AMBRETTOLIDE Chemical Properties

Boiling point:

185-190 °C16 mm Hg(lit.)

Density 

0.956 g/mL at 25 °C(lit.)

vapor pressure 

0.003Pa at 25℃

refractive index 

n20/D 1.479(lit.)

FEMA 

4145 | ISOAMBRETTOLIDE

Flash point:

>230 °F

storage temp. 

Refrigerator

solubility 

Chloroform (Sparingly), Methanol (Sparingly)

form 

Oil

color 

Clear Colorless

Odor

at 10.00 % in dipropylene glycol. sweet musk ambrette fruity waxy fatty

Odor Type

musk

Water Solubility 

15μg/L at 25℃

JECFA Number

1991

LogP

6.7 at 23℃

EPA Substance Registry System

Oxacycloheptadec-10-en-2-one (28645-51-4)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36

Safety Statements 

26-36

WGK Germany 

2

Toxicity

Both the acute oral LD₅₀ value in rats and the acute dermal LD₅₀ value in rabbits exceeded 5 g/kg(Wohl, 1974).

MSDS

• Language:English Provider:SigmaAldrich

AMBRETTOLIDE Usage And Synthesis

Chemical Properties

AMBRETTOLIDE is not reported as being found in nature, in contrast to (Z)-7-hexadecen-16-olide, which occurs in ambrette seed oil and which is also referred to as ambrettolide. It is a colorless to slightly yellow liquid, d²⁰₄ 0.949–0.957, n²⁰_D 1.477–1.482, with an intense and powerful musk odor. It is prepared by treating aleuritic acid (9,10,16-trihydroxyhexadecanoic acid) with trimethyl orthoformate to give a dioxolane derivative. Reaction with acetic anhydride yields ??-acetoxy (E)-9-hexadecenoic acid methyl ester. This is lactonized with potassium hydroxide to give the title compound .

Occurrence

Found in oil of ambrette seed[Givaudan Index, 1961).

Uses

Ambrettolide is a macrocyclic lactone that naturally occurs in ambrette seed oil. Ambrettolide is nontoxic, has a musky odour, and is commonly used as a fixative in perfume formulations.

Definition

ChEBI: Isoambrettolide is a macrolide.

Preparation

From bromohexadecenoic acid(Bedoukian, 1967).

Flammability and Explosibility

Not classified

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