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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:36:34 UTC
Update Date2019-07-23 06:14:28 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
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
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
DescriptionThis compound 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
  • Benzoate ester
  • Pyrogallol derivative
  • Benzylether
  • Benzenetriol
  • 1,2-diphenol
  • Benzoyl
  • Phenol
  • Polyol
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point150 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.5 mg/mL at 25 °CNot Available
LogP1.80Not Available
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-003r-1591200000-83ddc9d65f8d1fc4dc59JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003r-1591200000-83ddc9d65f8d1fc4dc59JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-3900000000-21920ec0bc1944203acdJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0300-3009200000-4c9cb5458fd589cfb9f5JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-3590000000-e327edc472bde7205749JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f6x-9610000000-d6337dfac07ea957e6daJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9700000000-019f1f6b94c68335f988JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1490000000-ff8794d740e2004569eaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-016r-1910000000-1acf485109a5d1fc39e6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fvi-3900000000-6045394c44a28e539509JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0uk9-2910000000-9f307d16268eddd77840JSpectraViewer | MoNA
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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 IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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
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.. .