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Record Information
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2019-01-11 19:16:50 UTC
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 ).
Isodecenoic acid vanillylamideChEBI
Isodecenoate vanillylamideGenerator
Isodecenoic acidHMDB
Link brand OF capsaicinMeSH
8 Methyl N vanillyl 6 nonenamideMeSH
Capsicum farmayaMeSH
Flemming brand OF capsaicinMeSH
Medicis brand OF capsaicinMeSH
Smaller brand OF capsaicinMeSH
Thompson brand OF capsaicinMeSH
Vinas brand OF capsaicinMeSH
Alacan brand OF capsaicinMeSH
Antiphlogistine rub a-535 capsaicinMeSH
Carter horner brand OF capsaicinMeSH
Centrum brand OF capsaicinMeSH
Elan brand OF capsaicinMeSH
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
InChI Identifier
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
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
  • 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
Physiological effect

Health effect:


Route of exposure:


Biological location:


Naturally occurring process:


Biological role:

Industrial application:

Physical Properties
Experimental Properties
Melting Point65 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
Water Solubility0.0084 g/LALOGPS
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-9860000000-4151cd60d08276e5122aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-9576000000-fb9f159d71790f546865View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0901000000-adba1bb6f254087febe8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF , negativesplash10-014i-0900000000-5be0e66854b20d7a5a03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-4337ff26dcbd2a77725eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014i-0900000000-c94a246143850aa73e44View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014r-0950000000-3d145ef428e054b3e535View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-014r-0950000000-c3ca097a6480ab798ff3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0900000000-4e8f98d1f848f30117d7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-58fab2fdd15893ea71e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-296a0cb1555da4f1ccd7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0209000000-a91e6403d5a0c0b67c2eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-03di-0209000000-dd0879d3f4f3a8b022c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0149000000-d6a9f6e70ae7cd7aec38View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-014i-0149000000-6fcf63c3bf44a4efc5bdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-06sl-0075690000-b562b766019cc7cbd98fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-01x3-0094560000-f354077f4cd51e45b945View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0002900000-ce1ea9819252343543cdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-004i-0002911000-6c37470f794c89a66410View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-00619747b8012ce6aa64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-000i-0900000000-3ca73f5212a7643b45d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0912000000-95e090cebb8f95d7fe89View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-6fb8b34936b848190c39View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f79-4900000000-ade1e8ba842adf972c83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0419000000-80bfd538da9be3f08fe0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0922000000-00b0b7b3e9df2464d425View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-7900000000-8b112ae03b8d84d338f3View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Normal Concentrations
FecesDetected but not Quantified Adult (>18 years old)Both
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB05318
Phenol Explorer Compound ID712
FoodDB 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
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 ]