Sobrerol

Sobrerol
Systematic (IUPAC) name

(1S)-5-(1-hydroxy-1-methylethyl)-2-methylcyclohex-2-en-1-ol
Clinical data
AHFS/Drugs.com	International Drug Names
Identifiers
CAS Number	42370-41-2^Y
ATC code	R05CB07
PubChem	CID 36089
UNII	AI0NX02O35^Y
Synonyms	trans-p-Menth-6-ene-2,8-diol; trans-sobrerol
Chemical data
Formula	C₁₀H₁₈O₂
Molar mass	170.249 g/mol
SMILES O[C@H]1CC(C\C=C1\C)C(O)(C)C
Physical data
Melting point	130–132 °C (266–270 °F)
Boiling point	270–271 °C (518–520 °F)
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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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