((E)-3,3-DIMETHOXY-PROPENYL)-BENZENE Property

Boiling point:

270.46°C (rough estimate)

Density 

1.0292 (rough estimate)

refractive index 

1.5103 (estimate)

form 

liquid

Odor

at 10.00 % in dipropylene glycol. fresh green spicy cinnamon herbal

Odor Type

spicy

LogP

2.689 (est)

EPA Substance Registry System

Benzene, (3,3-dimethoxy-1-propenyl)- (4364-06-1)

Safety

Toxicity

The acute oral LD₅₀ value in rats was reported as 3.7 g/kg (3.3-4.1 g/kg) (Moreno, 1972a). The acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Moreno, 1972b).

Hazard and Precautionary Statements (GHS)

((E)-3,3-DIMETHOXY-PROPENYL)-BENZENE Chemical Properties,Usage,Production

Chemical Properties

Almost colorless oily liquid. B.P. 239° C. Sp.Gr. 1.02. Fresh-green, spicy-herbaceous Cassia-cinnamon type odor, more Cassia-like than the Diethyl acetal, yet less harsh than the aldehyde. Sweet spicy -herbaceous taste, but not nearly as sweet as the alciehyde.

Occurrence

Has apparently not been reported to occur in nature.

Uses

((E)-3,3-DIMETHOXY-PROPENYL)-BENZENE is used as a lasting topnote ingredient in many types of “modem” fragrances, not only in copies of successful French perfumes, but also in general as a novelty along with aldehydic-floral or Oriental-spicy or sweet-woody fragrance types. It forms interesting topnotes with alifatic aldehydes in Rose-Jasmin fragrances, and gives pleasant variations of woody-Oakmoss types. Stable in soap and may introduce Cinnamon type odor when used at a sufficiently high level of concentration.

Uses

(E)-Cinnamaldehyde Dimethyl Acetal is synthesized from trans-cinnamaldehyde (C442020) and is used for the preparation of benzyl(aryl)triazoles and their selective human aromatase (cytochrome P 450 19A1) inhibitory activity.

Preparation

By the interaction of cinnamic aldehyde and methanol in the presence of a catalyst or by treating cinnamic aldehyde with trimethyl orthoformate.

Synthesis Reference(s)

The Journal of Organic Chemistry, 35, p. 1962, 1970 DOI: 10.1021/jo00831a052