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Bornyl acetate

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Bornyl acetate Basic information

Product Name:
Bornyl acetate
Synonyms:
  • 1-BORNYLACETATE
  • Acetic acid isobornyl ester
  • (1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl) acetate
  • Bicyclo[2.2.1]heptan-2-ol, 1,7,7-trimethyl-, acetate, (1R,2S,4R)-
  • 1,7,7-Trimethylbicyclo[2.2.1]heptane-2-yl=acetate
  • Acetic acid 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl
  • Acetic acid 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl ester
  • Acetic acid isobornyl
CAS:
76-49-3
MF:
C12H20O2
MW:
196.29
EINECS:
200-964-4
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Mol File:
76-49-3.mol
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Bornyl acetate Chemical Properties

Melting point:
29°C
alpha 
-41 º (neat)
Boiling point:
228-231 °C(lit.)
Density 
0.985 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.4635(lit.)
FEMA 
2159 | BORNYL ACETATE
Flash point:
192 °F
storage temp. 
Store at -20°C
solubility 
DMF: 25mg/mL; DMF:PBS (pH 7.2) (1:3): 0.25mg/mL; DMSO: 2mg/mL; Ethanol: 15mg/mL
form 
An oil
Odor
at 100.00 %. woody pine herbal cedar spice
Odor Type
balsamic
JECFA Number
1387
Merck 
13,1329
Dielectric constant
4.6(21℃)
LogP
3.86
CAS DataBase Reference
76-49-3
NIST Chemistry Reference
Bornyl acetate(76-49-3)
EPA Substance Registry System
Bornyl acetate (76-49-3)
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Safety Information

WGK Germany 
1

MSDS

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Bornyl acetate Usage And Synthesis

Chemical Properties

Bornyl acetate occurs in its optically active forms and as a racemate in many essential oils.
(1S,2R,4S)-(?)-Bornyl acetate is a characteristic component of most conifer oils. It has a camphoraceous, pine-needle-like odor. Both (1R,2S,4R)- (+)-bornyl acetate and (?)-bornyl acetate form colorless crystals; the racemate is a colorless liquid. Bornyl acetate is prepared by esterification of borneol with acetic anhydride or via the process described under borneol.
Due to its characteristic pine-needle odor, bornyl acetate is frequently used in conifer needle compositions, soaps, bath products, room sprays, and pharmaceutical products.

Chemical Properties

Bornyl acetate has a fresh, strong, piney odor and a fresh, burning taste.

Occurrence

Reported found in the oils of Abies canadensis, A. concolor, Picea canadensis, P. rubens, P. orientalis, Pinus densiflora, Larix americana, Callitris drum-mondi, Abies alba, Pinus punulio, Abies sibirica L., and in coriander, thyme and valerian oil; it has been identified in the essence from flowers of Chrysanthemum sincuse Sabin, in the distillate of Teucrium chamaedris L., and in the fresh rhizomes of Valeriana officinalis L.; d-bornyl acetate is found in the essential oils of Callitris glauca, C. robusta, C. gracilis, C. verrucosa and C. calcarata; the presence of acetate has been excluded from the essence of lavender and lavandin.

Uses

Antineoplastic; radioactive agent.

Aroma threshold values

Detection: 75 ppb to 1.38 ppm

Taste threshold values

Taste characteristics at 10 ppm: camphoreous, woody, mentholic, berry and seedy with soapy, woody nuances.

Synthesis

l-Bornyl acetate occurs naturally in many oils distilled from the leaves of plants of the family Pinaceae; d-bornyl acetate is found in the oils distilled from plants of the family Cupressaceae; bornyl acetate, therefore may be isolated by distillation and crystallization from these; however, it is commonly prepared by direct acetylation of borneol; the first synthesis dates to 1889.

Bornyl acetate Preparation Products And Raw materials

Raw materials

Bornyl acetateSupplier

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