Damascone

Damascones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascones belong to a family of chemicals known as rose ketones, which also includes damascenones and ionones. beta-Damascone is a contributor to the aroma of roses, despite its relatively low concentration, and is an important fragrance chemical used in perfumery.[2]

Not to be confused with Damascenone.
beta-Damascone[1]
Names
IUPAC name
(E)-1-(2,6,6-Trimethyl-1-cyclohexenyl)but-2-en-1-one
Other names
Rose ketones
Identifiers
3D model (JSmol)
3DMet
ChemSpider
ECHA InfoCard 100.041.660
EC Number
  • 245-842-1
UNII
  • InChI=1S/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7H,6,8-9H2,1-4H3/b7-5+ ☒N
    Key: BGTBFNDXYDYBEY-FNORWQNLSA-N ☒N
  • InChI=1/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7H,6,8-9H2,1-4H3/b7-5+
    Key: BGTBFNDXYDYBEY-FNORWQNLBE
  • O=C(/C1=C(/CCCC1(C)C)C)/C=C/C
Properties
C13H20O
Molar mass 192.30 g/mol
Density 0.934 g/mL
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H315, H317, H411
P261, P264, P272, P273, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P391, P501
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
alpha-Damascone
Names
IUPAC name
(E)-1-(2,6,6-trimethyl-1-cyclohex-2-enyl)but-2-en-1-one
Other names
Rose ketones
Identifiers
3D model (JSmol)
3DMet
2208707
ChEBI
ChemSpider
ECHA InfoCard 100.041.660
EC Number
  • InChI=1S/C13H20O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5,7-8,12H,6,9H2,1-4H3/b7-5+
    Key: CRIGTVCBMUKRSL-FNORWQNLSA-N
  • C/C=C/C(=O)C1C(=CCCC1(C)C)C
Properties
C13H20O
Molar mass 192.302 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation markGHS09: Environmental hazard
Warning
H302, H317, H411
P261, P264, P270, P272, P273, P280, P301+P312, P302+P352, P321, P330, P333+P313, P363, P391, P501
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

The damascones are derived from the degradation of carotenoids.[3][4]

See also

References
  1. β-Damascone at Sigma-Aldrich
  2. Rose (Rosa damascena), John C. Leffingwell
  3. Biogeneration of C13-norisoprenoid compounds: experiments supportive for an apo-carotenoid pathway in grapevines. R. Baumes, J. Wirth, S. Bureau, Y. Gunata and A. Razungles, Analytica Chimica Acta, 29 April 2002, Volume 458, Issue 1, pages 3–14, doi:10.1016/S0003-2670(01)01589-6
  4. Volatile Compounds Released by Enzymatic Hydrolysis of Glycoconjugates of Leaves and Grape Berries from Vitis vinifera Muscat of Alexandria and Shiraz Cultivars. Jérémie Wirth, Wenfei Guo, Raymond Baumes and Ziya Günata, J. Agric. Food Chem., 2001, 49 (6), pages 2917–2923, doi:10.1021/jf001398l

Further reading
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