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 Number	3691-12-1 (α) ; 88-84-6 (β) ; 3691-11-0 (δ) ;
3D model (JSmol)	(α): Interactive image; (β): Interactive image; (δ): Interactive image;
ChemSpider	4476575 (α) ; 16736689 (β) ; 85080 (δ) ;
PubChem CID	5317844 (α); 15560252 (β); 94275 (δ);
UNII	1D018Q907T (β) ;
	InChI (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;
	SMILES (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
Chemical formula	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]

References

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): 54–61. Cite journal requires |journal= (help)
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

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[thegoodscentscompany-1] 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 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

Guaiene

See also

References