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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2020-02-26 21:23:57 UTC
HMDB IDHMDB0002227
Secondary Accession Numbers
  • HMDB02227
Metabolite Identification
Common NameCapsaicin
DescriptionCapsaicin is identified as the primary pungent principle in Capsicum fruits. Hot chili peppers that belong to the plant genus Capsicum (family Solanaceae) are among the most heavily consumed spices throughout the world. The capsaicin content of green and red peppers ranges from 0.1 to 1%. Capsaicin evokes numerous biological effects and thus has been the target of extensive., investigations since its initial identification in 1919. One of the most recognized physiological properties of capsaicin is its selective effects on the peripheral part of the sensory nervous system, particularly on the primary afferent neurons. The compound is known to deplete the neurotransmitter of painful impulses known as substance P from the sensory nerve terminals, which provides a rationale for its use as a versatile experimental tool for studying pain mechanisms and also for pharmacotherapy to treat some peripheral painful states, such as rheumatoid arthritis, post-herpetic neuralgia, post-mastectomy pain syndrome and diabetic neuropathy. Considering the frequent consumption of capsaicin as a food additive and its current therapeutic application, correct assessment of any harmful effects of this compound is important from the public health standpoint. Ingestion of large amounts of capsaicin has been reported to cause histopathological and biochemical changes, including erosion of gastric mucosa and hepatic necrosis. However, there are contradictory data on the mutagenicity of capsaicin. A recent epidemiological study conducted in Mexico revealed that consumers of chili pepper were at higher risk for gastric cancer than non-consumers. However, it remains unclear whether capsaicin present in hot chili pepper is a major causative factor in the aetiology of gastric cancer in humans. A growing number of recent studies have focused on anticarcinogenic or antimutagenic phytochemicals, particularly those included in human diet. In summary, capsaicin has dual effects on chemically induced carcinogenesis and mutagenesis. Although a minute amount of capsaicin displays few or no deleterious effects, heavy ingestion of the compound has been associated with necrosis, ulceration and even carcinogenesis. Capsaicin is considered to be metabolized by cytochrome P-450-dependent mixed-function oxidases to reactive species. (PMID: 8621114 ).
Structure
Data?1582752237
Synonyms
ValueSource
(e)-8-Methyl-N-vanillyl-6-nonenamideChEBI
Isodecenoic acid vanillylamideChEBI
trans-8-Methyl-N-vanillyl-6-nonenamideChEBI
ZostrixChEBI
Isodecenoate vanillylamideGenerator
(e)-8-Methyl-N-vanillyl-6-nonenamide(8CL)HMDB
(e)8-Methyl-N-vanillyl-6-nonenamideHMDB
AxsainHMDB
e-CapsaicinHMDB
epsilon-CapsaicinHMDB
IsodecenoateHMDB
Isodecenoic acidHMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamideHMDB
StyptysatHMDB
TransacinHMDB
GelcenHMDB
Link brand OF capsaicinHMDB
8 Methyl N vanillyl 6 nonenamideHMDB
Capsicum farmayaHMDB
CapzasinHMDB
Flemming brand OF capsaicinHMDB
8-Methyl-N-vanillyl-6-nonenamideHMDB
CapsinHMDB
KatrumHMDB
Medicis brand OF capsaicinHMDB
Smaller brand OF capsaicinHMDB
Thompson brand OF capsaicinHMDB
Vinas brand OF capsaicinHMDB
Alacan brand OF capsaicinHMDB
Antiphlogistine rub a-535 capsaicinHMDB
CapsaicineHMDB
CapsidolHMDB
Carter horner brand OF capsaicinHMDB
Centrum brand OF capsaicinHMDB
Elan brand OF capsaicinHMDB
ZacinHMDB
Chemical FormulaC18H27NO3
Average Molecular Weight305.4119
Monoisotopic Molecular Weight305.199093735
IUPAC Name(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
Traditional Namecapsaicin
CAS Registry Number404-86-4
SMILES
COC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C1
InChI Identifier
InChI=1S/C18H27NO3/c1-14(2)8-6-4-5-7-9-18(21)19-13-15-10-11-16(20)17(12-15)22-3/h6,8,10-12,14,20H,4-5,7,9,13H2,1-3H3,(H,19,21)/b8-6+
InChI KeyYKPUWZUDDOIDPM-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
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0084 g/LALOGPS
logP3.8ALOGPS
logP3.75ChemAxon
logS-4.6ALOGPS
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 Count9ChemAxon
Refractivity90.32 m³·mol⁻¹ChemAxon
Polarizability36.32 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, Positivesplash10-052o-9860000000-4151cd60d08276e5122aSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-9576000000-fb9f159d71790f546865Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0901000000-adba1bb6f254087febe8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-014i-0900000000-5be0e66854b20d7a5a03Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-4337ff26dcbd2a77725eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-c94a246143850aa73e44Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014r-0950000000-3d145ef428e054b3e535Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014r-0950000000-c3ca097a6480ab798ff3Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-4e8f98d1f848f30117d7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-58fab2fdd15893ea71e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-296a0cb1555da4f1ccd7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0209000000-a91e6403d5a0c0b67c2eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0209000000-dd0879d3f4f3a8b022c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0149000000-d6a9f6e70ae7cd7aec38Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0149000000-6fcf63c3bf44a4efc5bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-06sl-0075690000-b562b766019cc7cbd98fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01x3-0094560000-f354077f4cd51e45b945Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0002900000-ce1ea9819252343543cdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0002911000-6c37470f794c89a66410Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-00619747b8012ce6aa64Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-3ca73f5212a7643b45d2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0912000000-95e090cebb8f95d7fe89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-6fb8b34936b848190c39Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-4900000000-ade1e8ba842adf972c83Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0419000000-80bfd538da9be3f08fe0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0922000000-00b0b7b3e9df2464d425Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7900000000-8b112ae03b8d84d338f3Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB06774
Phenol Explorer Compound ID712
FooDB IDFDB012411
KNApSAcK IDNot Available
Chemspider ID1265957
KEGG Compound IDC06866
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCapsaicin
METLIN IDNot Available
PubChem Compound1548943
PDB IDNot Available
ChEBI ID3374
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceGannett, Peter M.; Nagel, Donald L.; Reilly, Pam J.; Lawson, Terence; Sharpe, Jody; Toth, Bela. Capsaicinoids: their separation, synthesis, and mutagenicity. Journal of Organic Chemistry (1988), 53(5), 1064-71.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Surh YJ, Lee SS: Capsaicin in hot chili pepper: carcinogen, co-carcinogen or anticarcinogen? Food Chem Toxicol. 1996 Mar;34(3):313-6. [PubMed:8621114 ]
  2. Simpson DM, Estanislao L, Brown SJ, Sampson J: An open-label pilot study of high-concentration capsaicin patch in painful HIV neuropathy. J Pain Symptom Manage. 2008 Mar;35(3):299-306. Epub 2007 Oct 23. [PubMed:17959343 ]