Alpha and beta damascone

Greetings! Apparently, many of us like to aromatize ourselves especially ladies! Perfume (as according to thefreedictionary.com) is a substance that emits and diffuses a fragrant odor, especially a volatile liquid distilled from flowers or prepared synthetically and also a pleasing, agreeable scent or odor.

Perfume = Fragrance

So what actually perfumes you and I?

They are alpha and beta damascone, hedione, alpha and beta santatol which are some of the most important fragrance ingredients.

 They are all organic molecules and we love organic chemistry. Well,  let’s look into the first one, alpha and beta damascone.

With the suffix that ends with –one, it must be from a ketone family. Alpha and beta damascone are rose ketones derived from the Bulgarian rose oil. 

Molecules	Alpha damascone	Beta damascone
Structural formula
IUPAC name	1-(2,6,6-trimethyl-2-cyclohexene-1-yl)-but-2-ene-1-one	(E)-1-(2,6,6-trimethyl-1-cyclohexenyl)but-2-en-1-one
Empirical formula	C13H20O	C13H20O
Scent	a strong rose odor with a pronounced fruity green apples scent	A complex odour of rose, plum, blackcurrent, wine and tobacco
Solubility	Soluble in alcohol	Soluble in alcohol

What are the Uses of these damascones?

They are used in alcoholic solution, antiperspirant cream. Deodorant spray, shampoo, and soap. α-Damascone (rose -apple note) is highly effective in enriching odor of natural as well as artificial aromas. It is used to add a sweet floral woody odor with green berry undertones. Beta damascone emits a fruity floral blackcurrant plum rose honey tobacco. Beta-damascenone and Beta-damascone (blackcurrent- plum note) remain two of the most important  fragrance ingredients.

Ever wondered how are these damascone being synthesized?

One of the examples are preparing 1-(2,6,6-trimethyl-2-cyclohexene-1-yl)-but-2-ene-1-one ( alpha damascone) from 2,6,6 – trimethyl-1-cyclohexene.

2,6,6 – trimethyl-1-cyclohexene is added to the stirred suspension that consists of:

cyclohexane   

+    ZnCI        +

Crotonic anhydride

Cyclohexane- (100ml) + ZnCI (20gms) + (crotonic anhydride 150gms) for 45 minutes at 80 C. The mixture is cooled to room temperature and  (aq, 500 ml of 5%) is poured into the mixture.  The cyclohexane layer containing the product (II) is separated and washed with water to make it neutral. The organic layer is dried over with Na2SO4  followed by filtration and distillation under atmospheric pressure which is further fractionally distilled to obtain alpha damascone  (70 gms) and a purity of 95%.

alpha damascone

Who was one of the 1st fragrances to incorporate damascones into its rose veiled structure?

NahemaHYPERLINK "http://boisdejasmin.com/2005/05/nahema.html" by HYPERLINK "http://boisdejasmin.com/2005/05/nahema.html"Guerlain (1979) was one of the first fragrances to incorporate damascones into its rose veiled structure. Damascones decorate the rose notes in the way that gold jewelry enhances the beauty of princesses from the Arabian Nights tales by which Nahema was inspired. Indeed, one of the biggest successes of the 1980s was another damascone overdosed creation, Christian Dior Poison (1985). While alpha-damascone is fruity and floral, with a distinct camphorous element, beta-damascone can be described as gourmand, with floral and tobacco-like aspects. Its honeyed plum facet complements the spicy heart of Poison, while offering a beautiful sweet prelude to the ambery base.                                                                      

References:

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http://www.prasadorganics.com/AlphaDamascone.html

http://boisdejasmin.com/2006/02/fragrance_ingre.html

http://www.thegoodscentscompany.com/data/rw1000881.htmlhttp://www.chemicalbook.com/ChemicalProductProperty_EN_CB6755373.htm