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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:42:14 UTC
Update Date2019-07-23 06:16:57 UTC
HMDB IDHMDB0034780
Secondary Accession Numbers
  • HMDB34780
Metabolite Identification
Common NameCapsiate
DescriptionCapsiate, also known as dihydrocapsiate or capsiic acid, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. A carboxylic ester obtained by formal condensation of the carboxy group of (6E)-8-methylnon-6-enoic acid with the benzylic hydroxy group of vanillyl alcohol. Capsiate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Capsiate has been detected, but not quantified in, several different foods, such as yellow bell peppers, red bell peppers, italian sweet red peppers, orange bell peppers, and green bell peppers. This could make capsiate a potential biomarker for the consumption of these foods. A non-pungent analogue of capsaicin with a similar biological profile.
Structure
Data?1563862617
Synonyms
ValueSource
Vanillyl (6E)-8-methylnon-6-enoateChEBI
Vanillyl (6E)-8-methylnon-6-enoic acidGenerator
Capsiic acidGenerator
4-Hydroxy-3-methoxybenzyl 8-methyl-6-nonenoateHMDB
DihydrocapsiateHMDB
Nonanoic acid, 8-methyl-, (4-hydroxy-3-methoxyphenyl)methyl esterMeSH
Chemical FormulaC18H26O4
Average Molecular Weight306.3966
Monoisotopic Molecular Weight306.18310932
IUPAC Name(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate
Traditional Name(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1
InChI Identifier
InChI=1S/C18H26O4/c1-14(2)8-6-4-5-7-9-18(20)22-13-15-10-11-16(19)17(12-15)21-3/h6,8,10-12,14,19H,4-5,7,9,13H2,1-3H3/b8-6+
InChI KeyZICNYIDDNJYKCP-SOFGYWHQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Benzyloxycarbonyl
  • Methoxyphenol
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Methoxybenzene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Fatty acid ester
  • Alkyl aryl ether
  • Fatty acyl
  • Monocyclic benzene moiety
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.5ALOGPS
logP4.48ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.91ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity88.37 m³·mol⁻¹ChemAxon
Polarizability35.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-055u-5920000000-60d000d43b1f9096c192Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01t9-7965000000-9061c1d933cf836a3a4cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-0915000000-d19997b754042e7519cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-2900000000-f589d122afe9d7c95df2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-8900000000-45c9e4b9e1a49bb886d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0908000000-d0650030a37b0e1edd5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uxr-0901000000-41bf8df5d7f9f5c0de1dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9f-3900000000-ea96ed7aae0cb04b6649Spectrum
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 IDFDB013333
KNApSAcK IDNot Available
Chemspider ID8015237
KEGG Compound IDC20203
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9839519
PDB IDNot Available
ChEBI ID134190
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Macho A, Sancho R, Minassi A, Appendino G, Lawen A, Munoz E: Involvement of reactive oxygen species in capsaicinoid-induced apoptosis in transformed cells. Free Radic Res. 2003 Jun;37(6):611-9. [PubMed:12868488 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .