76-49-3 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 76-49-3 differently. You can refer to the following data:
1. 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.
2. 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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 76-49-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 6 respectively; the second part has 2 digits, 4 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 76-49:
(4*7)+(3*6)+(2*4)+(1*9)=63
63 % 10 = 3
So 76-49-3 is a valid CAS Registry Number.
InChI:InChI=1/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3
76-49-3Relevant articles and documents
Solvent-free Acetylation Procedure
Bhat, Sujata V.,Gupta, Manisha O.,Yadav, Jyoti K.,Vaze, Kedar R.
, p. 590 - 594 (2021/10/07)
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Simple Plug-In Synthetic Step for the Synthesis of (?)-Camphor from Renewable Starting Materials
Calderini, Elia,Drienovská, Ivana,Myrtollari, Kamela,Pressnig, Michaela,Sieber, Volker,Schwab, Helmut,Hofer, Michael,Kourist, Robert
, p. 2951 - 2956 (2021/06/18)
Racemic camphor and isoborneol are readily available as industrial side products, whereas (1R)-camphor is available from natural sources. Optically pure (1S)-camphor, however, is much more difficult to obtain. The synthesis of racemic camphor from α-pinene proceeds via an intermediary racemic isobornyl ester, which is then hydrolyzed and oxidized to give camphor. We reasoned that enantioselective hydrolysis of isobornyl esters would give facile access to optically pure isoborneol and camphor isomers, respectively. While screening of a set of commercial lipases and esterases in the kinetic resolution of racemic monoterpenols did not lead to the identification of any enantioselective enzymes, the cephalosporin Esterase B from Burkholderia gladioli (EstB) and Esterase C (EstC) from Rhodococcus rhodochrous showed outstanding enantioselectivity (E>100) towards the butyryl esters of isoborneol, borneol and fenchol. The enantioselectivity was higher with increasing chain length of the acyl moiety of the substrate. The kinetic resolution of isobornyl butyrate can be easily integrated into the production of camphor from α-pinene and thus allows the facile synthesis of optically pure monoterpenols from a renewable side-product.
'Clean' hydrolase reactions using commercial washing powder
Zhang, Jie,Tonin, Fabio,Zhang, Wuyuan,Hagedoorn, Peter-Leon,Mallée, Lloyd,Hollmann, Frank
, p. 24039 - 24042 (2019/08/15)
We report the use of commercial laundry powder as a biocatalyst for a range of lipase-catalysed reactions including (trans)esterification, ester hydrolysis and chemoenzymatic epoxidation reactions. The enzymatic laundry powder exhibited excellent stability and recyclability, making it a readily available and cheap biocatalyst for chemical transformations.
