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Butyric Acid

PubChem CID
264
Structure
Butyric Acid_small.png
Butyric Acid_3D_Structure.png
Molecular Formula
Synonyms
  • butyric acid
  • butanoic acid
  • 107-92-6
  • n-Butyric acid
  • n-Butanoic acid
Molecular Weight
88.11 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-25
Description
Butyric acid appears as a colorless liquid with a penetrating and unpleasant odor. Flash point 170 °F. Corrosive to metals and tissue. Density 8.0 lb /gal.
Butyric acid is a straight-chain saturated fatty acid that is butane in which one of the terminal methyl groups has been oxidised to a carboxy group. It has a role as a Mycoplasma genitalium metabolite and a human urinary metabolite. It is a straight-chain saturated fatty acid and a fatty acid 4:0. It is a conjugate acid of a butyrate.
A four carbon acid, CH3CH2CH2COOH, with an unpleasant odor that occurs in butter and animal fat as the glycerol ester.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Butyric Acid.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

butanoic acid
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

FERIUCNNQQJTOY-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCC(=O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C4H8O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

C4H8O2

CH3CH2CH2COOH

2.3 Other Identifiers

2.3.1 CAS

107-92-6

2.3.2 Deprecated CAS

879654-11-2

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 UN Number

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DrugBank ID

2.3.9 DSSTox Substance ID

2.3.10 FEMA Number

2.3.11 HMDB ID

2.3.12 ICSC Number

2.3.13 JECFA Number

87

2.3.14 KEGG ID

2.3.15 Lipid Maps ID (LM_ID)

2.3.16 Metabolomics Workbench ID

2.3.17 NCI Thesaurus Code

2.3.18 Nikkaji Number

2.3.19 NSC Number

2.3.20 Pharos Ligand ID

2.3.21 Wikidata

2.3.22 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Acid, Butanoic
  • Acid, Butyric
  • Butanoic Acid
  • Butyrate, Magnesium
  • Butyrate, Sodium
  • Butyric Acid
  • Butyric Acid Magnesium Salt
  • Butyric Acid, Sodium Salt
  • Dibutyrate, Magnesium
  • Magnesium Butyrate
  • Magnesium Dibutyrate
  • Sodium Butyrate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
88.11 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
88.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
88.052429494 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
37.3 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
6
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
49.5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

Butyric acid appears as a colorless liquid with a penetrating and unpleasant odor. Flash point 170 °F. Corrosive to metals and tissue. Density 8.0 lb /gal.
Liquid
Colorless, oily liquid with an unpleasant, rancid odor; [HSDB]
COLOURLESS OILY LIQUID WITH CHARACTERISTIC ODOUR.
colourless liquid/strong, rancid, butterlike odour

3.2.2 Color / Form

Oily liquid
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
Colorless liquid
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 183

3.2.3 Odor

Unpleasant, rancid odor
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
Penetrating and obnoxious odor
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 183

3.2.4 Taste

Butter-fat taste
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Volume 2. Boca Raton, Florida: CRC Press, Inc., 1980., p. 262

3.2.5 Boiling Point

326.3 °F at 760 mmHg (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
163.7 °C
PhysProp
163.5 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
164 °C

3.2.6 Melting Point

17.8 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
-5.7 °C
PhysProp
-7.9 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
-5.7 °C

3.2.7 Flash Point

170 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
72 °C
161 °F (72 °C) (Closed cup)
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 325-27
72 °C c.c.

3.2.8 Solubility

greater than or equal to 100 mg/mL at 66 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
60000 mg/L (at 25 °C)
HEMPHILL,L & SWANSON,WS (1964)
Miscible with ethanol, ether; slightly soluble in carbon tetrachloride
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 3-74
In water, 6.00X10+4 mg/L at 25 °C
Hemphill L, Swanson WS; Proc of the 18th Industrial Waste Conf, Eng Bull Purdue U, Lafayette, IN 18:204-17 (1964)
60.0 mg/mL
Solubility in water: miscible
miscible with alcohol, most fixed oils, propylene glycol, water

3.2.9 Density

0.958 at 68 °F (USCG, 1999) - Less dense than water; will float
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
0.959 at 20 °C/4 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
Relative density (water = 1): 0.96
0.952-0.956

3.2.10 Vapor Density

3.04 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
3.04 (Air= 1)
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. 662
Relative vapor density (air = 1): 3

3.2.11 Vapor Pressure

0.43 mmHg at 68 °F ; 1.4 mmHg at 86 °F (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
1.65 [mmHg]
1.65 mm Hg at 25 °C
Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press Inc., 1995-1996., p. 6-85
Vapor pressure, Pa at 20 °C: 57

3.2.12 LogP

0.79
HANSCH,C ET AL. (1995)
log Kow= 0.79
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 9
0.79
HANSCH,C ET AL. (1995)

3.2.13 LogS

-0.19
ADME Research, USCD

3.2.14 Stability / Shelf Life

It has good stability
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 490

3.2.15 Autoignition Temperature

842 °F (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
830 °F (443 °C)
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 325-27
452 °C

3.2.16 Viscosity

1.426 mPa-s at 25 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-176

3.2.17 Corrosivity

Corrosive material
Lewis, R.J. Sax's Dangerous Properties of Industrial Materials. 10th ed. Volumes 1-3 New York, NY: John Wiley & Sons Inc., 1999., p. 662

3.2.18 Heat of Combustion

521.87 kg cal/gm at 25 °C
Weast, R.C. (ed.) Handbook of Chemistry and Physics. 69th ed. Boca Raton, FL: CRC Press Inc., 1988-1989., p. D-274

3.2.19 Heat of Vaporization

40.45 kJ/mol at 25 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-100

3.2.20 Surface Tension

26.05 mN/m at 25 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-128

3.2.21 Odor Threshold

0.001 mg/cu m (Odor low) 9 mg/cu m (Odor high)
Ruth JH; Am Ind Hyg Assoc J 47: A-142-51 (1986)

3.2.22 Refractive Index

Index of refraction: 1.3991 at 20 °C/D
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
1.397-1.399

3.2.23 Dissociation Constants

pKa
4.82 (at 25 °C)
RIDDICK,JA ET AL. (1986)
pKa = 4.82 at 25 °C
Riddick, J.A., W.B. Bunger, Sakano T.K. Techniques of Chemistry 4th ed., Volume II. Organic Solvents. New York, NY: John Wiley and Sons., 1985., p. 1325

3.2.24 Kovats Retention Index

Standard non-polar
780 , 856 , 826 , 830 , 814 , 778 , 823 , 823 , 828 , 834 , 804 , 824 , 823 , 800 , 786 , 775.6 , 802 , 809 , 803 , 820 , 780 , 797 , 797 , 795
Semi-standard non-polar
789 , 822 , 790 , 823 , 822 , 821 , 850 , 840 , 824 , 831 , 841 , 848 , 790 , 815 , 817 , 844 , 820 , 823 , 818 , 812 , 780 , 804 , 808 , 818 , 818 , 780 , 834 , 815 , 826 , 821 , 790 , 820 , 802 , 829 , 821 , 835 , 821 , 820 , 795 , 785 , 821 , 773 , 777 , 789 , 802 , 784 , 803 , 803 , 793 , 790 , 793 , 821 , 821 , 821 , 856 , 788 , 763 , 781 , 786 , 780 , 791 , 821 , 821 , 821 , 821 , 779 , 804 , 795 , 805 , 820 , 821 , 788 , 788 , 779 , 787.5 , 820 , 796.2 , 769 , 817.6 , 779 , 775 , 814 , 778 , 825 , 821 , 784 , 829 , 829 , 796 , 783 , 784 , 792 , 811 , 779 , 784 , 784 , 821 , 789 , 791 , 783 , 803 , 793
Standard polar
1630 , 1637 , 1644 , 1641 , 1624 , 1653 , 1625 , 1576 , 1637 , 1637 , 1620 , 1620 , 1620 , 1644 , 1614 , 1627 , 1607 , 1647 , 1613 , 1625 , 1622 , 1622 , 1663 , 1625 , 1650 , 1661 , 1576 , 1628 , 1652 , 1629 , 1647 , 1657 , 1620 , 1625 , 1599 , 1648 , 1663 , 1610 , 1647 , 1652 , 1624 , 1624 , 1633 , 1617 , 1620 , 1616 , 1650 , 1637 , 1645 , 1607 , 1622 , 1613 , 1635 , 1670 , 1625 , 1604 , 1618 , 1616 , 1650 , 1627 , 1628 , 1617 , 1625 , 1604 , 1624 , 1618 , 1618 , 1610 , 1610 , 1625 , 1629 , 1613 , 1599 , 1611 , 1606 , 1618 , 1622 , 1599 , 1627 , 1597 , 1594 , 1637 , 1623 , 1624 , 1599 , 1600 , 1666 , 1612 , 1633 , 1622 , 1614 , 1646 , 1624 , 1623 , 1624 , 1624 , 1621 , 1612 , 1623 , 1631 , 1631 , 1635 , 1625 , 1630 , 1630 , 1598 , 1598 , 1606 , 1600 , 1596 , 1598 , 1599 , 1600 , 1598 , 1602 , 1591 , 1640 , 1627 , 1628 , 1576 , 1576 , 1581 , 1630 , 1648 , 1625 , 1633 , 1630 , 1642 , 1651 , 1620 , 1636 , 1636 , 1612 , 1606 , 1635 , 1652 , 1626 , 1621 , 1589 , 1641 , 1623 , 1626 , 1627 , 1619 , 1641 , 1620 , 1623 , 1625 , 1620 , 1646 , 1605 , 1618 , 1622 , 1645 , 1618 , 1629 , 1634 , 1625 , 1630 , 1619 , 1588 , 1659 , 1611 , 1634 , 1619 , 1619 , 1627 , 1634 , 1636 , 1609 , 1602 , 1623 , 1659 , 1602 , 1602 , 1634 , 1602 , 1636 , 1614 , 1613 , 1633 , 1639 , 1650 , 1599 , 1600 , 1641 , 1631 , 1616 , 1652 , 1642 , 1621 , 1610 , 1631 , 1642 , 1644 , 1647 , 1647 , 1642 , 1642 , 1647 , 1619 , 1650 , 1633 , 1646 , 1622 , 1627 , 1581 , 1646 , 1653 , 1640 , 1638.1 , 1614 , 1646 , 1620.5 , 1632.5 , 1622 , 1627 , 1596 , 1626 , 1620 , 1648 , 1625 , 1612 , 1612 , 1646 , 1614 , 1588 , 1618.5 , 1588 , 1621 , 1660 , 1644 , 1630 , 1630 , 1644 , 1639 , 1627 , 1629 , 1628 , 1628 , 1613 , 1616 , 1615 , 1615 , 1631 , 1620 , 1623 , 1620 , 1623 , 1616.1 , 1618.4 , 1623.6 , 1626.3 , 1629.5 , 1628 , 1625 , 1661 , 1630 , 1630 , 1598 , 1607 , 1609 , 1627 , 1645 , 1670.4 , 1613 , 1652 , 1610 , 1610 , 1628 , 1669 , 1628 , 1639 , 1638 , 1616 , 1642 , 1613 , 1623 , 1620.8 , 1620.8 , 1613 , 1630 , 1585 , 1600 , 1614 , 1637 , 1636 , 1581 , 1620 , 1620.8

3.2.25 Other Experimental Properties

Heat capacity = 178.6 J/mol-K at 25 °C. Heat capacity = 178.6 J/mol-K at 25 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 5-26
Critical molar volume = 292 cu cm/mol
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-42
Heat of fusion = 11.59 kJ/mol
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-113
Dielectric constant = 2.98 at 14 °C
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-137
For more Other Experimental Properties (Complete) data for n-BUTYRIC ACID (8 total), please visit the HSDB record page.

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Classes -> Organic Acids

3.4.1 Food Additives

ANTIOXIDANT, FLAVORING AGENT OR ADJUVANT, PH CONTROL AGENT -> FDA Substance added to food

3.4.2 Fragrances

Fragrance Ingredient (Butyric acid) -> IFRA transparency List

3.4.3 Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
1H NMR: 7312 (Sadtler Research Laboratories Spectral Collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 5
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Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
0.90:49.84, 1.58:4.10, 2.13:36.29, 1.51:4.51, 0.87:47.54, 0.88:100.00, 1.55:36.31, 2.14:64.06, 1.52:19.83, 2.16:31.68, 1.57:18.79, 1.54:36.96
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Spectra ID
Instrument Type
JEOL
Frequency
90 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
2.34:367.00, 2.26:331.00, 2.43:203.00, 1.64:183.00, 1.73:106.00, 1.06:263.00, 1.47:47.00, 11.51:1000.00, 0.88:157.00, 0.89:300.00, 1.55:151.00, 1.71:146.00, 1.05:489.00, 2.26:349.00, 1.79:127.00, 0.90:171.00, 0.98:966.00, 1.80:86.00, 1.62:218.00, 1.88:49.00, 1.63:175.00, 1.56:60.00, 2.34:455.00, 1.72:254.00, 1.78:40.00, 0.97:544.00, 2.42:222.00
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4.1.2 13C NMR Spectra

1 of 5
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Spectra ID
Instrument Type
Bruker
Frequency
125 MHz
Solvent
Water
pH
7.00
Shifts [ppm]:Intensity
15.93:78.92, 186.67:16.12, 42.28:69.20, 22.01:82.78, 0.00:11.49
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Spectra ID
Instrument Type
NEVA
Frequency
15.09 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
13.65:795.00, 18.36:1000.00, 36.18:972.00, 180.66:886.00
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4.1.3 17O NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 2D NMR Spectra

4.2.1 1H-13C NMR Spectra

2D NMR Spectra Type
1H-13C HSQC
Spectra ID
Instrument Type
Bruker
Frequency
600 MHz
Solvent
Water
pH
7.00
Shifts [ppm] (F2:F1):Intensity
2.15:42.35:1.00, 0.85:16.01:0.31, 0.91:15.92:0.37, 1.54:22.07:0.56
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 10
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

60.0 99.99

73.0 28.50

27.0 23.48

41.0 22.36

42.0 18.70

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Notes
instrument=HITACHI RMU-7M
2 of 10
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

60.0 99.99

27.0 32.60

73.0 30.27

41.0 24.41

42.0 21.65

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Notes
instrument=HITACHI M-80B

4.3.2 MS-MS

1 of 6
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Spectra ID
Instrument Type
EI-B (HITACHI RMU-7M)
Ionization Mode
Positive
Top 5 Peaks

60.0 1

73.0 0.29

27.0 0.24

41.0 0.22

42.0 0.19

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Spectra ID
Instrument Type
EI-B (HITACHI M-80B)
Ionization Mode
Positive
Top 5 Peaks

60.0 1

27.0 0.33

73.0 0.30

41.0 0.24

42.0 0.22

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4.3.3 LC-MS

1 of 8
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Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
10 V
Precursor m/z
87
Precursor Adduct
[M-H]-
Top 5 Peaks

87.1 999

43.1 1

57.9 1

42.2 1

104.9 1

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License
CC BY-NC-SA
2 of 8
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Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
NEGATIVE
Collision Energy
20 V
Precursor m/z
87
Precursor Adduct
[M-H]-
Top 5 Peaks

87.3 999

42.9 4

44 4

69.2 2

58.3 1

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License
CC BY-NC-SA

4.3.4 Other MS

1 of 6
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Other MS
MASS: 49308 (NIST/EPA/MSDC Mass Spectral Database 1990 version)
2 of 6
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Authors
TAJIMA S, GUNMA COLLEGE OF TECHNOLOGY
Instrument
HITACHI RMU-7M
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

60 999

73 285

27 235

41 224

42 187

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License
CC BY-NC-SA

4.4 UV Spectra

SADTLER REF NUMBER: 125 (IR, PRISM); 37 (IR, GRATING); MAX ABSORPTION (WATER): 208 NM (LOG E= 1.8), 270 (IR, PRISM); 37 (IR, GRATING); MAX ABSORPTION (WATER): 208 NM (LOG E= 1.8), 270 NM (SHOULDER) (LOG E= -0.8)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-221
UV: 2-21 (Philip et al, Organic Electronic Spectral Data, John Wiley & Sons, New York)
Lide, D.R., G.W.A. Milne (eds.). Handbook of Data on Organic Compounds. Volume I. 3rd ed. CRC Press, Inc. Boca Raton ,FL. 1994., p. V2: 1855

4.5 IR Spectra

IR Spectra
IR: 4820 (Coblentz Society Spectral Collection)

4.5.1 FTIR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
Neat
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L13189
Lot Number
10189625
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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Instrument Name
Bruker IFS 85
Technique
Cell
Source of Sample
Riedel de Haen AG, Seelze
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.5.2 ATR-IR Spectra

1 of 2
Technique
ATR-Neat
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L13189
Lot Number
10189625
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5.3 Near IR Spectra

1 of 2
Instrument Name
BRUKER IFS 88
Technique
NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=9330,REO=2,CNM=HEI,ZFF=2
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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Instrument Name
BRUKER IFS 88
Technique
NIR Spectrometer= INSTRUMENT PARAMETERS=INST=BRUKER,RSN=9330,REO=2,CNM=HEI,ZFF=2
Source of Spectrum
Prof. Buback, University of Goettingen, Germany
Copyright
Copyright © 1989, 1990-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.5.4 Vapor Phase IR Spectra

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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Technique
Vapor Phase
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
B103500
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.6 Raman Spectra

1 of 2
Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L13189
Lot Number
10189625
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Catalog Number
B103500
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

7.2 Clinical Trials

7.2.1 ClinicalTrials.gov

7.2.2 NIPH Clinical Trials Search of Japan

7.3 Therapeutic Uses

Mesh Heading: histamine antagonists
National Library of Medicine, SIS; ChemIDplus Record for Butyric Acid (107-92-6). Available from, as of April 13, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp

7.4 Biomarker Information

8 Food Additives and Ingredients

8.1 Food Additive Classes

Flavoring Agents
JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT;

8.2 FEMA Flavor Profile

Butter, Cheese, Sour

8.3 FDA Substances Added to Food

Substance
Used for (Technical Effect)
ANTIOXIDANT, FLAVORING AGENT OR ADJUVANT, PH CONTROL AGENT
Document Number (21 eCFR)
FEMA Number
2221
GRAS Number
3, 25
JECFA Flavor Number
87

8.4 Associated Foods

8.5 Evaluations of the Joint FAO / WHO Expert Committee on Food Additives - JECFA

Chemical Name
BUTYRIC ACID
Evaluation Year
1997
ADI
No safety concern at current levels of intake when used as a flavouring agent
Tox Monograph

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Histamine Antagonists
Drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only. (See all compounds classified as Histamine Antagonists.)

9.2 Bionecessity

Butyric acid as butyrates is formed in the human colon as a product of fiber fermentation, and this is suggested as a factor explaining why high fiber diets are protective in preventing colon cancer. Various hypotheses have been investigated regarding the possible mechanism of this relationship, including whether butyrate is important in maintaining normal phenotypic expression of the epithelial cells or enhancing removal of damaged cells through apoptosis. /Butyrates/
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:710
Butyric acid, a product of fermentation within the human colon, is a very important energy source for normal colorectal epithelium.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:709

9.3 Absorption, Distribution and Excretion

Butyric acid is readily absorbed from the gastrointestinal tract ...
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:709
A pharmacokinetics study was performed by injecting butyric acid as sodium or arginine salts for possible antitumor therapies. In the case of 1-(14)C-labelled butyrate, the appearance of radioactivity in the blood of injected mice is rapid and some of it is maintained for relatively long periods in different organs, mainly the liver. However, no precision can be given about the structure of radioactive compounds in blood and tissues. Using GLC, the metabolism of butyrate in both animals and man were studied. In mice and rabbits, the half-life is less than 5 min. In man, the butyric acid elimination curve can be divided into two parts corresponding to two half-lives: for the first (0.5 min), the slope suggests an accelerated excretion, while for the following (13.7 min), a slow plateau is observed. The rapid elimination of butyrate is a limiting factor for practical applications. However, the lack of toxicity supports its use in human therapy.
Daniel P et al; Clin Chim Acta 181 (3): 255-63 (1989)

9.4 Metabolism / Metabolites

Butyric acid is ... rapidly metabolized by the liver. In rats a considerable portion ... is metabolized to acetic acid. Butyric acid metabolism gives rise to ketone bodies (beta-hydroxybutyrate, acetoacetate, acetone) and acetic acid, which may be excreted in the urine or incorporated into normal processes of fat metabolism.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:709
The metabolism of carboxyl-labeled butyric acid by liver tissue was investigated in vitro. It was shown that the test substance was converted to ketone bodies mainly by fission into 2-carbon chains with subsequent recombination, and to a lesser extent by direct beta-oxidation.
European Chemicals Bureau; IUCLID Dataset, Butyric acid (107-92-6) (2000 CD-ROM edition). Available from, as of April 20, 2006: https://esis.jrc.ec.europa.eu/
In isolated animal tissues butyric acid was oxidized to acetoacetic and beta-hydroxybutyric acid. The formation of carbohydrate and complete oxidation were also reported. Besides the formation of beta-hydroxybutyric acid the formation of ketone bodies represents possibly an alternative path after oxidation at the beta-carbon atom of butyric acid.
European Chemicals Bureau; IUCLID Dataset, Butyric acid (107-92-6) (2000 CD-ROM edition). Available from, as of April 20, 2006: https://esis.jrc.ec.europa.eu/
... Following butyraldehyde intake ... it is oxidized by aldehyde dehydrogenase, largely in the liver but also in other tissues. Butyric acid undergoes further oxidation via the Krebs cycle, or it may be conjugated with glutathione.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:978
Paraoxonase (PON1) is a key enzyme in the metabolism of organophosphates. PON1 can inactivate some organophosphates through hydrolysis. PON1 hydrolyzes the active metabolites in several organophosphates insecticides as well as, nerve agents such as soman, sarin, and VX. The presence of PON1 polymorphisms causes there to be different enzyme levels and catalytic efficiency of this esterase, which in turn suggests that different individuals may be more susceptible to the toxic effect of OP exposure.

9.5 Mechanism of Action

Diet, especially the amount of starch and dietary fiber which escape digestion in the small intestine are major determinants of colon function in man. These carbohydrates are the principal substrates for fermentation by the large bowel flora. Carbohydrate fermentation results in lowered caecal pH and the production of short chain fatty acids of which butyric acid may protect the colon epithelium from dysplastic change. Protein digestion and amino acid fermentation also occur in the large bowel but the nature of its endproducts varies in relation to the amount of carbohydrate available. During active carbohydrate breakdown amino acid fermentation endproducts such as ammonia are used by the bacteria for protein synthesis during microbial growth, but in carbon limited fermentation amines, ammonia, phenols and indoles, etc, accumulate. Fermentation also results in changes in colon pH which alters the metabolism of bile acids, nitrate, sulfate and other substances. Fermentation is thus controlled to a great extent by substrate availability, especially of carbohydrates which are derived from the diet. The potential to induce mutagenic change in colon epithelial cells and promote tumor growth may readily be influenced by diet.
Cummings JH, Bingham SA; Cancer Surv 6 (4): 601-21 (1987)
Butyric acid has two contrasting functional roles. As a product of fermentation within the human colon, it serves as the most important energy source for normal colorectal epithelium. It also promotes the differentiation of cultured malignant cells. A switch from aerobic to anaerobic metabolism accompanies neoplastic transformation in the colorectum. The separate functional roles for n-butyrate may reflect the different metabolic activities of normal and neoplastic tissues. Deficiency of n-butyrate, coupled to the increased energy requirements of neoplastic tissue, may promote the switch to anaerobic metabolism.
Jass JR; Med Hypotheses 18 (2): 113-8 (1985)
Treatment of cultured HeLa cells with 5 mM butyrate caused an inhibition of growth as well as extensive chemical and morphological differentiation. Lysosomal enzyme activity changes are associated with both normal and neoplastic growth as well as many aspects of the neoplastic process. The comparative ultrastructural results showed that the butyrate treated cells had a more extensive internal membranous system than the untreated cells, whereas other organelles seemed unaffected. The histochemical localization of lysosomal acid phosphatase showed a 2-fold increase in particulate reaction product in the butyrate-treated HeLa cells. Butyrate treatment may prevent sublethal autolysis by arresting the leakage of the lysosomal enzymes from the lysosome into the cytosol and thus allowing the cell to differentiate chemically and morphologically.
Kelly RE; In Vitro 21 (7): 373-81 (1985)
Exposure of the rat glioma C6 cell line to butyric acid increased levels of L-triiodothyronine in the nuclear and extranuclear compartments. The increase in nuclear binding was not merely a reflection of the higher cellular hormone content, and Scatchard analysis of L-triiodothyronine binding to isolated nuclei revealed that butyric acid increased receptor number without changing affinity. The effect on the receptor was quantitatively important: a 48 hr incubation with 2 mM butyric acid increased nuclear binding by 2-3 fold, and 5 mM butyrate by 35 fold. Butyric acid increased receptor levels by decreasing receptor degradation, since the apparent half-life of receptor disappearance increased by approximately 3 fold in cells incubated with 2 mM butyric acid for 48 hr. Butyric acid had little effect in increasing the level of multiacetylated forms of H3 and H4 histone when studied in acid-urea gels, but it markedly inhibited the turnover of (3)H-acetate from the histone fraction. There was a striking similarity in the dose-response of butyric acid for increasing receptor levels and inhibiting histone deacetylation. Furthermore, a very close correlation between receptor levels and (3)H-acetate release was also found when different short-chain fatty acids were used.
Ortiz CJ et al; J Biol Chem 261 (30): 13997-4004 (1986)

9.6 Human Metabolite Information

9.6.1 Tissue Locations

  • Fibroblasts
  • Intestine
  • Kidney
  • Neuron
  • Prostate
  • Skeletal Muscle

9.6.2 Cellular Locations

  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria

9.6.3 Metabolite Pathways

9.7 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used as a flavoring agent (foods, perfumes, drugs) and chemical intermediate; also used in leather tanning (deliming hides) and as an additive to disinfectants, gasoline, and varnishes; [HSDB]
Industrial Processes with risk of exposure
Mesh Heading: histamine antagonists
National Library of Medicine, SIS; ChemIDplus Record for Butyric Acid (107-92-6). Available from, as of April 13, 2006: https://chem.sis.nlm.nih.gov/chemidplus/chemidlite.jsp
Chem int for cellulose derivatives in lacquers and plastics, for pharmaceuticals, emulsifiers and disinfectants; leather tanning agent for deliming and swelling hides, sweetening agent in gasolines.
SRI
Synthesis of butyrate ester perfume and flavor ingredients...
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 183
Butyric acid is used for body in butter, cheese, butterscotch, caramel, fruit, and nut flavors.
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 490
For more Uses (Complete) data for n-BUTYRIC ACID (8 total), please visit the HSDB record page.
This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

10.1.1 Use Classification

Food additives -> Flavoring Agents
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT; -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Hazard Classes and Categories -> Corrosives, Flammable - 2nd degree

10.1.2 Industry Uses

  • Fragrance
  • Intermediate
  • Processing aids, not otherwise listed

10.1.3 Consumer Uses

Fragrance

10.2 Methods of Manufacturing

Obtained as a by-product from the liquid phase oxidation of n-butane to acetic acid or by oxidation of n-butyl alcohol or normal-butyraldehyde
SRI
From n-propanol and carbon monoxide at 200 atm in the presence of Ni-(CO)4 and Ni-I2
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
Obtained by fermentation of starches and molasses with selective enzymes (Granulo saccharobutyricum). It is subsequently isolated as calcium salt.
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 3rd Edition, Volumes 1-2. Boca Raton, FL: CRC Press 1994-1995., p. 98
The reaction of butanol with concn alkali hydroxide at 275 °C yields hydrogen, butyric acid, and 2-ethylhexanoic acid.
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V4 338 (1978)
Oxidation of butyraldehyde to butyric acid is most commonly carried out employing air or oxygen as the oxidant. Alternatively, organic oxidants, eg, cumene hydroperoxide, can also be employed effectively to give high yields of butyric acid.
Kirk-Othmer Encyclopedia of Chemical Technology. 4th ed. Volumes 1: New York, NY. John Wiley and Sons, 1991-Present., p. V4 737 (1992)

10.3 Impurities

... Butyric acid is usually contaminated with acrylic acid.
Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. V1 124 (1978)

10.4 Formulations / Preparations

GRADES: 90%; 95%; 99%; edible; synthetic; reagent; Technical; FCC.
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 183
Grades or Purity: Commercial, 99.5+%
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.

10.5 U.S. Production

Aggregated Product Volume

2019: 20,000,000 lb - <100,000,000 lb

2018: 20,000,000 lb - <100,000,000 lb

2017: 20,000,000 lb - <100,000,000 lb

2016: 20,000,000 lb - <100,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).
EPA/Office of Pollution Prevention and Toxics; High Production Volume (HPV) Challenge Program. Available from, as of May 17, 2006: https://www.epa.gov/hpv/pubs/general/opptsrch.htm
(1986) >100 million-500 million pounds
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Butyric acid (107-92-6). Available from, as of May 16, 2006: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
(1990) >100 million-500 million pounds
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Butyric acid (107-92-6). Available from, as of May 16, 2006: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
(1994) >100 million-500 million pounds
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Butyric acid (107-92-6). Available from, as of May 16, 2006: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
For more U.S. Production (Complete) data for n-BUTYRIC ACID (6 total), please visit the HSDB record page.

10.6 General Manufacturing Information

Industry Processing Sectors
  • All Other Chemical Product and Preparation Manufacturing
  • All Other Basic Organic Chemical Manufacturing
EPA TSCA Commercial Activity Status
Butanoic acid: ACTIVE

11 Identification

11.1 Analytic Laboratory Methods

A gas chromatographic method that identifies sporeformers as the cause of spoilage in swollen cans of low-acid foods was collaboratively studied in 2 stages. Two organic compounds produced by sporeformers, D-(-)-2,3-butanediol and butyric acid, are measured in the upper phase after centrifugation of the liquid portion of the can contents. Each sample is assayed on 2 packed columns designed for the assay of aqueous solutions of volatile fatty acids, using flame ionization detectors.
Schafer ML et al; J Assoc Off Anal Chem 68 (4): 626-31 (1985)
Detection of organic acid sweetners, syrup carboxylic acids and carbohydrates by HPLC.
Mattiuz EL, Perone RA; LC-GC 4 (16): 552-61 (1986)
Carboxylate detection of /butyric acid in/ coffee, wine, and fruit juice by HPLC.
Badoud R, Pratz G; J Chromatogr 360 (1): 119-36 (1986)
Detection of cheese volatile substances by gas chromatography. Detection of odorous substances of cheese by gas chromatography.
Dunn HC, Lindsay RC; J Dairy Sci 68 (11): 2853-58 (1985)
For more Analytic Laboratory Methods (Complete) data for n-BUTYRIC ACID (11 total), please visit the HSDB record page.

11.2 Clinical Laboratory Methods

DETERMINATION IN FAT, COLUMN CHROMATOGRAPHIC METHOD, AND TITRATION
Association of Official Analytical Chemists. Official Methods of Analysis. 10th ed. and supplements. Washington, DC: Association of Official Analytical Chemists, 1965. New editions through 13th ed. plus supplements, 1982., p. 13/442 28.038
Gas chromatography seperation of mixtures of fatty acids, phenols, and indoles were effected with flexible fused silica capillary columns containing either volatile fatty acid, Carbowax 20M nondeactivated fused silica (VFA) or Carbowax 20M deactivated (Carbowax 20M), or SP-2100, Carbowax 20M deactivated (Methyl Silicone) and the respective chromatograms compared for artificial mixtures, for human urine, or for Persian cat feces. Optimum conditions for the column were detected and fair to good separations were achieved.
Hoshika Y; Glass Capillary Chromatogr Clin Med Pharmacol 315-28 (1985)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

1 of 4
View All
Pictogram(s)
Corrosive
Irritant
Signal
Danger
GHS Hazard Statements

H302 (12.7%): Harmful if swallowed [Warning Acute toxicity, oral]

H314 (99%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

H318 (11.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Precautionary Statement Codes

P260, P264, P264+P265, P270, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2102 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

12.1.2 Hazard Classes and Categories

Acute Tox. 4 (12.7%)

Skin Corr. 1B (99%)

Eye Dam. 1 (11.3%)

Skin corrosion - category 1B

12.1.3 NFPA Hazard Classification

NFPA 704 Diamond
3-2-0
NFPA Health Rating
3 - Materials that, under emergency conditions, can cause serious or permanent injury.
NFPA Fire Rating
2 - Materials that must be moderately heated or exposed to relatively high ambient temperatures before ignition can occur. Materials would not under normal conditions form hazardous atmospheres with air, but under high ambient temperatures or under moderate heating could release vapor in sufficient quantities to produce hazardous atmospheres with air.
NFPA Instability Rating
0 - Materials that in themselves are normally stable, even under fire conditions.

12.1.4 Health Hazards

Inhalation causes irritation of mucous membrane and respiratory tract; may cause nausea and vomiting. Ingestion causes irritation of mouth and stomach. Contact with eyes may cause serious injury. Contact with skin may cause burns; chemical is readily absorbed through the skin and may cause damage by this route. (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
ERG 2024, Guide 153 (Butyric acid)

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· Methyl bromoacetate (UN2643) is an eye irritant/lachrymator (causes flow of tears).

· Contact with molten substance may cause severe burns to skin and eyes.

· Avoid any skin contact.

· Fire may produce irritating, corrosive and/or toxic gases.

· Runoff from fire control or dilution water may be corrosive and/or toxic and cause environmental contamination.

12.1.5 Fire Hazards

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Corrosives in contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2024)

ERG 2024, Guide 153 (Butyric acid)

· Combustible material: may burn but does not ignite readily.

· When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards.

· Those substances designated with a (P) may polymerize explosively when heated or involved in a fire.

· Corrosives in contact with metals may evolve flammable hydrogen gas.

· Containers may explode when heated.

· Runoff may pollute waterways.

· Substance may be transported in a molten form.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Above 72 °C explosive vapour/air mixtures may be formed.

12.1.6 Hazards Summary

Corrosive to skin; [Quick CPC] A corrosive substance that can cause injury to the skin, eyes and respiratory tract; [ICSC]
Quick CPC - Forsberg K, Mansdorf SZ. Quick Selection Guide to Chemical Protective Clothing, 5th Ed. Hoboken, NJ: Wiley-Interscience, 2007.

12.1.7 Fire Potential

... Combustible liquid
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 49-35

12.1.8 Skin, Eye, and Respiratory Irritations

Vapor: Irritating to eyes, nose, and throat. If inhaled will cause coughing or difficult breathing. Liquid: Will burn skin and eyes.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.

12.2 Safety and Hazard Properties

12.2.1 Flammable Limits

Lower flammable limit: 2.0% by volume; Upper flammable limit: 10.0% by volume
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 325-27

12.2.2 Lower Explosive Limit (LEL)

2 % (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.2.3 Upper Explosive Limit (UEL)

10 % (NTP, 1992)
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.2.4 Critical Temperature & Pressure

Critical temperature = 342.05 °C; critical pressure = 4.06 MPa
Lide, D.R. CRC Handbook of Chemistry and Physics 86TH Edition 2005-2006. CRC Press, Taylor & Francis, Boca Raton, FL 2005, p. 6-42

12.2.5 Explosive Limits and Potential

Explosive limits , vol% in air: 2-10

12.3 First Aid Measures

Inhalation First Aid
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Skin First Aid
Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer for medical attention .
Eye First Aid
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Ingestion First Aid
Rinse mouth. Do NOT induce vomiting. Refer for medical attention .

12.3.1 First Aid

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas.

INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing.

INGESTION: DO NOT INDUCE VOMITING. Corrosive chemicals will destroy the membranes of the mouth, throat, and esophagus and, in addition, have a high risk of being aspirated into the victim's lungs during vomiting which increases the medical problems. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. Transport the victim IMMEDIATELY to a hospital. (NTP, 1992)

National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.
ERG 2024, Guide 153 (Butyric acid)

General First Aid:

· Call 911 or emergency medical service.

· Ensure that medical personnel are aware of the material(s) involved, take precautions to protect themselves and avoid contamination.

· Move victim to fresh air if it can be done safely.

· Administer oxygen if breathing is difficult.

· If victim is not breathing:

-- DO NOT perform mouth-to-mouth resuscitation; the victim may have ingestedor inhaled the substance.

-- If equipped and pulse detected, wash face and mouth, then give artificial respiration using a proper respiratory medical device (bag-valve mask, pocket mask equipped with a one-way valve or other device).

-- If no pulse detected or no respiratory medical device available, provide continuouscompressions. Conduct a pulse check every two minutes or monitor for any signs of spontaneous respirations.

· Remove and isolate contaminated clothing and shoes.

· For minor skin contact, avoid spreading material on unaffected skin.

· In case of contact with substance, remove immediately by flushing skin or eyes with running water for at least 20 minutes.

· For severe burns, immediate medical attention is required.

· Effects of exposure (inhalation, ingestion, or skin contact) to substance may be delayed.

· Keep victim calm and warm.

· Keep victim under observation.

· For further assistance, contact your local Poison Control Center.

· Note: Basic Life Support (BLS) and Advanced Life Support (ALS) should be done by trained professionals.

Specific First Aid:

· For corrosives, in case of contact, immediately flush skin or eyes with running water for at least 30 minutes. Additional flushing may be required.

· Removal of solidified molten material from skin requires medical assistance.

In Canada, an Emergency Response Assistance Plan (ERAP) may be required for this product. Please consult the shipping paper and/or the "ERAP" section.

12.4 Fire Fighting

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

SMALL FIRE: Dry chemical, CO2 or water spray.

LARGE FIRE: Dry chemical, CO2, alcohol-resistant foam or water spray. If it can be done safely, move undamaged containers away from the area around the fire. Dike runoff from fire control for later disposal.

FIRE INVOLVING TANKS, RAIL TANK CARS OR HIGHWAY TANKS: Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks in direct contact with flames. (ERG, 2024)

Use water spray, powder, alcohol-resistant foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

12.4.1 Fire Fighting Procedures

Use water spray, dry chemical, "alcohol resistant" foam, or CO2. Use water to keep fire-exposed containers cool. On large fires, solid streams of water may not be effective.
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 49-35
If material on fire or involved in fire: Use water in flooding quantities as fog. Solid streams of water may be ineffective. ... Apply water from as far a distance as possible.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, D.C.: Assoc. of American Railroads, Hazardous Materials Systems (BOE), 1987., p. 122

12.5 Accidental Release Measures

Public Safety: ERG 2024, Guide 153 (Butyric acid)

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· Keep unauthorized personnel away.

· Stay upwind, uphill and/or upstream.

· Ventilate closed spaces before entering, but only if properly trained and equipped.

Spill or Leak: ERG 2024, Guide 153 (Butyric acid)

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.

· Stop leak if you can do it without risk.

· Prevent entry into waterways, sewers, basements or confined areas.

· Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers.

· DO NOT GET WATER INSIDE CONTAINERS.

12.5.1 Isolation and Evacuation

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.

FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)

Evacuation: ERG 2024, Guide 153 (Butyric acid)

Immediate precautionary measure

· Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.

Spill

· For highlighted materials: see Table 1 - Initial Isolation and Protective Action Distances.

· For non-highlighted materials: increase the immediate precautionary measure distance, in the downwind direction, as necessary.

Fire

· If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions.

12.5.2 Spillage Disposal

Personal protection: complete protective clothing including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Cautiously neutralize remainder with soda lime. Then wash away with plenty of water.

12.5.3 Cleanup Methods

Land spill: Dig a pit, pond, lagoon, or holding area to contain liquid or solid material /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash or cement powder. Neutralize with agricultural lime (slaked lime), crushed limestone, or sodium bicarbonate.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, D.C.: Assoc. of American Railroads, Hazardous Materials Systems (BOE), 1987., p. 122
Water spill: Neutralize with agricultural lime (slaked lime), crushed limestone, or sodium bicarbonate. If dissolved, apply activated carbon at ten times the spilled amount in region of 10 ppm or greater concn. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, D.C.: Assoc. of American Railroads, Hazardous Materials Systems (BOE), 1987., p. 122
Air spill: Apply water spray or mist to knock down vapors. Vapor knockdown water is corrosive or toxic and should be diked for containment.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, D.C.: Assoc. of American Railroads, Hazardous Materials Systems (BOE), 1987., p. 122
Eliminate all ignition sources ... Protect personnel, and dilute spill to form nonflammable mixtures. Control runoff and isolate discharged material for proper disposal ...
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 49-35

12.5.4 Disposal Methods

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.
The following wastewater treatment technologies have been investigated for butyric acid: Concentration process: Biological treatment.
USEPA; Management of Hazardous Waste Leachate, EPA Contract No.68-03-2766 p.E-31 (1982)
The following wastewater treatment technologies have been investigated for butyric acid: Concentration process: Activated carbon.
USEPA; Management of Hazardous Waste Leachate, EPA Contract No.68-03-2766 p.E-129 (1982)
The following wastewater treatment technologies have been investigated for butyric acid: Concentration process: Resin adsorption.
USEPA; Management of Hazardous Waste Leachate, EPA Contract No.68-03-2766 p.E-184 (1982)

12.5.5 Preventive Measures

Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Use water spray to knock-down vapors. ... Avoid breathing vapors. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages without protective equipment. Wash away any material which may have contacted the body with copious amounts of water, or soap and water.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, D.C.: Assoc. of American Railroads, Hazardous Materials Systems (BOE), 1987., p. 122
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

12.6 Handling and Storage

12.6.1 Nonfire Spill Response

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area. Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2024)

12.6.2 Safe Storage

Separated from strong oxidants, strong bases and food and feedstuffs.

12.6.3 Storage Conditions

Store in cool, dry, well-ventilated location, away from any area where fire hazard may be acute.
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 49-32
Outside or detached storage is preferred. Separate from oxidizing materials, heat, oxidizers, and sunlight.
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 49-36

12.7 Exposure Control and Personal Protection

Protective Clothing: ERG 2024, Guide 153 (Butyric acid)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear chemical protective clothing that is specifically recommended by the manufacturer when there is NO RISK OF FIRE.

· Structural firefighters' protective clothing provides thermal protection but only limited chemical protection.

12.7.1 Emergency Response Planning Guidelines

Emergency Response: ERG 2024, Guide 153 (Butyric acid)

Small Fire

· Dry chemical, CO2 or water spray.

Large Fire

· Dry chemical, CO2, alcohol-resistant foam or water spray.

· If it can be done safely, move undamaged containers away from the area around the fire.

· Dike runoff from fire control for later disposal.

Fire Involving Tanks, Rail Tank Cars or Highway Tanks

· Fight fire from maximum distance or use unmanned master stream devices or monitor nozzles.

· Do not get water inside containers.

· Cool containers with flooding quantities of water until well after fire is out.

· Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank.

· ALWAYS stay away from tanks in direct contact with flames.

12.7.2 Inhalation Risk

No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.

12.7.3 Effects of Short Term Exposure

The substance is corrosive to the eyes, skin and respiratory tract.

12.7.4 Personal Protective Equipment (PPE)

Self-contained breathing apparatus; rubber gloves; vapor- proof plastic goggles; impervious apron and boots (USCG, 1999)
U.S. Coast Guard. 1999. Chemical Hazard Response Information System (CHRIS) - Hazardous Chemical Data. Commandant Instruction 16465.12C. Washington, D.C.: U.S. Government Printing Office.
Wear self-contained breathing apparatus; wear goggles if eye protection is not provided.
Fire Protection Guide to Hazardous Materials. 12 ed. Quincy, MA: National Fire Protection Association, 1997., p. 49-32
Wear boots and protective gloves. ... If contact with the material anticipated, wear full protective clothing.
Association of American Railroads. Emergency Handling of Hazardous Materials in Surface Transportation. Washington, D.C.: Assoc. of American Railroads, Hazardous Materials Systems (BOE), 1987., p. 122
Wear special protective clothing and positive pressure self-contained breathing apparatus.
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 49-35

12.7.5 Preventions

Fire Prevention
NO open flames. Above 72 °C use a closed system and ventilation.
Exposure Prevention
AVOID ALL CONTACT! IN ALL CASES CONSULT A DOCTOR!
Inhalation Prevention
Use ventilation, local exhaust or breathing protection.
Skin Prevention
Protective gloves. Protective clothing.
Eye Prevention
Wear face shield or eye protection in combination with breathing protection.
Ingestion Prevention
Do not eat, drink, or smoke during work.

12.8 Stability and Reactivity

12.8.1 Air and Water Reactions

Water soluble.

12.8.2 Reactive Group

Acids, Carboxylic

12.8.3 Reactivity Profile

BUTYRIC ACID can react with oxidizing agents. Incandescent reactions occur with chromium trioxide above 212 °F. Also incompatible with bases and reducing agents. May attack aluminum and other light metals (NTP, 1992).
National Toxicology Program, Institute of Environmental Health Sciences, National Institutes of Health (NTP). 1992. National Toxicology Program Chemical Repository Database. Research Triangle Park, North Carolina.

12.8.4 Hazardous Reactivities and Incompatibilities

May attack aluminum or other light metals with formation of flammable hydrogen gas.
U.S. Coast Guard, Department of Transportation. CHRIS - Hazardous Chemical Data. Volume II. Washington, D.C.: U.S. Government Printing Office, 1984-5.
/Butyric acid/ can react with oxidizing materials.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 650
A mixture of chromium trioxide and butyric acid became incandescent on heating to 100 °C. /Chromium trioxide/
Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 1070

12.9 Transport Information

12.9.1 DOT Emergency Guidelines

/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Health: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate enclosed areas.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
/GUIDE 153: SUBSTANCES - TOXIC and/or CORROSIVE (Combustible)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible.
U.S. Department of Transportation. 2012 Emergency Response Guidebook. Washington, D.C. 2012
For more DOT Emergency Guidelines (Complete) data for n-BUTYRIC ACID (8 total), please visit the HSDB record page.

12.9.2 Shipping Name / Number DOT/UN/NA/IMO

UN 2820; Butyric Acid
IMO 8.0; Butyric acid

12.9.3 Standard Transportation Number

49 314 14; Butyric acid

12.9.4 Shipment Methods and Regulations

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./
49 CFR 171.2; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of February 15, 2006: https://www.ecfr.gov
The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.
International Air Transport Association. Dangerous Goods Regulations. 47th Edition. Montreal, Quebec Canada. 2006., p. 155
The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.
International Maritime Organization. International Maritime Dangerous Goods Code. London, UK. 2004., p. 137

12.9.5 DOT Label

Corrosive

12.9.6 Packaging and Labelling

Do not transport with food and feedstuffs.

12.9.7 EC Classification

Symbol: C; R: 34; S: (1/2)-26-36-45

12.9.8 UN Classification

UN Hazard Class: 8; UN Pack Group: III

12.10 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Butanoic acid
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Butyric acid: Does not have an individual approval but may be used under an appropriate group standard

12.10.1 Atmospheric Standards

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Butyric acid is produced, as an intermediate or final product, by process units covered under this subpart.
40 CFR 60.489; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2006: https://www.ecfr.gov

12.10.2 Clean Water Act Requirements

Butyric acid is designated as a hazardous substance under section 311(b)(2)(A) of the Federal Water Pollution Control Act and further regulated by the Clean Water Act Amendments of 1977 and 1978. These regulations apply to discharges of this substance. This designation includes any isomers and hydrates, as well as any solutions and mixtures containing this substance.
40 CFR 116.4; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2006: https://www.ecfr.gov

12.10.3 CERCLA Reportable Quantities

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 5000 lb or 2270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
40 CFR 302.4; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2006: https://www.ecfr.gov

12.10.4 FDA Requirements

Synthetic flavoring substances and adjuvants /for human consumption/ that are generally recognized as safe for their intended use, withn the meaning of section 409 of the Act. Butyric acid is included on this list.
21 CFR 182.60; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2006: https://www.ecfr.gov
N-Butyric acid used as a synthetic flavoring substance or adjuvant in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.
21 CFR 582.60; U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of June 21, 2006: https://www.ecfr.gov

12.11 Other Safety Information

Chemical Assessment

IMAP assessments - Butanoic acid: Environment tier I assessment

IMAP assessments - Butanoic acid: Human health tier II assessment

12.11.1 Toxic Combustion Products

Products of combustion include carbon dioxide and carbon monoxide as well as irritating fumes.
Fire Protection Guide to Hazardous Materials. 13 ed. Quincy, MA: National Fire Protection Association, 2002., p. 49-36
When heated to decomposition it emits acrid smoke and irritating fumes.
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 650

12.11.2 Special Reports

Leung HW, Paustenbach DJ; Organic Acids and Bases: Review of Toxicological Studies; Am J Ind Med 18 (6): 717-35 (1990).

13 Toxicity

13.1 Toxicological Information

13.1.1 Toxicity Summary

Butyric acid is a cholinesterase or acetylcholinesterase (AChE) inhibitor. A cholinesterase inhibitor (or 'anticholinesterase') suppresses the action of acetylcholinesterase. Because of its essential function, chemicals that interfere with the action of acetylcholinesterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses, followed by muscle spasms and ultimately death. Nerve gases and many substances used in insecticides have been shown to act by binding a serine in the active site of acetylcholine esterase, inhibiting the enzyme completely. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop. Among the most common acetylcholinesterase inhibitors are phosphorus-based compounds, which are designed to bind to the active site of the enzyme. The structural requirements are a phosphorus atom bearing two lipophilic groups, a leaving group (such as a halide or thiocyanate), and a terminal oxygen.

13.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

13.1.3 Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Certain reproductive effects in fertility, growth, and development for males and females have been linked specifically to organophosphate pesticide exposure. Most of the research on reproductive effects has been conducted on farmers working with pesticides and insecticdes in rural areas. In females menstrual cycle disturbances, longer pregnancies, spontaneous abortions, stillbirths, and some developmental effects in offspring have been linked to organophosphate pesticide exposure. Prenatal exposure has been linked to impaired fetal growth and development. Neurotoxic effects have also been linked to poisoning with OP pesticides causing four neurotoxic effects in humans: cholinergic syndrome, intermediate syndrome, organophosphate-induced delayed polyneuropathy (OPIDP), and chronic organophosphate-induced neuropsychiatric disorder (COPIND). These syndromes result after acute and chronic exposure to OP pesticides.

13.1.4 Exposure Routes

The substance can be absorbed into the body by inhalation of its vapour.

13.1.5 Symptoms

Inhalation Exposure
Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed.
Skin Exposure
Pain. Redness. Blisters. Skin burns.
Eye Exposure
Pain. Redness. Severe deep burns. Loss of vision.
Ingestion Exposure
Burning sensation. Abdominal pain. Shock or collapse.
Symptoms of low dose exposure include excessive salivation and eye-watering. Acute dose symptoms include severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Hypertension, hypoglycemia, anxiety, headache, tremor and ataxia may also result.

13.1.6 Adverse Effects

Dermatotoxin - Skin burns.

13.1.7 Acute Effects

13.1.8 Toxicity Data

LC (rat) > 500 mg/m3

13.1.9 Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

13.1.10 Interactions

n-Butyrate was previously found to increase the epidermal growth factor receptor binding in primary cultures of rat hepatocytes. /It was shown/ that butyrate and dexamethasone synergistically modulate the surface expression of epidermal growth factor receptors. The butyrate-induced enhancement of high-affinity epidermal growth factor binding was only slight in the absence of glucocorticoid, but was strongly and dose-dependently amplified by dexamethasone. Butyrate counteracted the inhibition by insulin of the dexamethasone-induced increase in epidermal growth factor binding. The results indicate that the glucocorticoid has a permissive effect on a butyrate- sensitive process that determines the surface expression of the high-affinity class of epidermal growth factor receptors.
Gladhaug IP, Christoffersen T; FEBS Lett 243 (1): 21-4 (1989)
Butyrate inhibited differentiation of F9 mouse teratocarcinoma stem cells in the presence of retinoic acid, when added within 8 hr of retinoic acid addition.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:710

13.1.11 Antidote and Emergency Treatment

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist respirations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Activated charcoal is not effective ... . Do not attempt to neutralize because of exothermic reaction. Cover skin burns with dry, sterile dressings after decontamination ... . /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 176-7
/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Early intubation, at the first sign of upper airway obstruction, may be necessary. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Organic acids and related compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3Rd edition, Elsevier Mosby, St. Louis, MO 2005, p. 177

13.1.12 Human Toxicity Excerpts

/SIGNS AND SYMPTOMS/ Butyric acid can act as a mild skin irritant in humans ... Application to intact human skin elicits a moderate burning sensation only after 52 min, and erythema is hardly noticeable. Slight epidermal scaling may follow within 24 hr.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:710
/SIGNS AND SYMPTOMS/ No sensitization reaction, measured as a change in leukcocyte or eosinophil infiltration, was elicited in human volunteers injected subcutaneously with butyric acid for 2 wk.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:709
/SIGNS AND SYMPTOMS/ INHALATION: Sore throat. Cough. Burning sensation. Shortness of breath. Laboured breathing. Symptoms may be delayed. SKIN: Pain. redness. Blisters. Skin burns. EYES: Pain. Redness. Severe deep burns. Loss of vision. INGESTION: Burning sensation. Abdominal pain. Shock or collapse. /from table/
IPCS, CEC; International Chemical Safety Card on Butyric acid. (November 1998). Available from, as of April 13, 2006: https://www.inchem.org/documents/icsc/icsc/eics1334.htm

13.1.13 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ After a 90 min exposure to a butyric acid aerosol (40 mg/L), rabbits displayed increased lethargy and dyspnea. Signs of bronchial and capillary dilation and emphysema were evident upon necropsy.[Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:708]
/LABORATORY ANIMALS: Acute Exposure/ ... No lethalities /were reported/ when rats were exposed for 8 hr to air saturated with butyric acid vapor.[Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:708]
/LABORATORY ANIMALS: Acute Exposure/ The role of the autonomic innervation in the control of pancreatic endocrine responses to iv infusions of butyrate was investigated in conscious 4-6 month old weaned lambs. IV butyrate produced a small rise in mean arterial plasma pancreatic glucagon concentration which was unlikely to have had any physiological effect and produced no consistent or statistically significant changes in mean plasma pancreatic polypeptide concentration in any of the groups studied. In contrast, butyrate produced an abrupt and substantial rise in mean plasma insulin concentration which rose to a peak incremental value of about 300 pico mol/L in normal control.[Bloom SR, Edwards AV; J Physiol 364: 281-8 (1985)]
/LABORATORY ANIMALS: Acute Exposure/ ... HbF induction in response to butyrate was dependent on the dose and duration of treatment. Doses of butyrate less than 4 g/kg/d were associated with minimal toxicity (hypokalemia) and significant HbF induction in these nonanemic animals, with 1 g/kg/d producing an increase in HbF-containing reticulocytes (F reticulocytes) from 0.9% to 8.7% and an increase in HbF from 0.8% to 1.4%. A dose of 2 g/kg/d resulted in an increase in F reticulocytes from 2.1% to 27.8% and an increase in HbF from 0.7% to 2.2%. Doses of 4 g/kg/d in another animal produced an increase in F reticulocytes from 1% to 21.6% and in HbF from 1.9% to 5.3%. ... Prolonged infusions of high doses of butyrate (8 to 10 g/kg/d) were associated with peak F reticulocyte percentages reaching 38% to 64.5% and HbF reaching levels in excess of 20%.[Blau CA et al; Blood 81 (2): 529-37 (1993)]
For more Non-Human Toxicity Excerpts (Complete) data for n-BUTYRIC ACID (45 total), please visit the HSDB record page.

13.1.14 Non-Human Toxicity Values

LD50 Rat oral 8.79 g/kg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 268
LD50 Mouse iv 800 mg/kg /From table/
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:695
LD50 Mouse ip 3180 mg/kg /From table/
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:695
LD50 Mouse sc 3180 mg/kg /From table/
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 5:695
For more Non-Human Toxicity Values (Complete) data for n-BUTYRIC ACID (8 total), please visit the HSDB record page.

13.2 Ecological Information

13.2.1 Ecotoxicity Values

LC50 Daphnia magna (Water flea) 2750 mg/L/24 hr; static /formulated product/
Bringmann G, Kuhn R; Z Wasser-Abwasser-Forsch 10 (5): 161-166 (1977) Available from, as of April 20, 2006
LC50 Daphnia magna (Water flea) 61 mg/L/48 hr /Conditions of bioassay not specified/
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 414
LC50 Lepomis macrochirus (Bluegill) 200 mg/L/24 hr; static /formulated product/
Dowden BF, Bennett HJ; J Water Pollut Control Fed 37 (9): 1308-1316 (1965) Available from, as of April 20, 2006
LC50 Lepomis macrochirus (Bluegill sunfish) 5000 mg/L/24 hr /Conditions of bioassay not specified/ /Sodium salt/
Verschueren, K. Handbook of Environmental Data on Organic Chemicals. Volumes 1-2. 4th ed. John Wiley & Sons. New York, NY. 2001, p. 414
For more Ecotoxicity Values (Complete) data for n-BUTYRIC ACID (6 total), please visit the HSDB record page.

13.2.2 ICSC Environmental Data

The substance is harmful to aquatic organisms.

13.2.3 Environmental Fate / Exposure Summary

n-Butanoic acid's production and use as a material for the manufacture of perfume and flavor ingredients, in pharmaceuticals, deliming agents, disinfectants, emulsifying agents, for sweetening gasolines, for varnishes, in animal feeds, and as a decalcifier of hides may result in its release to the environment through various waste streams. n-Butanoic acid has been found in butter, essential oils, strawberry aroma, vegetable oils, and animal fluids, such as sweat, tissue fluids, and milk fat. n-Butanoic acid may also arise from natural fermentation processes occurring in sediment. If released to air, a vapor pressure of 1.65 mm Hg at 25 °C indicates n-butanoic acid will exist solely as a vapor in the atmosphere. Vapor-phase n-butanoic acid will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 7 days. n-Butanoic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight. If released to soil, n-butanoic acid is expected to have very high to high mobility based upon an estimated Koc of 64 and experimental Koc values of 19.1, 27.6, and 14.7 in mud, muddy sand, and sand. The pKa of n-butanoic acid is 4.82, indicating that this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil surfaces is expected to be slow based upon a Henry's Law constant of 5.35X10-7 atm-cu m/mole. n-Butanoic acid may volatilize from dry soil surfaces based upon its vapor pressure. If released into water, n-butanoic acid is not expected to adsorb to suspended solids and sediment based upon the estimated and experimental Koc values. n-Butanoic acid may be susceptible to biodegradation in the environment based on the observed degradation of 72% after 5 hours when incubated with activated sludge. Volatilization from water surfaces is expected to be slow based upon this compound's Henry's Law constant. Estimated volatilization half-lives for a model river and model lake are 64 and 471 days, respectively. An estimated BCF of 3.2 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Occupational exposure to n-butanoic acid may occur through inhalation and dermal contact with this compound at workplaces where n-butanoic acid is produced or used. Monitoring data indicate that the general population may be exposed to n-butanoic acid via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other products containing n-butanoic acid. (SRC)

13.2.4 Natural Pollution Sources

n-Butanoic acid is present in butter as an ester to the extent of 4-5%(1). It occurs as glyceride in animal milk fats(2). Butyric acid has been found in essential oils of: Citronella ceylon, Eucalyptus globulus, Araucaria cunninghamii, Lippia scaberrima, Monarda fistulosa, Cajeput, Heracleum giganteum, Lavender, Hedeoma pulegioides, Valerian, Nutmeg, Hops, Pastinaca sativa, and Spanish anise(3). It has also been identified in strawberry aroma(3). n-Butanoic acid is found in vegetable oils and in animal fluids, such as sweat, tissue fluids, and milk fat(4). Free n-butanoic acid is an important metabolite in the breakdown of carbohydrates, fats, and proteins(4). n-Butanoic acid may arise from natural fermentive processes occurring in sediment(5). It has also been detected as a volatile flavor component in the fruit of the deciduous palm Dalieb(6). n-Butanoic acid was the principal metabolite in a growth medium containing an aquatic actinomycete streptomyces species and represented the greatest potential as an odorous water pollutant under natural conditions(7).
(1) O'Neil MJ, ed; The Merck Index. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc. p. 268 (2001)
(2) Lewis RJ Sr, ed; Hawley's Condensed Chemical Dictionary. 14th ed. NY, NY: John Wiley & Sons, p. 183 (2001)
(3) Furia TE, Bellanca N, eds; Fenaroli's Handbook of Flavor Ingredients. Volume 2. 2nd ed. Cleveland, OH: The Chemical Rubber Co. p. 78 (1975)
(4) Reimenschneider W; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (2005). NY, NY: John Wiley & Sons; Carboxylic Acids, Aliphatic. Online Posting Date: June 15, 2000.
(5) Miller D et al; Marine Biol 50: 375-83 (1979)
(6) Harper DB et al; J Sci Food Agric 37: 685-8 (1986)
(7) Weete JD; Water Air Soil Pollution 11(Feb): 217 (1979)

13.2.5 Artificial Pollution Sources

n-Butanoic acid's production and use as a material for the manufacture of ester perfume and flavor ingredients, in pharmaceuticals, deliming agents, disinfectants, emulsifying agents, for sweetening gasolines, for varnishes, in animal feeds, and as a decalcifier of hides(1-3) may result in its release to the environment through various waste streams(SRC). n-Butanoic acid may also enter the environment as a result of the biological breakdown of other organic compounds(4).
(1) O'Neil MJ, ed; The Merck Index. 13th ed. Whitehouse Station, NJ: Merck and Co., Inc. p. 268 (2001)
(2) Lewis RJ Sr, ed; Hawley's Condensed Chemical Dictionary. 14th ed. NY, NY: John Wiley & Sons, p. 183 (2001)
(3) Clayton GD, Clayton FE, eds; Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C: Toxicology. 3rd ed. New York, NY: John Wiley Sons, p. 4915 (1982)
(4) Hoviuos JC et al; Anaerobic Treatment of Synthetic Organic Wastes, Washington, DC USEPA 12020 DIS (1972)

13.2.6 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 64(SRC), determined from a log Kow of 0.79(2) and a regression-derived equation(3), and experimental values of 19.1, 27.6, and 14.7 in mud, muddy sand, and sand(4), indicate that n-butanoic acid is expected to have very high to high mobility in soil(SRC). The pKa of n-butanoic acid is 4.82(5), indicating that this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). Volatilization of butyric acid from moist soil surfaces is expected to be slow(SRC) given a Henry's Law constant of 5.35X10-7 atm-cu m/mole(7). n-Butanoic acid is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.65 mm Hg(8). N-butanoic acid may be susceptible to biodegradation in terrestrial environments based on the observed degradation of 72% after 5 hours when incubated with activated sludge(9,10).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p.9 (1995)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9 (1990)
(4) Sansone FJ et al; Geochim Cosmochim Acta 51:1889-96 (1987)
(5) Riddick JA et al; Organic Solvents. Techniques of Chemistry 4th ed. New York, NY, Wiley-Interscience 2:pp. 1325 (1986)
(6) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(7) Butler JAV, Ramchandani CN; The Solubility of Non-Electrolytes. Part 2. J Chem Soc pp. 1952-5 (1935)
(8) Lide DR, ed; CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press (1995)
(9) Urano K, Katz Z; J Haz Mat 13: 147-59 (1986)
(10) Urano K, Katz Z; J Haz Mat 13: 135-45 (1986)
AQUATIC FATE: Based on a classification scheme(1), experimental Koc values of 19.1, 27.6, and 14.7 on a clastic mud (3.5% organic carbon), a lateritic muddy sand (1.3% organic carbon), and a fine carbonate sand (0.17% organic carbon), respectively(2), indicate that n-butanoic acid is not expected to adsorb to suspended solids and sediment(SRC). The pKa of n-butanoic acid is 4.82(5), indicating that this compound will primarily exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). Volatilization from water surfaces is expected to be slow(3) based upon a Henry's Law constant of 5.35X10-7 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 64 and 471 days, respectively(SRC). According to a classification scheme(7), an estimated BCF of 3.2(SRC), from a log Kow of 0.79(8) and a regression-derived equation(9), suggests the potential for bioconcentration in aquatic organisms is low(SRC). n-Butanoic acid may be susceptible to biodegradation in aquatic environments based on the observed degradation of 72% after 5 hours when incubated with activated sludge(10,11).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Sansone FJ et al; Geochim Cosmochim Acta 51:1889-96 (1987)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 4-9, 15-1 to 15-29 (1990)
(4) Butler JAV, Ramchandani CN; The Solubility of Non-Electrolytes. Part 2. J Chem Soc pp. 1952-5 (1935)
(5) Riddick JA et al; Organic Solvents. Techniques of Chemistry 4th ed. New York, NY, Wiley-Interscience 2:pp. 1325 (1986)
(6) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds, Boca Raton, FL: Lewis Publ (2000)
(7) Franke C et al; Chemosphere 29: 1501-14 (1994)
(8) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p.9 (1995)
(9) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(10) Urano K, Katz Z; J Haz Mat 13: 147-59 (1986)
(11) Urano K, Katz Z; J Haz Mat 13: 135-45 (1986)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), n-butanoic acid, which has a vapor pressure of 1.65 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase butyric acid is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 7 days(SRC), calculated from its rate constant of 2.40X10-12 cu cm/molecule-sec at 25 °C(3). n-Butanoic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lide DR, ed; CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press (1995)
(3) Atkinson R; Chem Rev 85:69-201 (1985)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

13.2.7 Environmental Biodegradation

AEROBIC: At an initial concentration of 100 mg/L, n-butanoic acid displayed a 72% theoretical biological oxygen demand (BODT) after 5 hours when incubated with activated sludge(1,2). n-Butanoic acid at an initial concentration of 5 ppm displayed a BODT of 76.6% in fresh water and 72.4% in sea water after 5 days(3). n-Butanoic acid had a BODT of 17.4%, 23.8%, 26.2%, and 27.7% after 6, 12, 18, and 24 hours, respectively, when incubated with an activated sludge seed at an initial concentration of 500 ppm(4). In a screening study, n-butanoic acid displayed a 46%, 48%, and 58% BODT after 2, 10, and 30 days, respectively, using a sewage seed(5). In a screening study using a sewage seed, n-butanoic acid had a 5 day BODT of 72-78% and a 20 day BODT of 92-99%(6,7). Several other screening studies with activated sludge inoculum have shown that n-butanoic acid is amenable to biodegradation under aerobic conditions(8-10).
(1) Urano K, Katz Z; J Haz Mat 13: 147-59 (1986)
(2) Urano K, Katz Z; J Haz Mat 13: 135-45 (1986)
(3) Takemoto S et al; Suishitsu Odaku Kenkyu 4: 80-90 (1981)
(4) Malaney GW, Gerhold RM; J Wat Pollut Control Fed 41: R18-33 (1969)
(5) Dias FF, Alexander M; App Microbiol 22: 1114-8 (1971)
(6) Gaffney PE, Heukelekian H; Sewage and Indust Waste 30: 673-9 (1958)
(7) Gaffney PE, Heukelekian H; J Wat Pollut Contr Fed 33: 1169-83 (1961)
(8) Dawson PSS, Jenkins SH; Sewage and Indust Waste 22: 490-507 (1950)
(9) Ishikawa T et al; Wat Res 13: 681-5 (1979)
(10) McKinney RE et al; Sewage and Ind Waste 28: 547-57 (1956)
ANAEROBIC: In two enriched methanogenic anaerobic microflora populations of two continuous laboratory digesters feed with acetate (6 g/L) or glucose (10 g/L) as the main carbon sources, the maximum degradation rate constant for n-butanoic acid (concentration range 0.4-2.5 g/L) was calculated to be 5.10 and 23.76 mg/L/hr, respectively(1). In the acetate inoculum, complete depletion of n-butanoic acid took about 8 days(1). n-Butanoic acid, present at 30 mg-C/L, reached 100% biodegradation in 7 days using a seeding bacteria at 100 mg-C/L under anaerobic conditions(2). In a screening study, methanogenic microbes raised on acetate were found to completely remove n-butanoic acid after a 3 day lag period at a rate of 284 mg/L/day, initial concentration not provided(3). In a laboratory experiment using a flow-through methanogenic digester with a sewage sludge seed, n-butanoic acid was found to be amenable to biodegradation under anaerobic conditions(4).
(1) Aguilar A et al; Wat Res 29: 505-9 (1995)
(2) Kameya T et al; Sci Total Environ 170: 43-51 (1995)
(3) Chou WL et al; Biotechnol Bioeng Symp 8: 391-414 (1979)
(4) Lin C et al; Water Res 20: 385-94 (1986)

13.2.8 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of n-butanoic acid with photochemically-produced hydroxyl radicals has been measured as 2.00X10-12 cu cm/molec-sec(1), 1.80X10-12 cu-cm/molec-sec(2) and 2.40X10-12 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 7 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(4). n-Butanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(5). n-Butanoic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(5).
(1) Daugaut P et al; Int J Chem Kinet 20: 331-8 (1988)
(2) Wallington TJ et al.; J Phys Chem 92: 5024-8 (1988)
(3) Atkinson R; Chem Rev 85:69-201 (1985)
(4) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(5) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 7-4, 7-5, 8-12 (1990)

13.2.9 Environmental Bioconcentration

An estimated BCF of 3.2 was calculated for n-butanoic acid(SRC), using a log Kow of 0.79(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).
(1) Hansch C et al; Exploring QSAR. Hydrophobic, Electronic, and Steric Constants. ACS Prof Ref Book. Heller SR, consult. ed., Washington, DC: Amer Chem Soc p.9 (1995)
(2) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(3) Franke C et al; Chemosphere 29: 1501-14 (1994)

13.2.10 Soil Adsorption / Mobility

The Koc of n-butanoic acid is estimated as 64(SRC), using a log Kow of 0.79(1) and a regression-derived equation(2). Experimental Koc values for n-butanoic acid on a clastic mud (3.5% organic carbon), a lateritic muddy sand (1.3% organic carbon), and a fine carbonate sand (0.17% organic carbon) were 19.1, 27.6, and 14.7, respectively(3). According to a classification scheme(4), these estimated and experimental Koc values suggest that n-butanoic acid is expected to have very high to high mobility in soil. The percent of n-butanoic acid sorbed to a kalonite or montmorillonite clay at 22 °C was 14.0% and 19.9% after 48 hours, respectively, which increased to 31.4% and 24.2%, respectively, after 144 hours(5). In a field study in which 100 ppm n-butanoic acid was injected underground, the retardation, relative to the linear ground-water velocity, was calculated to be 3%(6). N-butanoic acid is listed as a compound displaying an L-type adsorption isotherm, indicating that specific binding sites may be involved(7). Experimental studies in indicate that adsorption of n-butanoic acid to moist soil is dominated by attractive forces between the compound and soil and not by hydrophobic interactions(8). The pKa of n-butanoic acid is 4.82(9), indicating that this compound will primarily exist in the anion in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(10).
(1) Sansone FJ et al; Geochim Cosmochim Acta 51: 1889-96 (1987)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) Hemphill L et al; Proc 18th Indust Waste Conf 18: 204-17 (1964)
(4) Sutton PA, Barker JF; Ground Water 23: 10-6 (1985)
(5) Weber JB, Miller CT; Reactions and Movement of Organic Chemicals in Soils, SSSA Spec Publ No. 22: 305-33 (1989)
(6) Ulrich H et al; Env Sci Tech 22: 37-41 (1988)
(7) Riddick JA et al; Organic Solvents. Techniques of Chemistry 4th ed. New York, NY, Wiley-Interscience 2:pp. 1325 (1986)
(8) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)

13.2.11 Volatilization from Water / Soil

The Henry's Law constant for n-butanoic acid is measured as 5.35X10-7 atm-cu m/mole(1). This Henry's Law constant indicates that n-butanoic acid is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 64 days(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 471 days(SRC). A pKa of 4.82(3) indicates n-butanoic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(4). n-Butanoic acid's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). n-Butanoic acid is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.65 mm Hg(5).
(1) Butler JAV, Ramchandani CN; The Solubility of Non-Electrolytes. Part 2. J Chem Soc pp. 1952-5 (1935)
(2) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(3) Riddick JA et al; Organic Solvents. Techniques of Chemistry 4th ed. New York, NY, Wiley-Interscience 2 pp. 1325 (1986)
(4) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(5) Lide DR, ed; CRC Handbook of Chemistry and Physics. 76th ed. Boca Raton, FL: CRC Press (1995)

13.2.12 Environmental Water Concentrations

GROUNDWATER: Studies near a closed wood preserving facility in Pensacola, FL found n-butanoic acid concentrations in ground water ranging from 12.87 mg/L at 6 m depth and 0.17 mg/L at 18 m depth ca. 170 m from the plant site. At ca. 330 m from the site, butyric acid was not detected at any well tested (6-24 m depth)(1). Concentrations of n-butanoic acid in groundwater 0, 24, 36, 46, 56, 66, and 90 meters downgradient of the crude-oil body in Bemidji, Minnesota in 1990 were 0.031, 0.106, 0.053, 0.033, <0.020, 0.064, and 0.027 uM, respectively(2). Groundwater samples collected in 1985 from the sand aquifer at Pensacola, Florida contaminated from a wood-preserving plant that had operated on the site for over 80 years contained n-butanoic acid at a concentration of 20.6 mg/L at a depth of 6.1 meters(3). Groundwater from a different test well downgradient from direct contamination contained n-butanoic acid at concentrations of 2.20 and 1.50 mg/L at depths of 3.3 and 5.8 meters, respectively(3).
(1) Goerlitz DF et al; Environ Sci Technol 19: 955-61 (1985)
(2) Cozzarelli IM et al; Geochim Cosmochim Acta 58: 863-77 (1994)
(3) Goerlitz DF; Environ Sci Pollut Control Ser 4: 295-355 (1992)
DRINKING WATER: n-Butanoic acid was qualitatively identified in four water samples taken from a pilot plant in Evansville, Indiana, that uses various forms of chlorine dioxide treatment for the disinfection of drinking water(1).
(1) Richardson SD et al; Environ Sci Technol 28: 592-99 (1994)
SURFACE WATER: The concn of n-butanoic acid in the Ohio River, Little Miami River, and Tanners Creek ranged from 0.1-0.3 ug/L, 0.4-0.5 ug/L, and 0.5 ug/L, respectively(1).
(1) Murtauch JJ, Bunch RL; J WPCF 37: 410-5 (1965)

13.2.13 Effluent Concentrations

n-Butanoic acid was detected at a concentration range of 0.262 to 0.97 ppbv in gasoline engine exhaust samples from five different automobiles and was also found at a concentration of 0.42 ppbv in a diesel engine exhaust sample(1). Mean emission factors of butyric acid in smoldering smoke from litter and duff and from the self-sustained smoldering smoke from bark, litter, and duff (collected from ponderosa pine in northwestern Montana) fires were 0.08, 0.035, 0.14, 0.08, and 0.039 g/kg dry mass of fuel consumed, respectively(4). No n-butanoic acid was detected in the smoldering smoke from wood, needles, bark, and humus fires(2). n-Butanoic acid was qualitatively detected in kitchen waste exudate from household waste collected in Denmark(3).
(1) Kawamura K et al; Atmos Environ 34: 4175-91 (2000)
(2) McKenzie LM et al; Environ Sci Technol 29: 2047-54 (1995)
(3) Wilkins CK, Larsen K; J High Resol Chromatogr 18: 373-7 (1995)
n-Butanoic acid was detected in 1 of 7 aqueous effluent samples from energy-related processes at a concentration of 90 ppb(1). It was detected both in the primary and secondary effluent of sewage treatment plants at concentrations ranging from 17-1,540 ug/L, although the concentration was always lower in the secondary effluent(2). n-Butanoic acid was measured in the automobile exhaust at a concentration of 0.123 ppb(3). The effluent from a landfill in Norman, OK, 1972, contained n-butanoic acid at an estimated concentration of 1.5 ug/L(4,5). It was detected in solid waste leachates in the Netherlands, UK, Canada, France, and Spain representing from 0.34% to 8.5% of the volatile fatty acid fraction(6). It was also identified in the leachate from low-level radioactive waste disposal sites in KY and NY(7). n-Butanoic acid was detected in the leachate from a 1 year old simulated solid waste landfill at a concentration of 48.8 g/L, representing 65% of the acid fraction(8) and it has been detected in the leachate from a Barcelona, Spain, sanitary landfill(9). Australian oil shale retort water contained n-butanoic acid at a concentration of 174 mg/L(10).
(1) Pellizzari ED et al; ASTM Spec Tech Publ STP 686: 256-7 (1979)
(2) Murtauch JJ, Bunch RL; J WPCF 37:410-5 (1965)
(3) Kawamura K et al; Environ Sci Tech 19: 1082-6 (1985)
(4) Dunlap WJ et al; Organic Pollutants Contributed to Ground Water from a Landfill USEPA Off Res Dev USEPA-600/9-76-004 pp. 96-110 (1976)
(5) Dunlap WJ et al; pp. 453-7 in Identif Anal Org Pollut Water (1976)
(6) Lema JM et al; Water Air Soil Pollut 40: 223-50 (1988)
(7) Francis AJ et al; Nuc Tech 50: 158-63 (1980)
(8) Burrows WD, Rowe RS; J WPCF 47: 921-3 (1975)
(9) Albaiges J et al; Wat Res 20: 1153-59 (1986) (1O) Dobson KR et al; Wat Res 19: 849-56 (1985)

13.2.14 Sediment / Soil Concentrations

SEDIMENT: n-Butanoic acid was detected in the sediment of Loch Eil, Scotland, at a conc ranging from trace to 160 ug/g dry weight(1). Detected at a conc of 0.273 mg/g in the sediment of Lake Biwa, Japan, 1981(2).
(1) Miller D et al; Marine Biol 50: 375-83 (1979)
(2) Maeda H, Kawai A; Bull Jap Soc Sci Fish 52: 1205-8 (1986)

13.2.15 Atmospheric Concentrations

URBAN/SUBURBAN: n-Butanoic acid was detected at a concentration range of 0.009 to 0.050 ppbv in atmosphere samples collected in and around Los Angeles in Southern California in 1984(1). An average n-butanoic acid concentration of 0.58 ug/cu m was detected in the urban atmosphere across four sampling sites in Los Angeles, California during a photochemical smog episode in September 1993(2). The concentration of n-butanoic acid in Los Angeles, CA, July and September 1984, ranged from 0.014-0.083 ppb (8 samples)(3).
(1) Kawamura K et al; Atmos Environ 34: 4175-91 (2000)
(2) Nolte CG et al; Environ Sci Technol 33: 540-45 (1999)
(3) Kawamura K et al; Environ Sci Tech 19: 1082-6 (1985)
INDOOR: n-Butanoic acid was detected at concentrations of 0.0049 and 0.016 ppbv in air samples collected from a greenhouse at UCLA in 1984 during the night and day, respectively(1). n-Butanoic acid was qualitatively detected in 1 of 44 air samples taken from a chamber simulating indoor conditions containing wood-based furniture with different coatings(2). n-Butanoic acid was detected in indoor air samples taken from an established (more than 3 months old) school building at a mean concentration of 25 ug/cu m(3).
(1) Kawamura K et al; Atmos Environ 34: 4175-91 (2000)
(2) Salthammer T; Indoor Air 7: 189-97 (1997)
(3) Brown SK et al; Indoor Air 4: 123-34 (1994)
RURAL/REMOTE: n-Butanoic acid was detected at a mean concentration of 0.01 ug/cu m in atmosphere samples taken from San Nicolas Island, a remote site off the coast of Southern California, in September 1993(1).
(1) Nolte CG et al; Environ Sci Technol 33: 540-45 (1999)

13.2.16 Food Survey Values

n-Butanoic acid was qualitatively detected in the lipid volatile fraction of raw beef(1). Strawberry jam contained butyric acid at a concentration of 620.5 mg/kg(2). n-Butanoic acid was qualitatively identified as a flavor compound in pine sprout tea made with fresh pine sprouts for Korean red pine trees collected in May-June 1995(3). n-Butanoic acid was identified as a volatile component of baked potatoes(4). It has also been detected as a volatile flavor component in the fruit of the deciduous palm Dalieb at a concentration of 58 mg/kg pulp(5).
(1) King MF et al; J Agric Food Chem 41: 1974-81 (1993)
(2) Lesschaeve I et al; J Food Sci 56: 1393-8 (1991)
(3) Kim KY, Chung HJ; J Agric Food Chem 48: 1269-72 (2000)
(4) Coleman EC et al; J Agric Food Chem 29: 42-8 (1981)
(5) Harper DB et al; J Sci Food Agric 37: 685-8 (1986)
n-Butanoic acid was detected at a mean concentration of 243 ng/g in salt-fermented anchovy volatiles obtained from a fish market in Masan, Korea(1).
(1) Cha YJ, Cadwallader KR; J Food Sci 60: 19-24 (1995)
n-Butanoic acid was detected at concentrations of 0.08 and 109 ug/g (wet weight) in rotten mussels and fresh mussels, respectively, that were collected off the Oarai coast in Ibaraki, Japan in 1985(1).
(1) Yasuhara A; J Chromatogr 409: 251-8 (1987)

13.2.17 Probable Routes of Human Exposure

NIOSH (NOES Survey 1981-1983) has statistically estimated that 11,600 workers (3,391 of these are female) are potentially exposed to n-butanoic acid in the US(1). Occupational exposure to n-butanoic acid may occur through inhalation and dermal contact with this compound at workplaces where n-butanoic acid is produced or used(SRC). n-Butanoic acid has been detected as an emission during the welding of steel coated with protective paints(2). Monitoring data indicate that the general population may be exposed to n-butanoic acid via inhalation of ambient air, ingestion of food and drinking water, and dermal contact with this compound and other products containing n-butanoic acid(SRC).
(1) NIOSH; International Safety Cards. Butanoic Acid. 107-92-6. Available at http//www.cdc.gov/niosh/ipcs/nicstart.html as of Apr 20, 2006.
(2) Henriks-Eckerman M et al; Am Ind Hyg Assoc J 51: 241-4 (1990)

14 Associated Disorders and Diseases

Disease
Colorectal cancer
References

PubMed: 7482520, 19006102, 23940645, 24424155, 20156336, 19678709, 22148915, 25105552, 21773981, 25037050, 27015276, 27107423, 27275383, 28587349

Silke Matysik, Caroline Ivanne Le Roy, Gerhard Liebisch, Sandrine Paule Claus. Metabolomics of fecal samples: A practical consideration. Trends in Food Science & Technology. Vol. 57, Part B, Nov. 2016, p.244-255: http://www.sciencedirect.com/science/article/pii/S0924224416301984

Disease
Irritable bowel syndrome
References
Disease
Nonalcoholic fatty liver disease
References
PubMed: 23454028
Disease
Pervasive developmental disorder not otherwise specified
References
PubMed: 24130822
Disease
Bladder infections
References
Disease
Diverticular disease
References
Disease
Rheumatoid arthritis
References

PubMed: 6589104, 16277678, 15338487, 10361015, 15249323

Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70: https://link.springer.com/article/10.1007/s11306-016-1000-2

Disease
Enteritis
References
PubMed: 14684577
Disease
Eosinophilic esophagitis
References
Mordechai, Hien, and David S. Wishart

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Wiley References

15.6 Nature Journal References

15.7 Chemical Co-Occurrences in Literature

15.8 Chemical-Gene Co-Occurrences in Literature

15.9 Chemical-Disease Co-Occurrences in Literature

16 Patents

16.1 Depositor-Supplied Patent Identifiers

16.2 WIPO PATENTSCOPE

16.3 Chemical Co-Occurrences in Patents

16.4 Chemical-Disease Co-Occurrences in Patents

16.5 Chemical-Gene Co-Occurrences in Patents

17 Interactions and Pathways

17.1 Protein Bound 3D Structures

17.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

17.2 Chemical-Target Interactions

17.3 Pathways

18 Biological Test Results

18.1 BioAssay Results

19 Taxonomy

WormJam Metabolites Local CSV for MetFrag | DOI:10.5281/zenodo.3403364
WormJam: A consensus C. elegans Metabolic Reconstruction and Metabolomics Community and Workshop Series, Worm, 6:2, e1373939, DOI:10.1080/21624054.2017.1373939
The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

20 Classification

20.1 MeSH Tree

20.2 NCI Thesaurus Tree

20.3 ChEBI Ontology

20.4 LIPID MAPS Classification

20.5 KEGG: Metabolite

20.6 KEGG: Lipid

20.7 KEGG: Phytochemical Compounds

20.8 ChemIDplus

20.9 CAMEO Chemicals

20.10 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

20.11 ChEMBL Target Tree

20.12 UN GHS Classification

20.13 EPA CPDat Classification

20.14 NORMAN Suspect List Exchange Classification

20.15 EPA DSSTox Classification

20.16 EPA TSCA and CDR Classification

20.17 LOTUS Tree

20.18 EPA Substance Registry Services Tree

20.19 MolGenie Organic Chemistry Ontology

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CONTENTS