9-DECEN-1-OL Chemical Properties

Melting point:

-13 °C

Boiling point:

234-238 °C(lit.)

Density 

0.876 g/mL at 25 °C(lit.)

vapor pressure 

5Pa at 20℃

refractive index 

n20/D 1.447(lit.)

Flash point:

210 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform

form 

Liquid

pka

15.20±0.10(Predicted)

color 

Orange-red to red

Odor

at 10.00 % in dipropylene glycol. dewy rose waxy fresh clean aldehydic

Odor Type

floral

Water Solubility 

Soluble in water at 20°C 0.16g/L. Soluble in alcohol, dipropylene glycol, paraffin oil.

BRN 

1750928

Stability:

Stable. Combustible. Incompatible with strong oxidizing agents.

Cosmetics Ingredients Functions

FRAGRANCE
PERFUMING

LogP

3.9 at 40℃

CAS DataBase Reference

13019-22-2(CAS DataBase Reference)

EPA Substance Registry System

9-Decen-1-ol (13019-22-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

2

RTECS 

HE2095000

Hazard Note 

Irritant

TSCA 

TSCA listed

HS Code 

2905299090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

9-DECEN-1-OL Usage And Synthesis

Aroma

Powerful, fatty-oily, waxy-rosy odor of considerable tenacity. The rosy notes are particularly conspicuous in dilutions, best at 1% or lower, while higher concentrations bring about more waxy-oily notes.

Chemical Properties

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.

Physical properties

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

Occurrence

Apparently has not been reported to occur in nature.

Uses

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.

Uses

9-Decen-1-ol was used in the preparation of semifluorinated acids required for the synthesis of poly(styrene-b-semifluorinated isoprene) block copolymers with -CF₂H-terminated side groups.

Definition

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

Preparation

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

General Description

9-Decen-1-ol undergoes oxidation to give 9-decenoic in aqueous media (dioxane–water mixtures) in the presence of supported palladium or platinum catalysts.

Trade name

Rosalva (IFF), Trepanol® (Takasago).

Synthesis

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]

References

[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.

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