Sobrerol

Sobrerol
Clinical data
Other names	trans-p-Menth-6-ene-2,8-diol; trans-sobrerol
AHFS/Drugs.com	International Drug Names
ATC code	R05CB07 (WHO) ;
Identifiers
	IUPAC name (1S)-5-(1-hydroxy-1-methylethyl)-2-methylcyclohex-2-en-1-ol;
CAS Number	42370-41-2 ;
PubChem CID	36089;
UNII	AI0NX02O35;
CompTox Dashboard (EPA)	DTXSID60185983 ;
ECHA InfoCard	100.050.692
Chemical and physical data
Formula	C10H18O2
Molar mass	170.252 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	130–132 °C (266–270 °F)
Boiling point	270–271 °C (518–520 °F)
	SMILES O[C@H]1CC(C\C=C1\C)C(O)(C)C;
	(verify)

Sobrerol is a mucolytic.

History

Sobrerol was discovered by Ascanio Sobrero as an oxidation product of terpenes. Later the oxidation and reduction reactions of chiral pinene lead also to several possible isomers of carvone (the corresponding cyclohexyl ketone dehydrated at the isopropyl) and sobrerol, making it possible to determine reaction mechanism and the structural properties of pinene and of other terpenes.

References

G. G. Henderson; W. J. S. Eastburn (1909). "The conversion of pinene into sobrerol". J. Chem. Soc., Trans. 95: 1465–1466. doi:10.1039/CT9099501465.
H. E. Armstrong; W. J. Pope (1891). "Studies of the terpenes and allied compounds. Sobrerol, a product of the oxidation of terebenthene (oil of turpentine) in sunlight". J. Chem. Soc., Trans. 59: 315–320. doi:10.1039/CT8915900315.
H. Schmidt (1953). "Über cis- und trans-Sobrerol (optisch-aktives Pinolhydrat)". Chemische Berichte. 86 (11): 1437–1444. doi:10.1002/cber.19530861112.
Allegra L, Bossi R, Braga PC (1981). "Action of sobrerol on mucociliary transport". Respiration. 42 (2): 105–9. doi:10.1159/000194412. PMID 7313328.

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