| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:09 UTC |
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| Update date | 2019-11-26 03:06:44 UTC |
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| Primary ID | FDB012411 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Capsaicin |
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| Description | Flavouring ingredient. Pungent principle of various Capsicum subspecies (Solanaceae)
Capsaicin (pronounced /kæp?se??s?n/) (8-methyl-N-vanillyl-6-nonenamide, (CH3)2CHCH=CH(CH2)4CONHCH2C6H3-4-(OH)-3-(OCH3)) is the active component of chili peppers, which are plants belonging to the genus Capsicum. It is an irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related compounds are called capsaicinoids and are produced as a secondary metabolite by chili peppers, probably as deterrents against certain herbivores and fungi. Pure capsaicin is a hydrophobic, colorless, odorless, crystalline to waxy compound.; Capsaicin is a banned substance in equestrian sports because of its hypersensitizing and pain relieving properties. At the show jumping events of the 2008 Summer Olympics, four horses tested positive for the substance, resulting in disqualification.; Capsaicin is a highly irritant material requiring proper protective goggles, respirators, and proper hazardous material handling procedures. It is hazardous in cases of skin contact (irritant, sensitizer), of eye contact (irritant), of ingestion, of inhalation (lung irritant, lung sensitizer). Severe over-exposure to pure capsaicin can result in death; the lethal dose (LD50 in mice) is 47.2 mg/kg. Numerous other adverse health effects can occur in mammals.; 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. (PMID: 8621114); Prolonged activation of these neurons by capsaicin depletes presynaptic substance P, one of the body's neurotransmitters for pain and heat. Neurons that do not contain TRPV1 are unaffected. This causes extended numbness following surgery, and the patient does not feel pain as the capsaicin is applied under anesthesia.; 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 a receptor called the vanilloid receptor subtype 1 (VR1). First cloned in 1997, VR1 is an ion channel-type receptor. VR1, which can also be stimulated with heat and physical abrasion, 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.; The research team led by David Julius of UCSF showed in 1997 that capsaicin selectively binds to a protein known as TRPV1 that resides on the membranes of pain and heat sensing neurons. TRPV1 is a heat activated calcium channel, which opens between 37 and 45 °C. When capsaicin binds to TRPV1, it causes the channel to open below 37 °C (normal human body temperature), which is why capsaicin is linked to the sensation of heat. Capsaicin is found in many foods, some of which are pepper (c. annuum), red bell pepper, green bell pepper, and orange bell pepper. |
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| CAS Number | 404-86-4 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C18H27NO3 |
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| IUPAC name | (6Z)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enimidic acid |
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| 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- |
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| InChI Key | YKPUWZUDDOIDPM-VURMDHGXSA-N |
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| Isomeric SMILES | COC1=C(O)C=CC(CNC(=O)CCCC\C=C/C(C)C)=C1 |
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| Average Molecular Weight | 305.4119 |
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| Monoisotopic Molecular Weight | 305.199093735 |
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| Classification |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Phenols |
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| Sub Class | Methoxyphenols |
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| Direct Parent | Methoxyphenols |
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| Alternative Parents | |
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| 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
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Solid | |
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| Physical Description | Not Available | |
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| Mass Composition | C 70.79%; H 8.91%; N 4.59%; O 15.72% | DFC |
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| Melting Point | Mp 64-65° | DFC |
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| Boiling Point | Bp0.01 210-220° | DFC |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | 281 (e 2500) (MeOH) (Berdy) | DFC |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| Predicted GC-MS | Capsaicin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052o-9860000000-4151cd60d08276e5122a | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| MS/MS | LC-MS/MS Spectrum - , positive | splash10-000i-1900000000-b2bcbe6ef314218a9fca | 2017-09-14 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0912000000-95e090cebb8f95d7fe89 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900000000-6fb8b34936b848190c39 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0f79-4900000000-ade1e8ba842adf972c83 | 2017-07-25 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0419000000-80bfd538da9be3f08fe0 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0922000000-00b0b7b3e9df2464d425 | 2017-07-26 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-7900000000-8b112ae03b8d84d338f3 | 2017-07-26 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | 1265957 |
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| ChEMBL ID | CHEMBL294199 |
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| KEGG Compound ID | C06866 |
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| Pubchem Compound ID | 1548943 |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | 3374 |
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| Phenol-Explorer ID | 712 |
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| DrugBank ID | DB05318 |
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| HMDB ID | HMDB02227 |
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| CRC / DFC (Dictionary of Food Compounds) ID | HGT21-K:HGT21-K |
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| EAFUS ID | 1753 |
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| Dr. Duke ID | CAPSAICIN |
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| BIGG ID | Not Available |
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| KNApSAcK ID | Not Available |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | rw1027601 |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Capsaicin |
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| Phenol-Explorer Metabolite ID | Not Available |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| 5-lipoxygenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | | anaphylactic | | | DUKE | | anesthetic | | | DUKE | | anti aggregant | | | DUKE | | anti arrhythmic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | | anti colonospasmic | | | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti ischemic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti mastalgic | | | DUKE | | anti neuralgic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti neuritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti nitrosaminic | | | DUKE | | anti nociceptive | 35470 | A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. | DUKE | | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | | anti psoriatic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti tachycardic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | | calcium antagonist | 48706 | Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. | DUKE | | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | | cardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | | catabolic | | | DUKE | | cyclooxygenase inhibitor | 35544 | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. | DUKE | | cytochrome-P450 inhibitor | 50183 | An enzyme inhibitor that interferes with the activity of cytochrome P450 involved in catalysis of organic substances. | DUKE | | diaphoretic | | | DUKE | | digestive | | | DUKE | | endocrinactive | | | DUKE | | flavor | 48318 | A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. | DUKE | | hypothermic | | | DUKE | | irritant | | | DUKE | | neurotoxic | 50910 | A poison that interferes with the functions of the nervous system. | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | pyrogenic | | | DUKE | | repellent | | | DUKE | | respirasensitizer | | | DUKE | | rubefacient | | | DUKE | | sialogogue | | | DUKE | | thermogenic | | | DUKE | | vasodilator | 35620 | A drug used to cause dilation of the blood vessels. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | | Flavor | Citations |
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| mild |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | warm |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
| | herbal |
- The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
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| Files |
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| MSDS | show |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
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