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Isobornyl acetate information


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 Edit this at Wikidata
EC Number
  • 204-727-6
PubChem CID
  • 6950273
RTECS number
  • NP7350000
CompTox Dashboard (EPA)
  • DTXSID7042061 Edit this at Wikidata
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]

  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.

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Isobornyl acetate

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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...

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Camphene

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of fragrances and as a food additive for flavoring. These include isobornyl acetate. Camphene is biosynthesized from linalyl pyrophosphate via a sequence...

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Borneol

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derived from borneol by removal of hydroxyl and is also known as 2-bornyl. Isobornyl is the univalent radical C10H17 that is derived from isoborneol. The structural...

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Acetic acid

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synthetic camphor involves a Wagner-Meerwein rearrangement of camphene to isobornyl acetate; here acetic acid acts both as a solvent and as a nucleophile to trap...

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Isoborneol

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enantiomers. Isoborneol is synthesized commercially by hydrolysis of isobornyl acetate. The latter is obtained from treatment of camphene with acetic acid...

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Camphor

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