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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:36:34 UTC
Update Date2021-10-13 06:35:56 UTC
HMDB IDHMDB0033835
Secondary Accession Numbers
  • HMDB33835
Metabolite Identification
Common NamePropyl gallate
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
Structure
Data?1563862468
Synonyms
ValueSource
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
Chemical FormulaC10H12O5
Average Molecular Weight212.1993
Monoisotopic Molecular Weight212.068473494
IUPAC Namepropyl 3,4,5-trihydroxybenzoate
Traditional Namepropyl gallate
CAS Registry Number121-79-9
SMILES
CCCOC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling Point448.59 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility3.5 mg/mL at 25 °CNot Available
LogP1.80Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.71 g/LALOGPS
logP10(1.84) g/LALOGPS
logP10(1.95) g/LChemAxon
logS10(-2.1) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+149.9531661259
DarkChem[M-H]-148.6731661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Propyl gallateCCCOC(=O)C1=CC(O)=C(O)C(O)=C13042.8Standard polar33892256
Propyl gallateCCCOC(=O)C1=CC(O)=C(O)C(O)=C11988.5Standard non polar33892256
Propyl gallateCCCOC(=O)C1=CC(O)=C(O)C(O)=C11855.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Propyl gallate,1TMS,isomer #1CCCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C)=C11966.4Semi standard non polar33892256
Propyl gallate,1TMS,isomer #2CCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O)=C11956.2Semi standard non polar33892256
Propyl gallate,2TMS,isomer #1CCCOC(=O)C1=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C12001.2Semi standard non polar33892256
Propyl gallate,2TMS,isomer #2CCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C11972.3Semi standard non polar33892256
Propyl gallate,3TMS,isomer #1CCCOC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12031.6Semi standard non polar33892256
Propyl gallate,1TBDMS,isomer #1CCCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12221.6Semi standard non polar33892256
Propyl gallate,1TBDMS,isomer #2CCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C12221.0Semi standard non polar33892256
Propyl gallate,2TBDMS,isomer #1CCCOC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12461.6Semi standard non polar33892256
Propyl gallate,2TBDMS,isomer #2CCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12436.5Semi standard non polar33892256
Propyl gallate,3TBDMS,isomer #1CCCOC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12695.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Propyl gallate GC-MS (3 TMS)splash10-003r-1591200000-83ddc9d65f8d1fc4dc592014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Propyl gallate GC-MS (Non-derivatized)splash10-003r-1591200000-83ddc9d65f8d1fc4dc592017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propyl gallate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-21920ec0bc1944203acd2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propyl gallate GC-MS (3 TMS) - 70eV, Positivesplash10-0300-3009200000-4c9cb5458fd589cfb9f52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Propyl gallate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0uk9-2910000000-9f307d16268eddd778402014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 75V, Positive-QTOFsplash10-004u-1900000000-2c928c0529e1e856b4cf2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 90V, Positive-QTOFsplash10-020c-2900000000-6126b5c9249291690c342021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 75V, Negative-QTOFsplash10-004u-1900000000-3c677dc5e935ac8b92a72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 90V, Negative-QTOFsplash10-020c-2900000000-0f7125c76f6115f1a3622021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 30V, Negative-QTOFsplash10-03di-0490000000-801c27e3621d93ec37c12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 15V, Negative-QTOFsplash10-03di-0190000000-b3af9cab9a755c2515e02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 45V, Negative-QTOFsplash10-0400-0920000000-ee4ea381c88a5b7f07e32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Propyl gallate 60V, Negative-QTOFsplash10-004r-1900000000-fdda012f6b2915b52dde2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 10V, Positive-QTOFsplash10-03di-3590000000-e327edc472bde72057492016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 20V, Positive-QTOFsplash10-0f6x-9610000000-d6337dfac07ea957e6da2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 40V, Positive-QTOFsplash10-0f6x-9700000000-019f1f6b94c68335f9882016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 10V, Negative-QTOFsplash10-03di-1490000000-ff8794d740e2004569ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 20V, Negative-QTOFsplash10-016r-1910000000-1acf485109a5d1fc39e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 40V, Negative-QTOFsplash10-0fvi-3900000000-6045394c44a28e5395092016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 10V, Positive-QTOFsplash10-03di-0690000000-f4a4482ba53c556490b72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 20V, Positive-QTOFsplash10-0w90-1910000000-a11c00d19f2bc9ffbcde2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 40V, Positive-QTOFsplash10-0uxr-5900000000-7756697004244c98da582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 10V, Negative-QTOFsplash10-03di-0090000000-a3bb7cbc13a749439d3c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 20V, Negative-QTOFsplash10-0j4i-0930000000-524d0f46faeeb372fe282021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Propyl gallate 40V, Negative-QTOFsplash10-016s-9500000000-3ed22349cc0c3913984e2021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12450
Phenol Explorer Compound IDNot Available
FooDB IDFDB012003
KNApSAcK IDNot Available
Chemspider ID4778
KEGG Compound IDC11155
BioCyc IDCPD-6542
BiGG IDNot Available
Wikipedia LinkPropyl gallate
METLIN IDNot Available
PubChem Compound4947
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1034121
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
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. [PubMed:16356133 ]
  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. [PubMed:16660418 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .