Guaiene

Guaienes are a series of closely related natural chemical compounds that have been isolated from a variety of plant sources. The guaienes are sesquiterpenes with the molecular formula C15H24. α-Guaiene is the most common and was first isolated from guaiac wood oil from Bulnesia sarmientoi. The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.

Guaienes
α-Guaiene
β-Guaiene

δ-Guaiene
Names
IUPAC names
α: (1S,4S,7R)-1,4-Dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene
β: (1S,4S)-1,4-Dimethyl-7-(propan-2-ylidene)-1,2,3,4,5,6,7,8-octahydroazulene
δ: (3S,3aS,5R)-3,8-Dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene
Other names
Guajene
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • (α): InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+/m0/s1
    Key: ADIDQIZBYUABQK-RWMBFGLXSA-N
  • (β): InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h11-12H,5-9H2,1-4H3/t11-,12-/m0/s1
    Key: GIBQERSGRNPMEH-RYUDHWBXSA-N
  • (δ): InChI=1S/C15H24/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h12-13,15H,1,5-9H2,2-4H3/t12-,13+,15-/m0/s1
    Key: YHAJBLWYOIUHHM-GUTXKFCHSA-N
  • (α): C[C@H]1CCC2=C1C[C@H](C(C)=C)CC[C@@H]2C
  • (β): C[C@H]1CCC2=C1C/C(CC[C@@H]2C)=C(C)\C
  • (δ): C[C@H]1CCC2=C(C)CC[C@@H](C(C)=C)C[C@]21[H]
Properties
C15H24
Molar mass 204.357 g·mol−1
Boiling point α: 281-282 °C
α: 78-79 °C (@ 2.5 Torr)
β: 281 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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