Damascenone

• CAT Number: R064347
• CAS Number: 23696-85-7
• Molecular Formula: C13H18O
• Molecular Weight: 190.286
• Purity: ≥95%
• Storage: Store at +4C
• IUPAC Name: (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one
• 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+
• InChIKey: POIARNZEYGURDG-FNORWQNLSA-N
• SMILES: CC=CC(=O)C1=C(C=CCC1(C)C)C

Damascenone (CAS 23696-85-7) belongs to the class of organic compounds known as enones.  It has a role as a fragrance, a volatile oil component and a plant metabolite. It is also an apo carotenoid monoterpenoid and a cyclic monoterpene ketone. The damascenones are derived from the degradation of carotenoids.

Reference

1. Food Chem Toxicol. 2007;45 Suppl 1:S172-8. doi: 10.1016/j.fct.2007.09.056. Epub 2007 Sep 14.Fragrance material review on damascenone.Lapczynski A(1), Lalko J, McGinty D, Bhatia S, Letizia CS, Api AM.A toxicologic and dermatologic review of damascenone when used as a fragrance ingredient is presented.

 

2. J Agric Food Chem. 2011 Feb 23;59(4):1338-43. doi: 10.1021/jf103741n. Epub 2011 Jan 21.Formation of Damascenone under both commercial and model fermentation conditions.Lloyd ND(1), Capone DL, Ugliano M, Taylor DK, Skouroumounis GK, Sefton MA, Elsey GM.


The fermentations, at a commercial winery, of six different grape musts encompassing the varieties Riesling, Chardonnay, Sauvignon blanc, Shiraz, Grenache, and Pinot noir were monitored for damascenone concentration. In every case, the concentration of damascenone increased during fermentation from low or undetectable levels to concentrations of several parts per billion. Further increases in damascenone concentration were observed during barrel aging of three of these wines. Two ketones, megastigma-4,6,7-triene-3,9-dione (4) and 3-hydroxymegastigma-4,6,7-trien-9-one (5), were synthesized and subjected to fermentation conditions using two yeasts, AWRI 796, and AWRI 1537. In the case of the former compound, 4, synthesis confirmed the original, tentative assignment of the structure and confirmed 4 as a natural product, isolated from honey. Both compounds, under the action of both yeasts, produced appreciable amounts of damascenone (1), with ketone 5 and AWRI 796 yeast yielding the highest concentration of 1.

3. Isoe, Sachihiko, Shigeo Katsumura, and Takeo Sakan. "The Synthesis of Damascenone and β‐Damascone and the possible mechanism of their formation from carotenoids." Helvetica Chimica Acta 56.5 (1973): 1514-1516.