3,7-dimethyloct-6-en-1-yn-3-ol Property

Boiling point:

198 °C

Density 

0.879 at 20℃

vapor pressure 

3.8Pa at 25℃

refractive index 

1.46

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Oil

pka

13.29±0.29(Predicted)

color 

Clear Colourless

Odor

at 100.00 %. sweet musk waxy ambrette dry woody

Odor Type

musk

InChI

InChI=1S/C10H16O/c1-5-10(4,11)8-6-7-9(2)3/h1,7,11H,6,8H2,2-4H3

InChIKey

YWTIDNZYLFTNQQ-UHFFFAOYSA-N

SMILES

C#CC(C)(O)CC/C=C(\C)/C

LogP

2.61 at 25℃ and pH7

EPA Substance Registry System

Dehydrolinalool (29171-20-8)

Safety

HS Code 

2905299090

Toxicity

mouse,LD50,intraperitoneal,200mg/kg (200mg/kg),BEHAVIORAL: ATAXIABEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)LUNGS, THORAX, OR RESPIRATION: DYSPNEA,National Technical Information Service. Vol. OTS0543729,

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3,7-dimethyloct-6-en-1-yn-3-ol Chemical Properties,Usage,Production

Description

3,7-dimethyl-6-octen-1-yn-3-ol, also known as Dehydrolinalool, is a derivative of methyl heptenone and acetylene. It is used in small amounts for the production of chemical fragrances for daily use. Industrial-grade dehydrolinalool (content 92–96%) is mainly used to synthesize a series of perfumes such as linalool, nerolidol, citral and ionone, which are also important intermediates for the synthesis of vitamin A, E and K. Dehydrolinalool has a strong ability to mask bad odors, especially for disgusting hydrogen sulfide, garlic preparations and polysulfide odors. In addition, it also has the role of mosquito repellent. A sterol compound such as dehydrolinalool has excellent antibacterial activity against Escherichia coli, Enterobacter faecalis, Proteus and the like. Dehydrolinalool has high added value and is a fine chemical product with broad market prospects.

Chemical Properties

Dehydrolinalool is an acyclic monoterpene alcohol compound with a pleasant floral vanilla aroma and a spicy and lavender-like fragrance. Its boiling point is 89–93°C at 1.6 kPa. The constant pressure heat capacity is 385.2 J·mol^-1·K^-1 at 313.55 K. The enthalpies of vaporization are 50.4 kJ·mol^-1 at 407 K and 52.1 kJ·mol^-1 at 421 K.

Uses

3,7-Dimethyl-6-octen-1-yn-3-ol is a useful synthetic intermediate in the synthesis of Methylisopseudoionone (M314920); a derivative of Ionone (I731275) which is an aroma compound found in essential oils such as rose oil, and thus can be used in the perfumery industry.

Definition

ChEBI: Dehydrolinalool is a ynone.

Application

3,7-dimethyl-6-octen-1-yn-3-ol is an important intermediate for the preparation of β-ionone and vitamin E. It can be used to produce a series of fragrances such as linalool and nerolidol. Furthermore, dehydrolinalool is a fragrance ingredient used in decorative cosmetics, fine fragrances, shampoos, toilet soaps and other toiletries as well as in non-cosmetic products such as household cleaners and detergents

Synthesis

3,7-dimethyl-6-octen-1-yn-3-ol(Dehydrolinalool) is obtained by ethynylation of methylheptenone with acetylene in the presence of potassium hydroxide and liquid ammonia.
The specific process is as follows: open the valves of ammonia and acetylene gas cylinders, respectively, add ammonia gas and acetylene to the mixed gas cabinet, and adjust the ratio of the two gases so that the content of acetylene in the mixed gas cabinet is about 20–25%. The gas mixture is compressed to 2.0–2.5 MPa by a compressor, liquefied in a high-position cooling tower and enters the reaction tower through a bottom discharge pipe, and a methylheptene solution containing potassium hydroxide is introduced into the reaction tower through a metering pump. The reaction temperature is 35–40°C, the reaction pressure is 2.0–2.5 MPa and the reaction time is 2–3 h. The reaction liquid enters the flash tank through the discharge tube of the reaction tower, and the flashing temperature is 50–70°C. Excess acetylene and ammonia are flashed and recycled back to the mixing gas cabinet, and the reaction product overflows from the bottom of the flash tank to the storage tank. By distillation under reduced pressure, dehydrolinalool having a mass fraction of more than 98% can be obtained and the yield can reach 92–94%.