Damascenone

*beta*-Damascenone
Names
	IUPAC name (E)-1-(2,6,6-Trimethyl-1-cyclohexa-1,3-dienyl)but-2-en-1-one
Identifiers
CAS Number	23726-93-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:67251 ;
ChemSpider	4517997 ;
ECHA InfoCard	100.041.662
PubChem CID	5366074;
CompTox Dashboard (EPA)	DTXSID90885242 ;
	InChI InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ Key: POIARNZEYGURDG-FNORWQNLSA-N ; InChI=1/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ Key: POIARNZEYGURDG-FNORWQNLBV;
	SMILES O=C(\C1=C(\C=C/CC1(C)C)C)/C=C/C;
Properties
Chemical formula	C13H18O
Molar mass	190.28 g/mol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Damascenones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascenones belong to a family of chemicals known as rose ketones, which also includes damascones and ionones. beta-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery.^[1]

The damascenones are derived from the degradation of carotenoids.^[2]

In 2008, (E)-β-damascenone was identified as a primary odorant in Kentucky Bourbon.^[3]

Biosynthesis

References

^ Rose (Rosa damascena), John C. Leffingwell
^ Sachihiko Isoe; Shigeo Katsumura; Takeo Sakan (1973). "The Synthesis of Damascenone and beta-Damascone and the possible mechanism of their formation from carotenoids". Helvetica Chimica Acta. 56 (5): 1514–1516. doi:10.1002/hlca.19730560508.
^ LUIGI POISSON; PETER SCHIEBERLE (2008). "Characterization of the Most Odor-Active Compounds in an American Bourbon Whisky by Application of the Aroma Extract Dilution Analysis". J. Agric. Food Chem. 56 (14): 5813–5819. doi:10.1021/jf800382m.

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[1] Rose (Rosa damascena), John C. Leffingwell

[2] Sachihiko Isoe; Shigeo Katsumura; Takeo Sakan (1973). "The Synthesis of Damascenone and beta-Damascone and the possible mechanism of their formation from carotenoids". Helvetica Chimica Acta. 56 (5): 1514–1516. doi:10.1002/hlca.19730560508.

[3] LUIGI POISSON; PETER SCHIEBERLE (2008). "Characterization of the Most Odor-Active Compounds in an American Bourbon Whisky by Application of the Aroma Extract Dilution Analysis". J. Agric. Food Chem. 56 (14): 5813–5819. doi:10.1021/jf800382m.

[1]

[2]

[3]

Biosynthesis

See also

References