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9-DECEN-1-OL

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CAS:13019-22-2
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9-DECEN-1-OL Basic information
Aroma
Product Name:9-DECEN-1-OL
Synonyms:ROSALVA;Dec-9-en-1-ol;Decylenic alcohol;decylenicalcohol;omega-Decen-1-ol;omega-Decenol;1-Decen-10-ol;9-Decenol
CAS:13019-22-2
MF:C10H20O
MW:156.27
EINECS:235-878-6
Product Categories:omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;omega-Unsaturated Alkanols;Acyclic;Alkenes;Organic Building Blocks
Mol File:13019-22-2.mol
9-DECEN-1-OL Structure
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.)
Fp 210 °F
storage temp. Sealed in dry,Room Temperature
solubility Chloroform
form Liquid
pka15.20±0.10(Predicted)
color Orange-red to red
Odorat 10.00 % in dipropylene glycol. dewy rose waxy fresh clean aldehydic
Odor Typefloral
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 FunctionsFRAGRANCE
PERFUMING
InChI1S/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h2,11H,1,3-10H2
InChIKeyQGFSQVPRCWJZQK-UHFFFAOYSA-N
SMILESOCCCCCCCCC=C
LogP3.9 at 40℃
CAS DataBase Reference13019-22-2(CAS DataBase Reference)
EPA Substance Registry System9-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
Storage Class11 - Combustible Solids
Hazard ClassificationsEye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
ALFA English
9-DECEN-1-OL Usage And Synthesis
AromaPowerful, 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 Properties9-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 properties9-DECEN-1-OL is colorless oily Iiquid. Practically insoluble in water, soluble in alcohol and oils.
OccurrenceApparently has not been reported to occur in nature.
UsesIt 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.
Uses9-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.
PreparationFrom 1,10-decamethylene glycol (Arctander, 1969).
DefinitionChEBI: 9-Decen-1-ol is an aliphatic alcohol.
General Description9-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 nameRosalva (IFF), Trepanol® (Takasago).
SynthesisThe 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.
9-DECEN-1-OL
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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