Borneol
Title: Borneol
CAS Registry Number: 507-70-0
CAS Name: endo-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol
Additional Names: endo-2-bornanol; endo-2-camphanol; endo-2-hydroxycamphane; bornyl alcohol; Baros camphor; Sumatra camphor; Borneo camphor; Dryobalanops camphor; Bhimsaim camphor; Malayan camphor; camphol
Molecular Formula: C10H18O
Molecular Weight: 154.25
Percent Composition: C 77.87%, H 11.76%, O 10.37%
Literature References: The dextrorotatory form which predominates occurs in the oil from Dryobalanops aromatica Gaertn., Dipterocarpaceae, and in many other plants; the levorotatory form comes from Blumea balsamifera (L.) DC., Compositae: E. Gildemeister, F. Hoffman, Die ätherischen Ole (Schimmel, Leipzig, 3rd ed., 1928) pp 475-481. Racemic borneol is prepd synthetically by reduction of camphor: Truett, Moulton, J. Am. Chem. Soc. 73, 5913 (1951); Ziegler et al., Ann. 623, 9 (1959); Ziegler, GB 803178 (1958); from pinene: Schwyzer, Pharm. Ztg. 75, 1275 (1930). Configuration (isoborneol = exo-form; borneol = endo-form): Toivonen et al., Acta Chem. Scand. 3, 991 (1949). Toxicity data: R. C. Beier, Rev. Environ. Contam. Toxicol. 113, 47-127 (1990). Review: J. L. Simonsen, The Terpenes vol. II (University Press, Cambridge, 2nd ed., 1949) pp 349-365.
 
Derivative Type: d-Form
Properties: Hexagonal plates from petr ether, mp 208°. Peculiar peppery odor and burning taste somewhat resembling that of mint. Sublimes, but is less volatile than camphor. d420 1.011. bp 212°. [a]D20 +37.7° (c = 5 in alc); [a]22546 +44.4° (c = 0.5 in toluene). Almost insol in water. Sol in alc (176 parts dissolve in 100 parts w/w of abs alc), ether, petr ether (about 1:6), benzene (about 1:5), toluene, acetone, decalin, tetralin. LD orally in rabbits: 2000 mg/kg (Beier).
Melting point: mp 208°
Boiling point: bp 212°
Optical Rotation: [a]D20 +37.7° (c = 5 in alc); [a]22546 +44.4° (c = 0.5 in toluene)
Density: d420 1.011
Toxicity data: LD orally in rabbits: 2000 mg/kg (Beier)
 
Derivative Type: l-Form
Properties: Hexagonal plates, mp 204°. bp779 210°. [a]D20 -37.7° (c = 5 in alc); [a]22546 -44.4° (c = 0.5 in toluene).
Melting point: mp 204°
Boiling point: bp779 210°
Optical Rotation: [a]D20 -37.7° (c = 5 in alc); [a]22546 -44.4° (c = 0.5 in toluene)
 
Derivative Type: dl-Form
Properties: mp 206-207°.
Melting point: mp 206-207°
 
CAUTION: May cause nausea, vomiting, mental confusion, dizziness, convulsions.
Use: Primarily in the manuf of its esters. Some free borneol and isoborneol is used in perfumery and in incense making.

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