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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-05-22 14:17:43 UTC
Update Date2022-03-07 02:49:13 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
Disposition
ProcessNot Available
Role
Industrial applicationBiological roleIndirect biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling Point210.00 to 220.00 °C. @ 0.01 mm HgThe Good Scents Company Information System
Water Solubility4.41 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.327 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM183.030932474
[M+H]+Not Available181.643http://allccs.zhulab.cn/database/detail?ID=AllCCS00000834
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+176.18931661259
DarkChem[M-H]-175.03131661259
DeepCCS[M+H]+188.74830932474
DeepCCS[M-H]-186.3930932474
DeepCCS[M-2H]-219.27730932474
DeepCCS[M+Na]+194.84130932474
AllCCS[M+H]+177.332859911
AllCCS[M+H-H2O]+174.332859911
AllCCS[M+NH4]+180.132859911
AllCCS[M+Na]+180.932859911
AllCCS[M-H]-178.632859911
AllCCS[M+Na-2H]-179.432859911
AllCCS[M+HCOO]-180.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CapsaicinCOC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C13625.3Standard polar33892256
CapsaicinCOC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C12497.8Standard non polar33892256
CapsaicinCOC1=C(O)C=CC(CNC(=O)CCCC\C=C\C(C)C)=C12555.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Capsaicin,1TMS,isomer #1COC1=CC(CNC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C2635.9Semi standard non polar33892256
Capsaicin,1TMS,isomer #2COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O2521.3Semi standard non polar33892256
Capsaicin,2TMS,isomer #1COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2552.7Semi standard non polar33892256
Capsaicin,2TMS,isomer #1COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2531.4Standard non polar33892256
Capsaicin,2TMS,isomer #1COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2803.1Standard polar33892256
Capsaicin,1TBDMS,isomer #1COC1=CC(CNC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2879.1Semi standard non polar33892256
Capsaicin,1TBDMS,isomer #2COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2749.9Semi standard non polar33892256
Capsaicin,2TBDMS,isomer #1COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C3019.0Semi standard non polar33892256
Capsaicin,2TBDMS,isomer #1COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2927.3Standard non polar33892256
Capsaicin,2TBDMS,isomer #1COC1=CC(CN(C(=O)CCCC/C=C/C(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2975.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Capsaicin GC-MS (Non-derivatized) - 70eV, Positivesplash10-052o-9860000000-4151cd60d08276e5122a2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsaicin GC-MS (1 TMS) - 70eV, Positivesplash10-03mi-9576000000-fb9f159d71790f5468652017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsaicin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Capsaicin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin LC-ESI-QTOF , negative-QTOFsplash10-014i-0901000000-adba1bb6f254087febe82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin LC-ESI-ITTOF , negative-QTOFsplash10-014i-0900000000-5be0e66854b20d7a5a032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOFsplash10-014i-0900000000-4337ff26dcbd2a77725e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOFsplash10-014i-0900000000-c94a246143850aa73e442017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOFsplash10-014r-0950000000-3d145ef428e054b3e5352017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , negative-QTOFsplash10-014r-0950000000-c3ca097a6480ab798ff32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin LC-ESI-QTOF , positive-QTOFsplash10-000i-0900000000-4e8f98d1f848f30117d72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-000i-0900000000-58fab2fdd15893ea71e72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-000i-0900000000-296a0cb1555da4f1ccd72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-03di-0209000000-a91e6403d5a0c0b67c2e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-03di-0209000000-dd0879d3f4f3a8b022c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-014i-0149000000-d6a9f6e70ae7cd7aec382017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-014i-0149000000-6fcf63c3bf44a4efc5bd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-06sl-0075690000-b562b766019cc7cbd98f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-01x3-0094560000-f354077f4cd51e45b9452017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-004i-0002900000-ce1ea9819252343543cd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-004i-0002911000-6c37470f794c89a664102017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-000i-0900000000-00619747b8012ce6aa642017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Capsaicin Linear Ion Trap , positive-QTOFsplash10-000i-0900000000-3ca73f5212a7643b45d22017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsaicin 10V, Positive-QTOFsplash10-0udi-0912000000-95e090cebb8f95d7fe892016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsaicin 20V, Positive-QTOFsplash10-0udi-0900000000-6fb8b34936b848190c392016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsaicin 40V, Positive-QTOFsplash10-0f79-4900000000-ade1e8ba842adf972c832016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsaicin 10V, Negative-QTOFsplash10-0udi-0419000000-80bfd538da9be3f08fe02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsaicin 20V, Negative-QTOFsplash10-0udi-0922000000-00b0b7b3e9df2464d4252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Capsaicin 40V, Negative-QTOFsplash10-0006-7900000000-8b112ae03b8d84d338f32016-08-03Wishart LabView Spectrum
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 IDC00052221
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 IDNot Available
Good Scents IDrw1027601
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 ]