Resiniferatoxin
| Names | |
|---|---|
| IUPAC name
[(1R,2R,6R,10S,11R,13R,15R,17R)-13-Benzyl-6-hydroxy-4,17-dimethyl-5-oxo-15-(prop-1-en-2-yl)-12,14,18-trioxapentacyclo[11.4.1.01,10.02,6.011,15]octadeca-3,8-dien-8-yl]methyl 2-(4-hydroxy-3-methoxyphenyl)acetate
| |
| Other names
RTX
| |
| Properties | |
| C37H40O9 | |
| Molar mass | 628.718 g/mol |
| Appearance | Colorless crystalline solid |
| Odor | Irritant |
| Density | 1.35 g/cm3 |
| Melting point | 64–67 °C (147–153 °F; 337–340 K) [1] |
| Insoluble | |
| Solubility | Soluble in acetone, chloroform, dichloromethane, DMSO, ethanol, ethyl acetate, isopropanol, methanol Insoluble in heptane, hexane |
| Vapor pressure | ~0 mmHg |
| Hazards | |
| Safety data sheet | ThermoFisher Scientific |
| Lethal dose or concentration (LD, LC): | |
| LD50 (Median dose)
|
148 mg/kg (rat, oral) |
| Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Resiniferatoxin (RTX) is a naturally occurring chemical found in resin spurge (Euphorbia resinifera), a cactus-like plant commonly found in Morocco, and in Euphorbia poissonii found in northern Nigeria. It is a potent functional analog of capsaicin, the active ingredient in chili peppers.
Contents
Properties
Chemical
Resiniferatoxin has been shown to have a score of 16 billion Scoville heat units, making pure resiniferatoxin about 500 to 1000 times hotter than pure capsaicin.
Physical
RTX is a white crystalline solid, insoluble in water, but soluble in organic solvents.
Availability
RTX is sold by a few chemical suppliers around the world, in mg quantities, at a high price.
Preparation
Resiniferatoxin can be extracted from the resin spurge plant.[2]
Total synthesis of this complicated is too expensive for the hobby chemist.
Projects
- Spiciest substance known
- Compound collecting
Handling
Safety
At 16 billion Scoville units, resiniferatoxin is rather toxic and can inflict chemical burns in minute quantities. The primary action of resiniferatoxin is to activate sensory neurons responsible for the perception of pain. It is currently the most potent TRPV1 agonist known, with ~500x higher binding affinity for TRPV1 than capsaicin, the active ingredient in hot chili peppers such as those produced by Capsicum annuum.
Storage
Due to its hazards, this compound is best stored in a glass ampoule.
Disposal
Can be destroyed with an oxidizing solution, like bleach.
References
- ↑ Hashimoto, Satoshi; Katoh, Shun-Ichiro; Kato, Takehiro; Urabe, Daisuke; Inoue, Masayuki; Journal of the American Chemical Society; vol. 139; nb. 45; (2017); p. 16420 - 16429
- ↑ Fattorusso, Ernesto; Lanzotti, Virginia; Taglialatela-Scafati, Orazio; Tron, Gian Cesare; Appendino, Giovanni; European Journal of Organic Chemistry; nb. 1; (2002); p. 71 - 78
