File:Capsaicin.svg · Wikimedia Commons · See Wikimedia Commons
capsaicin
Sign in to saveAlso known as Qutenza®, Zostrix, (E)-8-Methyl-N-vanillyl-6-nonenamide, Isodecenoic acid vanillylamide, trans-8-Methyl-N-vanillyl-6-nonenamide
Capsaicin ('8-methyl-N-vanillyl-6-nonenamide') (, commonly ) is a toxin that is the main active component of chili peppers and gives them their distinct pungent, "spicy" or "hot" taste. It is a potent irritant for mammals for which it produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against eating by mammals and against the growth of fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent (i.e., spicy) crystalline solid.
OverviewAI-generated
Capsaicin is a chemical compound with the formula C₁₈H₂₇NO₃. Its IUPAC name is (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide. The substance has a mass of 305.199 and a weight of 305.4. It possesses a melting point of 63.5 and a Scoville grade of 16000000.
Chemical properties include a charge of 0, an xlogp of 3.6, and a tpsa of 58.6. The molecule contains two hydrogen bond donors and three hydrogen bond acceptors. Its canonical SMILES representation is CC(C)C=CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC, while the isomeric SMILES is CC(C)/C=C/CCCCC(=O)NCC1=CC(=C(C=C1)O)OC.
The compound is referenced by 788 other encyclopedia articles. A search for capsaicin in PubMed yields a count of 18091 entries.
Synthesized by Vinony from 20 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Pepper <! The given scoville rating is for the pure chemical compound, this should not be mistaken for food. >.heat
- Above peak
- Pepper <! The given scoville rating is for the pure chemical compound, this should not be mistaken for food. >.scoville
- 16,000,000
via Wikipedia infobox
Chemical data
- Formula
- C18H27NO3
- Molecular weight
- 305.4 g/mol
- IUPAC name
- (E)-N-[(4-hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
- SMILES
- CC(C)/C=C/CCCCC(=O)NCC1=CC(=C(C=C1)O)OC
- InChIKey
- YKPUWZUDDOIDPM-SOFGYWHQSA-N
- XLogP
- 3.6
- Polar surface area
- 58.6 Ų
- H-bond donors
- 2
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
18,091 papers- Capsaicin, The Vanilloid Receptor TRPV1 Agonist in Neuroprotection: Mechanisms Involved and Significance.Neurochemical research · 2023
- Fight fire with fire: Neurobiology of capsaicin-induced analgesia for chronic pain.Pharmacology & therapeutics · 2021
- Capsaicin alleviates cisplatin-induced muscle loss and atrophy in vitro and in vivo.Journal of cachexia, sarcopenia and muscle · 2023
- Capsaicin: A Novel Approach to the Treatment of Functional Dyspepsia.Molecular nutrition & food research · 2023
- Capsaicin: TRPV1-independent mechanisms and novel therapeutic possibilities.European journal of pharmacology · 2020
via PubMed
~18 min read
Encyclopedic overview
27 sectionsContents
- Natural function
- Uses
- Food
- Research
- Pepper spray and pests
- Equestrian sports
- Irritant effects
- Acute health effects
- Treatment after exposure
- Weight loss and regain
- Peptic ulcer
- Death
- Mechanism of action
- History
- Capsaicinoids
- Biosynthesis
- History
- Biosynthetic pathway
- Evolution
- Antifungal properties
- Insecticidal properties
- Seed dispersion and deterrents against granivorous mammals
- Adaptation to varying moisture levels
- References
- Notes
- Further reading
- External links
Capsaicin ('8-methyl-N-vanillyl-6-nonenamide') (, commonly ) is a toxin that is the main active component of chili peppers and gives them their distinct pungent, "spicy" or "hot" taste. It is a potent irritant for mammals for which it produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against eating by mammals and against the growth of fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent (i.e., spicy) crystalline solid.
== Natural function == Capsaicin is present in large quantities in the placental tissue (which holds the seeds), the internal membranes and, to a lesser extent, the other fleshy parts of the fruits of plants in the genus Capsicum. The seeds themselves do not produce any capsaicin, although the highest concentration of capsaicin can be found in the white pith of the inner wall, where the seeds are attached.
Excerpted from Wikipedia’s “capsaicin” article, available under the CC BY-SA 4.0 licence.