Sobrerol

Sobrerol

Sobrerol
Systematic (IUPAC) name
(1S)-5-(1-hydroxy-1-methylethyl)-2-methylcyclohex-2-en-1-ol
Clinical data
AHFS/Drugs.com
Legal status
?
Identifiers
CAS number  Y
ATC code R05
PubChem
UNII  Y
Synonyms trans-p-Menth-6-ene-2,8-diol; trans-sobrerol
Chemical data
Formula C10H18O2 
Mol. mass 170.249 g/mol
Physical data
Melt. point 130-132 °C (-76 °F)
Boiling point 270-271 °C (-186 °F)
 Y   

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. PMID 7313328. doi:10.1159/000194412.