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

Aroma

Colorless, somewhat viscous oil with rich and extremely tenacious floral-musky, sweet odor.
Ambrettolide is one of the finest fixatives among the distinguished group of those showing a synergistic and amplifying effect upon perfumes and flavors. At the same time it increases the diffusiveness of fragrances in which it is incorporated. Its fixative effect is easily recognized by the fact that solutions of 0.01% ~ Ambrettolide (or even less) in slightly diluted alcohol show practically no odor of alcohol, only a faint, floral-musky, sweet and pleasant odor of the lactone. A. is particularly useful in fragrance types of delicately floral, mildly animal or Ambre-like type.

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).

Production Methods

Many patented methods are known, few are commercially feasible. From Bromo hexadecenoic acid, or from Dihydroxy palmitic acid, or from Aleuritic acid, or from Juniperic acid, etc.

Flammability and Explosibility

Not classified

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