TRANS,CIS-2,6-NONADIEN-1-OL Chemical Properties

Boiling point:

96-100 °C(lit.)

Density 

0.873 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.468(lit.)

FEMA 

2780 | 2,6-NONADIEN-1-OL

Flash point:

203 °F

storage temp. 

0-6°C

form 

clear liquid

pka

14.41±0.10(Predicted)

color 

White to yellow liquid

Odor

powerful, vegetable odor

Odor Type

green

JECFA Number

1184

LogP

2.71

EPA Substance Registry System

2,6-Nonadien-1-ol, (2E,6Z)- (28069-72-9)

Safety Information

Hazard Codes 

Xi

Risk Statements 

38

Safety Statements 

26-36-38

WGK Germany 

2

RTECS 

RA5394000

HS Code 

29052990

Toxicity

skn-gpg 100%/24H MOD FCTOD7 20,771,82

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

TRANS,CIS-2,6-NONADIEN-1-OL Usage And Synthesis

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.

Uses

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

Uses

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is a primary allylic alcohol that is (2E,6Z)-nona-2,6-diene in which a hydrogen at position 1 has been replaced by a hydroxy group.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.

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