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Record Information
Version1.0
Creation Date2014-09-11 05:19:10 UTC
Update Date2016-11-09 01:09:13 UTC
Accession NumberCHEM003806
Identification
Common NamePropyl gallate
ClassSmall Molecule
DescriptionPropyl gallate is found in corn. Propyl gallate is an antioxidant used in foods especially animal fats and vegetable oils. Synergistic with other antioxidants such as Butylated hydroxyanisole DNB28-K and 2,6-Di-tert-butyl-4-methylphenol HCH42-H. Especially effective with polyunsaturated fats. Indirect food additive arising from paper or board packaging, adhesives and food contact polymers Propyl gallate is an anti-oxidant. It protects against oxidation by hydrogen peroxide and oxygen free radicals, in a catalytic manner similar to superoxide dismutase. Propyl gallate, or propyl 3,4,5-trihydroxybenzoate is an ester formed by the condensation of gallic acid and propanol. It is an antioxidant added to foods containing oils and fats to prevent oxidation.[citation needed] As a food additive, it is used under the E number E310. Propyl gallate has been shown to exhibit pro-oxidant and radical scavenger functions (1, 2).
Contaminant Sources
  • EAFUS Chemicals
  • FooDB Chemicals
  • HPV EPA Chemicals
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Ester
  • Ether
  • Food Additive
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
Chemical Structure
Thumb
Synonyms
ValueSource
Propyl gallic acidGenerator
3,4,5-Trihydroxybenzene-1-propylcarboxylateHMDB
3,4,5-Trihydroxybenzoic acid N-propyl esterHMDB
3,4,5-Trihydroxybenzoic acid propyl esterHMDB
3,4,5-Trihydroxybenzoic acid, propyl esterHMDB
Benzoic acid, 3,4,5-trihydroxy-, propyl esterHMDB
e310HMDB
FEMA 2947HMDB
Gallate, propylHMDB
Gallic acid N-propyl esterHMDB
Gallic acid propyl esterHMDB
Gallic acid, propyl esterHMDB
N-Propyl 3,4,5-trihydroxybenzoateHMDB
N-Propyl ester OF 3,4,5-trihydroxybenzoic acidHMDB
N-Propyl gallateHMDB
N-Propyl-3,4,5-trihydroxybenzoateHMDB
N-Propyl-gallateHMDB
Nipa 49HMDB
Nipagallin pHMDB
Nipanox S 1HMDB
PGHMDB
Pro gallin pHMDB
Progallin pHMDB
Propyl 3,4,5-trihydroxybenzoateHMDB
Propyl galiateHMDB
Propyl gallate (NF)HMDB
Propylester kyseliny galloveHMDB
Sustane PGHMDB
Tenox PGHMDB
Propyl gallateKEGG
N-Propyl gallic acidGenerator
Chemical FormulaC10H12O5
Average Molecular Mass212.199 g/mol
Monoisotopic Mass212.068 g/mol
CAS Registry Number121-79-9
IUPAC Namepropyl 3,4,5-trihydroxybenzoate
Traditional Namepropyl gallate
SMILESCCCOC(=O)C1=CC(O)=C(O)C(O)=C1
InChI IdentifierInChI=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
InChI KeyZTHYODDOHIVTJV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentGalloyl esters
Alternative Parents
Substituents
  • Galloyl ester
  • P-hydroxybenzoic acid alkyl ester
  • M-hydroxybenzoic acid ester
  • P-hydroxybenzoic acid ester
  • Benzoate ester
  • Benzenetriol
  • Pyrogallol derivative
  • Benzoyl
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Polyol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point150 °C
Boiling PointDecomposes
Solubility3.5 mg/mL at 25 °C
Predicted Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP1.84ALOGPS
logP1.95ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)8.11ChemAxon
pKa (Strongest Basic)-5.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity53.3 m³·mol⁻¹ChemAxon
Polarizability21.21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-003r-1591200000-83ddc9d65f8d1fc4dc59View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSsplash10-0udi-3900000000-21920ec0bc1944203acdView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-003r-1591200000-83ddc9d65f8d1fc4dc59View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS)splash10-0300-3009200000-4c9cb5458fd589cfb9f5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3590000000-e327edc472bde7205749View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-9610000000-d6337dfac07ea957e6daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9700000000-019f1f6b94c68335f988View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1490000000-ff8794d740e2004569eaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-1910000000-1acf485109a5d1fc39e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvi-3900000000-6045394c44a28e539509View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0uk9-2910000000-9f307d16268eddd77840View in MoNA
1D NMR13C NMR SpectrumNot Available
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB12450
HMDB IDHMDB0033835
FooDB IDFDB012003
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-6542
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkPropyl gallate
Chemspider ID4778
ChEBI IDNot Available
PubChem Compound ID4947
Kegg Compound IDC11155
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSLink
General References
1. Kawanishi S, Oikawa S, Murata M: Evaluation for safety of antioxidant chemopreventive agents. Antioxid Redox Signal. 2005 Nov-Dec;7(11-12):1728-39.
2. Baker JE, Lieberman M, Anderson JD: Inhibition of ethylene production in fruit slices by a rhizobitoxine analog and free radical scavengers. Plant Physiol. 1978 Jun;61(6):886-8.
3. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.