Sobrerol
Clinical data
Other namestrans-p-Menth-6-ene-2,8-diol; trans-sobrerol
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
  • (1S)-5-(1-hydroxy-1-methylethyl)-2-methylcyclohex-2-en-1-ol
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.050.692 Edit this at Wikidata
Chemical and physical data
FormulaC10H18O2
Molar mass170.252 g·mol−1
3D model (JSmol)
Melting point130–132 °C (266–270 °F)
Boiling point270–271 °C (518–520 °F)
  • O[C@H]1CC(C\C=C1\C)C(O)(C)C
  (verify)

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

  • Henderson GG, Eastburn WJ (1909). "CLXIV — The conversion of pinene into sobrerol". Journal of the Chemical Society, Transactions. 95: 1465–1466m. doi:10.1039/CT9099501465.
  • Armstrong HE, Pope WJ (1891). "XXXVI — Studies of the terpenes and allied compounds. Sobrerol, a product of the oxidation of terebenthene (oil of turpentine) in sunlight". Journal of the Chemical Society, Transactions. 59: 315–320. doi:10.1039/CT8915900315.
  • Schmidt H (November 1953). "Über cis-und trans-Sobrerol (optisch-aktives Pinolhydrat)" [About cis- and trans-sobrerol (optically active pinol hydrate)]. Chemische Berichte (in German). 86 (11): 1437–1444. doi:10.1002/cber.19530861112.
  • Allegra L, Bossi R, Braga PC (1981). "Action of sobrerol on mucociliary transport". Respiration; International Review of Thoracic Diseases. 42 (2): 105–109. doi:10.1159/000194412. PMID 7313328.
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