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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:05:29 UTC
Update Date2021-10-13 06:32:21 UTC
HMDB IDHMDB0033375
Secondary Accession Numbers
  • HMDB33375
Metabolite Identification
Common NameOctyl gallate
DescriptionOctyl gallate, also known as octyl gallic acid, 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. Octyl gallate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Octyl gallate.
Structure
Data?1563862396
Synonyms
ValueSource
Gallic acid octyl esterChEBI
N-Octyl gallateChEBI
Gallate octyl esterGenerator
N-Octyl gallic acidGenerator
Octyl gallic acidGenerator
3,4,5-Trihydroxybenzoic acid octyl esterMeSH
Octyl gallate dihydrateMeSH
Benzoic acid, 3,4,5-trihydroxy-, octyl esterHMDB
e311HMDB
GA 8HMDB
Gallic acid, octyl esterHMDB
N-Octyl ester OF 3,4,5-trihydroxybenzoic acidHMDB
N-OctylgallateHMDB
Octyl 3,4,5-trihydroxybenzoateHMDB
OctylgallateHMDB
Oktylester kyseliny galloveHMDB
Progallin OHMDB
Stabilizer ga 8HMDB
Chemical FormulaC15H22O5
Average Molecular Weight282.3322
Monoisotopic Molecular Weight282.146723814
IUPAC Nameoctyl 3,4,5-trihydroxybenzoate
Traditional Nameoctyl gallate
CAS Registry Number1034-01-1
SMILES
CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C1
InChI Identifier
InChI=1S/C15H22O5/c1-2-3-4-5-6-7-8-20-15(19)11-9-12(16)14(18)13(17)10-11/h9-10,16-18H,2-8H2,1H3
InChI KeyNRPKURNSADTHLJ-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

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94 - 95 °CNot Available
Boiling Point482.86 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.036 mg/mL at 20 °CNot Available
LogP3.66Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.26 g/LALOGPS
logP10(4.1) g/LALOGPS
logP10(4.17) g/LChemAxon
logS10(-3) 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 Count9ChemAxon
Refractivity76.3 m³·mol⁻¹ChemAxon
Polarizability31.8 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]+170.4331661259
DarkChem[M-H]-168.00531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Octyl gallateCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C13628.9Standard polar33892256
Octyl gallateCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C12492.3Standard non polar33892256
Octyl gallateCCCCCCCCOC(=O)C1=CC(O)=C(O)C(O)=C12426.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Octyl gallate,1TMS,isomer #1CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C)=C12445.5Semi standard non polar33892256
Octyl gallate,1TMS,isomer #2CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O)=C12425.2Semi standard non polar33892256
Octyl gallate,2TMS,isomer #1CCCCCCCCOC(=O)C1=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C12455.7Semi standard non polar33892256
Octyl gallate,2TMS,isomer #2CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12422.9Semi standard non polar33892256
Octyl gallate,3TMS,isomer #1CCCCCCCCOC(=O)C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12468.2Semi standard non polar33892256
Octyl gallate,1TBDMS,isomer #1CCCCCCCCOC(=O)C1=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12698.7Semi standard non polar33892256
Octyl gallate,1TBDMS,isomer #2CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C12683.5Semi standard non polar33892256
Octyl gallate,2TBDMS,isomer #1CCCCCCCCOC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C12942.0Semi standard non polar33892256
Octyl gallate,2TBDMS,isomer #2CCCCCCCCOC(=O)C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12916.5Semi standard non polar33892256
Octyl gallate,3TBDMS,isomer #1CCCCCCCCOC(=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)=C13164.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Octyl gallate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0udi-4900000000-878a0a7a4a67ed06c0ff2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octyl gallate GC-MS (3 TMS) - 70eV, Positivesplash10-01c0-5209400000-3d5229f775270bdd88682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octyl gallate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Octyl gallate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 45V, Positive-QTOFsplash10-019r-0920000000-dd0646e49d169d2d39a42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 90V, Negative-QTOFsplash10-020c-2900000000-2dfd6a3290e77879474e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 45V, Negative-QTOFsplash10-017i-0920000000-b750c5426d2367f6bfda2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 30V, Negative-QTOFsplash10-001i-0190000000-eb4afbede645135b76632021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 60V, Negative-QTOFsplash10-004i-1900000000-34fdedc0e3ae08ef6c4c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 75V, Negative-QTOFsplash10-004u-1900000000-41eaaa406b8a3f84606b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 15V, Negative-QTOFsplash10-001i-0090000000-6eb2ef731eb900efa48a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 40V, Positive-QTOFsplash10-0a59-9500000000-25e3c2fbd78d072d820b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 10V, Positive-QTOFsplash10-00di-1900000000-f97f06cdbe5ca99b4bae2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Octyl gallate 20V, Positive-QTOFsplash10-0pdi-3900000000-169a117fdd40fbb3f66b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 10V, Positive-QTOFsplash10-001i-0790000000-1a568cbe925ce46780bc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 20V, Positive-QTOFsplash10-0ik9-2910000000-32a6f3e83cb258626b0a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 40V, Positive-QTOFsplash10-0kbf-9600000000-c74166cded4e492c3e242016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 10V, Negative-QTOFsplash10-001i-0590000000-150fabd6eb0d5e81d0b92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 20V, Negative-QTOFsplash10-016r-0910000000-652ef7ed882c584e38792016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 40V, Negative-QTOFsplash10-0fvi-1900000000-0a04645a38fadbbab6922016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 10V, Negative-QTOFsplash10-001i-0290000000-c333499f784512ab55492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 20V, Negative-QTOFsplash10-0fw9-0930000000-d3463202c650e369f74d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 40V, Negative-QTOFsplash10-00vi-5900000000-e9a5b02eb650d4f7a67c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 10V, Positive-QTOFsplash10-001i-0590000000-18e43656b88b6abb544e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 20V, Positive-QTOFsplash10-0f89-3950000000-cb1f00495f16a31abcb02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Octyl gallate 40V, Positive-QTOFsplash10-0udi-8900000000-38f3d1a994ec952bab6a2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Biological Properties
Cellular Locations
  • Membrane
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
FooDB IDFDB011405
KNApSAcK IDNot Available
Chemspider ID55194
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkOctyl_gallate
METLIN IDNot Available
PubChem Compound61253
PDB IDNot Available
ChEBI ID83631
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1270671
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yamasaki H, Uozaki M, Katsuyama Y, Utsunomiya H, Arakawa T, Higuchi M, Higuti T, Koyama AH: Antiviral effect of octyl gallate against influenza and other RNA viruses. Int J Mol Med. 2007 Apr;19(4):685-8. [PubMed:17334645 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .