Vetivones
Title: Vetivones
Molecular Formula: C15H22O
Molecular Weight: 218.33
Percent Composition: C 82.52%, H 10.16%, O 7.33%
Literature References: Ketonic components of vetiver oil; from roots of Vetiveria zizanioides (Andropogon muricatus Retz., Gramineae). Two isomers, the a-form having the stronger odor. Isoln and structure: Pfau, Plattner, Helv. Chim. Acta 22, 640 (1939); Naves, Perrottet, ibid. 24, 3 (1941).
 
Derivative Type: a-Vetivone
CAS Registry Number: 15764-04-2
CAS Name: (4R-cis)-4,4a,5,6,7,8-Hexahydro-4,4a-dimethyl-6-(1-methylethylidene)-2(3H)-naphthalenone
Additional Names: 4bH,5a-eremophila-1(10),7(11)-dien-2-one; isonootkatone
Literature References: Structure: Endo, DeMayo, Chem. Commun. 1967, 89; Marshall, Andersen, Tetrahedron Lett. 1967, 1611. Total syntheses of the racemate: Marshall et al., Chem. Commun. 1967, 753; Marshall, Warne, J. Org. Chem. 36, 178 (1971); Vandergen et al., Rec. Trav. Chim. 90, 1034, 1045 (1971); Dastur, J. Am. Chem. Soc. 96, 2605 (1974).
Properties: Crystals from pentane, strong agreeable odor. mp 51.5° (Naves, Perrottet); mp of racemate 30-35° (Marshall, Andersen). nD20 1.5384. [a]D20 +248° (chloroform). d420 1.003 (liquid, supercooled). uv max (ethanol): 233 nm (e 13200).
Melting point: mp 51.5° (Naves, Perrottet); mp of racemate 30-35° (Marshall, Andersen)
Optical Rotation: [a]D20 +248° (chloroform)
Index of refraction: nD20 1.5384
Absorption maximum: uv max (ethanol): 233 nm (e 13200)
Density: d420 1.003 (liquid, supercooled)
 
Derivative Type: b-Vetivone
CAS Registry Number: 18444-79-6
CAS Name: (5R-cis)-6,10-Dimethyl-2-(1-methylethylidene)spiro[4.5]dec-6-en-8-one
Additional Names: 2-isopropylidene-6,10-dimethylspiro[4.5]dec-6-en-8-one
Literature References: Structure: Marshall et al., J. Am. Chem. Soc. 89, 2748, 2750 (1967). Syntheses of racemate: Marshall, Johnson, Chem. Commun. 1968, 391; eidem, J. Org. Chem. 35, 192 (1970); K. Uneyama et al., Chem. Lett. 1977, 493; S. Torii et al., Bull. Chem. Soc. Jpn. 51, 3590 (1978); E. Wenkert et al., J. Am. Chem. Soc. 100, 1267 (1978). Stereospecific synthesis of (-)-b-vetivone: Deighton et al., Chem. Commun. 1975, 662; M. Asaoka et al., Chem. Lett. 1988, 1225.
Properties: Crystals from pentane, mp 44-46°. d420 1.000 (liquid, supercooled). d445 0.9804. [a]D20 -38.9° (c = 10 in alcohol). nD20 1.5309 (liquid, supercooled), nD45 1.5216.
Melting point: mp 44-46°
Optical Rotation: [a]D20 -38.9° (c = 10 in alcohol)
Index of refraction: nD20 1.5309 (liquid, supercooled); nD45 1.5216
Density: d420 1.000 (liquid, supercooled); d445 0.9804
 
Use: Of potential interest in the perfume industry.

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