ContaminantDB: Capsaicin

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (6)XML

Record Information

Version

1.0

Creation Date

2009-07-23 18:26:09 UTC

Update Date

2026-05-14 18:24:11 UTC

Accession Number

CHEM002422

Identification

Common Name

Capsaicin

Class

Small Molecule

Description

Capsaicin 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. (1).

Contaminant Sources

EAFUS Chemicals
FooDB Chemicals
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amide
Amine
Ether
Food Toxin
Household Toxin
Human Neurotoxin
Lachrymator
Metabolite
Natural Compound
Organic Compound
PFAS
Phytotoxin
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-8-Methyl-N-vanillyl-6-nonenamide	ChEBI
Isodecenoic acid vanillylamide	ChEBI
trans-8-Methyl-N-vanillyl-6-nonenamide	ChEBI
Zostrix	ChEBI
Isodecenoate vanillylamide	Generator
(e)-8-Methyl-N-vanillyl-6-nonenamide(8CL)	HMDB
(e)8-Methyl-N-vanillyl-6-nonenamide	HMDB
Axsain	HMDB
e-Capsaicin	HMDB
epsilon-Capsaicin	HMDB
Isodecenoate	HMDB
Isodecenoic acid	HMDB
N-(4-Hydroxy-3-methoxybenzyl)-8-methylnon-trans-6-enamide	HMDB
Styptysat	HMDB
Transacin	HMDB
Gelcen	HMDB
Link brand OF capsaicin	HMDB
8 Methyl N vanillyl 6 nonenamide	HMDB
Capsicum farmaya	HMDB
Capzasin	HMDB
Flemming brand OF capsaicin	HMDB
8-Methyl-N-vanillyl-6-nonenamide	HMDB
Capsin	HMDB
Katrum	HMDB
Medicis brand OF capsaicin	HMDB
Smaller brand OF capsaicin	HMDB
Thompson brand OF capsaicin	HMDB
Vinas brand OF capsaicin	HMDB
Alacan brand OF capsaicin	HMDB
Antiphlogistine rub a-535 capsaicin	HMDB
Capsaicine	HMDB
Capsidol	HMDB
Carter horner brand OF capsaicin	HMDB
Centrum brand OF capsaicin	HMDB
Elan brand OF capsaicin	HMDB
Zacin	HMDB

Chemical Formula

C₁₈H₂₇NO₃

Average Molecular Mass

305.412 g/mol

Monoisotopic Mass

305.199 g/mol

CAS Registry Number

404-86-4

IUPAC Name

(6E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide

Traditional Name

capsaicin

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 Key

YKPUWZUDDOIDPM-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.

Kingdom

Super Class

Class

Sub Class

Direct Parent

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 Framework

Aromatic homomonocyclic compounds

External Descriptors

capsaicinoid (CHEBI:3374 )
Capsaicinoids and derivatives (C06866 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

non-narcotic analgesic

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	65°C
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.0084 g/L	ALOGPS
logP	3.8	ALOGPS
logP	3.75	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	9.93	ChemAxon
pKa (Strongest Basic)	-0.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	58.56 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	90.32 m³·mol⁻¹	ChemAxon
Polarizability	36.32 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052o-9860000000-4151cd60d08276e5122a	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-03mi-9576000000-fb9f159d71790f546865	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-014i-0901000000-adba1bb6f254087febe8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITTOF , negative	splash10-014i-0900000000-5be0e66854b20d7a5a03	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0900000000-4337ff26dcbd2a77725e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014i-0900000000-c94a246143850aa73e44	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014r-0950000000-3d145ef428e054b3e535	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-014r-0950000000-c3ca097a6480ab798ff3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-000i-0900000000-4e8f98d1f848f30117d7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-58fab2fdd15893ea71e7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-296a0cb1555da4f1ccd7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0209000000-a91e6403d5a0c0b67c2e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-03di-0209000000-dd0879d3f4f3a8b022c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014i-0149000000-d6a9f6e70ae7cd7aec38	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-014i-0149000000-6fcf63c3bf44a4efc5bd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-06sl-0075690000-b562b766019cc7cbd98f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-01x3-0094560000-f354077f4cd51e45b945	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-004i-0002900000-ce1ea9819252343543cd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-004i-0002911000-6c37470f794c89a66410	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-00619747b8012ce6aa64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-000i-0900000000-3ca73f5212a7643b45d2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0912000000-95e090cebb8f95d7fe89	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-6fb8b34936b848190c39	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-4900000000-ade1e8ba842adf972c83	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0419000000-80bfd538da9be3f08fe0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0922000000-00b0b7b3e9df2464d425	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-7900000000-8b112ae03b8d84d338f3	Spectrum

Toxicity Profile

Route of Exposure

Oral (ingestion) (5) ; dermal (5)

Mechanism of Toxicity

The burning and painful sensations associated with capsaicin result from its chemical interaction with sensory neurons. Capsaicin, as a member of the vanilloid family, binds to the vanilloid receptor 1 (VR1). VR1 permits cations to pass through the cell membrane and into the cell when activated. The resulting depolarization of the neuron stimulates it to signal the brain. By binding to the VR1 receptor, the capsaicin molecule produces the same sensation that excessive heat or abrasive damage would cause, explaining why the spiciness of capsaicin is described as a burning sensation. (4)

Metabolism

Not Available

Toxicity Values

LD50: 47200 ug/kg (Oral, Mouse) (6) LD50: 6500 ug/kg (Intraperitoneal, Mouse) (6) LD50: 9000 ug/kg (Subcutaneous, Mouse) (6) LD50: 400 ug/kg (Intravenous, Mouse) (6) LD50: 7800 ug/kg (Intramuscular, Mouse) (6) LD50: 1600 ug/kg (Intratracheal, Mouse) (6)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

Capsaicin is the active component of chili peppers (genus Capsicum). It is a powerful irritant that is commonly used in food products to give them added spice. Capsaicin is also used in topical ointments to relieve the pain of peripheral neuropathy and can be found in pepper spray. (4)

Minimum Risk Level

Not Available

Health Effects

Capsaicin is a powerful irritant and severe over-exposure can result in death. (4)

Symptoms

Capsaicin is a powerful irritant and causes burning or stinging pain to the skin. Ingestion of large amounts can cause nausea, vomiting, abdominal pain and burning diarrhea. Eye exposure produces intense tearing, pain, conjunctivitis and blepharospasm. (4)

Treatment

Capsaicin should be washed off the skin using soap, shampoo, or other detergents, or rubbed off with oily compounds such as vegetable oil, paraffin oil, petroleum jelly, creams, or polyethylene glycol. Burning and pain symptoms can be effectively relieved by cooling from ice, cold water, cold surfaces, or a flow of air. In severe cases, eye burn might be treated symptomatically with topical ophthalmic anaesthetics, while mucous membrane burn can be treated with lidocaine gel. Capsaicin-induced asthma might be treated with nebulized bronchodilators or oral antihistamines or corticosteroids. (4)

Concentrations

Not Available

External Links

DrugBank ID

HMDB ID

FooDB ID

Phenol Explorer ID

KNApSAcK ID

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Gannett, 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.

MSDS

Link

General References

1. Gannett, 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.

2. Gannett, 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.

3. Surh YJ, Lee SS: Capsaicin in hot chili pepper: carcinogen, co-carcinogen or anticarcinogen? Food Chem Toxicol. 1996 Mar;34(3):313-6.

4. 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.

Capsaicin (CHEM002422)

Structure for CHEM002422: Capsaicin