trans,cis-2,6-Nonadien-1-ol

Chemical properties

CLEAR COLOURLESS LIQUID

Chemical properties

(2E,6Z)-2,6-Nonadien-1-ol occurs, for example, in cucumber oil, violet leaf oil, and violet blossom oil. It is a colorless liquid with an intense, heavy, fatty, green odor, reminiscent of violet leaves. The starting material for the synthesis of (2E,6Z)-2,6-nonadien-l-ol is (Z)-3-hexen- 1-ol, which is converted via its halide into the corresponding Grignard reagent. The Grignard reagent is reacted with acrolein to give 1,6-nonadien-3-ol, which is converted into (2E,6Z)-2,6-nonadien-l-ol by allylic rearrangement.
Nonadienal is a powerful fragrance substance. It is used in fine fragrances to create refined violet odors and to impart interesting notes to other blossom compositions. In aroma compositions, it is used for fresh, green cucumber notes.

The Uses of trans,cis-2,6-Nonadien-1-ol

trans,cis-2,6-Nonadien-1-ol can be used as antimicrobial compositions for personal care products.

The Uses of trans,cis-2,6-Nonadien-1-ol

Food additive/natural product.

Definition

ChEBI: (2E,6Z)-nona-2,6-dien-1-ol is a primary allylic alcohol that is (2E,6Z)-nona-2,6-diene in which a hydrogen at position 1 has been replaced by a hydroxy group. It has a role as a flavouring agent, a plant metabolite and a fragrance. It is an alkenyl alcohol, a volatile organic compound, a primary allylic alcohol and a medium-chain primary fatty alcohol.

Preparation

When natural Hexenol is used as a starting material, the preferred isomer will result. This is called "natural" because it is evidently identical to the naturally occurring alcohol. If synthetic Hexenol is used, the less desirable isomer will result. It has a more dry, less pleasant-oily character. There are several methods in use for the production of trans,cis-2,6-Nonadien-1-ol.

Synthesis Reference(s)

Synthesis, p. 528, 1978 DOI: 10.1055/s-1978-24798

Hazard

Low toxicity by ingestion and skin contact. A skin irritant.

Safety Profile

Low toxicity by ingestion and skin contact. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.