Record Information
Version1.0
Creation date2010-04-08 22:13:20 UTC
Update date2019-11-26 03:15:17 UTC
Primary IDFDB017816
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameDihydrocapsaicin
DescriptionPotential nutriceutical Dihydrocapsaicin is a capsaicinoid and analog and congener of capsaicin in chili peppers (Capsicum). Like capsaicin it is an irritant. Dihydrocapsaicin accounts for about 22% of the total capsaicinoids mixture and has about the same pungency as capsaicin. Pure dihydrocapsaicin is a lipophilic colorless odorless crystalline to waxy compound. It is soluble in dimethyl sulfoxide and 100 % ethanol. Dihydrocapsaicin is found in many foods, some of which are green bell pepper, pepper (c. frutescens), pepper (c. annuum), and yellow bell pepper.
CAS Number19408-84-5
Structure
Thumb
Synonyms
SynonymSource
6,7-DihydrocapsaicinChEBI
8-Methyl-N-vanillylnonanamideChEBI
8-Methyl dihydrocapsaicinHMDB
8-Methyl-N-vanillyl-nonanamideHMDB
DihydrocapsacineHMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methyl-nonanamideHMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-8-methylnonanamideHMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnonanamideHMDB
8-methyl dihydrocapsaicinbiospider
8-METHYL-N-VANILLYLNONANAMIDEbiospider
Dihydrocapsaicindb_source
N-(4-hydroxy-3-methoxybenzyl)-8-methylnonanamidebiospider
Nonanamide, 8-methyl-N-vanillyl-biospider
Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-8-methyl-biospider
Predicted Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP4.56ALOGPS
logP4.11ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity89.2 m³·mol⁻¹ChemAxon
Polarizability36.55 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC18H29NO3
IUPAC nameN-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnonanamide
InChI IdentifierInChI=1S/C18H29NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h10-12,14,20H,4-9,13H2,1-3H3,(H,19,21)
InChI KeyXJQPQKLURWNAAH-UHFFFAOYSA-N
Isomeric SMILESCOC1=C(O)C=CC(CNC(=O)CCCCCCC(C)C)=C1
Average Molecular Weight307.4278
Monoisotopic Molecular Weight307.214743799
Classification
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
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Carboximidic acid
  • Carboximidic acid derivative
  • Ether
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 70.32%; H 9.51%; N 4.56%; O 15.61%DFC
Melting PointMp 65.5-65.8°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-000i-3900000000-abaed17f1bd3fe1a957eSpectrum
Predicted GC-MSDihydrocapsaicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9740000000-b2eb8f7656281d7d739bSpectrum
Predicted GC-MSDihydrocapsaicin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ox-9435000000-166a1615c9c7debf8fa6Spectrum
Predicted GC-MSDihydrocapsaicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-00di-3900100000-8f8a87e8debee126c12cSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-4bf71c20819da305ce70Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-a53f7cfa19d20f2105dfSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-c74b426a1681b495fc33Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-00di-0900000000-63e5d3c7e068d4720104Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-b598b9d57b30dd108b5aSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00di-0900000000-ecfc83244dd3376f1dc2Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0920000000-dd441af4b60bf0f654e5Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-000i-0920000000-f9315d39cf7d630a0a41Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-4daa3f6ecd5e6c49d89aSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-fd7dab103a28c7b4cd09Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-fe825b62fd7353a50762Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0079-0900000000-e9d6137ffa4c454a8d59Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-9ef8e6281ac1b6fd2096Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-91e3f4f1c04e0772032dSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-3b7d7910c5a1504b8050Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-bdb490ed777f216f71d0Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-a00fce3e02396fdc17f0Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0910000000-c6908fb6b7708aae4a18Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0912000000-cf4ec19a423958fe8e9fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-c3c2399bfb1327178596Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-4900000000-2fd58142b38c01ad2de2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0419000000-9533cc5af6d3e015e122Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0ab9-0922000000-b9327ebe541844193dcfSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-6900000000-0173e704c2d335e9b9daSpectrum
NMR
TypeDescriptionView
ChemSpider ID97096
ChEMBL IDCHEMBL311158
KEGG Compound IDC16952
Pubchem Compound ID107982
Pubchem Substance IDNot Available
ChEBI ID46932
Phenol-Explorer ID716
DrugBank IDNot Available
HMDB IDHMDB38457
CRC / DFC (Dictionary of Food Compounds) IDHGT21-K:LBD66-I
EAFUS IDNot Available
Dr. Duke IDDIHYDROCAPSAICIN
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDDihydrocapsaicin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
hypocholesterolemicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).