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Guaiene information


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) checkY
  • 88-84-6 (β) checkY
  • 3691-11-0 (δ) checkY
3D model (JSmol)
  • (α): Interactive image
  • (β): Interactive image
  • (δ): Interactive image
ChemSpider
  • 4476575 (α) ☒N
  • 16736689 (β) ☒N
  • 85080 (δ) ☒N
PubChem CID
  • 5317844 (α)
  • 15560252 (β)
  • 94275 (δ)
UNII
  • ABQ2CB7VAC (α) ☒N
  • 1D018Q907T (β) ☒N
  • 2U8L6FYE8U (δ) ☒N
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).
☒N verify (what is checkY☒N ?)
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]

  1. ^ a b 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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Guaiene

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Guaienes are a series of closely related natural chemical compounds that have been isolated from a variety of plant sources. The guaienes are sesquiterpenes...

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Oil of guaiac

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primarily composed of 42–72% guaiol, bulnesol, δ-bulnesene, β-bulnesene, α-guaiene, guaioxide and β-patchoulene. It is considered non-irritating, non-sensitizing...

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Salvia leucantha

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found it to be rich in the sesquiterpene hydrocarbons ; β-caryophyllene, α-guaiene, cis-muurola-3,5-diene, germacrene D, and bicyclogermacrene. Bornyl acetate...

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Lippia alba

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caryophyllene, camphor, eucalyptol, limonene, carvone, germacrene, α-guaiene, β-ocimene, linalool, or myrcene. The leaves are used for flavoring foods...

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C15H24

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Humulene Zingiberene Amorpha-4,11-diene Aristolochene Cadinene Caryophyllene Guaiene Selinene Thujopsene Valencene Capnellene Cedrene Copaene Cubebene Gurjunene...

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Vitex negundo

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constituents of the oil are sabinene, linalool, terpinen-4-ol, β-caryophyllene, α-guaiene and globulol constituting 61.8% of the oil.[citation needed] Purified extracts...

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Terpene

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acetate α-Ylangene α-Copaene Aromadendrene Eremophilene Longifolene β-Guaiene Valencene β-Bisabolene γ-Cadinene β-Selinene Neophytadiene Ferruginol Aristolone...

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Hash oil

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terpinolene, and terpineol. Sesquiterpenes (~ 5%): β-caryophyllene, humulene, δ-guaiene, γ-cadinene, eudesma-3,7(11)-diene, and elemene. The hash oils made in...

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Guaiol

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a deep purple color when treated with electrophilic bromine reagents. Guaiene The Merriam-Webster Dictionary. Wolfram Alpha Guaiol Hillig, Karl W (2004-10-01)...

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Longifolene

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acetate α-Ylangene α-Copaene Aromadendrene Eremophilene Longifolene β-Guaiene Valencene β-Bisabolene γ-Cadinene β-Selinene Neophytadiene Ferruginol Aristolone...

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Valencene

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Hypericum hircinum

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the flowers are monoterpenes. Some dominant compounds of the oil include guaiene, selinene, limonene, and pinene. The most active and useful oil components...

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Cryptocarya agathophylla

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Cajanus scarabaeoides

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and compared with that of cultivated pigeonpea. The β-carophyllene and guaiene that is emitted from cultivated pigeonpea, which attracts H. armigera,...

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Cucurbitane

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Selinum carvifolia

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in Bosnia and Croatia. Selinum carvifolia has been found to contain a guaiene, certain trimethylbenzaldehydes (see also pages aldehyde and benzaldehyde)...

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