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[1]
α: 78-79 °C (@ 2.5 Torr)[2]
β: 281 °C[3]
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

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.[4] The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.[1][5]

See also

References

  1. 1 2 Alpha-guaiene, The Good Scents Company
  2. ↑ Takeda, Kenichi (1961). "Studies on sesquiterpenoids—III, Some derivatives of guaiol". Tetrahedron. 13 (4): 308–318. doi:10.1016/S0040-4020(01)92224-0.
  3. ↑ Won, Mi-Mi (2009). "Analytica Chimica Acta". 631 (1): 54–61. {{cite journal}}: Cite journal requires |journal= (help)
  4. ↑ Bates, R. B.; Slagel, R. C. (1962). "Terpenoids. VI. β-Bulnesene, α-guaiene, β-patchoulene, and guaioxide in essential oils". Chemistry & Industry: 1715–1716.
  5. ↑ Guaiene, Joint FAO/WHO Expert Committee on Food Additives
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