Isobornyl acetate

Isobornyl acetate

Names
IUPAC name [(1S,2S,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate
Identifiers
CAS Number	125-12-2 (+)
3D model (JSmol)	Interactive image
ChemSpider	5323219
ECHA InfoCard	100.004.298
EC Number	204-727-6
PubChem CID	6950273
RTECS number	NP7350000
CompTox Dashboard (EPA)	DTXSID7042061
InChI InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9-,10-,12+/m0/s1 Key: KGEKLUUHTZCSIP-JBLDHEPKSA-N
SMILES CC(=O)O[C@H]1C[C@@H]2CC[C@]1(C2(C)C)C
Properties
Chemical formula	C12H20O2
Molar mass	196.290 g·mol−1
Appearance	colorless liquid
Density	0.9841 g/cm3
Boiling point	102–103 °C (216–217 °F; 375–376 K) 13 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Isobornyl acetate is an organic compound consisting of the acetate ester or the terpenoid isoborneol. It is a colorless liquid with a pleasant pine-like scent, and it is produced on a multi-ton scale for this purpose. The compound is prepared by reaction of camphene with acetic acid in the presence of a strongly acidic catalyst such as sulfuric acid. Hydrolysis of isobornyl acetate gives isoborneol, a precursor to camphor. ^[1]

Like many plant exudates, isobornyl acetate appears to have antifeedant properties. ^[2]

References

1. Panten, Johannes; Surburg, Horst (2015). "Flavors and Fragrances, 2. Aliphatic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–55. doi:10.1002/14356007.t11_t01. ISBN   9783527306732.
2. Andrews, R. E.; Parks, L. W.; Spence, K. D. (1980). "Some Effects of Douglas Fir Terpenes on Certain Microorganisms". Applied and Environmental Microbiology. 40 (2): 301–304. Bibcode:1980ApEnM..40..301A. doi:10.1128/aem.40.2.301-304.1980. PMC   291570 . PMID   16345609.