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Behenic Acid

PubChem CID
8215
Structure
Behenic Acid_small.png
Molecular Formula
Synonyms
  • Docosanoic acid
  • Behenic acid
  • 112-85-6
  • 1-Docosanoic acid
  • N-DOCOSANOIC ACID
Molecular Weight
340.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2004-09-16
  • Modify:
    2025-01-18
Description
Docosanoic acid is a straight-chain, C22, long-chain saturated fatty acid. It has a role as a plant metabolite. It is a straight-chain saturated fatty acid and a long-chain fatty acid. It is a conjugate acid of a behenate.
Docosanoic acid has been reported in Calodendrum capense, Arisaema tortuosum, and other organisms with data available.
Behenic Acid is a saturated very long-chain fatty acid with a 22-carbon backbone. Behenic acid is a major component of ben oil, extracted from the seeds of the moringa tree.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Behenic Acid.png

1.2 3D Status

Conformer generation is disallowed since too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C22H44O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h2-21H2,1H3,(H,23,24)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

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

2.2 Molecular Formula

C22H44O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

112-85-6

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Lipid Maps ID (LM_ID)

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 NSC Number

2.3.15 RXCUI

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • behenic acid
  • behenic acid, aluminum salt
  • behenic acid, barium salt
  • behenic acid, cadmium salt
  • behenic acid, ferrium (+3) salt
  • behenic acid, lithium salt
  • behenic acid, potassium salt
  • behenic acid, silver (+1) salt
  • behenic acid, sodium salt
  • behenic acid, zinc salt
  • docosanoic acid

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
340.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
9.6
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
20
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
340.334130642 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
340.334130642 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
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
250
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

Pellets or Large Crystals; Other Solid; Liquid, Other Solid; Liquid
White to cream or yellow solid; [CHEMINFO] White crystalline powder; [MSDSonline]
Solid

3.2.2 Color / Form

Waxy solid
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
Needles
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. V3: 2534

3.2.3 Boiling Point

306 °C at 60 mm Hg
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169

3.2.4 Melting Point

79.95 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
81 °C

3.2.5 Solubility

0.102 g are sol in 100 g of 90% ethanol at 17 °C;0.218 g are sol in 100 ml of 91.5% ethanol at 25 °C; 0.116 g are sol in 100 ml of 86.2% ethanol at 25 °C; 0.011 g are sol in 100 ml of 63.07% ethanol at 25 °C; 0.1922 g are sol in 100 g of ether at 16 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
Slightly soluble in water, ethanol, ethyl ether
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. V3: 2534
In water, 160 mg/L, temp not specified
OECD; Environment Directorate. OECD Guideline Test. Screening Information Data Set ... for Docosanoic acid (CAS-No. 112-85-6).13-May-2004. Available from, as of Feb 27, 2008: https://www.oecd.org/findDocument/0,3354,en_2649_34379_1_119666_1_50_1,00.html
1.6e-05 mg/mL

3.2.6 Density

0.8221 at 100 °C/4 °C
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169

3.2.7 Vapor Pressure

0.00000007 [mmHg]

3.2.8 LogP

9.910
The Good Scents Company Information System

3.2.9 Refractive Index

Index of refraction: 1.4270 at 100 °C/D
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169

3.2.10 Collision Cross Section

193.1 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Sample Type: Human bronchoalveolar lavage fluid (BALF); Dataset: Unambiguous Lipids]
191.18 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

3.2.11 Kovats Retention Index

Semi-standard non-polar
2567 , 2564 , 2569 , 2564

3.2.12 Other Experimental Properties

Neutralization value: 164.73
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
mp 54 °C /Methyl ester/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
mp 50 °C; bp 185 °C at 0.2 mm Hg /Ethyl ester/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
mp 111-112 °C /Amide/
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169

3.3 Chemical Classes

Other Classes -> Organic Acids

3.3.1 Cosmetics

Cosmetic ingredients (Behenic Acid) -> CIR (Cosmetic Ingredient Review)
Emulsifying
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

3.3.2 Lipids

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

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Spectra ID
Instrument Type
Varian
Frequency
500 MHz
Solvent
CDCl3
pH
7.0
Shifts [ppm]:Intensity
1.61:0.73, 2.34:3.09, 1.63:2.03, 2.37:2.81, 0.87:3.48, 1.64:2.61, 2.35:5.40, 0.90:3.30, 1.66:1.73, 0.89:7.05, 1.26:100.00, 1.67:0.57
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
216941
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 3
View All
Spectra ID
Instrument Type
Varian
Frequency
25.16 MHz
Solvent
CDCl3
Shifts [ppm]:Intensity
14.12:95.00, 31.98:105.00, 29.74:1000.00, 29.12:120.00, 180.26:65.00, 29.42:165.00, 22.73:115.00, 24.72:105.00, 29.48:160.00, 34.12:80.00, 29.28:155.00
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2 of 3
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Source of Sample
Analabs, Inc., North Haven, Connecticut
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. 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
CD3OD
pH
7.00
Shifts [ppm] (F2:F1):Intensity
1.59:26.26:0.04, 1.32:30.27:0.09, 1.28:32.90:0.03, 1.28:30.59:1.00, 1.30:23.61:0.01, 0.90:14.31:0.01, 2.26:35.22:0.06
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4.3 Mass Spectrometry

4.3.1 GC-MS

1 of 17
View All
Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

43.0 99.99

57.0 70.20

41.0 70.10

60.0 69.40

73.0 65.60

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Notes
instrument=HITACHI M-80B
2 of 17
View All
Spectra ID
Instrument Type
GC-EI-TOF
Ionization Mode
positive
Top 5 Peaks

117.0 100

132.0 53.75

129.0 46.05

145.0 31.63

133.0 14.31

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Notes
instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies

4.3.2 MS-MS

1 of 7
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

339.3276 100

340.33 21.72

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2 of 7
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

339.3276 100

340.3303 23.42

341.3316 1

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4.3.3 LC-MS

1 of 12
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Retention Time
0.143 min
Precursor m/z
339.3269
Precursor Adduct
[M-H]-
Top 5 Peaks

339.3281 999

101.2462 2

337.3147 2

319.2998 1

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License
CC BY
2 of 12
View All
Authors
da Silva KM, Iturrospe E, van de Lavoir M, Robeyns R, University of Antwerp, Belgium
Instrument
Agilent 6560 QTOF
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Retention Time
0.143 min
Precursor m/z
339.3269
Precursor Adduct
[M-H]-
Top 5 Peaks

339.3275 999

321.3147 9

241.2877 1

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License
CC BY

4.3.4 Other MS

1 of 5
View All
Other MS
MASS: 63742 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
2 of 5
View All
Authors
SODA AROMATIC CO., LTD.
Instrument
HITACHI M-80B
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 70 eV
Top 5 Peaks

43 999

57 702

41 701

60 694

73 656

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License
CC BY-NC-SA

4.4 IR Spectra

IR Spectra
IR: 860 (Coblentz Society Spectral Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
MELT (CRYSTALLINE PHASE)
Source of Sample
Witco Corporation, Humko Chemical Division
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
MELT (CRYSTALLINE PHASE)
Source of Sample
AC Humko Corporation, Memphis, Tennessee
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
TCI Chemicals India Pvt. Ltd.
Catalog Number
B1248
Lot Number
83B4E-ES
Copyright
Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
216941
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Catalog Number
216941
Copyright
Copyright © 2017-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2017-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.6 Other Spectra

SADTLER REFERENCE NUMBER: 15645 (IR, PRISM); 644 (HR, GRATING)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-280

6 Chemical Vendors

7 Drug and Medication Information

7.1 Biomarker Information

8 Food Additives and Ingredients

8.1 Associated Foods

9 Pharmacology and Biochemistry

9.1 Human Metabolite Information

9.1.1 Tissue Locations

Placenta

9.1.2 Cellular Locations

  • Extracellular
  • Membrane

9.2 Biochemical Reactions

10 Use and Manufacturing

10.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Behenic Acid
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 in cosmetics, waxes, plasticizers, stabilizers and as a chemical intermediate; [HSDB] Used in lubricating oils and to retard solvent evaporation in paint removers; A minor constituent of most seed fats, animal milk fats, and marine animal oils; [Merck Index]
Merck Index - O'Neil MJ, Heckelman PE, Dobbelaar PH, Roman KJ (eds). The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 15th Ed. Cambridge, UK: The Royal Society of Chemistry, 2013.
In lubricating oils, as solvent evaporation retarder in paint removers. Amide as anti-foam in the manufacture of detergents, in floor polishes, in dripless candles
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
Cosmetics; waxes; plasticizers; chemicals; stabilizers
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 131
SRI
SRI
For more Uses (Complete) data for DOCOSANOIC ACID (7 total), please visit the HSDB record page.

10.1.1 Use Classification

EPA Safer Chemical Functional Use Classes -> Surfactants
Safer Chemical Classes -> Green circle Green circle - The chemical has been verified to be of low concern
Cosmetics -> Emulsifying
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

10.1.2 Industry Uses

  • Lubricants and lubricant additives
  • Intermediates
  • Emulsifier
  • Intermediate
  • Fuel
  • Other
  • Softener and conditioner
  • Lubricating agent
  • Solids separation agents

10.1.3 Consumer Uses

  • Solids separation agents
  • Paint additives and coating additives not described by other categories
  • Softener and conditioner
  • Lubricating agent
  • Other
  • Emulsifier
  • Not Known or Reasonably Ascertainable
  • Lubricants and lubricant additives

10.1.4 Household Products

Household & Commercial/Institutional Products

Information on 33 consumer products that contain Behenic acid in the following categories is provided:

• Personal Care

10.2 Methods of Manufacturing

Prepn from erucic acid by catalytic reduction
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
HYDROGENATION OF RAPESEED OR FISH OIL FOLLOWED BY HYDROLYSIS AND FRACTIONAL DISTILLATION; HYDROGENATION OF ERUCIC ACID (CIS-13-DOCOSENOIC ACID)
SRI

10.3 Impurities

(C14-C20) fatty acids ca. 11 %; C24 fatty acid ca. 2 %
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.22 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html

10.4 Formulations / Preparations

Grades: Technical, 99%
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 131

10.5 U.S. Production

Aggregated Product Volume

2019: 1,000,000 lb - <20,000,000 lb

2018: 1,000,000 lb - <20,000,000 lb

2017: 1,000,000 lb - <20,000,000 lb

2016: 1,000,000 lb - <20,000,000 lb

(1977) AT LEAST 4.54X10+8 GRAMS
SRI
(1981) No Data
SRI
Production volumes for non-confidential chemicals reported under the Inventory Update Rule.
Year
1986
Production Range (pounds)
>1 million - 10 million
Year
1990
Production Range (pounds)
>1 million - 10 million
Year
1994
Production Range (pounds)
>1 million - 10 million
Year
1998
Production Range (pounds)
>1 million - 10 million
Year
2002
Production Range (pounds)
>1 million - 10 million
US EPA; Non-confidential Production Volume Information Submitted by Companies for Chemicals Under the 1986-2002 Inventory Update Rule (IUR). Docosanoic Acid (112-85-6). Available from, as of January 14, 2008: https://www.epa.gov/oppt/iur/tools/data/2002-vol.html
Docosanoic acid is listed as a High Production Volume (HPV) chemical (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 the Database Query page at: https://www.epa.gov/hpv/pubs/general/opptsrch.htm on Docosanoic Acid (112-85-6) as of February 4, 2008

10.6 U.S. Imports

(1979) No Data
SRI
(1981) No Data
SRI

10.7 U.S. Exports

(1979) No Data
SRI
(1981) No Data
SRI

10.8 General Manufacturing Information

Industry Processing Sectors
  • Paper Manufacturing
  • Plastics Product Manufacturing
  • All Other Chemical Product and Preparation Manufacturing
  • Soap, Cleaning Compound, and Toilet Preparation Manufacturing
  • Cyclic Crude and Intermediate Manufacturing
  • Petroleum Lubricating Oil and Grease Manufacturing
  • All Other Basic Organic Chemical Manufacturing
  • Other (requires additional information)
EPA TSCA Commercial Activity Status
Docosanoic acid: ACTIVE
Straight chain saturated fatty acid. /From table/
Ullmann's Encyclopedia of Industrial Chemistry. 6th ed.Vol 1: Federal Republic of Germany: Wiley-VCH Verlag GmbH & Co. 2003 to Present, p. V13 77 (2003)

11 Identification

11.1 Analytic Laboratory Methods

EIGHTY SPECIFIC COMPOUNDS WERE IDENTIFIED IN RAW AND TREATED WASTEWATER BY GAS CHROMATOGRAPHY/MASS SPECTROMETRY.
GARRISON AW ET AL; GC/MS ANALYSIS OF ORGANIC COMPOUNDS IN DOMESTIC WASTEWATERS; IDENTIF ANAL ORG POLLUT WATER (CHEM CONGR NORTH AM CONT) 1ST: 517 (1976)
SOYBEAN OIL FATTY ACIDS DETERMINED BY HPLC.
JASELSKIS B ET AL; DETERMINATION OF THE FATTY ACID COMPOSITION OF SOYBEAN OIL BY HIGH-PRESSURE LIQUID CHROMATOGRAPHY; TALANTA 29(1) 54 (1982)
THE FATTY ACID COMPOSITION OF ROOT OIL OF CURCULIGO ORCHIOIDES (USED MEDICINALLY IN INDIA) WAS DETERMINED BY TLC-GAS CHROMATOGRAPHY TECHNIQUES. BEHENIC ACID WAS A MAIN COMPONENT ACID.
MEHTA BK ET AL; STUDY OF ROOT OIL: COMPONENT FATTY ACIDS OF CURCULIGO ORCHIOIDES ROOTS; INDIAN DRUGS 18(3) 109 (1980)
BEHENIC ACID (2.62%) WAS ISOLATED FROM THE OIL OBTAINED FROM THE MEDICINAL PLANT ERYTHRINA SUBEROSA ROXB SEEDS AND IDENTIFIED BY THIN LAYER CHROMATOGRAPHY.
JOSHI R, GARG BD; THE SEED OIL OF ERYTHRINA SUBEROSA ROXB; J SCI RES (BHOPAL, INDIA) 3(1) 11 (1981)

11.2 Clinical Laboratory Methods

Analyte: behenic acid; matrix: blood (plasma); procedure: high-performance liquid chromatography with fluorescence detection at 360 nm (excitation) and 420 nm (emission); limit of detection: 50 ng
Baty JD et al; J Chromatogr 395: 403-411 (1987). As cited in: Lunn G; HPLC and CE Methods for Pharmaceutical Analysis. CD-ROM. New York, NY: John Wiley & Sons (2000)

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 97.1% (168 of 173) of all reports. Pictograms displayed are for 2.9% (5 of 173) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 168 of 173 companies (only 2.9% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 173 reports by companies from 2 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 168 of 173 reports by companies. For more detailed information, please visit ECHA C&L website.

There is 1 notification provided by 5 of 173 reports by companies with hazard statement code(s).

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

Not Classified

12.1.3 EPA Safer Chemical

Chemical: Docosanoic acid

Green circle Green circle - The chemical has been verified to be of low concern based on experimental and modeled data.

12.1.4 Hazards Summary

No data available on effects as an irritant or sensitizer; In a feeding study of rats at doses up to 1000 mg/kg/day for 42 days, negative for toxic effects and no reproductive or developmental adverse effects; [OECD SIDS: Docosanoic acid - 2001] An irritant; [MSDSonline]

12.1.5 Fire Potential

Combustible
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 15th Edition. John Wiley & Sons, Inc. New York, NY 2007., p. 131

12.2 Accidental Release Measures

12.2.1 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.
Dissolved or mixed the material with a combustible solvent and burned in a chemical incinerator equipped with an afterburner and scrubber.
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.24 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html

12.3 Regulatory Information

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

12.4 Other Safety Information

Chemical Assessment

IMAP assessments - Docosanoic acid: Human health tier I assessment

IMAP assessments - Docosanoic acid: Environment tier I assessment

12.4.1 Special Reports

Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) (November 6 - 9, 2001). Available from the Database Query page at: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html as of January 24, 2008.

13 Toxicity

13.1 Toxicological Information

13.1.1 Toxicity Summary

Oral LD50 value of docosanoic acid for rats is greater than 2,000 mg/kg. There are no available data for irritation and sensitization. In an oral study using the OECD combined repeated dose and reproductive/developmental toxicity test [OECD TG 422], docosanoic acid was administered to rats at doses of 0, 100, 300, 1,000 mg/kg/day for at least 42 days . No deaths occurred and also no substance related toxic effects were observed in any parameters. Therefore, the NOAEL is considered to be 1,000 mg/kg/day for both repeated dose toxicity and reproductive/developmental toxicity. The chemical was negative in both a bacterial mutation test [OECD TG 471, 472] and a chromosomal aberration test in vitro [OECD TG 473]. ... Acute toxicity values of docosanoic acid on alga (Selenastrum capricornutum), aquatic invertebrate (Daphnia magna) or fish (Oryzias latipes) are greater than its water solubility (0.016 mg/L). The NOEC in a 21-day reproduction test with Daphnia magna is also greater than its water solubility. No significant effects are observed in any tests conducted at extremely high concentrations by using dispersant under OECD test guidelines [TG201, 202, 203, 204, or 211]. There is information that some fatty acids with shorter carbon chain caused no mortality at saturated concentration in certain aquatic organisms (gammarus in freshwater; Medaka in seawater condition). Considering from these data and additional information, it is reasonable to assume that docosanoic acid is not toxic to aquatic organisms at the concentration less than its water solubility (0.016 mg/L). A PNEC is not calculated since NOEC values obtained are above the water solubility of the substance.
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.3 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html

13.1.2 Interactions

THE BLOOD PLATELET AGGREGATING EFFECT OF BEHENIC ACID ON WASHED PIG BLOOD PLATELETS WAS ENHANCED BY THE ADDITION OF CALCIUM IONS. LINOLENIC ACID COMPLETELY INHIBITED THE EFFECT OF BEHENIC ACID WHEN BOTH WERE ADDED IN EQUIMOLAR CONCENTRATIONS.
MAHADEVAN V ET AL; EFFECTS OF SATURATED AND UNSATURATED FATTY ACIDS ON BLOOD PLATELET AGGREGATION IN VITRO; PROC SOC EXP BIOL MED 121(1) 82 (1966)

13.1.3 Antidote and Emergency Treatment

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /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
/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

13.1.4 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ ... In a randomized, crossover, metabolic-ward study, 7 mildly hypercholesterolemic men were fed 3 natural-food diets supplemented with behenate oil, palm oil, or high-oleic acid sunflower oil. Mean serum lipid and lipoprotein concentrations and plasma triacylglycerol fatty acid composition were determined from fasting blood drawn during the final 4 days of each 3-wk diet period. ... Behenate oil produced mean concentrations of total cholesterol (5.87+/-0.8 mmol/L) and LDL cholesterol (4.40+/-0.8 mmol/L) not significantly different from those produced by palm oil (5.84+/-0.7 and 4.42+/-0.7 mmol/L, respectively) but significantly higher than those produced by high-oleic acid sunflower oil (5.12+/-0.5 and 3.70+/-0.6 mmol/L, respectively). There were no significant differences in triacylglycerol or HDL-cholesterol concentrations. ... /Behenate oil/
Cater NB, Denke MA: Am J Clin Nutr 73 (1): 41-4 (2001)
/CASE REPORTS/ A 53-year-old librarian had recurrent palpable purpura on her ankles and legs that was found to be caused by the fumes released from heat-activated photocopy paper at her place of employment. Behenic acid was identified as the responsible chemical component through a series of challenge studies that simulated her work exposure. Behenic acid, a fatty acid, is volatilized when heat-activated photocopy paper is developed. Absorption through the upper respiratory mucosa was the likely route of entry of this agent. The mechanism of this reaction is unclear. Skin biopsies, complement studies, and immune complex assays failed to confirm a type III immune response. /SRP: Results of this report has been questioned/
Tencati JR, Novey HS; Ann Intern Med 98 (3): 320-2 (1983)

13.1.5 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ /Crj:CD(SD)/ rats were administered orally (gavage) at 0 or 2,000 mg/kg of docosanoic acid. No deaths occurred for either males or females in the treated groups. No treatment-related effects were found on clinical signs, body weight changes or autopsy findings. /Purity 85.9 %; Impurities: (C14-C20) fatty acids 10.9 %, C24 fatty acid 2.3 %/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.13, 37 & 69 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Male and female SD rats were orally administered (gavage) at doses of 0, 100, 300 and 1,000 mg/kg/day. In male rats, the administration period was two weeks prior to mating, 2 weeks of mating and 2 weeks after the completion of the mating period. In females, in addition to maximum four weeks pre-mating and mating period, they were exposed through pregnancy until day 3 of post delivery. No deaths or abnormalities in clinical signs were observed in any male and female animals. Also, there were no adverse effects related to the substance in body weights and food consumption. No treatment-related effects were found for hematological, biochemical, gross findings, organ weights and histopathological examinations ... The NOAEL for repeated dose toxicity in rats is considered to be 1,000 mg/kg/day in both sexes. /Purity 85.9 %; Impurities: (C14-C20) fatty acids 10.9 %, C24 fatty acid 2.3 %/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.13, 37 & 71 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
/LABORATORY ANIMALS: Developmental or Reproductive Toxicity/ Male and female SD rats were orally administered (gavage) at doses of 0, 100, 300 and 1,000 mg/kg/day. In male rats, the administration period was two weeks prior to mating, 2 weeks of mating and 2 weeks after the completion of the mating period. In females, in addition to maximum four weeks pre-mating and mating period, they were exposed through pregnancy until day 3 of post delivery ... Parameters to evaluate developmental toxicity were limited to only body weights at day 0 and day 4 after birth, and autopsy findings at day 4. This chemical showed no adverse effects on copulation or fertility indexes. No changes related to the dosing of substance were observed in gestation length and any parameters during gestation, delivery and lactation periods. The chemical also did not show any adverse effects on the sex ratio, body weight or viability of pups ... No morphological abnormalities in external and visceral observation in pups were observed in any of the treated groups ... The NOAEL values for both parental and F1 offspring in reproductive toxicity are considered to be 1,000 mg/kg/day. As for developmental toxicity, the NOAEL for F1 offspring is estimated to be 1,000 mg/kg/day. /Purity 85.9 %; Impurities: (C14-C20) fatty acids 10.9 %, C24 fatty acid 2.3 %/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.14, 38 & 74 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
/GENOTOXICITY/ Docosanoic acid showed negative results /in the reverse gene mutation assay/ in Salmonella typhimurium TA100, TA1535, TA98, TA1537 and Escherichia coli WP2 uvrA at concentrations up to 5 mg/plate with or without metabolic activation system. /Purity 85.9 %; Impurities: (C14-C20) fatty acids 10.9 %, C24 fatty acid 2.3 %/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.14, 39 & 77 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
For more Non-Human Toxicity Excerpts (Complete) data for DOCOSANOIC ACID (6 total), please visit the HSDB record page.

13.1.6 Non-Human Toxicity Values

LD50 Rats oral >2,000 mg/kg /Purity 85.9 %; Impurities: (C14-C20) fatty acids 10.9 %, C24 fatty acid 2.3 %/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.13&37 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html

13.2 Ecological Information

13.2.1 Ecotoxicity Values

EC50 Selenastrum capricornutum (algae) >5.00 mg/L/72 hr; Conditions: static, 22.5 to 23.4 °C; Effect: growth rate. /Purity 96.5%/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.11, 35 & 62 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
EC50 Daphnia magna (water flea) >5.00 mg/L/48 hr; Conditions: static, 20.4 to 20.7 °C, pH=7.7 to 7.9; Effect: immobilization. /Purity 96.5%/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.11, 34 & 62 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
EC50 Daphnia magna (water flea) >0.84 mg/L/14 or 21 days; Conditions: semi-static (water renewal: 3 times a week), 19.9 to 20.6 °C, pH=7.0 to 8.0; Effect: reproduction. /Purity 96.5%/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.11, 35 & 67 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
LC50 Daphnia magna (water flea) >0.84 mg/L/14 or 21 days; Conditions: semi-static (water renewal: 3 times a week), 19.9 to 20.6 °C, pH=7.0 to 8.0. /Purity 96.5%/
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.11, 35 & 67 (November 6 - 9, 2001). Available from, as of January 25, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
For more Ecotoxicity Values (Complete) data for DOCOSANOIC ACID (6 total), please visit the HSDB record page.

13.2.2 Ecotoxicity Excerpts

/AQUATIC SPECIES/ In a chronic toxicity test with Daphnia magna, conducted at 0.30, 0.55 and 1.00 mg/L under semi-static conditions (water renewal: 3 times a week), the measured concentrations in groups tested at 21 day were different over 20% from their corresponding nominal concentration. Thus, the concentrations were expressed using time-weighted averages: 0.24, 0.49 and 0.84 mg/L, respectively. The parental mortalities observed in controls and treated groups were within the range of 20% and no effects by dispersant were observed. EC50 and NOEC values in this chronic toxicity test to Daphnia magna on reproduction were greater than 0.84 mg/L.
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.11 (November 6 - 9, 2001). Available from, as of January 24, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html
/AQUATIC SPECIES/ Toxicity studies of docosanoic acid have been conducted using dispersant in a limited number of representative aquatic organisms: algae (Selenastrum capricornutum), aquatic invertebrates (Daphnia magna), and fish (Oryzias latipes) ... In all tests, no significant effect was observed at considerably higher concentration than its water solubility (0.016 mg/L).
Organization for Economic Cooperation and Development; Screening Information Data Set for Docosanoic acid (CAS #112-85-6) p.12 (November 6 - 9, 2001). Available from, as of January 24, 2008: https://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html

13.2.3 Environmental Fate / Exposure Summary

Docosanoic acid's production and use in cosmetics, waxes, plasticizers, chemicals and stabilizers may result in its release to the environment through various waste streams. Docosanoic acid was found as a natural minor constituent of most seed fats, animal milk fats and marine animal oils, and in large amounts in jamba oil, mustard seed oil, and rape oil. Docosanoic acid is a fatty acid and occurs naturally in many essential oils. Fatty acids are widely distributed in nature as components of animal and vegetable fats and are an important part of the normal daily diet of mammals, birds and invertebrates. If released to air, an estimated vapor pressure of 7.1X10-8 mm Hg at 25 °C indicates docosanoic acid will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase docosanoic 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 14 hours. Particulate-phase docosanoic acid will be removed from the atmosphere by wet or dry deposition. Docosanoic 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, undissociated docosanoic acid is expected to have no mobility based upon an estimated Koc of 1.4X10+5 for the free acid. The estimated pKa of docosanoic acid is 4.7, indicating that this compound will exist almost entirely in anion form in the environment and anions do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize. Biodegradation of 69% of the theoretical BOD using a modified closed bottle Blok test employing a sewage inoculum incubated 28 days suggests that biodegradation may be an important environmental fate process in soil. If released into water, undissociated docosanoic acid is expected to adsorb to suspended solids and sediment based upon the estimated Koc. A half life of 1.7 days in freshwater after a 29 days suggests that biodegradation may be an important environmental fate process in water. The estimated pKa indicates docosanoic 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. An estimated BCF of 3 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 docosanoic acid may occur through dermal contact with this compound at workplaces where docosanoic acid is produced or used. Monitoring and use data indicate that the general population may be exposed to docosanoic acid via inhalation of ambient air, ingestion of food, and dermal contact with this compound and other consumer products containing docosanoic acid. (SRC)

13.2.4 Natural Pollution Sources

Minor constituent of most seed fats, animal milk fats and marine animal oils.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169
Occurs in bean oil
Lewis, R.J. Sr.; Hawley's Condensed Chemical Dictionary 14th Edition. John Wiley & Sons, Inc. New York, NY 2001., p. 120
THE HIGHEST CONCENTRATION OF BEHENIC ACID WAS FOUND IN GARCINIA MANGOSTANA AND VENTILAGO MADRASPATANA SEEDS.
DAULATABAD CD, ANKALGI RF; THE COMPONENT ACIDS OF TEN SEED OILS; J OIL TECHNOL ASSOC INDIA 10(2) 36 (1978)
BEHENIC ACID (2.62%) WAS ISOLATED FROM THE OIL OBTAINED FROM THE MEDICINAL PLANT ERYTHRINA SUBEROSA ROXB SEEDS.
JOSHI R, GARG BD; THE SEED OIL OF ERYTHRINA SUBEROSA ROXB; J SCI RES (BHOPAL, INDIA) 3(1) 11 (1981)
Docosanoic acid is a carboxylic acid that is also known as a fatty acid because fatty acids were first isolated by the hydrolysis of naturally occurring fats(1). Fatty acids are widely distributed in nature as components of animal and vegetable fats(2) including lipids such as oils and fats, waxes, sterol esters and other minor compounds(1).
(1) Gutsche CD, Pasto DJ; Fundamentals of Organic Chemistry. Englewood Cliffs, NJ: Prentice-Hall p. 369 (1975)
(2) Anneken DJ et al; Ullmann's Encyclopedia of Industrial Chemistry. 7th ed. (2008). NY, NY: John Wiley & Sons; Fatty Acids. Online Posting Date: Dec 15, 2006.

13.2.5 Artificial Pollution Sources

Docosanoic acid's production and use in cosmetics, waxes, plasticizers, chemicals and stabilizers(1) may result in its release to the environment through various waste streams(SRC).
(1) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary 14th ed John Wiley & Sons, Inc. New York, NY p. 120 (2001)
Large amt (approx 50%) are found in (possibly hydrogenated ?) jamba oil, mustard seed oil and rape oil.
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Whitehouse Station, NJ: Merck and Co., Inc., 2006., p. 169

13.2.6 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+5(SRC), determined from a structure estimation method(2), indicates that undissociated docosanoic acid is expected to be immobile in soil(SRC). The estimated pKa of docosanoic acid is 4.7(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization from moist soil is not expected because the acid exists as an anion and anions do not volatilize(SRC). Docosanoic is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.1X10-8 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation of 69% of the theoretical BOD using a modified closed bottle Blok test employing a sewage inoculum incubated 28 days(6) suggests that biodegadation may be an important environmental fate process in soil(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) SPARC; pKa/property server. Ver 3. Jan, 2006. Available at https://ibmlc2.chem.uga.edu/sparc/ as of Jan 2008.
(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) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(6) Gerike P; Chemosphere : 169-90 (1984)
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1.4X10+5 for the free acid(SRC), determined from a structure estimation method(2), indicates that undissociated docosanoic acid is expected to adsorb to suspended solids and sediment(SRC). An estimated pKa of 4.7(3) indicates docosanoic 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). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of 9.91(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A half life of 1.7 days in freshwater after a 29 days(8) suggests that biodegradation may be an important environmental fate process in water(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(3) SPARC; pKa/property server. Ver 3. Jan, 2006. Available at https://ibmlc2.chem.uga.edu/sparc/ as of Jan 2008.
(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) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (1995)
(7) Meylan WM et al; Environ Toxicol Chem 18: 664-72 (1999)
(8) Matsumoto G; Water Res 17: 1803-10 (1983)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), docosanoic acid, which has an estimated vapor pressure of 7.1X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase docosanoic 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 14 hours(SRC), calculated from its rate constant of 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase docosanoic acid may be removed from the air by wet or dry deposition(SRC). Docosanoic acid does not contain chromophores that absorb at wavelengths >290 nm(4) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)
(3) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(4) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 8-12 (1990)

13.2.7 Environmental Biodegradation

AEROBIC: During a 29-day incubation period of freshwater from the Tama River, Japan, docosanoic acid displayed a first order rate biodegradation constant of 0.41/day(1), suggesting a half-life of approximately 1.7 days(SRC). Docosanoic acid added at a concentration of 20 mg/L, exhibited a 69% of theoretical BOD using the modified closed bottle Blok test using a sewage inoculum and incubated for 28 days(2). Sodium-docosanate had a 5-day BOD of 43% and a 10-day BOD of 75% using a closed bottle screening test(3).
(1) Matsumoto G; Water Res 17: 1803-10 (1983)
(2) Gerike P; Chemosphere : 169-90 (1984)
(3) Steber J, Berger H; pp. 134-82 in Biodegrad Surfactants, Glasgow, UK: Karsa DR, Porter MR eds (1995)

13.2.8 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of docosanoic acid with photochemically-produced hydroxyl radicals has been estimated as 2.8X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 14 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Docosanoic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Docosanoic acid does not contain chromophores that absorb at wavelengths >290 nm(2) and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).
(1) Meylan WM, Howard PH; Chemosphere 26: 2293-99 (1993)
(2) 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 was calculated in fish for docosanoic acid(SRC), using an estimated log Kow of 9.91(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) Meylan WM, Howard PH; J Pharm Sci 84: 83-92 (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

Using a structure estimation method based on molecular connectivity indices(1), the Koc of undissociated docosanoic acid can be estimated to be 1.4X10+5(SRC). According to a classification scheme(2), this estimated Koc value suggests that docosanoic acid is expected to be immobile in soil(SRC). The estimated pKa of docosanoic acid is 4.7(3), indicating that this compound will exist almost entirely in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).
(1) Meylan WM et al; Environ Sci Technol 26: 1560-67 (1992)
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) SPARC; pKa/property server. Ver 3. Jan, 2006. Available at https://ibmlc2.chem.uga.edu/sparc/ as of Jan 2008.
(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)

13.2.11 Volatilization from Water / Soil

An estimated pKa of 4.7(1) indicates docosanoic 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(2). Docosanoic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.1X10-8 mm Hg(SRC), determined from a fragment constant method(3).
(1) SPARC; pKa/property server. Ver 3. Jan, 2006. Available at https://ibmlc2.chem.uga.edu/sparc/ as of Jan 2008.
(2) Doucette WJ; pp. 141-188 in Handbook of Property Estimation Methods for Chemicals. Boethling RS, Mackay D, eds. Boca Raton, FL: Lewis Publ (2000)
(3) Lyman WJ; p. 31 in Environmental Exposure From Chemicals Vol I, Neely WB, Blau GE, eds, Boca Raton, FL: CRC Press (1985)

13.2.12 Effluent Concentrations

Water samples taken from the effluent of a kraft paper mill located on the shore of Lake Saimaa, Lappeenranta, Finland were found to contain docosanoic acid concns ranging from 1 to 37 ug/L over a 9 day period(1). Docosanoic acid was identified in a tire manufacturing plant wastewater at 1 mg/L(2).
(1) Oikari A et al; Pap Puu 62: 193-202 (1980)
(2) Jungclaus GA et al; Anal Chem 48: 1894-6 (1976)
Docosanoic acid was found in candle smoke from paraffin and beeswax at 0.15 and 1.21 mg/g of organic compounds(1). Docosanoic acid was found in wood smoke from yellow poplar, white ash, sweet gum, mockernut hickory, loblolly pine, and slash pine(2). Docosanoic acid was detected in wood smoke from pine, oak and synthetic logs at 7.98, 4.63 and 0.99 mg/kg of wood burnt(3). Docosanoic acid was found at 20.8, 7.61 and 5.09 mg/kg of burnt pine, oak and eucalyptus wood, respectively, in the particulate phase(4). Docosanoic acid was found in extract from a pine wood burning campfire at 628 ng/g(5). Docosanoic acid was found at 17 ug/g from heated roofing tar pot fumes(6).
(1) Fine PM et al; Environ Sci Technol 33: 2352-62 (1999)
(2) Fine PM et al; Environ Sci Technol 36: 1442-51 (2002)
(3) Rogge WF et al; Environ Sci Technol 32: 13-22 (1998)
(4) Schauer JJ et al; Environ Sci Tech 35: 1716-28 (2001)
(5) Simoneit BRT et al; Chemosphere - Global Change Science 2: 107-22 (2000)
(6) Rogge WF et al; Environ Sci Technol 31: 2726-30 (1997)
Docosanoic acid was not detected in tire wear particles, and in brake lining particles and road dust particles at concns of 2.1 ug/g and 70.2 ug/g of particle sample, respectively(1). Docosanoic acid was emitted at 350 ug/kg of cooked meat in the particulate phase(2). Fine particle emission of docosanoic acid from a natural gas-fired water heater and a natural gas-fired space heater were not detected(3).
(1) Rogge WF et al; Environ Sci Technol 27: 1892-1904 (1993)
(2) Schauer JJ et al; Environ Sci Technol 33:1566-77 (1999)
(3) Rogge WF et al; Environ Sci Technol 27: 2736-44 (1993)

13.2.13 Sediment / Soil Concentrations

SEDIMENT: Docosanoic acid was identified in sediment samples taken Sept 1995 at the mouth of 3 rivers and in 1 port in Niigata, Japan(1). Sediment samples from the Tarawera River in the Eastern Bay of Plenty region, New Zealand were found to contain an average of 15.5 ppm of docosanoic acid(2).
(1) Kawata K et al; Bull Environ Contam Toxicol 65: 660-7 (2000)
(2) Wilkins AL et al; Bull Environ Contam Toxicol 57: 434-41 (1996)

13.2.14 Atmospheric Concentrations

URBAN/SUBURBAN: Sampling of particulate matter and gaseous pollutants was conducted for three weeks between October 7 and 29, 1976 in Belgium; docosanoic acid was identified in particulate samples with an average concn of 13.68 ug/1000 cu m(1). Aerosol samples collected in the Tsukuba area, northeast of Tokyo, Japan on April 28-29, 1985 contained docosanoic acid in unknown concns(2). Aerosol samples were collected systematically throughout a complete annual cycle (1982) at four urban sites in southern California. Ambient annual concns of docosanoic acid ranged from 5.7 to 9.9 ng/cu m(3). Docosanoic acid had an average concentration of 2.6 ng/cu m in 4 urban sites from southern CA from samples taken Sept 8-9, 1993(4). A southern CA atmospheric study gave concns of docosanoic acid at 2.33, 5.41, 2.08, 2.01 and 2.8 ng/cu m for Long Beach, Mira Loma, Riverside, San Dimas and Upland, respectively(5). Docosanoic acid was found in atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Fresno, CA at 160 and 48.1 ng/cu m and samples taken in Bakersfield had 43.1 and 53.6 ng/cu m, respectively(6). n-Docosanoic acid was found in atmospheric samples from North Birmingham, AL; Jefferson Street, Atlanta, GA; Gulfport, MS; Pensacola, FL; and OLF#8 (suburban site 20 km NW of downtown Pensacola), FL at concns of 4.12; 2.44; 1.60; 2.98; and 1.75 ng/cu m, respectively(7). Docosanoic acid was found in Antwerp, Belgium at concns of 3.2 to 8.4 ug/1000 cu m(8). Atmospheric concns of docosanoic acid in Algiers City, Algeria May 27 to Sept 2, 1998 averaged 4.7 ng/cu m(9).
(1) Cautreels W, VanCauwenberghe K; Atmos Environ 12: 1133-41 (1978)
(2) Yokouchi Y, Ambe Y; Atmos Environ 20: 1727-34 (1986)
(3) Rogge WF et al; Atmos Environ 27A: 1309-30 (1993)
(4) Fraser MP et al; Environ Sci Technol 37: 446-53 (2003)
(5) Manchester-Neesvig JB et al; J Air Waste Mange Assoc 53: 1065-79 (2003)
(6) Schauer JJ, Cass GR; Environ Sci Technol 34: 1821-32 (2000)
(7) Zheng M et al; Environ Sci Technol 36: 2361-71 (2002)
(8) Cautreels W et al; Sci Total Environ 8: 79-88 (1977)
(9) Yassaa N et al; Atmos Environ 35: 1843-51 (2001)
RURAL/REMOTE: Docosanoic acid was found on aerosols obtained over the southern North Atlantic Ocean with a mean concn of 1.1 ng/cu m and over Chacaltaya, Bolivia with a mean concn of 0.49 ng/cu m(1). A southern CA atmospheric study gave concns of docosanoic acid as 1.14, 2.32, 5.28, 0.77, 1.72, 2.99 and 2.21 ng/cu m for Lompoc, Alpine, Atascadero, Lake Arrowhead, Lake Elsinore, Lancaster and Santa Maria, respectively(2). Atmospheric samples taken Dec 26-28, 1995 and Jan 4-6, 1996 in Kern Wildlife Refuge, CA had 4.10 and 4.30 ng/cu m of docosanoic acid(3). Docosanoic acid concns of 2.83, 2.02 and 2.59 ng/cu m were found in Centreville, AL, Yorkville, GA and Oak Grove, MS, respectively(4). Docosanoic acid was found in LaPaz, Bolivia at concns of 0.29 to 0.69 ug/1000 cu m(5). Docosanoic acid was found at San Nicolas Island July to Sept, 1982 at an average concn of 0.39 ng/cu m(6).
(1) Duce RA et al; Rev Geophysics Space Physics 21: 921-52 (1983)
(2) Manchester-Neesvig JB et al; J Air Waste Mange Assoc 53: 1065-79 (2003)
(3) Schauer JJ, Cass GR; Environ Sci Technol 34: 1821-32 (2000)
(4) Zheng M et al; Environ Sci Technol 36: 2361-71 (2002)
(5) Cautreels W et al; Sci Total Environ 8: 79-88 (1977)
(6) Rogge WF et al; Atmos Environ 27A: 1309-30 (1993)

13.2.15 Food Survey Values

Docosanoic acid was identified as a volatile component of roasted and boiled Chinese chestnuts (Castanea molissima)(1).
(1) Morini G, Maga JA; Lebensm Wiss U Technol 28: 638-40 (1995)

13.2.16 Plant Concentrations

Docosanoic acid is found as a minor constituent of most seed fats and in large amounts in jamba oil, mustard seed oil and rape oil(1). Docosanoic acid occurs in bean oil, hydrogenated mustard oil, and rapeseed oil(2). Docosanoic acid was found in fine particulate abrasion products from green leaves at a concn of 152.2 ug/g and from dead leaves at a concn of 212.4 ug/g; samples collected were from trees characteristic of the Los Angeles, CA area(3).
(1) O'Neil MJ ed; The Merck Index. 14th ed. Whitehouse Station, NJ: Merck and Co Inc p. 169 (2006)
(2) Lewis RJ Sr; Hawley's Condensed Chemical Dictionary 14th ed John Wiley & Sons, Inc. New York, NY (2001)
(3) Rogge WF et al; Environ Sci Technol 27: 2700-11 (1993)

13.2.17 Fish / Seafood Concentrations

Docosanoic acid was detected in Sydney rock oysters (Saccostrea commercialis) deployed in mesh bags in the Redhead and Hunter regions of New South Wales, Australia; docosanoic acid was detected in 0.097% lipid material in 83 control samples from the Redhead region which is not directly exposed to sources of sewage pollution(1). The compound was detected in 0.81% lipid material of 59 samples taken in the Huneter region, an area of extended sewage outfall(1). Docosanoic acid is found as a minor constituent of marine animal oils(2).
(1) Avery EL et al; Arch Environ Contam Toxicol 35:229-35 (1998)
(2) O'Neil MJ ed; The Merck Index. 14th ed. Whitehouse Station, NJ: Merck and Co Inc p. 169 (2006)

13.2.18 Milk Concentrations

ENVIRONMENTAL: Docosanoic acid is found as a minor constituent of animal milk fats(1).
(1) O'Neil MJ ed; The Merck Index.14th ed Whitehouse Station, NJ: Merck and Co Inc p. 169 (2006)

13.2.19 Other Environmental Concentrations

Docosanoic acid was found in unburned paraffin and beeswax at 0.15 and 3.34 mg/g of wax(1).
(1) Fine PM et al; Environ Sci Technol 33: 2352-62 (1999)

13.2.20 Probable Routes of Human Exposure

THE LONG CHAIN SATURATED MONOCARBOXYLIC ACIDS.../INCLUDING BEHENIC ACID/ ARE OF A VERY LOW ORDER OF TOXICITY AND NO PROBLEMS ARE LIKELY IN INDUSTRIAL USE.
International Labour Office. Encyclopedia of Occupational Health and Safety. Volumes I and II. New York: McGraw-Hill Book Co., 1971., p. 29
NIOSH (NOES Survey 1981-1983) has statistically estimated that 5,191 workers (2,194 of these were female) were potentially exposed to docosanoic acid in the US(1). Occupational exposure to docosanoic acid may occur through dermal contact with this compound at workplaces where n-docosanoic acid is produced or used. Monitoring and use data indicate that the general population may be exposed to docosanoic acid via inhalation of ambient air, ingestion of food, and dermal contact with this compound and other consumer products containing docosanoic acid(SRC).
(1) NIOSH; NOES. National Occupational Exposure Survey conducted from 1981-1983. Estimated numbers of employees potentially exposed to specific agents by 2-digit standard industrial classification (SIC). Available at https://www.cdc.gov/noes/ as of Dec 2007.

13.2.21 Average Daily Intake

Fatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.
USEPA/OPPTS; R.E.D Facts. Soap Salts. Reregistration Eligibility Decisions (REDs) Database. EPA-738-F-92-013. Sept 1992. Available from the Database Query page at https://www.epa.gov/pesticides/reregistration/status.htm as of Sept 8, 2008.

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
Obesity
References

PubMed: 15899597, 16253646, 2401584, 17264178, 1783639, 26505825, 17408529, 18997681, 24740590, 23108202, 26910390

Metabolomics reveals determinants of weight loss during lifestyle intervention in obese children

15 Literature

15.1 Consolidated References

15.2 NLM Curated PubMed Citations

15.3 Springer Nature References

15.4 Thieme References

15.5 Chemical Co-Occurrences in Literature

15.6 Chemical-Gene Co-Occurrences in Literature

15.7 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 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
A metabolome atlas of the aging mouse brain. Nat Commun. 2021 Oct 15;12(1):6021. DOI:10.1038/s41467-021-26310-y. PMID:34654818; PMCID:PMC8519999.
The Metabolome Atlas of the Aging Mouse Brain: https://mouse.atlas.metabolomics.us

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 EPA Safer Choice

20.9 ChemIDplus

20.10 ChEMBL Target Tree

20.11 UN GHS Classification

20.12 EPA CPDat Classification

20.13 NORMAN Suspect List Exchange Classification

20.14 CCSBase Classification

20.15 EPA DSSTox Classification

20.16 Consumer Product Information Database Classification

20.17 EPA TSCA and CDR Classification

20.18 LOTUS Tree

20.19 EPA Substance Registry Services Tree

20.20 CCS Classification - Baker Lab

20.21 MolGenie Organic Chemistry Ontology

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  13. Baker Lab, Chemistry Department, The University of North Carolina at Chapel Hill
    FA 22:0
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    https://tarheels.live/bakerlab/
  14. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  15. LIPID MAPS
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    https://www.lipidmaps.org/
  16. ChEBI
  17. LOTUS - the natural products occurrence database
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    docosanoic acid
  26. KNApSAcK Species-Metabolite Database
  27. Natural Product Activity and Species Source (NPASS)
  28. West Coast Metabolomics Center-UC Davis
    FA 22:0; (behenic acid)
  29. EPA Safer Choice
    EPA Safer Chemical Ingredients Classification
    https://www.epa.gov/saferchoice
  30. FooDB
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  37. MarkerDB
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  38. Metabolomics Workbench
  39. NLM RxNorm Terminology
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  51. PATENTSCOPE (WIPO)
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CONTENTS