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Propyl Gallate

PubChem CID
4947
Structure
Propyl Gallate_small.png
Propyl Gallate_3D_Structure.png
Molecular Formula
Synonyms
  • propyl gallate
  • 121-79-9
  • Propyl 3,4,5-trihydroxybenzoate
  • N-Propyl gallate
  • Progallin P
Molecular Weight
212.20 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Propyl gallate appears as fine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150 °C. Insoluble in water. Slightly bitter taste.
N-propyl gallate is a trihydroxybenzoic acid.
Propyl Gallate is under investigation in clinical trial NCT01450098 (A Study of LY2484595 in Healthy Subjects).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Propyl Gallate.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

propyl 3,4,5-trihydroxybenzoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCOC(=O)C1=CC(=C(C(=C1)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H12O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

121-79-9

2.3.2 Deprecated CAS

56274-95-4

2.3.3 European Community (EC) Number

204-498-2

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 FEMA Number

2.3.10 HMDB ID

2.3.11 KEGG ID

2.3.12 Metabolomics Workbench ID

2.3.13 NCI Thesaurus Code

2.3.14 Nikkaji Number

2.3.15 NSC Number

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Gallate, Propyl
  • Propyl Gallate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
212.20 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
1.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
212.06847348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
212.06847348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
87 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
206
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

Propyl gallate appears as fine white to creamy-white crystalline powder. Odorless or with a faint odor. Melting point 150 °C. Insoluble in water. Slightly bitter taste.
White to creamy-white, crystalline, odourless solid
Colorless or white odorless solid; [HSDB] Faintly beige crystals; [MSDSonline]
Solid

3.2.2 Color / Form

White to creamy-white crystalline powder
Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1223
Colorless crystals
Larranaga, M.D., Lewis, R.J. Sr., Lewis, R.A.; Hawley's Condensed Chemical Dictionary 16th Edition. John Wiley & Sons, Inc. Hoboken, NJ 2016., p. 1143
Needles in water
Haynes, W.M. (ed.). CRC Handbook of Chemistry and Physics. 95th Edition. CRC Press LLC, Boca Raton: FL 2014-2015, p. 3-470
Fine, ivory powder or crystals
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. 3792

3.2.3 Odor

Odorless
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. 3792
Odorless or with a faint odor
NOAA; CAMEO Chemicals. Database of Hazardous Materials. Propyl Gallate (121-79-9). Natl Ocean Atmos Admin, Off Resp Rest; NOAA Ocean Serv. Available from, as of Oct 21, 2016: https://cameochemicals.noaa.gov/

3.2.4 Taste

Slightly bitter taste
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. 3792

3.2.5 Boiling Point

Decomposes (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.

3.2.6 Melting Point

302 °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.
Between 146 °C and 150 °C after drying at 110 °C for four hours
147-149 °C
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. 3792
150 °C

3.2.7 Flash Point

368 °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.
187 °C (369 °F) - closed cup
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

3.2.8 Solubility

less than 1 mg/mL at 68 °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.
Slightly soluble in water, freely soluble in ethanol, ether and propane-1,2-diol
In water, 3490 mg/L at 25 deg, 2790 mg/L at 20 °C, 3790 mg/L at 30 °C
Yalkowsky, S.H., He, Yan, Jain, P. Handbook of Aqueous Solubility Data Second Edition. CRC Press, Boca Raton, FL 2010, p. 690
Solubility at 25 °C: in water 0.35 g/100 mL
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1455
Slightly soluble in acetone and 2-butanol
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 12th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2012., p. 3792
Solubility at 25 °C: in alcohol 103 g/100 g, in ether 83 g/100 g; Solubility at 30 °C: in cottonseed oil at 30 °C 1.23 g/100 g, in lard at 45 °C 1.14 g/100 g
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1455
3.5 mg/mL at 25 °C

3.2.9 Density

1.21 (NTP, 1992) - Denser than water; will sink
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.
1.21
NOAA; CAMEO Chemicals. Database of Hazardous Materials. Propyl Gallate (121-79-9). Natl Ocean Atmos Admin, Off Resp Rest; NOAA Ocean Serv. Available from, as of Oct 21, 2016: https://cameochemicals.noaa.gov/

3.2.10 Vapor Density

7.3 (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.

3.2.11 LogP

log Kow = 1.80
Hansch, C., Leo, A., D. Hoekman. Exploring QSAR - Hydrophobic, Electronic, and Steric Constants. Washington, DC: American Chemical Society., 1995., p. 73
1.80

3.2.12 Stability / Shelf Life

Stable under recommended storage conditions.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

3.2.13 Decomposition

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. 3084

3.2.14 pH

pH = 6.3 (0.05% aqueous solution); pH = 5.9 (0.1% aqueous solution); pH = 5.7 (0.2% aqueous solution)
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1455

3.2.15 Dissociation Constants

pKa = 7.94
Shahidi F, ed; Handbook of Antioxidants for Food Preservation. Waltham, MA: Woodhead Publishing, p. 54 (2015)

3.2.16 Other Experimental Properties

Darkens in presence of iron and iron salts
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1455
Synergic with acids, BHA, BHT
O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. Cambridge, UK: Royal Society of Chemistry, 2013., p. 1455
Propyl gallate can react with oxidizing agents. Incompatible with strong acids, strong bases and strong reducing agents.
NOAA; CAMEO Chemicals. Database of Hazardous Materials. Propyl Gallate (121-79-9). Natl Ocean Atmos Admin, Off Resp Rest; NOAA Ocean Serv. Available from, as of Oct 21, 2016: https://cameochemicals.noaa.gov/
Henry's Law constant = 2.1X10-11 atm-cu m/mol at 25 °C /Estimated from vapor pressure and water solubility/
US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools

3.3 Chemical Classes

Other Uses -> Preservatives
Antioxidant
S120 | DUSTCT2024 | Substances from Second NORMAN Collaborative Dust Trial | DOI:10.5281/zenodo.13835254

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.3.1.1 Animal Drugs
Pharmaceuticals -> UK Veterinary Medicines Directorate List
S104 | UKVETMED | UK Veterinary Medicines Directorate's List | DOI:10.5281/zenodo.7802119

3.3.2 Cosmetics

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

3.3.3 Food Additives

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

3.3.4 Fragrances

Fragrance Ingredient (Propyl gallate) -> IFRA transparency List

4 Spectral Information

4.1 1D NMR Spectra

1 of 2
1D NMR Spectra
NMR: 18733 (Sadtler Research Laboratories Spectral Collection)
2 of 2
1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian A-60D
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
P53306
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
D2O
Shifts [ppm]:Intensity
144.83:432.00, 21.73:562.00, 110.25:1000.00, 168.41:213.00, 121.54:248.00, 9.81:482.00, 138.21:139.00, 66.87:656.00
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2 of 3
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Source of Sample
Eastman Organic Chemicals, Rochester, New York
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 7
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

281.0 1

239.0 0.58

428.0 0.47

133.0 0.28

179.0 0.27

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2 of 7
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MS Category
Experimental
MS Type
GC-MS
Instrument Type
GC-MS
Top 5 Peaks

281.0 1

239.0 0.58

428.0 0.47

133.0 0.28

179.0 0.27

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4.2.2 MS-MS

1 of 8
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

125.0244 100

140.0115 81.98

139.0037 52.65

111.0088 48.75

136.988 35.64

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2 of 8
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Spectra ID
Ionization Mode
Positive
Top 5 Peaks

140.0115 100

125.0244 91.99

139.0037 66.57

111.0088 60.46

123.0088 44.14

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4.2.3 LC-MS

1 of 9
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
15
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
14.149 min
Precursor m/z
211.0612
Precursor Adduct
[M-H]-
Top 5 Peaks

211.0611 999

169.0143 88

168.0065 42

125.0244 20

124.0169 9

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License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).
2 of 9
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
30
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
14.149 min
Precursor m/z
211.0612
Precursor Adduct
[M-H]-
Top 5 Peaks

211.0611 999

169.0143 204

168.0065 103

125.0244 75

140.0116 27

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License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).

4.2.4 Other MS

Other MS
MASS: 70022 (NIST/EPA/MSDC Mass Spectral Database, 1990 Version)

4.3 UV Spectra

Max absorption (alcohol): 275 nm; 9163 (IR, Prism)
Weast, R.C. (ed.). Handbook of Chemistry and Physics. 60th ed. Boca Raton, Florida: CRC Press Inc., 1979., p. C-199
The UV spectrum of propyl gallate in water has two characteristic bands: maximum #1 at 217 nm and maximum #2 at 274 nm
Szymula M; J Cosmet Sci 55: 281-289 (2004). Available from, as of Oct 24, 2016: https://journal.scconline.org/pdf/cc2004/cc055n03/p00281-p00289.pdf

4.3.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 IR Spectra

IR Spectra
IR: 2023 (Coblentz Society Spectral Collection)

4.4.1 FTIR Spectra

1 of 2
Technique
BETWEEN SALTS
Source of Sample
The Harshaw Chemical Company
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Technique
KBr WAFER
Source of Sample
Eastman Chemcial Products, Inc., Kingsport, 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 (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
A10877
Lot Number
10158862
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Source of Sample
Aldrich
Catalog Number
P53306
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

1 of 2
Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
P53306
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

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
A10877
Lot Number
10158862
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Therapeutic Uses

/EXPL THER/ In addition to the hepatocellular edema and cytoplasmic eosinophilia, sludging of blood was present in liver of mice exposed to trinitrotoluene (TNT). Single necrosis of the partical liver cell was seen occasionally. Liver damage induced by TNT was significantly alleviated by orally administrated propyl gallate (PG). Futhermore, PG can promote the regeneration of the hepatocytes following TNT-exposed mice. The results suggest that PG showed a protective effect on the histopathologic changes of liver injury induced by TNT.
Li Z et al; Wei Sheng Yan Jiu 27 (3): 151-3 (1998)
/EXPL THER/ Phosgene, widely used in industrial processes, can cause life-threatening pulmonary edema and acute lung injury. One mechanism of protection against phosgene-induced lung injury may involve the use of antioxidants. The present study focused on dietary supplementation in mice using n-propyl gallate (nPG)--a gallate acid ester compound used in food preservation--and vitamin E. Five groups of male mice were studied: group 1, control-fed with Purina rodent chow 5002; group 2, fed 0.75% nPG (w/w) in 5002; group 3, fed 1.5% nPG (w/w) in 5002; group 4 fed 1% (w/w) vitamin E in 5002; and group 5, fed 2% (w/w) vitamin E also in 5002. Mice were fed for 23 days. On day 23 mice were exposed to 32 mg m-3 (8 ppm) phosgene for 20 min (640 mg. min m-3) in a whole-body exposure chamber. Survival rates were determined at 12 and 24 hr. In mice that died within 12 h, the lungs were removed and lung wet weights, dry weights, wet/dry weight ratios, lipid peroxidation (thiobarbituric acid reactive substances, TBARS) and glutathione (GSH) were assessed. Vitamin E had no positive effect on any outcome measured. There was no significant difference between 1.5% nPG and any parameter measured or survival rate compared with 5002 + phosgene. However, dietary treatment with 0.75% nPG significantly increased survival rate (p
Sciuto AM, Moran TS; J Appl Toxicol 21 (1): 33-9 (2001)
/EXPL THER/ ... In the present study we explored the role of oxidants present in ambient particles in causing damage to the mucociliary epithelium. We explored the protective effects of pretreatment with three substances (n-propyl gallate, DL-alpha-tocopherol acetate, and EDTA) on the frog palate exposed to residual oil fly ash (ROFA). The parameters analyzed were mucociliary transport (MCT) and ciliary beating frequency (CBF) after 0, 10, 20, 30, 60, and 120 min of exposure. MCT was decreased significantly by ROFA (p<0.001), with a significant interaction effect (p=0.02) between the duration of exposure and treatment with antioxidants. The inhibitory effects on MCT of the substances tested were significantly different (p=0.002); vitamin E was similar to control (Ringer) and different from all other groups. CBF showed no significant effect of duration of exposure (p=0.465), but a significant interaction between duration of exposure and treatments was observed (p=0.011). Significant differences were detected among treatments (p<0.001), with ROFA and n-propyl gallate at concentrations of 50 uM presenting a short-lived increase in CBF, which was not observed in the remaining groups. The results showed that both MCT and CBF were affected within a short period (100 min) of exposure to ROFA and that the presence of antioxidant substances, such as vitamin E (4 mg/mL) and n-propyl gallate (300 uM), protected against the mucociliary impairment induced by ROFA on the frog palate.
Carvalho-Oliveira R et al; Environ Res 98 (3): 349-54 (2005)
/EXPL THER/ Ca(2+) sensitizers are cardiotonic agents that directly increase the Ca(2+) sensitivity of cardiac myofilament. To find a novel Ca(2+) sensitizer, we have screened a group of phenolic compounds by examining their effects on the Ca(2+)-dependent force generation in cardiac muscle fibers. We found that propyl gallate, a strong antioxidant, increased the Ca(2+) sensitivity of cardiac myofilament in a dose-dependent and reversible manner. The present study indicates that propyl gallate is a novel type of Ca(2+) sensitizer with antioxidant activity, which might be more beneficial for the treatment of congestive heart failure associated with oxidative stress than existing Ca(2+) sensitizers.
Tadano N et al; J Pharmacol Sci 109 (3): 456-8 (2009)
For more Therapeutic Uses (Complete) data for PROPYL GALLATE (8 total), please visit the HSDB record page.

8 Food Additives and Ingredients

8.1 Food Additive Classes

JECFA Functional Classes
Food Additives -> ANTIOXIDANT;

8.2 FDA Substances Added to Food

Used for (Technical Effect)
ANTIOXIDANT, FLAVORING AGENT OR ADJUVANT
FEMA Number
2947
GRAS Number
3

8.3 Associated Foods

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

Chemical Name
PROPYL GALLATE
Evaluation Year
1996
ADI
0-1.4 mg/kg bw (1993)
Comments
The 1993 ADI was maintained at the forty-sixth meeting (1996)

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Antioxidants
Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

9.2 Absorption, Distribution and Excretion

Propyl gallate was quickly metabolized and excreted when administered orally to rats and rabbits. ...When fed to rats, most of the propyl gallate was passed in the feces as the original ester. The urinary components detected were the original ester and gallic acid, and these were excreted completely within 24 hours. When administered orally to rabbits, 79 percent of the administered dose of propyl gallate was excreted in the urine, 72 percent as 4-methoxygallic acid glucuronide and 6.7 percent as unconjugated phenolic compounds. Minor metabolites included pyrogallol (free and conjugated) and free 4-methoxy gallic acid.
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
In rats, /SRP: some/ of an oral dose of propyl gallate is absorbed in the GI tract. In vivo, the gallate esters are hydrolized to gallic acid and free alcohol. Free alcohol is metabolized through the Krebs cycle, and most of the gallic acid is converted into 4-O-methyl gallic acid. Free gallic acid or a conjugated derivative of 4-O-methyl gallic acid is excreted in the urine. Significant amounts of unchanged esters are excreted in the feces of rats.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 731

9.3 Metabolism / Metabolites

Propyl gallate was quickly metabolized and excreted when administered orally to rats and rabbits. ...When fed to rats, most of the propyl gallate was passed in the feces as the original ester. The urinary components detected were the original ester and gallic acid, and these were excreted completely within 24 hours. When administered orally to rabbits, 79 percent of the administered dose of propyl gallate was excreted in the urine, 72 percent as 4-methoxygallic acid glucuronide and 6.7 percent as unconjugated phenolic compounds. Minor metabolites included pyrogallol (free and conjugated) and free 4-methoxy gallic acid.
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
In rats, /SRP: some/ of an oral dose of propyl gallate is absorbed in the GI tract. In vivo, the gallate esters are hydrolized to gallic acid and free alcohol. Free alcohol is metabolized through the Krebs cycle, and most of the gallic acid is converted into 4-O-methyl gallic acid. Free gallic acid or a conjugated derivative of 4-O-methyl gallic acid is excreted in the urine. Significant amounts of unchanged esters are excreted in the feces of rats. In pigs, the metabolism is similar to rats.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 731
The available evidence indicates that the gallate esters are hydrolyzed in the body to gallic acid. Most of the gallic acid is converted into 4-O-methyl gallic acid. Free gallic acid or a conjugated derivative of 4-O-methyl gallic acid is excreted in the urine. Conjugation of the 4-O-methyl gallic acid with glucuronic acid was demonstrated ... .
International Programme on Chemical Safety/World Health Organization; Food Additives Series 32, Gallates (1993). Available from, as of October 10, 2016: https://www.inchem.org/documents/jecfa/jecmono/v32je02.htm
In vitro incubations with propyl, octyl and dodecyl gallate were performed using homogenates of liver, mucosa of the small intestine, and contents of caecum/colon as a source of intestinal microflora. The various homogenates were incubated at 37 °C with the individual gallate esters. At various time points up to 24 hr, samples were taken and analyzed by HPLC. ... All test substances were extensively metabolized by the homogenate of the intestinal mucosa. ... Furthermore, the caecum and colon contents also showed a high metabolic capacity, especially towards propyl gallate. The amt of gallic acid detected in the incubations was always much smaller than the total decrease of the amt of ester. It seems likely that apart from hydrolysis of the ester bond, other biotransformation routes ... are of major importance for all three gallate esters.
International Programme on Chemical Safety/World Health Organization; Food Additives Series 32, Gallates (1993). Available from, as of October 10, 2016: https://www.inchem.org/documents/jecfa/jecmono/v32je02.htm

9.4 Mechanism of Action

The present study aimed to assess anti-inflammatory activity and underlying mechanism of n-propyl gallate, the n-propyl ester of gallic acid. n-Propyl gallate was shown to contain anti-inflammatory activity using two experimental animal models, acetic acid-induced permeability model in mice, and air pouch model in rats. It suppressed production of nitric oxide and induction of inducible nitric oxide synthase and cyclooxygenase-2 in the lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. It was able to diminish reactive oxygen species level elevated in the LPS-stimulated RAW264.7 macrophage cells. It also suppressed gelatinolytic activity of matrix metalloproteinase-9 enhanced in the LPS-stimulated RAW264.7 macrophage cells. It inhibited inhibitory kappaB-aplha degradation and enhanced NF-kappaB promoter activity in the stimulated macrophage cells. It was able to suppress phosphorylation of c-Jun NH(2)-terminal kinase 1/2 (JNK1/2) and activation of c-Jun promoter activity in the stimulated macrophage cells. In brief, n-propyl gallate possesses anti-inflammatory activity via down-regulation of NF-kappaB and JNK pathways.
Jung HJ et al; Inflammation 34 (5): 352-61 (2011)
... In the present study, we demonstrate that propyl gallate (PG) reduced cell viability in THP-1, Jurkat, and HL-60 leukemia cells and induced apoptosis in THP-1 cells. PG activated caspases 3, 8, and 9 and increased the levels of p53, Bax, Fas, and Fas ligand. PG activated mitogen-activated protein kinases (MAPKs), inhibited nuclear translocation of the nuclear factor erythroid 2-related factor 2 (Nrf-2) and induced intracellular glutathione (GSH) depletion. In addition, PG increased superoxide dismutase-1 expression and decreased intracellular levels of reactive oxygen species. Our data show ... that an early event of PG-induced apoptosis is MAPKs/Nrf-2-mediated GSH depletion and that PG induced apoptosis via multiple pathways in human leukemia. PG might serve as a potential chemotherapeutic agent or food supplement for human leukemia patients.
Chen CH et al; Food Chem Toxicol 49 (2): 494-501 (2011)

9.5 Human Metabolite Information

9.5.1 Cellular Locations

  • Cytoplasm
  • Extracellular

9.6 Transformations

10 Use and Manufacturing

10.1 Uses

Cosmetic Ingredient Review Link
CIR ingredient: Propyl Gallate
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 antioxidant to prevent rancidity in fats, oils, and other food products; Also used as a laboratory reagent and stabilizer for synthetic vitamin A; [HSDB] Used as an antioxidant for cosmetics, ethers, emulsions, waxes, and transformer oils; [Merck Index] Contact dermatitis documented in a baker and confectioner; [Kanerva, p. 1830]
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.
Kanerva - Rustemeyer L, Elsner P, John SM, Maibach HI (eds). Kanerva's Occupational Dermatology, 2nd Ed. Berlin: Springer-Verlag, 2012., p. 1830

Reported uses (ppm):

Table: Reported uses (ppm): (Flavor and Extract Manufacturers' Association, 1994)

Food Category
Baked goods
Usual
0.00
Max.
0.03
Food Category
Fats, oils
Usual
0.06
Max.
0.15
Food Category
Meat products
Usual
0.03
Max.
0.10
Food Category
Nut products
Usual
0.01
Max.
0.01
Food Category
Snack foods
Usual
0.01
Max.
0.03

Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1755
It is used as an antioxidant for foods and cosmetics; especially fats, oils, emulsions, and waxes. It is also used in transformer oils and as a stabilizer for synthetic vitamin A.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 730
Reactive peroxides in povidone often lead to degradation of oxidation-labile drugs. ... The antioxidants ascorbic acid, propyl gallate, and sodium sulfite reduced the peroxide concentration in povidone ... .
Narang AS et al; J Pharm Sci 101 (1): 127-39 (2012)
Synthetic antioxidants commonly used in food include butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), propyl gallate (PG), and tert-butylhydroquinone (TBHQ).
Somosyi L; Food Additives. Kirk-Othmer Encyclopedia of Chemical Technology (1999-2016). John Wiley & Sons, Inc. Online Posting Date: June 15, 2015
MEDICATION

10.1.1 Use Classification

Food additives
Fragrance Ingredients
Food Additives -> ANTIOXIDANT; -> JECFA Functional Classes
Cosmetics -> Antioxidant
S13 | EUCOSMETICS | Combined Inventory of Ingredients Employed in Cosmetic Products (2000) and Revised Inventory (2006) | DOI:10.5281/zenodo.2624118

10.1.2 Household Products

Household & Commercial/Institutional Products

Information on 8 consumer products that contain Propyl gallate in the following categories is provided:

• Personal Care

10.2 Methods of Manufacturing

Propyl gallate is manufactured via a reaction of n-propanol with 3,4,5-trihydroxybenzoic acid.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. V6 730
Produced commercially by the esterification of gallic acid with propyl alcohol followed by distillation to remove the excess alcohol.
Burdock, G.A. (ed.). Fenaroli's Handbook of Flavor Ingredients. 6th ed.Boca Raton, FL 2010, p. 1755
SRI

10.3 Formulations / Preparations

Trade Names: NIPA 49; Nipagallin P; Progallin P; and Tenox PG.
Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 729
The antioxidant formulations most commonly used in edible products contain various combinations of BHA, BHT, and/or propyl gallate together with citric acid in a suitable solvent.
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 202

10.4 U.S. Production

(1975) PROBABLY GREATER THAN 9.08X10+5 GRAMS
SRI
Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: Benzoic acid, 3,4,5-trihydroxy-, propyl ester. National Production Volume: 232,076 lb/yr.
USEPA/Pollution Prevention and Toxics; 2012 Chemical Data Reporting Database. Benzoic acid, 3,4,5-trihydroxy-, propyl ester (121-79-9). Available from, as of October 26, 2016: https://java.epa.gov/oppt_chemical_search/

10.5 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzoic acid, 3,4,5-trihydroxy-, propyl ester: ACTIVE
The Panel on Food Additives and Nutrient Sources added to Food (ANS), European Food Safety Authority (EFSA), concluded in a 2014 report, that the use of propyl gallate as food additive at the current uses and use levels is not of safety concern.
EFSA; Scientific Opinion on the re-evaluation of propyl gallate (E 310) as a food additive; ESFA Journal 12: 3642 (2014). Available from, as of Oct 24, 2016: https://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2014.3642/pdf
Propyl gallate is used as an antioxidant in pesticide formulations at typical concentrations of 0.25% or less.
USEPA; Inert Reassessment Propyl Gallate (CAS Reg. No. 121-79-9), December 2005. Available from, as of Oct 24, 2016: https://www.epa.gov/sites/production/files/2015-04/documents/propyl.pdf
Used in foods restricted to 0.02% of fat content.
Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 12th ed. New York, NY: Van Nostrand Rheinhold Co., 1993, p. 972
The antioxidant formulations most commonly used in edible products contain various combinations of BHA, BHT, and/or propyl gallate together with citric acid in suitable solvent.
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 202
Tocopherols, gum guaiac, and similar natural antioxidants usually lack potency in most products compared to combinations of BHA /butylated hydroxyanisole/, BHT /butylated hydroxytoluene/, and propyl gallate.
Furia, T.E. (ed.). CRC Handbook of Food Additives. 2nd ed. Cleveland: The Chemical Rubber Co., 1972., p. 203

11 Identification

11.1 Analytic Laboratory Methods

A simple and fast luminescent method is used ... to resolve a mixture of two synthetic antioxidants, propyl gallate (PG) and butylated hydroxyanisole (BHA), by the joint use of the stopped-flow mixing technique and a T-format luminescence spectrometer. The determination of these compounds involves two different and independent reactions. On the one hand, PG determination is based on an energy transfer process that involves the formation of a lanthanide chelate with terbium in the presence of Triton X-100 and tri-n-octylphosphine oxide. On the other hand, BHA is determined using a reaction between the oxidized form of Nile Blue and the antioxidant. Both systems are excited at the same excitation wavelength (310 nm), and the emission wavelengths are 545 and 665 nm for PG and BHA, respectively. The absence of overlap in the emission spectra makes it possible to measure separately the analytes in each channel of the instrument. Initial rate and equilibrium signal are used as analytical parameters and measured in 0.1 and 1 s for PG and BHA, respectively. Calibration graphs are linear over the range 0.09-3.5 ug/mL for PG and 0.3-15 ug/mL for BHA. The relative standard deviations of both systems are close to 2%. The proposed method is applied to the determination of these two antioxidants in several commercial food samples with recoveries ranging between 94.8 and 102.9% for PG and between 94.1 and 102.1% for BHA.
Aguilar-Caballos MP et al; J Agric Food Chem 48 (2): 312-7 (2000)
An accurate and rapid method for simultaneous determination of antioxidants butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and propyl gallate (PG) in food by reversed-phase high performance liquid chromatography was established. The sample was extracted with hexane. Being filtrated and dried by N2, the residues in evaporator was dissolved in a certain amount of water-C2H5OH (1:4, V/V) and filtered with 0.5 micron of filter membrane for HPLC analysis. The chromatographic conditions were Radial-PAK C12 column, methanol-water (92:8, V/V) mobile phase adjusted to pH = 3 with phosphoric acid and UV-280 nm detector. By using external standard method the analytical results showed that the coefficients of variation of PG,BHA and BHT were 0.61, 0.08 and 1.44 respectively, linear correlation coefficients were more than 0.999 and recoveries were 92%-98% (n = 6). The lowest detection limit was 0.5 mg/L.
Li G et al; Se Pu 16 (3): 276-7 (1998)
A flow-through optosensor with solid phase UV spectroscopic detection is proposed for the direct determination of single antioxidants, namely butylated hydroxyanisole (BHA) and n-propyl gallate (n-PG), without previous derivatization. The methods are based on the transient retention behavior of these compounds in a flow-through cell packed with C-18 silica using ethanol-water mixtures as a carrier, and on the intrinsic absorbance monitored at 290 and 283 nm, respectively. After recording the analytical signal, the antioxidants were easily and quickly desorbed from the solid support by the same carrier. For BHA, calibration graphs were linear over the range 1.0-300.0 mg/L using area as the analytical parameter. The relative standard deviation (RSD) was between 0.5 and 1.6%. For n-PG, calibration graphs were linear over the range 1.0-300.0 mg/L in area and the RSD was between 1.4 and 1.5%. The methods were applied to the determination of these antioxidants in several food and cosmetics samples, and were validated using the standard additions method and an HPLC reference method.
Capitan-Vallvey LF et al; Analyst 126 (6): 897-902 (2001)
An HPLC method with fluorescence detection was developed for the determination of propyl gallate, nordihydroguaiaretic acid, butylated hydroxyanisole (2- and 3-tert-butyl-4-hydroxyanisole), tert-butylhydroquinone and octyl gallate in edible oils and foods. The antioxidants in edible oil were isolated directly with acetonitrile saturated with n-hexane. The antioxidants in food were extracted with ethyl acetate and the extract was concentrated under vacuum. They were isolated from the residue with acetonitrile saturated with n-hexane. The acetonitrile layer was centrifuged at 5,000 rpm for 10 min. The HPLC separation was performed on a Symmetry C18 column (3.5 microns, 4.6 mm i.d. x 150 mm) using a mixture of 5% acetic acid-acetonitrile-methanol (4:3:3, v/v/v) as the mobile phase and monitored by using a fluorescence detector with time programming. Sample peaks were identified by comparison of the fluorescence spectra with those of antioxidant standards. Average recoveries of fortified antioxidants at 100 micrograms/g were 72.1-99.6%. Coefficients of variation were 0.7-7.2%.
Oishi M et al; Shokuhin Eiseigaku Zasshi 43 (2): 104-9 (2002)
For more Analytic Laboratory Methods (Complete) data for PROPYL GALLATE (12 total), please visit the HSDB record page.

12 Safety and Hazards

12.1 Hazards Identification

12.1.1 GHS Classification

1 of 6
View All
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H317 (> 99.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

Precautionary Statement Codes

P261, P264, P270, P272, P280, P301+P317, P302+P352, P321, P330, P333+P317, P362+P364, 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 1768 reports by companies from 8 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 (100%)

Skin Sens. 1 (> 99.9%)

Acute toxicity - category 4

Skin sensitisation - category 1

12.1.3 Health Hazards

SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes, mucous membranes and upper respiratory tract. Other symptoms include gasping respirations and convulsions. Brief skin contact may dry the skin. Prolonged or repeated contact can cause dermatitis and sensitization of the skin. Aspiration into the lungs may cause chemical pneumonia.

ACUTE/CHRONIC HAZARDS: This compound may be harmful by inhalation or ingestion. It is an irritant of the skin, eyes, mucous membranes and upper respiratory tract. When heated to decomposition it emits acrid smoke, irritating fumes and toxic fumes of carbon monoxide and carbon dioxide. (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.

12.1.4 Fire Hazards

This chemical is combustible. (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.

12.1.5 Hazards Summary

Cause allergic contact dermatitis in bakers and other workers; [HSDB] A skin, eye, mucous membrane, and upper respiratory tract irritant; May cause skin sensitization; [CAMEO] Causes convulsions in lethal dose studies of rats; [RTECS] May cause skin sensitization; [eChemPortal: ESIS] Does not increase birth defects in animal experiments; [REPROTOX] ADI = 0-1.4 mg/kg when used as an antioxidant in food; [JECFA]
REPROTOX - Scialli AR, Lione A, Boyle Padgett GK. Reproductive Effects of Chemical, Physical, and Biological Agents. Baltimore: The Johns Hopkins University Press, 1995.

12.1.6 Fire Potential

Combustible when exposed to heat or flame ... .
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3084

12.1.7 Skin, Eye, and Respiratory Irritations

/LABORATORY ANIMALS: Acute Exposure/ Guinea pig: 10% /propyl gallate/ in propylene glycol applied to shaved skin for 48 hours /resulted in/ no local lesions or primary irritation. /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
/LABORATORY ANIMALS: Acute Exposure/ Rabbit: <1 percent /propyl gallate/ in a lipstick. Primary skin irritation test - applied to intact and abraded skin, three 24-hour applications. Not a primary irritant. /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
/LABORATORY ANIMALS: Acute Exposure/ Rabbit: Lipstick containing <7% propyl gallate. Nonirritant /to eyes/. /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 6 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/

12.2 First Aid Measures

12.2.1 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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.

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. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. IMMEDIATELY transport the victim 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.

12.3 Fire Fighting

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (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.

12.3.1 Fire Fighting Procedures

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

12.4 Accidental Release Measures

12.4.1 Cleanup Methods

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

12.4.2 Disposal Methods

SRP: 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 air, soil or water; effects on animal, aquatic and plant life; and conformance with environmental and public health regulations. If it is possible or reasonable use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination.
Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber; Contaminated packaging: Dispose of as unused product.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

12.4.3 Preventive Measures

ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Do not let product enter drains.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.

12.5 Handling and Storage

12.5.1 Nonfire Spill Response

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

STORAGE PRECAUTIONS: You should store this chemical under ambient temperatures, and keep it away from oxidizing materials. (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.

12.5.2 Storage Conditions

Keep container tightly closed in a dry and well-ventilated place.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

12.6 Exposure Control and Personal Protection

12.6.1 Allowable Tolerances

Residues of propyl gallate are exempted from the requirement of a tolerance when used as an antioxidant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
40 CFR 180.910 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 24, 2016: https://www.ecfr.gov
Residues of propyl gallate are exempted from the requirement of a tolerance when used as a antioxidant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
40 CFR 180.930 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 24, 2016: https://www.ecfr.gov

12.6.2 Personal Protective Equipment (PPE)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (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.
Eye/face protection: Face shield and safety glasses. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
Skin protection: Handle with gloves.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
Body Protection: Complete suit protecting against chemicals. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator. For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

12.7 Stability and Reactivity

12.7.1 Air and Water Reactions

Insoluble in water.

12.7.2 Reactive Group

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Phenols and Cresols

12.7.3 Reactivity Profile

PROPYL GALLATE can react with oxidizing agents. Incompatible with strong acids, strong bases and strong reducing agents. Darkens in the presence of iron and iron salts. Contact with metals should be avoided (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.

12.7.4 Hazardous Reactivities and Incompatibilities

Incompatible materials: Strong oxidizing agents, strong acids, strong bases, strong reducing agents
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html
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. 3084

12.8 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Benzoic acid, 3,4,5-trihydroxy-, propyl ester
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Propyl gallate: Does not have an individual approval but may be used under an appropriate group standard

12.8.1 FIFRA Requirements

Residues of propyl gallate are exempted from the requirement of a tolerance when used as an antioxidant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest.
40 CFR 180.910 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 24, 2016: https://www.ecfr.gov
Residues of propyl gallate are exempted from the requirement of a tolerance when used as a antioxidant in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals.
40 CFR 180.930 (USEPA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 24, 2016: https://www.ecfr.gov

12.8.2 FDA Requirements

The food additive chewing gum base may be safely used in the manufacture of chewing gum in accordance with the following prescribed conditions: (a) The food additive consists of one or more of the following substances that meet the specifications and limitations prescribed in this paragraph, used in amounts not to exceed those required to produce the intended physical or other technical effect. Propyl gallate is included on this list. Not to exceed antioxidant content of 0.1% when used alone or in any combination.
21 CFR 172.615 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 21, 2016: https://www.ecfr.gov
Substances classified as antioxidants, when migrating from food-packaging material (limit of addition to food, 0.005 percent) shall include: propyl gallate.
21 CFR 181.24 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 21, 2016: https://www.ecfr.gov
Substance added directly to human food affirmed as generally recognized as safe (GRAS). ... Good manufacturing practice results in a maximum total content of antioxidants of 0.02 percent of the fat or oil content, including the essential (volatile) oil content, of the food.
21 CFR 184.1660 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 21, 2016: https://www.ecfr.gov
This substance is generally recognized as safe for use in food when the total content of antioxidants is not over 0.02 percent of fat or oil content, including essential (volatile) oil content of the food, provided the substance is used in accordance with good manufacturing or feeding practice.
21 CFR 582.3660 (USFDA); U.S. National Archives and Records Administration's Electronic Code of Federal Regulations. Available from, as of October 21, 2016: https://www.ecfr.gov

12.9 Other Safety Information

12.9.1 Toxic Combustion Products

Special hazards arising from the substance or mixture: Carbon oxides
Sigma-Aldrich; Safety Data Sheet for Propyl gallate. Product Number: P3130, Version 4.4 (Revision Date 06/28/2014). Available from, as of October 7, 2016: https://www.sigmaaldrich.com/safety-center.html

12.9.2 Special Reports

DHHS/NTP; Toxicology & Carcinogenesis Studies of Propyl Gallate in F344/N Rats and B6C3F1 Mice (Feed Study) Technical Report Series No. 240 (1982) NIH Publication No. 83-1796[Available from, as of October 10, 2016: https://ntp.niehs.nih.gov/]
International Programme on Chemical Safety/World Health Organization; Food Additives Series 32, Gallates (1993)[Available from, as of October 10, 2016: http://www.inchem.org/documents/jecfa/jecmono/v32je02.htm]

13 Toxicity

13.1 Toxicological Information

13.1.1 Toxicity Summary

IDENTIFICATION AND USE: Propyl gallate is white to creamy-white crystalline powder. It is used as an antioxidant for foods and cosmetics; especially fats, oils, emulsions, and waxes. It is used in transformer oils and as a stabilizer for synthetic vitamin A. It is also used as experimental medication. HUMAN EXPOSURE AND TOXICITY: Statistically significant increase in propyl gallate-positive rates on patch testing over the last decade have been reported. Propyl gallate produced contact dermatitis in 5 of 10 patients. Patients applied 20% in 70% ethyl alcohol to forearm daily for 24 days. 5 patients complained of pruritus and erythema. Propyl gallate was investigated in vitro at concentration of 0.5, 5.0 and 50 ug/mL employing WI-38 human embryonic lung cells for anaphase abnormalities. Propyl gallate was not mutagenic. ANIMAL STUDIES: In a 4-week oral toxicity study, rats ingested 0%, 0.1%, 0.5%, or 2.5% propyl gallate in feed. In rats ingesting the highest dose, a decrease in weight gain of more than 10%, dirty tails, thickening of the stomach wall, necrosis, and ulceration of the stomach mucosa, a moderate to severe granulomatous inflammatory response in the submucosa and muscular wall of the stomach, anemia, hyperplastic tubuli in the outer medulla of the kidneys, and increased activity of several microsomal and cytoplasmic drug-metabolizing enzymes in the liver were observed. Increased activity of hepatic drug metabolizing enzymes was also noted in rats treated with 0.5% propyl gallate. No effects were noted in those ingesting 0.1%. Guinea pigs fed 0.02% propyl gallate in the diet for 14 months and dogs fed 0.01% for a year showed no signs of toxicity. Administration to rats of 2.5% propyl gallate in the diet caused maternal toxicity and slight retardation of fetal development, but no teratogenic effects. In dose levels up to 250 mg/kg/day, propyl gallate had no effects on organogenesis in rabbits. At a concentration of 0-0.1 mg/plate, propyl gallate was mutagenic in S. typhimurium strain TA102, in the presence, but not the absence, of metabolic activation. An intraperitoneal injection of 900 mg/kg propyl gallate caused a positive result in a mouse micronucleus test. Propyl gallate was found to be negative when tested for mutagenicity using the Salmonella/microsome preincubation assay with 5 Salmonella typhimurium strains (TA1535, TA1537, TA97, TA98, and TA100) in the presence and absence of metabolic activation. ECOTOXICITY STUDIES: The toxic effects of propyl gallate on aquatic organisms were investigated, using five model systems from four trophic levels. The most sensitive system was the hepatoma fish cell line PLHC-1 according to total protein content, with an EC(50) of 10 uM and a NOAEL of 1 uM at 72 hours, followed by the immobilization of Daphnia magna, the inhibition of bioluminescence of Vibrio fischeri, the salmonid fish cell line RTG-2 and the inhibition of the growth of Chlorella vulgaris.

13.1.2 Carcinogen Classification

1 of 2
NTP Technical Report
TR-240: Carcinogenesis Bioassay of Propyl Gallate (CASRN 121-79-9) in F344/N Rats and B6C3F1 Mice (Feed Study) (1982 )
Peer Review Date
Conclusion for Male Rat
Equivocal Evidence Equivocal Evidence
Conclusion for Female Rat
No Evidence No Evidence
Conclusion for Male Mice
Equivocal Evidence Equivocal Evidence
Conclusion for Female Mice
No Evidence No Evidence
Summary
Under the conditions of this bioassay, propyl gallate was not considered carcinogenic for F344/N rats, although there was evidence of an increased proportion of low-dose male rats with preputial gland tumors, islet-cell tumors of the pancreas, and pheochromocytomas of the adrenal glands; rare tumors of the brain occurred in two low-dose females. Propyl gallate was not considered to be carcinogenic for B6C3F1 mice of either sex, although the increased incidence of malignant lymphoma in male mice may have been related to the dietary administration of propyl gallate.
2 of 2
Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

13.1.3 Adverse Effects

Neurotoxin - Other CNS neurotoxin

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

13.1.4 Acute Effects

13.1.5 Interactions

The antioxidant propyl gallate (PG) induced lipid peroxidation in combination with non-toxic Cu(II) concentrations in human fibroblasts. This was measured by the thiobarbituric acid assay (TBA assay) and by detection of accumulating fluorescent products after a 1-hr treatment of cells with CuCl2/PG at concentrations higher than 0.125 mM. PG alone led to a significant reduction of thiobarbituric acid-reactive substances (TBARS) demonstrating its antioxidative properties. Time course studies of lipid peroxidation by PG/Cu(II) showed that formation of TBARS was preceded by a lag phase of 60 min. Thereafter, the TBARS value increased rapidly for 1 hr and then reached a constant maximum or slightly decreased. The induction of lipid peroxidation by PG/Cu(II) is probably due to the formation of reactive species like reactive oxygen species (ROS), Cu(I) and semiquinone radicals which are able to participate in initiation and propagation of lipid peroxidation. Combination effects of PG/Cu(II) were demonstrated also on inhibition of membrane-bound succinate dehydrogenase. Cytosolic esterases were affected only slightly. The greater susceptibility of membrane-bound enzymes is in accordance with the lipid peroxidation-inducing effects of PG/Cu(II).
Jacobi H et al; Toxicol Lett 110 (3): 183-90 (1999)
We looked at the in vitro effect of an antioxidant, propyl gallate (PG), on the antifungal activity of miconazole sulphosalicylate, econazole sulphosalicylate and ketoconazole against 40 clinical isolates of Candida albicans. The combination of imidazole and PG gave MIC values 10-150 times lower than those of imidazole alone. The optimal conditions for this enhanced activity were pH 6.2-8.0 and a fungal cell concentration lower than 3 x 10(5) cells/mL. The mechanism of the interaction between imidazole and PG is not known but may be as a result of an effect of PG on the P-450 cytochrome. ...
Strippoli V et al; Int J Antimicrob Agents 16 (1): 73-6 (2000)
Partial protection against liver damage by single oral doses of 2.5 or 0.25 ml/kg of chloroform was provided by ip injection of 150 mg/kg bw of propyl gallate ... .
International Programme on Chemical Safety/World Health Organization; Food Additives Series 32, Gallates (1993). Available from, as of October 10, 2016: https://www.inchem.org/documents/jecfa/jecmono/v32je02.htm
Pregnant New Zealand white rabbits (on gestation day 12) were injected sc with propyl gallate (362-900 mg/kg bw) and hydroxyurea (600-750 mg/kg bw). The materials were injected either simultaneously or mixed over periods of 45 min. The extent of amelioration of the teratogenic effects of hydroxyurea was dependent on the dose of propyl gallate. There was a significant linear decrease in both resorptions and specific malformations with increasing doses of propyl gallate ... .
International Programme on Chemical Safety/World Health Organization; Food Additives Series 32, Gallates (1993). Available from, as of October 10, 2016: https://www.inchem.org/documents/jecfa/jecmono/v32je02.htm
For more Interactions (Complete) data for PROPYL GALLATE (22 total), please visit the HSDB record page.

13.1.6 Antidote and Emergency Treatment

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 if 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. /Phenols and Related Compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 276-7
Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations 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 ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Administer activated charcoal ... . Dilution may be contraindicated because it may increase absorption. Do not use emetics ... . Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and Related Compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 277
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. Positive-pressure ventilation techniques with a bag-valve-mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W TKO. 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 ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. DIRECT PHYSICIAN ORDER ONLY ... . Treat seizures with diazepam (Valium) or lorazepam (Ativan) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and Related Compounds/
Currance, P.L. Clements, B., Bronstein, A.C. (Eds).; Emergency Care For Hazardous Materials Exposure. 3rd revised edition, Elsevier Mosby, St. Louis, MO 2007, p. 277

13.1.7 Human Toxicity Excerpts

/HUMAN EXPOSURE STUDIES/ ... The objectives were to assess the prevalence of allergic contact dermatitis to propyl gallate in our center from 1988 to 2005. From 1988 to 2005, 9529 patients were patch tested to the face series, 6973 were females and 2556 were males. Patch tests were read at 2 D and 4 D. Positive reactions were scored as per International Contact Dermatitis Research Group recommendations as negative, +, ++, and +++ reactions. Propyl gallate was used at a 1% petrolatum (pet.). A total of 55 patients had positive reactions to propyl gallate 1% pet. (0.57%), 46 were female (0.65%) and 9 were male (0.33%). Using chi-square, there was a significant difference (p<0.05) in the positivity rates between the 1988-96 period (0.45%) and the 1997-2005 period (0.77%). A review of our face series performed in the last 18 years has shown a statistically significant increase in propyl gallate-positive rates on patch testing over the last decade. An increase in its use in the cosmetic industry may well be the explanation for this. Nevertheless, a concomitant reduction of propyl gallate as an antioxidant in food, with oral tolerance being less likely to develop, may also be a contributing factor in the increasing trend of allergic contact dermatitis caused by propyl gallate.
Perez A et al; Contact Dermatitis 58 (1): 47-8 (2008)
/HUMAN EXPOSURE STUDIES/Propyl gallate produced contact dermatitis in 5 of 10 patients. Patients applied 20% in 70% ethyl alc to forearm daily for 24 days. 5 Patients complained of pruritus and erythema.
Kahn G et al; Arch Dermatol 109 (Apr): 506-9 (1974)
/CASE REPORTS/ A 29-year-old Turkish woman with allergic contact cheilitis from a lipstick was misdiagnosed as herpes labialis and subsequently worsened with the application of Zovirax cream. Patch tests were positive to Zovirax cream, propylene glycol, the patient's favorite lipstick and propyl gallate. No reaction was seen with Zovirax ophthalmic ointment and Zovirax tablet. The propylene glycol component of the Zovirax cream and the propyl gallate component of the lipstick were regarded as the responsible contact sensitizers. The differential diagnosis was challenging due to concomitant contact sensitization with these agents.
Ozkaya E et al; Australas J Dermatol 48 (3): 190-2 (2007)
/CASE REPORTS/ A 62-year-old man, with a 20-year history of seborrhoeic dermatitis, presented with a worsening of his dermatitis. He had previously been demonstrated to be allergic to various topical corticosteroids, so he had been using an emollient cream (Sebclair), containing piroctone olamine and various anti-inflammatory substances, for 6 months, with good effect. Patch testing to the cream and its ingredients revealed positive reactions to both propyl gallate and pentylene glycol. A positive reaction to propylene glycol was also detected, whereas patch testing to butylene glycol was negative. Complete remission followed avoidance of the offending substances.
Foti C et al; Australas J Dermatol 51 (2): 147-8 (2010)
For more Human Toxicity Excerpts (Complete) data for PROPYL GALLATE (20 total), please visit the HSDB record page.

13.1.8 Non-Human Toxicity Excerpts

/LABORATORY ANIMALS: Acute Exposure/ Guinea pig: 10% /propyl gallate/ in propylene glycol applied to shaved skin for 48 hours /resulted in/ no local lesions or primary irritation. /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
/LABORATORY ANIMALS: Acute Exposure/ Rabbit: <1 percent /propyl gallate/ in a lipstick. Primary skin irritation test - applied to intact and abraded skin, three 24-hour applications. Not a primary irritant. /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
/LABORATORY ANIMALS: Acute Exposure/ Rabbit: 0.003 percent /propyl gallate/ in suntan cream. Primary skin irritation- intact and abraded, three 24-hour applications. No edema, not a primary skin irritant. /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
/LABORATORY ANIMALS: Acute Exposure/ Rabbit: 0.003 percent /propyl gallate/ in suntan oil. Primary skin irritation- intact, three 6-hour applications. Practically nonirritating. /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 6 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
For more Non-Human Toxicity Excerpts (Complete) data for PROPYL GALLATE (59 total), please visit the HSDB record page.

13.1.9 Non-Human Toxicity Values

LD50 Rat oral 2100 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3084
LD50 Mouse oral 1700 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3084
LD50 Cat oral 400 mg/kg
Lewis, R.J. Sr. (ed) Sax's Dangerous Properties of Industrial Materials. 11th Edition. Wiley-Interscience, Wiley & Sons, Inc. Hoboken, NJ. 2004., p. 3084
LD50 Pig oral > 2-6 g/kg bw /from table/
EPA/Office of Prevention, Pesticides, and Toxic Substances; Memorandum: Reassessment of Two Exemptions from the Requirement of a Tolerance For Propyl Gallate (CAS Reg. No. 121-79-9) p. 5 (2005). Available from, as of October 12, 2016: https://www3.epa.gov/
For more Non-Human Toxicity Values (Complete) data for PROPYL GALLATE (9 total), please visit the HSDB record page.

13.1.10 Ongoing Test Status

EPA has released the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assays/[USEPA; ICSS Dashboard Application; Available from, as of September 8, 2016: http://actor.epa.gov/dashboard/]
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page for propyl gallate, which tabulates all of the "Short-Term Toxicity Studies," "Long-term Carcinogenicity Studies," and "Genetic Toxicology Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp.niehs.nih.gov/testing/status/agents/ts-10564-y.html]

13.1.11 National Toxicology Program Studies

A carcinogenesis bioassay of propyl gallate was conducted by feeding diets containing 6,000 or 12,000 ppm propyl gallate to groups of 50 F344/N rats and 50 B6C3F1 mice of each sex for 103 wk. Groups of 50 untreated rats and 50 untreated mice of each sex served as controls. ... Under the conditions of this bioassay, propyl gallate was not considered to be carcinogenic for F344/N rats, although there was evidence of an incr proportion of low dose male rats with preputial gland tumors, islet cell tumors of the pancreas, and pheochromocytomas of the adrenal glands; rare tumors of the brain occurred in two low dose females. Propyl gallate was not considered to be carcinogenic for B6C3F1 mice of either sex, although the incr incidence of malignant lymphoma in male mice may have been related to dietary admin of propyl gallate.
DHHS/NTP; Toxicology & Carcinogenesis Studies of Propyl Gallate in F344/N Rats and B6C3F1 Mice (Feed Study) Technical Report Series No. 240 (1982) NIH Publication No. 83-1796. Available from, as of October 10, 2016: https://ntp.niehs.nih.gov/

13.2 Ecological Information

13.2.1 Ecotoxicity Values

EC50; Species: Dreissena polymorpha (Zebra Mussel) shell length 5-8 mm; Conditions: freshwater, static, 17.0 °C (16.3-17.4 °C), pH 8.0 (7.3-8.7), hardness 146 mg/L CaCO3 (136-156 mg/L CaCO3), alkalinity 109 mg/L CaCO3 (98-120 mg/L CaCO3), dissolved oxygen 8.3 mg/L (6.0-11.2 mg/L); Concentration: 17800 ug/L for 48 hr (95% confidence interval: 11700-23800 ug/L); Effect: behavior, increased ability to detach from substrate /formulation/
Cope WG et al; Environ Toxicol Chem 16 (9): 1930-4 (1997) as cited in the ECOTOX database. Available from, as of October 5, 2016

13.2.2 Ecotoxicity Excerpts

/AQUATIC SPECIES/ ... The toxic effects /of propyl gallate on aquatic organisms/ were investigated, using five model systems from four trophic levels. The most sensitive system was the hepatoma fish cell line PLHC-1 according to total protein content, with an EC(50) of 10 uM and a NOAEL of 1 uM at 72 hr, followed by the immobilization of Daphnia magna, the inhibition of bioluminescence of Vibrio fischeri, the salmonid fish cell line RTG-2 and the inhibition of the growth of Chlorella vulgaris. Although protein content, neutral red uptake, methylthiazol metabolization and acetylcholinesterase activity were reduced in PLHC-1 cells, stimulations were observed for lysosomal function, succinate dehydrogenase, glucose-6-phosphate dehydrogenase and ethoxyresorufin-O-deethylase activities. No changes were observed in metallothionein levels. The main morphological observations were the loss of cells and the induction of cell death mainly by necrosis but also by apoptosis. The protective and toxic effects of propyl gallate were evaluated. General antioxidants and calcium chelators did not modify the toxicity of propyl gallate, but an iron-dependent lipid peroxidation inhibitor gave 22% protection. The results also suggest that propyl gallate cytotoxicity is dependent on glutathione levels, which were modulated by malic acid diethyl ester and 2-oxothiazolidine-4-carboxylic acid. According to the results, propyl gallate should be classified as toxic to aquatic organisms.
Zurita JL et al; Water Res 41 (12): 2599-611 (2007)

13.2.3 Environmental Fate / Exposure Summary

Propyl gallate's production and use as an antioxidant for cosmetics, foods, fats, oils, ethers, emulsifiers, waxes and transformer oils may result in its release to the environment through various waste streams. Propyl gallate's use as an antioxidant in pesticide formulations will result in its direct release to the environment. Propyl gallate has been detected in corn seed. If released to air, an estimated vapor pressure of 2.6X10-7 mm Hg at 25 °C indicates propyl gallate will exist in both the vapor and particulate phases in the atmosphere. Vapor-phase propyl gallate 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 4.2 hours. Particulate-phase propyl gallate will be removed from the atmosphere by wet and dry deposition. Propyl gallate absorbs at wavelengths >290 nm and, therefore, may be susceptible to direct photolysis by sunlight. If released to soil, propyl gallate is expected to have moderate mobility based upon an estimated Koc of 490. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 2.1X10-11 atm-cu m/mole. Propyl gallate is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Propyl gallate is reported to be biodegradable in the environment with ultimate aerobic degradation estimated to be weeks and primary degradation in days. If released into water, propyl gallate is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 7 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis half-lives of 12 and 1.2 years have been estimated at pH values of 7 and 8, respectively, at 25 °C. Photo-oxidation may have some importance in surface waters exposed to sunlight. Occupational exposure to propyl gallate may occur through inhalation and dermal contact with this compound at workplaces where propyl gallate is produced or used. Use data indicate that the general population may be exposed to propyl gallate via ingestion of food and dermal contact with consumer products containing propyl gallate. Propyl gallate is used as an antioxidant in a reported 167 cosmetic products. (SRC)

13.2.4 Natural Pollution Sources

Propyl gallate was detected, not quantified in corn kernels (Zea mays, Poceae)(1).
(1) US Dept Agric; US Dept Agric, Agric Res Service. 1992-2016. Dr. Duke's Phytochemical and Ethnobotanical Databases. n-Propyl Gallate. Available from, as of Oct 25, 2016: https://phytochem.nal.usda.gov/phytochem/search

13.2.5 Artificial Pollution Sources

Propyl gallate's production and use as an antioxidant for cosmetics, foods, fats, oils, ethers, emulsifiers, waxes and transformer oils(1) may result in its release to the environment through various waste streams(SRC). Propyl gallate's use as an antioxidant in pesticide formulations, with typical concentrations of 0.25% or less(2), will result in its direct release to the environment(SRC).
(1) O'Neil MJ, ed; The Merck Index. 15th ed., Cambridge, UK: Royal Society of Chemistry, p. 1455 (2013)
(2) USEPA; Inert Reassessment Propyl Gallate (CAS Reg. No. 121-79-9), December 2005. Available from, as of Oct 24, 2016: https://www.epa.gov/sites/production/files/2015-04/documents/propyl.pdf

13.2.6 Environmental Fate

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 490(SRC), determined from a structure estimation method(2), indicates that propyl gallate is expected to have moderate mobility in soil(SRC). Volatilization of propyl gallate from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-11 atm-cu m/mole(SRC), derived from its estimated vapor pressure, 2.6X10-7 mm Hg(2), and water solubility, 3490 mg/L(3). Propyl gallate is not expected to volatilize from dry soil surfaces(SRC) based upon its estimated vapor pressure(2). Propyl gallate is reported to be biodegradable in the environment(4) with ultimate aerobic degradation estimated to be weeks and primary degradation in days(5).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools
(3) Yalkowsky SH et al; Handbook of Aqueous Solubility Data 2nd ed., Boca Raton, FL: CRC Press, p. 690 (2010)
(4) Quinchia LA et al; J Agric Food Chem 59: 12917-12924 (2011)
(5) USEPA; Inert Reassessment Propyl Gallate (CAS Reg. No. 121-79-9), December 2005. Available from, as of Oct 24, 2016: https://www.epa.gov/sites/production/files/2015-04/documents/propyl.pdf
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 490(SRC), determined from a structure estimation method(2), indicates that propyl gallate is expected to adsorb moderately to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-11 atm-cu m/mole(SRC) derived from its estimated vapor pressure, 2.6X10-7 mm Hg(2), and water solubility, 3490 mg/L(4). According to a classification scheme(5), an estimated BCF of 7(SRC), from its log Kow of 1.80(6) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Propyl gallate is reported to be biodegradable in the environment(7) with ultimate aerobic degradation estimated to be weeks and primary degradation in days(8). A base-catalyzed second-order hydrolysis rate constant of 0.018 L/mole-sec(SRC) was estimated using a structure estimation method(2); this corresponds to half-lives of 12 and 1.2 years at pH values of 7 and 8, respectively(2). Propyl gallate is reported to react readily with photo-oxidant radicals in aqueous media(9); therefore, photo-oxidation may have some importance in surface waters exposed to sunlight(SRC).
(1) Swann RL et al; Res Rev 85: 17-28 (1983)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)
(4) Yalkowsky SH et al; Handbook of Aqueous Solubility Data 2nd ed., Boca Raton, FL: CRC Press, p. 690 (2010)
(5) Franke C et al; Chemosphere 29: 1501-14 (1994)
(6) 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. 73 (1995)
(7) Quinchia LA et al; J Agric Food Chem 59: 12917-12924 (2011)
(8) USEPA; Inert Reassessment Propyl Gallate (CAS Reg. No. 121-79-9), December 2005. Available from, as of Oct 24, 2016: https://www.epa.gov/sites/production/files/2015-04/documents/propyl.pdf
(9) Medina ME et al; Phys Chem Chem Phys 15: 13137-13146 (2013)
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), propyl gallate, which has an estimated vapor pressure of 2.6X10-7 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 propyl gallate 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 4.2 hours(SRC), calculated from its rate constant of 9.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(2). Particulate-phase propyl gallate may be removed from the air by wet and dry deposition(SRC). Propyl gallate absorbs at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
(1) Bidleman TF; Environ Sci Technol 22: 361-367 (1988)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools
(3) Szymula M; J Cosmet Sci 55: 281-289 (2004). Available from, as of Oct 24, 2016: https://journal.scconline.org/pdf/cc2004/cc055n03/p00281-p00289.pdf

13.2.7 Environmental Biodegradation

AEROBIC: Propyl gallate is reported to be a biodegradable antioxidant effective in oxidatively stabilizing vegetable oils according to REACH (Registration, Evaluation, Authorization and Restriction of Chemicals) biodegradability regulations(1). Propyl gallate is expected to biodegrade in the environment with ultimate aerobic degradation estimated to be weeks and primary degradation in days(2).
(1) Quinchia LA et al; J Agric Food Chem 59: 12917-12924 (2011)
(2) USEPA; Inert Reassessment Propyl Gallate (CAS Reg. No. 121-79-9), December 2005. Available from, as of Oct 24, 2016: https://www.epa.gov/sites/production/files/2015-04/documents/propyl.pdf

13.2.8 Environmental Abiotic Degradation

The rate constant for the vapor-phase reaction of propyl gallate with photochemically-produced hydroxyl radicals has been estimated as 9.2X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 4.2 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). A base-catalyzed second-order hydrolysis rate constant of 0.018 L/mole-sec(SRC) was estimated using a structure estimation method(1); this corresponds to half-lives of 12 and 1.2 years at pH values of 7 and 8, respectively(1). The UV spectrum of propyl gallate in water has two characteristic bands: maximum #1 at 217 nm and maximum #2 at 274 nm with decreasing absorbance extending to nearly 330 nm(2); therefore, propyl gallate may be susceptible to direct photolysis by sunlight(SRC). Propyl gallate is reported to react readily with photo-oxidant radicals in aqueous media(3); therefore, photo-oxidation may have some importance in surface waters exposed to sunlight(SRC). With respect to reaction fate in foods, it is reported that propyl gallate is stable in neutral or slightly acidic chemical environments but unstable when heated or in mild alkaline environment(4).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools
(2) Szymula M; J Cosmet Sci 55: 281-289 (2004). Available from, as of Oct 24, 2016: https://journal.scconline.org/pdf/cc2004/cc055n03/p00281-p00289.pdf
(3) Medina ME et al; Phys Chem Chem Phys 15: 13137-13146 (2013)
(4) EFSA; Scientific Opinion on the re-evaluation of propyl gallate (E 310) as a food additive; ESFA Journal 12: 3642 (2014). Available from, as of Oct 24, 2016: https://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2014.3642/pdf

13.2.9 Environmental Bioconcentration

An estimated BCF of 7 was calculated in fish for propyl gallate(SRC), using a log Kow of 1.80(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. 73 (1995)
(2) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools
(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 propyl gallate can be estimated to be 490(SRC). According to a classification scheme(2), this estimated Koc value suggests that propyl gallate is expected to have moderate mobility in soil.
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools
(2) Swann RL et al; Res Rev 85: 17-28 (1983)
(3) Shahidi F, ed; Handbook of Antioxidants for Food Preservation. Waltham, MA; Woodhead Publishing, p. 54 (2015)

13.2.11 Volatilization from Water / Soil

The Henry's Law constant for propyl gallate is estimated as 2.1X10-11 atm-cu m/mole(SRC) derived from its estimated vapor pressure, 2.6X10-7 mm Hg(1), and water solubility, 3490 mg/L(2). This Henry's Law constant indicates that propyl gallate is expected to be essentially nonvolatile from water surfaces(3). Propyl gallate's estimated Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Propyl gallate is not expected to volatilize from dry soil surfaces based upon its vapor pressure(SRC).
(1) US EPA; Estimation Program Interface (EPI) Suite. Ver. 4.11. Nov, 2012. Available from, as of Oct 24, 2016: https://www2.epa.gov/tsca-screening-tools
(2) Yalkowsky SH et al; Handbook of Aqueous Solubility Data 2nd ed., Boca Raton, FL: CRC Press, p. 690 (2010)
(3) Lyman WJ et al; Handbook of Chemical Property Estimation Methods. Washington, DC: Amer Chem Soc pp. 15-1 to 15-29 (1990)

13.2.12 Plant Concentrations

Propyl gallate was detected, not quantified in corn kernels (Zea mays, Poceae)(1).
(1) US Dept Agric; US Dept Agric, Agric Res Service. 1992-2016. Dr. Duke's Phytochemical and Ethnobotanical Databases. n-Propyl Gallate. Available from, as of Oct 25, 2016: https://phytochem.nal.usda.gov/phytochem/search

13.2.13 Probable Routes of Human Exposure

According to the 2012 TSCA Inventory Update Reporting data, 1 reporting facility estimates the number of persons reasonably likely to be exposed during the manufacturing, processing, or use of propyl gallate in the United States may be as low as 10-24 workers and as high as 10-24 workers per plant; the data may be greatly underestimated due to confidential business information (CBI) or unknown values(1).
(1) US EPA; Chemical Data Reporting (CDR). Non-confidential 2012 Chemical Data Reporting information on chemical production and use in the United States. Available from, as of Oct 21, 2016: https://java.epa.gov/oppt_chemical_search/
Occupational exposure to propyl gallate may occur through inhalation and dermal contact with this compound at workplaces where propyl gallate is produced or used. Use data indicate that the general population may be exposed to propyl gallate via ingestion of food and dermal contact with consumer products containing propyl gallate(SRC). Propyl gallate is used as an antioxidant in a reported 167 cosmetic products, with a maximum concentration of 0.1%(1).
(1) American College of Toxicology; International Journal of Toxicology (May 2007) 26: 89-118 (2007). Available from, as of Oct 24, 2016: https://ijt.sagepub.com/content/26/3_suppl/89

13.2.14 Average Daily Intake

Average daily intake assessment: 0.25 - 1.11 mg/kg bw/day in adults(1). Propyl gallate has an ADI of 0-1.4 mg/kg bw/day established by the Joint FAO/WHO Expert Committee on Food Additives(JECFA)(2).
(1) EFSA; Scientific Opinion on the re-evaluation of propyl gallate (E 310) as a food additive; ESFA Journal 12: 3642 (2014). Available from, as of Oct 24, 2016: https://onlinelibrary.wiley.com/doi/10.2903/j.efsa.2014.3642/pdf
(2) USEPA; Inert Reassessment Propyl Gallate (CAS Reg. No. 121-79-9), December 2005. Available from, as of Oct 24, 2016: https://www.epa.gov/sites/production/files/2015-04/documents/propyl.pdf

14 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

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 Chemical Co-Occurrences in Literature

15.7 Chemical-Gene Co-Occurrences in Literature

15.8 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 Chemical-Target Interactions

18 Biological Test Results

18.1 BioAssay Results

19 Taxonomy

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 ChemIDplus

20.5 CAMEO Chemicals

20.6 ChEMBL Target Tree

20.7 UN GHS Classification

20.8 EPA CPDat Classification

20.9 NORMAN Suspect List Exchange Classification

20.10 EPA DSSTox Classification

20.11 Consumer Product Information Database Classification

20.12 EPA TSCA and CDR Classification

20.13 LOTUS Tree

20.14 EPA Substance Registry Services Tree

20.15 MolGenie Organic Chemistry Ontology

21 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Benzoic acid, 3,4,5-trihydroxy-, propyl ester
    https://services.industrialchemicals.gov.au/search-inventory/
  2. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
    CAMEO Chemical Reactivity Classification
    https://cameochemicals.noaa.gov/browse/react
  3. EU Food Improvement Agents
  4. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  7. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  8. EPA Chemicals under the TSCA
    Benzoic acid, 3,4,5-trihydroxy-, propyl ester
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  9. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  10. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    Propyl 3,4,5-trihydroxybenzoate
    https://chem.echa.europa.eu/100.004.090
  11. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  12. Hazardous Substances Data Bank (HSDB)
  13. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  14. International Fragrance Association (IFRA)
    LICENSE
    (c) The International Fragrance Association, 2007-2021. All rights reserved.
    https://ifrafragrance.org/links/copyright
  15. New Zealand Environmental Protection Authority (EPA)
    LICENSE
    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  16. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  17. ChEBI
  18. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  19. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  20. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  21. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  22. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  23. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  24. Consumer Product Information Database (CPID)
    LICENSE
    Copyright (c) 2024 DeLima Associates. All rights reserved. Unless otherwise indicated, all materials from CPID are copyrighted by DeLima Associates. No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://www.whatsinproducts.com/contents/view/1/6
    Consumer Products Category Classification
    https://www.whatsinproducts.com/
  25. Cosmetic Ingredient Review (CIR)
  26. EPA Chemical and Products Database (CPDat)
  27. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Propyl Gallate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  29. Joint FAO/WHO Expert Committee on Food Additives (JECFA)
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) licence.
    https://www.who.int/about/policies/publishing/copyright
  30. Hazardous Chemical Information System (HCIS), Safe Work Australia
  31. NITE-CMC
    Propyl 3,4,5-trihydroxybenzoate - FY2011 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/11-mhlw-0077e.html
    Propyl 3,4,5-trihydroxybenzoate - FY2023 (Revised classification)
    https://www.chem-info.nite.go.jp/chem/english/ghs/23-jniosh-2074e.html
  32. Regulation (EC) No 1272/2008 of the European Parliament and of the Council
    LICENSE
    The copyright for the editorial content of this source, the summaries of EU legislation and the consolidated texts, which is owned by the EU, is licensed under the Creative Commons Attribution 4.0 International licence.
    https://eur-lex.europa.eu/content/legal-notice/legal-notice.html
    propyl 3,4,5-trihydroxybenzoate
    https://eur-lex.europa.eu/eli/reg/2008/1272/oj
  33. FDA Substances Added to Food
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  34. Flavor and Extract Manufacturers Association (FEMA)
  35. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  36. NMRShiftDB
  37. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  38. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  39. SpectraBase
    BENZOIC ACID, 3,4,5-TRIHYDROXY-, PROPYL ESTER
    https://spectrabase.com/spectrum/2vBT61bbCtS
    Benzoic acid, 3,4,5-trihydroxy-, propyl ester
    https://spectrabase.com/spectrum/1uvy25pWiH0
    n-Propyl 3,4,5-trihydroxybenzoate
    https://spectrabase.com/spectrum/dSqzo0Fxxt
    n-Propyl 3,4,5-trihydroxybenzoate
    https://spectrabase.com/spectrum/HkVkeuLynCw
  40. Japan Chemical Substance Dictionary (Nikkaji)
  41. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  42. Natural Product Activity and Species Source (NPASS)
  43. MassBank Europe
  44. Metabolomics Workbench
  45. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  46. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  47. NTP Technical Reports
  48. Springer Nature
  49. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  50. Wikidata
  51. Wikipedia
  52. Wiley
  53. Medical Subject Headings (MeSH)
    LICENSE
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    https://www.nlm.nih.gov/copyright.html
  54. PubChem
  55. GHS Classification (UNECE)
  56. EPA Substance Registry Services
  57. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  58. PATENTSCOPE (WIPO)
CONTENTS