Menthyl isovalerate

Structural formula
General
Surname	Menthyl isovalerate
other names	(1 R , 2 S , 5 R ) -2-isopropenyl-5-methylcyclohexyl isovalerate; Mementhyl valerate; Validol;
Molecular formula	C 15 H 28 O 2
Brief description	colorless liquid with a burning bitter taste
External identifiers / databases
ECHA InfoCard	100,036,766
PubChem	565690
Wikidata	Q12831520
properties
Molar mass	240.38 g mol −1
Physical state	liquid
density	0.909 g cm −3 (25 ° C)
boiling point	260–262 ° C (1000 hPa)
solubility	practically insoluble in water; soluble in ethanol and carbon trichloride;
Refractive index	1.4481 (20 ° C)
safety instructions
GHS labeling of hazardous substances Caution
H and P phrases	H: 315-319-335
	P: 261-305 + 351 + 338
Toxicological data	> 5000 mg kg −1 ( LD 50 , rat , oral ) ; > 5000 mg kg −1 ( LD 50 , rabbit , transdermal ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Menthyl isovalerate is an ester of menthol and isovaleric acid .

Occurrence

Black Catnip ( Nepeta mussini )

Menthyl isovalerate occurs naturally in the herb oil from Nepeta mussini as well as various peppermint oils (e.g. peppermint , cornmint and nutmeg ).

Extraction and presentation

The acid-catalyzed esterification of menthol with iso- valeryl chloride at around 100 ° C yields menthol isovalerate.

properties

Menthyl isovalerate is a clear, colorless liquid with a burning bitter taste, the smell of which allows the two components to be recognized. It decomposes on contact with bases.

use

Menthyl isovalerate is used as a flavoring agent. It is offered as a dietary food and anxiolytic under the names Validol and Anti-Stress VL . Depending on how it is manufactured, it contains around 50% menthyl isovalerate, 15 to 40% menthol and other esters of isovaleric acid and menthol compounds. However, no information is currently available on the pharmacological effects of the compounds.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Franz v. Bruchhausen, Siegfried Ebel, Eberhard Hackenthal, Ulrike Holzgrabe: Hager's Handbook of Pharmaceutical Practice, Volume 5: Substances LZ . Springer-Verlag, 2013, ISBN 978-3-642-58388-9 , pp. 115 ( limited preview in Google Book search).
↑ ^a ^b ^c ^d ^e ^f ^g data sheet Menthyl isovalerate, ≥98%, FG at Sigma-Aldrich , accessed on September 11, 2016 ( PDF ).
↑ ^a ^b ^c ^d George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9412-6 , pp. 1682 ( limited preview in Google Book search).
↑ Kh. A. Suerbaev, N. Zh. Kudaibergenov, NO Appazov, G. Zh. Zhaksylykova: Synthesis of L-menthyl isovalerate by esterification of isovaleric acid with L-menthol under microwave irradiation. In: Russian Journal of Organic Chemistry. 52, 2016, p. 585, doi: 10.1134 / S1070428016040205 .
↑ antistress-vl.de: ANTI STRESS VL , accessed: September 11, 2016.
↑ rupharma.com: VALIDOL , accessed: September 11, 2016.
↑ DZ Yaskina, VI Trubnikov, LA Kheifits, NE Kologrivova, IV Shumskaya, VP Pakhomov, AV Luk'yanov: A study of the composition of validol obtained from different types of raw materials. In: Pharmaceutical Chemistry Journal. 8, 1974, p. 252, doi: 10.1007 / BF00777002 .

[Franz_v._Bruchhausen,_Siegfried_Ebel,_Eberhard_Hackenthal,_Ulrike_Holzgrabe-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Franz v. Bruchhausen, Siegfried Ebel, Eberhard Hackenthal, Ulrike Holzgrabe: Hager's Handbook of Pharmaceutical Practice, Volume 5: Substances LZ . Springer-Verlag, 2013, ISBN 978-3-642-58388-9 , pp. 115 ( limited preview in Google Book search).

[Sigma-2] ↑ ^a ^b ^c ^d ^e ^f ^g data sheet Menthyl isovalerate, ≥98%, FG at Sigma-Aldrich , accessed on September 11, 2016 ( PDF ).

[George_A._Burdock-3] George A. Burdock: Encyclopedia of Food and Color Additives . CRC Press, 1997, ISBN 978-0-8493-9412-6 , pp. 1682 ( limited preview in Google Book search).

[DOI10.1134/S1070428016040205-4] Kh. A. Suerbaev, N. Zh. Kudaibergenov, NO Appazov, G. Zh. Zhaksylykova: Synthesis of L-menthyl isovalerate by esterification of isovaleric acid with L-menthol under microwave irradiation. In: Russian Journal of Organic Chemistry. 52, 2016, p. 585, doi: 10.1134 / S1070428016040205 .

[antistress-vl.de-5] tistress-vl.de: ANTI STRESS VL , accessed: September 11, 2016.

[6] rupharma.com: VALIDOL , accessed: September 11, 2016.

[DOI10.1007/BF00777002-7] DZ Yaskina, VI Trubnikov, LA Kheifits, NE Kologrivova, IV Shumskaya, VP Pakhomov, AV Luk'yanov: A study of the composition of validol obtained from different types of raw materials. In: Pharmaceutical Chemistry Journal. 8, 1974, p. 252, doi: 10.1007 / BF00777002 .