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Menthyl isovalerate

From Wikipedia, the free encyclopedia
Menthyl isovalerate
Names
IUPAC name
(1R,3R,4S)-p-Menthan-3-yl 3-methylbutanoate
Systematic IUPAC name
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 3-methylbutanoate
Other names
Validolum; Valofin; Validol; Menthoval
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard100.036.766Edit this at Wikidata
UNII
  • InChI=1S/C15H28O2/c1-10(2)8-15(16)17-14-9-12(5)6-7-13(14)11(3)4/h10-14H,6-9H2,1-5H3/t12-,13+,14-/m1/s1
    Key: VYQSSWZYPCCBRN-HZSPNIEDSA-N
  • InChI=1/C15H28O2/c1-10(2)8-15(16)17-14-9-12(5)6-7-13(14)11(3)4/h10-14H,6-9H2,1-5H3/t12-,13+,14-/m1/s1
    Key: VYQSSWZYPCCBRN-HZSPNIEDBT
  • C[C@@H]1CC[C@H]([C@@H](C1)OC(=O)CC(C)C)C(C)C
Properties
C15H28O2
Molar mass240.387 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Menthyl isovalerate, also known asvalidolum, is thementhylester ofisovaleric acid. It is a transparent oily, colorless liquid with a smell of menthol. It is very slightly soluble inethanol, while practically insoluble in water. It is used as afood additive forflavor and fragrance.[1]

Medical use

[edit]

In Poland, Bulgaria, Romania and the former Soviet Union states including Russia, menthyl isovalerate mixed with roughly 25% menthol is sold as ananxiolytic under various trade names including Extravalerianic, Validol, Valofin, and Menthoval.[2][3][4]

Validol, the anxiety medication containing a roughly 25% solution of menthol in menthyl isovalerate is prepared essentially in one step, in which the amount of menthol added before conducting the acid catalysed esterification is in an excess such that the resulting solution of the yielded ester has around 25% menthol, simplifying the procedure. Work up might consist of several washings, including one with aqueoussodium bicarbonate to neutralize traces of acid catalyst and unreacted isovaleric acid, anddistillation.[citation needed]

See also

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References

[edit]
  1. ^Menthyl isovalerate.
  2. ^Russian Medications List and Possible Side Effects[dead link]
  3. ^"Farmak Product Information - Validol"(PDF). Archived fromthe original(PDF) on 2016-03-15. Retrieved2013-04-05.
  4. ^Bondarenko IP, Liashenko MM, Chirkov SN, Ermakovich II (1996). "A comparative evaluation of the antianginal action of commercially and noncommercially produced validol in neurocirculatory dystonia and stenocardia".Lik Sprava.Mar–Apr (3–4):110–113.PMID 9035841.
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Retrieved from "https://en.wikipedia.org/w/index.php?title=Menthyl_isovalerate&oldid=1335668396"
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