1339. Bornyl Acetate

Nomenclature

CAS number: 76-49-3
(1R,2S,4R)-rel-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-ol 2-acetate; borneol acetate; dl-bornyl acetate; (±)-bornyl acetate.
C12H20O2; mol wt 196.29.
C 73.43%, H 10.27%, O 16.30%.

Description and references

Constituent of essential oils of various plants; both d- and l- forms are naturally occurring. Prepn by acylation of borneol: M. A. Haller, Compt. Rend. 109, 29 (1889); K. Sisido et al., J. Am. Chem. Soc. 82, 125 (1960) DOI. Properties: W. J. Considine, J. Org. Chem. 25, 671 (1960) DOI.

Chemical structure

Properties

Crystals, mp 7.0°.

Derivative

d-Form.

Nomenclature

CAS number: 20347-65-3
(1R,2S,4R)-Bornyl acetate.

Properties

Crystals, mp 24° (Haller); also reported as mp 26.5°(Considine). bp 225-226°; bp8 92-93°. d 0.99. nD22 1.4623. [α]D +44.38° (Haller); [α]D +41.2° (Considine); [α]D14 +44.72°, neat (Sisido). Very slightly sol in water; sol in alcohol, ether.

Derivative

l-Form.

Nomenclature

CAS number: 5655-61-8
(1S,2R,4S)-Bornyl acetate.

Properties

Crystals, mp 24° (Haller); also reported as mp 27° (Considine). bp14 103°. [α]D 44.45° (Haller); [α]D 42.0° (Considine).

Use

In flavors and fragrances.