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Rose (Rosa damascena)

A Review by John C. Leffingwell, Ph.D.

This a part of our series on aroma materials produced by carotenoid degradation.

From the time of the Romans (and probably before) the aroma of the rose was valued for its fragrant perfume.

Chemists have known for over 100 years that the main constituent of Rose oil is citronellol, but it wasn't until work in the 1960's & 70's that the trace constituents so essential to a rose fragrance were reported. Of the more than 275 constituents of Bulgarian rose oil, Ohloff reviewed the aroma contribution of both major and minor components [Perfumer & Flavorist, 3, 1, 11-22 (1978); Ohloff, G.; Scent and Fragrances, The fascination of odors and their chemical perspectives; translated by W. Pickenhagen and B. Lawrence, Springer-Verlag, Pub., Berlin - Heidelberg;, 1994, pp. 154-158. ]. Utilizing the Odor unit concept of Guadagni, Buttery & Harris [J. Sci. Food. Agric., 17, 142-144 (1966)] in which an "Odor unit" value is assigned based on dividing the concentration of a component (in ppb) by the components detection threshold level ( in ppb), Ohloff calculated the relative odor contribution for both major and minor components:

Component
% of Oil
Threshold in ppb
Odor Units x 10-3
Rel. % of odor units

(-)-Citronellol

38
40
9500
4.3

C14 - C16 Paraffins

16
-
-
-

Geraniol

14
75
1860
0.8

Nerol

7
300
233
0.1

Phenethyl alcohol

2.8
750
37
0.016

Eugenol methyl ether

2.4
820
29
0.013

Eugenol

1.2
30
400
0.18

Farnesol

1.2
20
600
0.27

Linalool

1.4
6
2300
1.0

(-)-Rose oxide

0.46
0.5
9200
4.1

(-)-Carvone

0.41
50
82
0.036

Rose furan

0.16
200
8
0.003

beta-Damascenone

0.14
0.009
156000
70.0

beta-Ionone

0.03
0.007
42860
19.2

As should be noted, the minor constituents beta-damascenone and beta-ionone provide a significant majority of the odor contribution.

This research by Firmenich led to the discovery of the so-called Rose Ketones, beta-Damascenone and beta-Damascone (also a trace constituent), two of the most important fragrance & flavor chemicals of this century; both of which (along with beta-ionone), are derived from carotenoid degradation.

.

The importance of the rose ketones has allowed the creation of dramatically new type perfumes [as exemplified by by Diors "Poison" (1985)], wherein damascenone and the alpha- & beta-damascones may be used at quite high levels.

Although not a carotenoid degradation product, the terpenoid ether (Rose oxide) was another significant discovery from Firmenich that contributes to rose aroma. A discovery that warranted a USSR postage stamp.

 


Rose Oxide

 

Story of the Rose from Shiseido

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