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α-Vetivone

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α-Vetivone
Names
IUPAC name 4α,5α-Eremophila-1(10),7(11)-dien-2-one
Systematic IUPAC name (4R,4aS)-4,4a-Dimethyl-6-(propan-2-ylidene)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.036.217 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11H,5-7,9H2,1-4H3/t11-,15+/m1/s1Key: NIIPDXITZPFFTE-ABAIWWIYSA-N
  • InChI=1/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11H,5-7,9H2,1-4H3/t11-,15+/m1/s1Key: NIIPDXITZPFFTE-ABAIWWIYBZ
SMILES
  • O=C2\C=C1\CC/C(=C(/C)C)C1(C)(C)C2
Properties
Chemical formula C15H22O
Molar mass 218.335
Appearance colourless solid
Density 0.962 g/mL
Boiling point 270.5 °C (518.9 °F; 543.6 K)
Solubility in water practically insoluble
Solubility in ethanol soluble
Solubility in diethyl ether soluble
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

α-Vetivone is an organic compound that is classified as a sesquiterpene (derived from three isoprene units). It is a major component of the oil of vetiver, which is used to prepare certain high value perfumes.

α-Vetivone is isolated by steam distillation of the roots of the grass Vetiveria zizanioides. Two other components of this distillate are the sesquiterpenes khusimol and β-vetivone shown below.

  • Structure of khusimol, another fragrant component of the oil of vetiver. Structure of khusimol, another fragrant component of the oil of vetiver.
  • Structure of β-vetivone, another fragrant component of the oil of vetiver. Structure of β-vetivone, another fragrant component of the oil of vetiver.

References

  1. Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim: 2002. Published online: 15 January 2003; doi:10.1002/14356007.a11_141.
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