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Record Information
Version3.6
Creation Date2006-05-22 14:17:43 UTC
Update Date2016-02-11 01:05:28 UTC
HMDB IDHMDB02227
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
(e)-8-Methyl-N-vanillyl-6-nonenamideChEBI
Isodecenoic acid vanillylamideChEBI
trans-8-Methyl-N-vanillyl-6-nonenamideChEBI
ZostrixChEBI
(e)-8-Methyl-N-vanillyl-6-nonenamide(8CL)HMDB
(e)8-Methyl-N-vanillyl-6-nonenamideHMDB
AxsainHMDB
CapsaicinHMDB
e-CapsaicinHMDB
epsilon-CapsaicinHMDB
IsodecenoateHMDB
Isodecenoic acidHMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamideHMDB
StyptysatHMDB
TransacinHMDB
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 KeyInChIKey=YKPUWZUDDOIDPM-SOFGYWHQSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as methoxyphenols. These are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Methoxybenzene
  • Phenylmethylamine
  • Phenol ether
  • Benzylamine
  • Anisole
  • Alkyl aryl ether
  • Fatty acyl
  • N-acyl-amine
  • Fatty amide
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Ether
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity90.32 m3·mol-1ChemAxon
Polarizability36.32 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05318
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID712
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB012411
KNApSAcK IDNot Available
Chemspider ID1265957
KEGG Compound IDC06866
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCapsaicin
NuGOwiki LinkHMDB02227
Metagene LinkHMDB02227
METLIN IDNot Available
PubChem Compound1548943
PDB IDNot Available
ChEBI ID3374
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. [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. [17959343 ]