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Updating {{chembox}} (changes to verified fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation]...
m Added Missing UNIIs, not yet published
 
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{{Chembox
{{Chembox
| Verifiedfields = changed
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459443626
| verifiedrevid = 459443626
| Name = Guaienes
| Name = Guaienes
| ImageFileL1 = Alpha-guaiene.svg
| ImageFileL1 = Alpha-guaiene.svg
⚫
| ImageCaptionL1 = α-Guaiene
| ImageSizeL1 = 100px
⚫
| ImageCaptionL1 = α-Guaiene
| ImageFileR1 = Beta-guaiene.svg
| ImageFileR1 = Beta-guaiene.svg
⚫
| ImageCaptionR1 = β-Guaiene
| ImageSizeR1 = 100px
⚫
| ImageCaptionR1 = β-Guaiene
| ImageFile2 = Delta-guaiene.svg
| ImageFile2 = Delta-guaiene.svg
| ImageSize2 = 100px
| ImageSize2 = 100px
| ImageCaption2 = δ-Guaiene
| ImageCaption2 = δ-Guaiene
| IUPACName = α: (1''S'',4''S'',7''R'')-1,4-Dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene<br>β: (1''S'',4''S'')-1,4-Dimethyl-7-(propan-2-ylidene)-1,2,3,4,5,6,7,8-octahydroazulene<br>δ: (3''S'',3a''S'',5''R'')-3,8-Dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene
| IUPACName = α: (1''S'',4''S'',7''R'')-1,4-Dimethyl-7-(prop-1-en-2-yl)-1,2,3,4,5,6,7,8-octahydroazulene<br>β: (1''S'',4''S'')-1,4-Dimethyl-7-(propan-2-ylidene)-1,2,3,4,5,6,7,8-octahydroazulene<br>δ: (3''S'',3a''S'',5''R'')-3,8-Dimethyl-5-(prop-1-en-2-yl)-1,2,3,3a,4,5,6,7-octahydroazulene
| IUPACName_hidden = yes
| OtherNames = Guajene
| OtherNames = Guajene
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
⚫
| CASNo_Ref = {{cascite|correct|}}
| CASNo = 3691-12-1
| CASNo = 3691-12-1
⚫
| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Comment = (α)
| CASNo_Comment = (α)
⚫
| CASNo1_Ref = {{cascite|correct|}}
| CASNo1 = 88-84-6
| CASNo1 = 88-84-6
⚫
| CASNo1_Ref = {{cascite|correct|}}
| CASNo1_Comment = (β)
| CASNo1_Comment = (β)
⚫
| CASNo2_Ref = {{cascite|correct|}}
| CASNo2 = 3691-11-0
| CASNo2 = 3691-11-0
⚫
| CASNo2_Ref = {{cascite|correct|}}
| CASNo2_Comment = (δ)
| CASNo2_Comment = (δ)
| UNII_Ref = {{fdacite|changed|FDA}}
⚫
| PubChem =
| UNII = ABQ2CB7VAC
⚫
| SMILES = C[C@H]1CCC2=C1C[C@H](C(C)=C)CC[C@@H]2C
| SMILES_Comment = (α)
| UNII_Comment = (α)
| UNII1_Ref = {{fdacite|changed|FDA}}
⚫
| SMILES1 = C[C@H]1CCC2=C1C/C(CC[C@@H]2C)=C(C)\C
| UNII1 = 1D018Q907T
⚫
| SMILES1_Comment = (β)
| UNII1_Comment = (β)
⚫
| SMILES2 = C[C@H]1CCC2=C(C)CC[C@@H](C(C)=C)C[C@]21[H]
| UNII2_Ref = {{fdacite|changed|FDA}}
⚫
| SMILES2_Comment = (δ)
| UNII2 = 2U8L6FYE8U
| UNII2_Comment = (δ)
⚫
| PubChem = 5317844
| PubChem_Comment = (α)
| PubChem1 = 15560252
| PubChem1_Comment = (β)
| PubChem2 = 94275
| PubChem2_Comment = (δ)
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4476575
| ChemSpiderID_Comment = (α)
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 16736689
| ChemSpiderID1_Comment = (β)
| ChemSpiderID2_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID2 = 85080
| ChemSpiderID2_Comment = (δ)
⚫
| SMILES = C[C@H]1CCC2=C1C[C@H](C(C)=C)CC[C@@H]2C
| SMILES_Comment = (α)
⚫
| SMILES1 = C[C@H]1CCC2=C1C/C(CC[C@@H]2C)=C(C)\C
⚫
| SMILES1_Comment = (β)
⚫
| SMILES2 = C[C@H]1CCC2=C(C)CC[C@@H](C(C)=C)C[C@]21[H]
⚫
| SMILES2_Comment = (δ)
| 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
| InChI_Comment = (α)
| InChIKey = ADIDQIZBYUABQK-RWMBFGLXSA-N
| InChI1 = 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
| InChI1_Comment = (β)
| InChIKey1 = GIBQERSGRNPMEH-RYUDHWBXSA-N
| InChI2 = 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
| InChI2_Comment = (δ)
| InChIKey2 = YHAJBLWYOIUHHM-GUTXKFCHSA-N
}}
}}
| Section2 = {{Chembox Properties
|Section2={{Chembox Properties
| C=15|H=24
| C=15 | H=24
| Appearance =
| Appearance =
| Density =
| Density =
| MeltingPt =
| MeltingPt = α: 281-282 °C<ref name=thegoodscentscompany>[http://www.thegoodscentscompany.com/data/rw1054351.html Alpha-guaiene], The Good Scents Company</ref><br>α: 78-79 °C (@ 2.5 Torr)<ref>{{cite journal | author = Takeda, Kenichi | journal = Tetrahedron | year = 1961 | volume = 13 | pages = 308–318 | doi = 10.1016/S0040-4020(01)92224-0 | title = Studies on sesquiterpenoids—III, Some derivatives of guaiol | issue = 4}}</ref><br>β: 281 °C<ref>{{cite journal | author = Won, Mi-Mi | title = Analytica Chimica Acta | year = 2009 | volume = 631 | issue = 1 | pages = 54–61}}</ref>
| BoilingPt = α: 281-282 °C<ref name=thegoodscentscompany>[http://www.thegoodscentscompany.com/data/rw1054351.html Alpha-guaiene], The Good Scents Company</ref><br>α: 78-79 °C (@ 2.5 Torr)<ref>{{cite journal | author = Takeda, Kenichi | journal = Tetrahedron | year = 1961 | volume = 13 | pages = 308–318 | doi = 10.1016/S0040-4020(01)92224-0 | title = Studies on sesquiterpenoids—III, Some derivatives of guaiol | issue = 4}}</ref><br>β: 281 °C<ref>{{cite journal | author = Won, Mi-Mi | title = Analytica Chimica Acta | year = 2009 | volume = 631 | issue = 1 | pages = 54–61}}</ref>
| BoilingPt =
| Solubility = }}
| Solubility = }}
| Section3 = {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards =
| MainHazards =
| FlashPt =
| FlashPt =
| Autoignition = }}
| AutoignitionPt = }}
}}
}}


⚫
'''Guaienes''' are a series of closely related natural chemical compounds that have been isolated from a variety of plant sources. The guaienes are [[sesquiterpene]]s with the molecular formula C<sub>15</sub>H<sub>24</sub>. α-Guaiene is the most common and was first isolated from [[Oil of guaiac|guaiac wood oil]] from ''[[Bulnesia sarmientoi]]''.<ref>{{cite journal |author1=Bates, R. B. |author2=Slagel, R. C. | title = Terpenoids. VI. β-Bulnesene, α-guaiene, β-patchoulene, and guaioxide in essential oils | journal = Chemistry & Industry | year = 1962 | pages = 1715–1716}}</ref> The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.<ref name=thegoodscentscompany/><ref>[http://www.fao.org/ag/agn/agns/jecfa_index_en.asp Guaiene], Joint FAO/WHO Expert Committee on Food Additives</ref>


==See also==
⚫
'''Guaienes''' are a series of closely related natural chemical compounds that have been isolated from a variety of plant sources. The guaienes are [[sesquiterpene]]s with the molecular formula C<sub>15</sub>H<sub>24</sub>. α-Guaiene is the most common and was first isolated from [[Oil of guaiac|guaiac wood oil]] from ''[[Bulnesia sarmientoi]]''.<ref>{{cite journal | author = Bates, R. B.; Slagel, R. C. | title = Terpenoids. VI. β-Bulnesene, α-guaiene, β-patchoulene, and guaioxide in essential oils | journal = Chemistry & Industry | year = 1962 | pages = 1715–1716}}</ref> The guaienes are used in the fragrance and flavoring industries to impart earthy, spicy aromas and tastes.<ref name=thegoodscentscompany/><ref>[http://www.fao.org/ag/agn/agns/jecfa_index_en.asp Guaiene], Joint FAO/WHO Expert Committee on Food Additives</ref>
* [[Guaiol]]


==References==
==References==

Latest revision as of 20:46, 20 December 2021

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).
☒N verify (what is checkY☒N ?)

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

[edit]

References

[edit]
  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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