Damascone

beta-Damascone[1]
Names
IUPAC name
(E)-1-(2,6,6-Trimethyl-1-cyclohexenyl)but-2-en-1-one
Other names
Rose ketones
Identifiers
CAS Number
  • 23726-91-2 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • L01258
ChemSpider
  • 4524302 ☒N
ECHA InfoCard 100.041.660 Edit this at Wikidata
EC Number
  • 245-842-1
PubChem CID
  • 5374527
UNII
  • I75J0X33Q6 checkY
CompTox Dashboard (EPA)
  • DTXSID7051890 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C13H20O
Molar mass 192.30 g/mol
Density 0.934 g/mL
Hazards
GHS labelling:
Pictograms
 GHS07: Exclamation markGHS09: Environmental hazard
Warning
Hazard statements
 H315, H317, H411
Precautionary statements
 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
Chemical compound
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
CAS Number
  • 24720-09-0 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • L01257
2208707
ChEBI
  • CHEBI:53220
ChemSpider
  • 4518000
ECHA InfoCard 100.041.660 Edit this at Wikidata
EC Number
  • 246-430-4 correct ECHA infocard 100.042.195
  • 5366077
  • DTXSID8051912
  • 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
Chemical compound

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]

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

  • Charles S. Sell. (2003). A fragrant introduction to terpenoid chemistry. Cambridge: RSC, Royal Society of Chemistry. pp. 256–257. ISBN 978-0-85404-681-2.
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