Sobrerol

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Sobrerol
Sobrerol.png
Systematic (IUPAC) name
(1S)-5-(1-hydroxy-1-methylethyl)-2-methylcyclohex-2-en-1-ol
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
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Identifiers
CAS number 42370-41-2 YesY
ATC code R05CB07
PubChem CID 36089
UNII AI0NX02O35 YesY
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)
 YesY (what is this?)  (verify)

Sobrerol is a mucolytic.

History[edit]

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[edit]

  • 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.