3,3,5-Trimethylcyclohexanol

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3,3,5-Trimethylcyclohexanol
3,3,5-trimethylcyclohexanol.svg
Names
IUPAC name
3,3,5-trimethylcyclohexan-1-ol
Other names
Homomenthol
Identifiers
3D model (JSmol)
2203314
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.748
EC Number 204-122-7
PubChem CID
UNII
Properties
C9H18O
Molar mass 142.242 g·mol−1
Density 0.878 at 20 °C
Melting point 37.0 °C (98.6 °F; 310.1 K)
Boiling point 198 °C (388 °F; 471 K)
Hazards
GHS pictograms GHS-pictogram-exclam.svg
GHS signal word Warning
H315, H319, H412
P264, P273, P280, P302+352, P305+351+338, P321, P332+313, P337+313, P362, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

3,3,5-Trimethylcyclohexanol is a precursor to the vasodilator cyclandelate, the sunscreen component homosalate and the VP nerve agent. [1] [2] It can be synthesized by hydrogenation of isophorone. [3] It has a mint flavour.

Cyclandelate chemical compound

Cyclandelate is a vasodilator used in the treatment of claudication, arteriosclerosis and Raynaud's disease. It is also used to treat nighttime leg cramps, and has been investigated for its effect against migraine. It is orally administered.

Homosalate chemical compound

Homosalate is an organic compound used in some sunscreens. It is made by the Fischer–Speier esterification of salicylic acid and 3,3,5-trimethylcyclohexanol, the latter being a hydrogenated derivative of isophorone. Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter. The salicylic acid portion of the molecule absorbs ultraviolet rays with a wavelength from 295 nm to 315 nm, protecting the skin from sun damage. The hydrophobic trimethyl cyclohexane functional group provides greasiness that prevents it from dissolving in water.

Nerve agents, sometimes also called nerve gases, are a class of organic chemicals that disrupt the mechanisms by which nerves transfer messages to organs. The disruption is caused by the blocking of acetylcholinesterase, an enzyme that catalyzes the breakdown of acetylcholine, a neurotransmitter.

See also

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References

  1. Bell, GD; Clegg, RJ; Ellis, WR; Middleton, B; White, DA (January 1984). "The effects of 3,5,5-trimethylcyclohexanol on hepatic cholesterol synthesis, bile flow and biliary lipid secretion in the rat". British Journal of Pharmacology. 81 (1): 183–7. doi:10.1111/j.1476-5381.1984.tb10759.x. PMC   1986967 . PMID   6704580.
  2. "3-Pyridyl phosphonates". US3903098A.
  3. "Fragrance raw materials monographs". Food and Cosmetics Toxicology. 12 (7–8): 1007. December 1974. doi:10.1016/0015-6264(74)90227-2.