10-Undecenal

Chemical properties

Clear colorless liquid

Chemical properties

10-Undecenal was identified, for example, in coriander leaf extract. It is a colorless liquid with a fatty, green, slightly metallic, heavy, floral odor. The aldehyde can be synthesized from undecylenic acid, for example, by hydrogenation of the acid chloride (Rosenmund reduction) or by reaction with formic acid in the vapor phase in the presence of titanium dioxide. In perfumery, 10-undecenal is one of the aldehydes essential for creating the “aldehydic note.”
Mixtures containing undecenals with the double bond in other positions (9-, 8-, 7-) are also marketed and used in fragrances, for example, Aldehyde C₁₁ Iso (Givaudan), Intreleven aldehyde (IFF).

Chemical properties

10-Undecenal has a characteristic fatty, rose odor on dilution. It has an unpleasant sweet, fatty taste. This compound tends to polymerize.

Occurrence

Reported found in coriander leaf (Coriandrum sativum L.).

The Uses of 10-Undecenal

10-Undecylenic Aldehyde is derived from the reduction of Undecylenic Acid (U788820) which is used for the manufacture of pharmaceuticals, cosmetics and perfumery, including antidandruff shampoos, antimicrobial powders and as a musk in perfumes and aromas.

Preparation

By oxidation of the corresponding alcohol or reduction of the corresponding acid; by passing vapors of formic acid and undecylenic acid over TiO2 at 250°C under pressure; by passing vapors of undecylenic acid and methanol over a manganese dioxidebased catalyst; or by reduction of ethyl undecylenate with lithium hydride and sodium in tetrahydrofuran solution at very low temperature (–50°C).

Definition

ChEBI: 10-undecenal is an undecenal.

Taste threshold values

Taste characteristics at 2.5 ppm: fatty, oily and aldehydic with a mandarin, citrus nuance.

Synthesis Reference(s)

The Journal of Organic Chemistry, 47, p. 4534, 1982 DOI: 10.1021/jo00144a026
Synthetic Communications, 12, p. 839, 1982 DOI: 10.1080/00397918208065961

Flammability and Explosibility

Non flammable

Safety Profile

LOW toxicity by ingestion and skin contact. A skin irritant. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALDEHYDES.