Damascenone

Description

What is more evocative of Valentine’s Day than roses? But did you ever wonder about the compounds in roses that are responsible for the flower’s wonderful scent? Writing in the?Journal of Chemical Education?in 2011, Albrecht Mannschreck and Erwin von Angerer* at the University of Regensburg (Germany) gave a full accounting of roses’ aroma constituents.
According to the authors, geraniol, (–)-citronellol, and β-damascenone (Figures 1, 2, and 3, respectively) are three major components of rose scent. Geraniol is monoterpene alcohol that is a main ingredient of rose oil; it also is present in many other essential oils. It was first isolated by O. Jacobsen in 1871. Its structure is similar to that of nerol, also a rose scent ingredient.
Citronellol exists in nature as two enantiomers, designated (+) and (–). The (+)-isomer is more common and takes its name from citronella oils. The (–) isomer, however, is the one that occurs in the oils of roses and geraniums. The citronellols are also monoterpene alcohols; they are the hydrogenated forms of geraniol.
β-Damascenone is different: It belongs to a family of unsaturated ketones known as rose ketones. Its concentration in rose oil is very small, but it contributes significantly to the aroma.
All three of these compounds are articles of commerce as fragrance ingredients used by the perfume industry. So if you give your loved one perfume instead of roses for Valentine’s Day, she or he will likely get a whiff of one of them.

Occurrence

Reported found in raspberry oil, Burley tobacco, apple, lemon balm, summer savory, anise, hyssop, apple juice, cooked apple, apricot, sweet and sour cherry, black currant berries, fresh blackberry, strawberry jam, hop oil rum, white wine, red wine, black tea, tomato, rye bread, blue cheese, cow, goat and sheep milk, hop oil, beer, cognac, rum, whiskies, scotch, cider, grape wines, coffee, tea, popcorn, oatmeal, soybean, plum, prune, beans, starfruit, mango, tamarind, dill seed, corn oil, okra, cape gooseberry, anise hyssop and Roman chamomile oil.

The Uses of Damascenone

Damascenone is a fragrance ingredient that can be used in shampoos, fine fragrances, decorative cosmetics, toilet soaps as well as non-cosmetic products like household cleaners and detergents.

Preparation

By treating the corresponding ethyl safranate with allyl lithium, followed by catalytic isomerization of the reaction product; also from the oxirane derivative of β-damascone by an acid-catalyzed reaction.

Definition

ChEBI: Beta-damascenone is a cyclic monoterpene ketone that is 2,6,6-trimethylcyclohexa-1,3-diene substituted at position 1 by a crotonoyl group. It has a role as a fragrance, a volatile oil component and a plant metabolite. It is an enone, an apo carotenoid monoterpenoid and a cyclic monoterpene ketone.

Aroma threshold values

Detection: 0.0007 to 0.009 ppb. Aroma characteristics at 1.0%: sweet, brown woody, tobacco, davana-like fruity, with a spicy balsamic undernote.

Taste threshold values

Taste characteristics at 1 to 5 ppm: sweet brown, tea-like, davana dried fruity, with jamy berry, strawberry and raspberry nuances, woody, floral, herbal, green and fruity with spicy tobacco nuances.

General Description

Damascenone is a norisoprenoid ketone mainly found in red wines. It occurs naturally in tomato and grapes.

Biochem/physiol Actions

Taste at 1-5 ppm