Title: Sobrerol
CAS Registry Number: 498-71-5
CAS Name: 5-Hydroxy-a,a,4-trimethyl-3-cyclohexene-1-methanol
Additional Names: p-menth-6-ene-2,8-diol; 6,8-carvomenthenediol; 1-p-menthene-6,8-diol; pinol hydrate
Molecular Formula: C10H18O2
Molecular Weight: 170.25
Percent Composition: C 70.55%, H 10.66%, O 18.80%
Literature References: An oxidation product of oil of turpentine formed by the autooxidation of a-pinene, q.v., in the presence of water and especially in sunlight. First obtained by Margueron in 1797. Confused with terpin hydrate, q.v., until fully characterized by Sobrero in 1851. The naturally occurring form is the trans-form. For a review of early structure and prepn work, see J. L. Simonsen, The Terpenes vol. II (University Press, Cambridge, 2nd ed., 1949) pp 137-138. Summary of general methods of prepn: Lombard, Heywang, Bull. Soc. Chim. Fr. 1954, 1210. Prepn of dl-trans-form: Ward, J. Am. Chem. Soc. 60, 325 (1938); Schenck et al., Ann. 584, 177 (1953); Moore et al., J. Am. Chem. Soc. 78, 1173 (1956); Brook, Wright, J. Org. Chem. 22, 1314 (1957); of l-trans-form: Klein, US 2815378 (1958 to Glidden). Prepn of cis- and trans-forms and analysis of stereochemistry: Blumann, Wood, J. Chem. Soc. 1952, 4420; H. Schmidt, Ber. 86, 1437 (1953). Pharmacology and chemistry of dl-trans-form: GB 1176817; C. Corvi-Mora, US 3592908 (1970, 1971 to Camillo Corvi); V. Dalla Valle, Boll. Chim. Farm. 109, 761 (1970). Clinical evaluation: C. F. Marchioni, G. Monzali, Clin. Ter. 60, 135 (1972). Activity on mucociliary transport: P. Braga, Clin. Trials J. 18, 30 (1981). Pharmacokinetics: P. C. Braga et al., Eur. J. Clin. Pharmacol. 24, 209 (1983). Metabolism: P. Ventura et al., Xenobiotica 13, 139 (1983); eidem, ibid. 15, 317 (1985). GLC determn in human plasma: U. A. Shulka, J. Chromatogr. 308, 189 (1984).
Derivative Type: dl-trans-Form
Trademarks: Lysmucol (Schering); Sobrepin (Corvi)
Properties: Crystals, mp 130-131.5°. bp 270-271°. Soly in water: 3.3 g/100 ml (15°). LD50 in rats, mice (mg/kg): both 580 i.v. (Dalla Valle).
Melting point: mp 130-131.5°
Boiling point: bp 270-271°
Toxicity data: LD50 in rats, mice (mg/kg): both 580 i.v. (Dalla Valle)
Derivative Type: d-trans-Form
Properties: mp 148-149°. [a]D20 +150° (Schmidt).
Melting point: mp 148-149°
Optical Rotation: [a]D20 +150° (Schmidt)
Derivative Type: l-trans-Form
Properties: mp 148-149°. [a]D20 -150° (Schmidt).
Melting point: mp 148-149°
Optical Rotation: [a]D20 -150° (Schmidt)
Therap-Cat: Mucolytic.
Keywords: Mucolytic.

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