Capsaicin
| Names | |
|---|---|
| IUPAC name
(6E)-N-[(4-Hydroxy-3-methoxyphenyl)methyl]-8-methylnon-6-enamide
| |
| Other names
8-methyl-N-vanillyl-6-nonenamide
8-Methyl-N-vanillyl-trans-6-nonenamide (E)-Capsaicin Axsain Capsicin Capsicine CPS Mioton Zostrix trans-8-Methyl-N-vanillylnon-6-enamide | |
| Properties | |
| C18H27NO3 | |
| Molar mass | 305.418 g/mol |
| Appearance | Colorless solid |
| Odor | Pungent, spicy |
| Melting point | 62–65 °C (144–149 °F; 335–338 K) |
| Boiling point | 210–220 °C (410–428 °F; 483–493 K) |
| 0.0013 g/100 ml | |
| Solubility | Soluble in benzene, cyclohexane, dibutyl ether, diethyl ether, diisopropyl ether, ethanol Slightly soluble in carbon disulfide, chloroform, hexane, petroleum ether |
| Vapor pressure | 1.32·10−8 mmHg at 25 °C |
| Hazards | |
| Safety data sheet | Sigma-Aldrich |
| Flash point | 113 °C (235 °F; 386 K) |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
47.2 mg/kg (oral, mice) |
| Related compounds | |
| Related compounds
|
Phenylacetylrinvanil |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Capsaicin or 8-methyl-N-vanillyl-6-nonenamide is an organic chemical compound, the active component of chili peppers (Capsicum). It is a chemical irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact, although at low concentrations this occurs mostly in mouth, nose or other sensitive areas.
Capsaicin only causes irritation to mammals, as they posses capsaicin receptors, while other animals like birds or reptiles are unaffected, due to the lack of said receptors.
Contents
Properties
Chemical
Capsaicin can be decomposed using strong oxidizers.
Due to the presence of the OH group bonded to the aromatic ring, it's possible to produce and ester using acyl chlorides.
Physical
Capsaicin is a colorless waxy solid, practically insoluble in water, but soluble in many non-polar solvents like aromatic hydrocarbons.
Capsaicin and its related capsaicinoids' spiciness are measured on the Scoville scale, with pure capsaicin having 16 million Scoville heat units (SHU).
Availability
Capsaicin can be bought from chemical suppliers.
Capsaicin is readily found in chili peppers, and can be extracted from them. The extraction process however, has been described as "nasty", so you absolutely must wear the best protection if you really plan on doing this.
Preparation
Capsaicin can be synthesized from vanilamine and 8-methyl-6-nonenoyl-CoA.
If other acyl-CoA compounds are used, the end product will be different capsaicinoids.
Projects
- Make spicy stuff
- Compound collecting
Handling
Safety
Capsaicin is an extremely strong irritant, requiring proper protective goggles, respirators, and proper hazardous material-handling procedures. Capsaicin takes effect upon skin contact (irritant, sensitizer), eye contact (irritant), ingestion, and inhalation (lung irritant, lung sensitizer).
When capsaicin is ingested, cold milk is an effective way to relieve the burning sensation, mainly due to the milk from the fat, as well as the caseins, proteins found in milk, having a detergent-like effect on capsaicin. A sugar solution (10 %) at 20 °C (68 °F) is almost as effective. Avoid alcohol, as it does not remove capsaicin effectively, and it will defat the tissues, causing further irritation. Alcohol works best to remove capsaicin from objects, without damaging them.
Storage
In airtight bottles, preferably in glass ampoules if possible.
Disposal
Capsaicin on itself is not very harmful for the environment, so it can be poured down the drain, with lots of detergent.
