13019-22-2

9-Decen-1 (cipher)-ol has been identified as a trace constituent of cognac. It is a colorless liquid with a fresh, dewy, rose note that can be prepared by partial dehydration of 1,10-decanediol. It is used in rosy, floral soap perfumes.

colourless liquid

9-DECEN-1-OL is colorless oily Iiquid. Practically insoluble in water, soluble in alcohol and oils.

Apparently has not been reported to occur in nature.

It finds it uses in a wide range of fragrances, especially in fine fragrances and soaps, in floral, rose petal or herbal fragrances. 9-Decen-1-ol is used in the preparation of semifluorinated acids required for the synthesis of poly(styrene-b-semi fluorinated isoprene) block copolymers with -CF2H-terminated side groups.

ChEBI: 9-Decen-1-ol is an aliphatic alcohol.

From 1,10-decamethylene glycol (Arctander, 1969).

Rosalva (IFF), Trepanol® (Takasago).

The synthesis of 9-decenol was conducted in three phases, and undecylenic acid was used as initial substance in this synthetic procedure. The key phase in this synthesis is the oxidative decarboxylation of undecylenic acidup to 9-decyl-chloride, as shown on the scheme.

In a round flask of 50ml, equipped with reverse condenser and a magnetic mixer, 1.9g (0.01mol) of 9-decenyl-acetate is placed, 0.56g (0.01 mol) of potassiumhydroxide, 3ml H2O and 2ml of methanol. The mixture is heated and left to boil for 1- 2 hours on the oil bath. After the completion of the reaction, the solution is cooled down, 3ml of water is added and the then it is acidified with diluted hydrochloric acid. The organic layer is extracted with ether and left to dry with anhydrous sodium-sulfate. Ether and methanol are separated with normal pressure distillation, and the rest of the solution is distilled under the lowered pressure. Unsaturated alcohol, 9-decenol (4) is distilled at T=155℃ or at 120℃  under the pressure of 533.289 Pa. The obtained 9-decenol is 1.575g (86%) in comparison to the used ether, that is 30.48% in comparison to the initial undecylenic acid.^[1]

[1] SUNCICA JOVIC  Lidija J S. Synthesis of 9-decen-1-ol[J]. Journal of Process Management New Technologies, 2018, 6 1: 27-31. DOI:10.5937/JOUPROMAN6-16258.