Sobrerol

Chemical compound

Pharmaceutical compound

Sobrerol
Clinical data

Other names	trans-p-Menth-6-ene-2,8-diol; trans-sobrerol
AHFS/Drugs.com	International Drug Names
ATC code	R05CB07 (WHO )
Identifiers
IUPAC name (1S)-5-(1-hydroxy-1-methylethyl)-2-methylcyclohex-2-en-1-ol
CAS Number	42370-41-2 ^checkY
PubChem CID	36089
UNII	AI0NX02O35
CompTox Dashboard (EPA)	DTXSID60185983 Edit this at Wikidata
ECHA InfoCard	100.050.692 Edit this at Wikidata
Chemical and physical data
Formula	C₁₀H₁₈O₂
Molar mass	170.252 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	130–132 °C (266–270 °F)
Boiling point	270–271 °C (518–520 °F)
SMILES O[C@H]1CC(C\C=C1\C)C(O)(C)C
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Sobrerol is a mucolytic.

History

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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

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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.