Capsiate (CHEM028790)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:42:01 UTC
Update Date2016-11-09 01:18:45 UTC
Accession NumberCHEM028790
Identification
Common NameCapsiate
ClassSmall Molecule
DescriptionA 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. A non-pungent analogue of capsaicin with a similar biological profile.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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
DihydrocapsiateMeSH, HMDB
Nonanoic acid, 8-methyl-, (4-hydroxy-3-methoxyphenyl)methyl esterMeSH
Chemical FormulaC18H26O4
Average Molecular Mass306.397 g/mol
Monoisotopic Mass306.183 g/mol
CAS Registry Number205687-01-0
IUPAC Name(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate
Traditional Name(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate
SMILESCOC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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 GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0900000000-3af65de2869b973825d6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0v6r-1900000000-973956f425d4207c3559Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3912000000-fa5e9b2552f99de0f277Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-7fa0654d4ef4c85920a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-1900000000-f6058625f5a778bf7299Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-3900000000-97d9169adb4f26f974b8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0034780
FooDB IDFDB013333
Phenol Explorer IDNot Available
KNApSAcK IDC00053980
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID8015237
ChEBI ID134190
PubChem Compound ID9839519
Kegg Compound IDC20203
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12726827
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12959953
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=16636441
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17264228
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=17971242
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=18172315
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=19773740
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=20102390
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=20123015
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=21071592
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=21878735
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21883144
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21928164
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=22038945
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23026494
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24026939
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24102723
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24644244
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=25806854
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=26030806
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=28001433
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=28230360
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=28569248
24.
25. 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.
26. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.