Sobrerol

Sobrerol
Systematic (IUPAC) name
(1S)-5-(1-hydroxy-1-methylethyl)-2-methylcyclohex-2-en-1-ol
Identifiers
CAS number	42370-41-2
ATC code	R05CB07
PubChem	36089
Chemical data
Formula	C10H18O2
Mol. mass	170.249 g/mol
SMILES	eMolecules & PubChem
Synonyms	trans-p-Menth-6-ene-2,8-diol; trans-sobrerol
Physical data
Melt. point	130-132 °C (-76 °F)
Boiling point	270-271 °C (-186 °F)
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status
Routes	?

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. 

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