TRANS-2-NONENAL Chemical Properties

Melting point:

-28°C (estimate)

Boiling point:

88-90 °C12 mm Hg(lit.)

Density 

0.846 g/mL at 25 °C(lit.)

vapor density 

>1 (vs air)

refractive index 

n20/D 1.453(lit.)

FEMA 

3213 | 2-NONENAL

Flash point:

184 °F

storage temp. 

Refrigerator (+4°C)

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Liquid

color 

Clear colorless to pale yellow

Odor

at 1.00 % in dipropylene glycol. fatty green cucumber aldehydic citrus

Odor Type

fatty

biological source

synthetic

Water Solubility 

Soluble in Alcohol , and oils. Insoluble in water.

Sensitive 

Air Sensitive

Merck 

14,6676

JECFA Number

1362

Major Application

cleaning products
cosmetics
flavors and fragrances
food and beverages
personal care

Cosmetics Ingredients Functions

PERFUMING

InChI

1S/C9H16O/c1-2-3-4-5-6-7-8-9-10/h7-9H,2-6H2,1H3/b8-7+

InChIKey

BSAIUMLZVGUGKX-BQYQJAHWSA-N

SMILES

[H]C(=O)C(\[H])=C(/[H])CCCCCC

LogP

3.17

CAS DataBase Reference

18829-56-6(CAS DataBase Reference)

EPA Substance Registry System

2-Nonenal, (2E)- (18829-56-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RIDADR 

NA 1993 / PGIII

WGK Germany 

3

RTECS 

RA8509050

TSCA 

TSCA listed

HazardClass 

3

PackingGroup 

II

HS Code 

29121900

Storage Class

10 - Combustible liquids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

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

TRANS-2-NONENAL Usage And Synthesis

Chemical Properties

CLEAR COLOURLESS TO PALE YELLOW LIQUID

Uses

trans-2-Nonenal is an unsaturated aldehyde that is a product of fatty acid peroxidation (and also has a grassy, cucumber smell). trans-2-Nonenal is naturally found in mushrooms, coffee and is also a constituent of carrot root. It also exhibits insecticidal effects.

Definition

ChEBI: (E)-non-2-enal is a monounsaturated fatty aldehyde that is (2E)-non-2-ene which is carrying an oxo group at position 1. It has a role as a plant metabolite. It is a monounsaturated fatty aldehyde, an enal and a medium-chain fatty aldehyde.

Synthesis Reference(s)

Tetrahedron Letters, 24, p. 4829, 1983 DOI: 10.1016/S0040-4039(00)94018-8

General Description

trans-2-Nonenal (T2N) is a volatile unsaturated aldehyde with an unpleasant greasy odor, present in low concentrations in barley, malt, and certain vegetables. It is utilized as an insect repellent, insecticide, and flavor compound. T2N is one of the basic components contributing to the off-flavor and odor in stored beer.

Synthesis

(1), the synthesis of ??-phenylthio-nonenal
Take n-nonynyl (0.12 g, 1 mmol), phenylthiophenol (2a) (0.33 g, 3 mmol) was dissolved in chloroform, the reaction was carried out at 20 ??; the reaction was tracked by TLC until it was completely finished; the crude product obtained at the end of the reaction was separated by column chromatography (petroleum ether: ethyl acetate=10:1), the target product was obtained (yield 84%);

(2) Synthesis of target product (E)-2-nonenal

Weighing ??-phenylthio-nonenal (3f) (0.25 g, 1 mmol) was dissolved in 10 mL of dichloromethane, and aqueous hydrogen peroxide (0.22 g, 2 mmol, 30%) was added drop by drop at 0 ?? with continued stirring for 3 h. Ten milliliters of water was added, and the reaction was carried out under 30 ?? with stirring. The reaction was stirred and followed by TLC until the complete completion of the reaction; after the reaction, the reaction solution was poured into a saturated solution of sodium bicarbonate, the aqueous phase was extracted by adding dichloromethane, the organic layers were combined, washed by adding saturated solution of sodium bicarbonate, and then dried and concentrated with anhydrous magnesium sulfate. The crude product was separated by column chromatography (petroleum ether:ethyl acetate=10:1) to obtain the target product (E)-2-nonenal (83% yield)

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