Capsaicin

Capsaicin
Compound Structure:
Synonyms: Capsaicin;404-86-4;(E)-Capsaicin;Zostrix;Qutenza;CAPSAICINE;Styptysat;Axsain;Isodecenoic acid vanillylamide;Ausanil;trans-Capsaicin;E-CAPSAICIN;Mioton;NGX-4010;trans-8-Methyl-N-vanillyl-6-nonenamide;Dolenon;Ovocap;(E)-8-Methyl-N-vanillyl-6-nonenamide
Compound ID: NMPC-722
PubChem ID:

1548943

Molecular Formula: C18H27NO3
Canonical SMILES: CC(C)C=CCCCCC(=O)NCC1=CC(=C(C=C1)O)OC
InChIKey: YKPUWZUDDOIDPM-SOFGYWHQSA-N
About the compound:

Capsaicin is the active component of chili peppers, which belong to the genus Capsicum. It is a chemical irritant and a neurotoxin for mammals, including humans, and is known for producing a sensation of burning when it comes into contact with various tissues. Capsaicin and related compounds, known as capsaicinoids, are produced by chili peppers primarily as a defense mechanism against certain mammals and fungi. Chemically, capsaicin (8-methyl-N-vanillyl-6-nonenamide) is a hydrophobic, colorless solid that is highly pungent and crystalline to waxy in form. It is found in large quantities in the placental tissue, internal membranes, and, to a lesser extent, the other fleshy parts of the fruits of Capsicum plants. Interestingly, the seeds themselves do not produce capsaicin, but the highest concentration is found in the white pith to which the seeds are attached. Capsaicin serves various purposes in both plants and animals. It is believed to have evolved as a deterrent against herbivores and pathogens like the Fusarium fungus. Additionally, it is instrumental in seed dispersal, particularly by birds, which are unaffected by its irritant properties unlike mammals. In human use, capsaicin is widely recognized for its culinary and medicinal applications. It is commonly used in food products to add spiciness or "heat," measured on the Scoville scale. Capsaicin is a popular ingredient in chili pepper and hot sauces, such as Tabasco and Mexican salsa. It is also known to induce pleasurable and euphoric effects in some individuals when ingested. Medicinally, capsaicin is used as an analgesic in topical ointments, dermal patches, and creams to relieve pain, particularly for conditions like arthritis, strains, sprains, and peripheral neuropathies such as post-herpetic neuralgia and diabetic neuropathy. The capsaicin transdermal patch, Qutenza, is one such FDA-approved treatment for post-herpetic neuralgia. Capsaicin is also studied for its potential effects on cholesterol levels and various disorders like obesity, diabetes, cancer, and cardiovascular diseases, though more research is needed to confirm these effects. Beyond medicinal and culinary uses, capsaicinoids are active ingredients in riot control and personal defense pepper sprays, causing pain and breathing difficulty upon contact with skin, especially the eyes and mucous membranes. Additionally, capsaicin is used as a pest deterrent against various mammals and in some insect-repellent formulas, although its efficacy in the latter is debated. Capsaicin, as a capsaicinoid, functions as a non-narcotic analgesic, a voltage-gated sodium channel blocker, and a TRPV1 agonist. Its role in pain management, especially for neuropathic pain, is significant, leading to the development of various pharmaceutical formulations, including the high-concentration capsaicin patch Qutenza.

https://en.wikipedia.org/wiki/Capsaicin

GHS Hazard Statements

H301 (21.07%): Toxic if swallowed [Danger Acute toxicity, oral]

H302 (78.82%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (99.72%): Causes skin irritation [Warning Skin corrosion/irritation]

H318 (97.32%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

305.4 g/mol

XLogP3-AA

3.6

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

3

Rotatable Bond Count

9

Exact Mass

305.19909372 g/mol

Monoisotopic Mass

305.19909372 g/mol

Topological Polar Surface Area

58.6²

Heavy Atom Count

22

Formal Charge

0

Complexity

341

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Dark red solid with a volatile pungent odor; [HSDB] Formulated as dry powder, liquid, and liquid spray; [Reference #1] White crystalline solid; [Sigma-Aldrich MSDS]

Boiling Point

210-220

Melting Point

65 °C

Solubility 

Freely soluble in alcohol, ether, benzene. Slightly soluble in carbon disulfide, Insoluble in cold water

Vapor Pressure

0.00000001 [mmHg]

Source: PubChem

Source Species: Talinum triangulare
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