Record Information
Version1.0
Creation date2010-04-08 22:09:56 UTC
Update date2019-11-26 03:05:56 UTC
Primary IDFDB012003
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePropyl gallate
DescriptionAntioxidant used in foods especies 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. Especies 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 is found in corn.
CAS Number121-79-9
Structure
Thumb
Synonyms
SynonymSource
Propyl gallic acidGenerator
Gallate, propylMeSH
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
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
3,4,5-Trihydroxybenzoic acid n-propyl esterbiospider
E310db_source
Gallic acid n-propyl esterbiospider
n-Propyl 3,4,5-trihydroxybenzoatebiospider
n-Propyl ester of 3,4,5-trihydroxybenzoic acidbiospider
N-propyl gallatebiospider
n-Propyl-3,4,5-Trihydroxybenzoatebiospider
N-propyl-gallatebiospider
Nipagallin pbiospider
Pro gallin pbiospider
Progallin pbiospider
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12O5
IUPAC namepropyl 3,4,5-trihydroxybenzoate
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
Isomeric SMILESCCCOC(=O)C1=CC(O)=C(O)C(O)=C1
Average Molecular Weight212.1993
Monoisotopic Molecular Weight212.068473494
Classification
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
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 56.60%; H 5.70%; O 37.70%DFC
Melting PointMp 150° (147-148°)DFC
Boiling PointNot Available
Experimental Water Solubility3.5 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logP1.80HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0uk9-2910000000-9f307d16268eddd77840Spectrum
GC-MSPropyl gallate, 3 TMS, GC-MS Spectrumsplash10-003r-1591200000-83ddc9d65f8d1fc4dc59Spectrum
GC-MSPropyl gallate, non-derivatized, GC-MS Spectrumsplash10-003r-1591200000-83ddc9d65f8d1fc4dc59Spectrum
Predicted GC-MSPropyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udi-3900000000-21920ec0bc1944203acdSpectrum
Predicted GC-MSPropyl gallate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0300-3009200000-4c9cb5458fd589cfb9f5Spectrum
Predicted GC-MSPropyl gallate, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-004u-1900000000-2c928c0529e1e856b4cfSpectrum
MS/MSLC-MS/MS Spectrum - 90V, Positivesplash10-020c-2900000000-6126b5c9249291690c34Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-004u-1900000000-3c677dc5e935ac8b92a7Spectrum
MS/MSLC-MS/MS Spectrum - 90V, Negativesplash10-020c-2900000000-0f7125c76f6115f1a362Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-03di-0490000000-801c27e3621d93ec37c1Spectrum
MS/MSLC-MS/MS Spectrum - 15V, Negativesplash10-03di-0190000000-b3af9cab9a755c2515e0Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-0400-0920000000-ee4ea381c88a5b7f07e3Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-004r-1900000000-fdda012f6b2915b52ddeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3590000000-e327edc472bde7205749Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-9610000000-d6337dfac07ea957e6daSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9700000000-019f1f6b94c68335f988Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1490000000-ff8794d740e2004569eaSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-1910000000-1acf485109a5d1fc39e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvi-3900000000-6045394c44a28e539509Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0690000000-f4a4482ba53c556490b7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w90-1910000000-a11c00d19f2bc9ffbcdeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uxr-5900000000-7756697004244c98da58Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-a3bb7cbc13a749439d3cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0j4i-0930000000-524d0f46faeeb372fe28Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-016s-9500000000-3ed22349cc0c3913984eSpectrum
NMR
TypeDescriptionView
1D NMR13C NMR SpectrumSpectrum
ChemSpider ID4778
ChEMBL IDCHEMBL7983
KEGG Compound IDC11155
Pubchem Compound ID4947
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33835
CRC / DFC (Dictionary of Food Compounds) IDBFL35-I:HCL42-B
EAFUS ID3219
Dr. Duke IDN-PROPYL-GALLATE
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1034121
SuperScent IDNot Available
Wikipedia IDPropyl_3,4,5-trihydroxybenzoate
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bland
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).