Sobrerol

Sobrerol
Clinical data

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
Synonyms	trans-p-Menth-6-ene-2,8-diol; trans-sobrerol
CAS Number	42370-41-2^Y
PubChem (CID)	36089
UNII	AI0NX02O35^Y
ECHA InfoCard	100.050.692
Chemical and physical data
Formula	C₁₀H₁₈O₂
Molar mass	170.249 g/mol
3D model (Jmol)	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
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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.

Cough and cold preparations (R05)

Expectorants

Mucolytics

Cough suppressants

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