Guaiene

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

CAS Registry Number

3691-12-1 (α)^N
88-84-6 (β)^Y
3691-11-0 (δ)^Y

ChemSpider

4476575 (α)^N
16736689 (β)^N
85080 (δ)^N

InChI

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 (α)
Key: ADIDQIZBYUABQK-RWMBFGLXSA-N
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 (β)
Key: GIBQERSGRNPMEH-RYUDHWBXSA-N
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 (δ)
Key: YHAJBLWYOIUHHM-GUTXKFCHSA-N

Jmol-3D images

Image

(α)
Image (β)
Image (δ)

PubChem

5317844 (α)
15560252 (β)
94275 (δ)

SMILES

C[C@H]1CCC2=C1C[C@H](C(C)=C)CC[C@@H]2C (α)
C[C@H]1CCC2=C1C/C(CC[C@@H]2C)=C(C)\C (β)
C[C@H]1CCC2=C(C)CC[C@@H](C(C)=C)C[C@]21[H] (δ)

Properties

Molecular formula

C₁₅H₂₄

Molar mass

204.35 g·mol⁻¹

Boiling point

α: 281-282 °C^[1]
α: 78-79 °C (@ 2.5 Torr)^[2]
β: 281 °C^[3]

Except where noted otherwise, data is 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]

References

↑ 1.0 1.1 Alpha-guaiene, The Good Scents Company
↑ Takeda, Kenichi (1961). "Studies on sesquiterpenoids—III, Some derivatives of guaiol". Tetrahedron 13 (4): 308–318. doi:10.1016/S0040-4020(01)92224-0.
↑ Won, Mi-Mi (2009). "Analytica Chimica Acta" 631 (1). pp. 54–61.
↑ Bates, R. B.; Slagel, R. C. (1962). "Terpenoids. VI. β-Bulnesene, α-guaiene, β-patchoulene, and guaioxide in essential oils". Chemistry & Industry: 1715–1716.
↑ Guaiene, Joint FAO/WHO Expert Committee on Food Additives

Guaiene

See also

References