Difference between revisions of "Resiniferatoxin"

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(Created page with "{{Chembox | Name = Resiniferatoxin | Reference = | IUPACName = [(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-trioxapenta...")
 
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Resiniferatoxin can be extracted from the resin spurge plant.<ref>Fattorusso, Ernesto; Lanzotti, Virginia; Taglialatela-Scafati, Orazio; Tron, Gian Cesare; Appendino, Giovanni; European Journal of Organic Chemistry; nb. 1; (2002); p. 71 - 78</ref>
 
Resiniferatoxin can be extracted from the resin spurge plant.<ref>Fattorusso, Ernesto; Lanzotti, Virginia; Taglialatela-Scafati, Orazio; Tron, Gian Cesare; Appendino, Giovanni; European Journal of Organic Chemistry; nb. 1; (2002); p. 71 - 78</ref>
  
Total synthesis of this complicated is too expensive for the hobby chemist.
+
Total synthesis of this compound is too complicated is too expensive for the hobby chemist.
  
 
==Projects==
 
==Projects==

Latest revision as of 20:00, 27 December 2023

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):
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.

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 compound is too 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

  1. 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
  2. Fattorusso, Ernesto; Lanzotti, Virginia; Taglialatela-Scafati, Orazio; Tron, Gian Cesare; Appendino, Giovanni; European Journal of Organic Chemistry; nb. 1; (2002); p. 71 - 78

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