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
3D model (Jmol)	Interactive image
ChemSpider	4524302
ECHA InfoCard	100.041.660
PubChem	5374527
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+ Key: BGTBFNDXYDYBEY-FNORWQNLSA-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
SMILES 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
R-phrases	R43
S-phrases	S36/37
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
CAS Number	24720-09-0
3D model (Jmol)	Interactive image
ECHA InfoCard	100.041.660
SMILES C/C=C/C(=O)C1/C(C)=C\CCC(C)(C)1
Properties
Chemical formula	C13H20O
Molar mass	192.30 g·mol^−1
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

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

• Rose oil

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.