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.
Bornyl Acetate Bornyl Chloride Bornyl Salicylate Boromycin Boron Carbide

Borneol
Borneol Borneol-3D-balls.png
Identifiers
CAS number 507-70-0 YesY
PubChem 6552009
ChemSpider 5026296 YesY
UNII M89NIB437X YesY
KEGG C01411 YesY
ChEBI CHEBI:15393 YesY
ChEMBL CHEMBL486208 YesY
Jmol-3D images Image 1
Properties
Molecular formula C10H18O
Molar mass 154.25 g mol−1
Appearance colorless to white lumps
Odor pungent, camphor-like
Density 1.011 g/cm3 (20 °C)[1]
Melting point 208 °C; 406 °F; 481 K
Boiling point 213 °C; 415 °F; 486 K
Solubility in water slightly soluble (D-form)
Solubility soluble in chloroform, ethanol, acetone, ether, benzene, toluene, decalin, tetralin
Hazards
MSDS External MSDS
NFPA 704
NFPA 704.svg
2
2
0
Flash point 65 °C; 149 °F; 338 K
Related compounds
Related compounds Bornane (hydrocarbon)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Borneol is a bicyclic organic compound and a terpene. The hydroxyl group in this compound is placed in an endo position. Borneol exists as two enantiomers which have two different CAS numbers. Naturally occurring d-(+)-borneol is optically active.