Methyl trans-2-nonenoate Chemical Properties

Melting point:

-89.9°C (estimate)

Boiling point:

115 °C21 mm Hg(lit.)

Density 

0.895 g/mL at 25 °C(lit.)

vapor pressure 

13.33hPa at 95.84℃

refractive index 

n20/D 1.444(lit.)

FEMA 

2725 | METHYL 2-NONENOATE

Flash point:

196 °F

storage temp. 

Sealed in dry,Room Temperature

Odor

at 100.00 %. sweet green waxy violet pear fruity melon vegetable

Odor Type

green

Water Solubility 

52.1mg/L at 25℃

JECFA Number

1813

LogP

3.6 at 25℃

CAS DataBase Reference

111-79-5(CAS DataBase Reference)

NIST Chemistry Reference

2-Nonenoic acid, methyl ester(111-79-5)

EPA Substance Registry System

2-Nonenoic acid, methyl ester (111-79-5)

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36/38-51/53

Safety Statements 

26-61

RIDADR 

UN 3082 9/PG 3

WGK Germany 

2

RTECS 

RA9470000

Toxicity

Both the acute oral LD₅₀ value in rats and the acute dermal LD₅₀ value in rabbits exceeded 5 g/kg (Moreno, 1975)

MSDS

• Language:English Provider:SigmaAldrich

Methyl trans-2-nonenoate Usage And Synthesis

Description

Methyl 2-nonenoate has a characteristic violet-like odor. May be obtained in quantitative yields by treating methyl P-chlorocaproate with sodium acetate, or by dehydrogenating the corresponding saturated ester.

Physical properties

Methyl trans-2-nonenoate is colorless to slightly yellow liquid;strong violet-leaf odor. Stable; soluble in alco-hol. Combustible.

Chemical Properties

Methyl 2-Nonenoate is a colorless to pale yellow liquid with a green, floral note. It imparts freshness to floral fragrance compositions and is recommended as a substitute for methyl 2-octynoate.The synthesis consists of a condensation of heptanal withmalonic acid, decarboxylation, and subsequent esterification with methanol.

Occurrence

Methyl trans-2-nonenoate has apparently not been reported to occur in nature.

Uses

Perfumes.

Definition

ChEBI: Methyl 2-nonenoate is a fatty acid ester.

Preparation

Obtained in quantitative yields by treating methyl β-chlorocaproate with sodium acetate, or by dehydrogenating the corresponding saturated ester.

Taste threshold values

Taste characteristics at 5 ppm: green, waxy, oily, fruity, watermelon rind, pear- and apple-like.

Synthesis Reference(s)

The Journal of Organic Chemistry, 54, p. 1831, 1989 DOI: 10.1021/jo00269a017
Synthetic Communications, 24, p. 2069, 1994 DOI: 10.1080/00397919408010217
Tetrahedron Letters, 30, p. 6555, 1989 DOI: 10.1016/S0040-4039(01)89020-1

Flammability and Explosibility

Not classified

Trade name

Neofolione (Givaudan).

Metabolism

2-Nonenoic acid produced by the hydrolysis of methyl nonylenate will presumably pass through the normal pathways of fatty acid metabolism (Lehninger, 1970)

Methyl trans-2-nonenoate(111-79-5)Related Product Information

• ETHYL TRANS-2-DECENOATE
• OLIGOMYCIN B
• DIGOXIN
• GITOXIN
• Digitoxin
• LANATOSIDE B
• GITOXIGENIN
• DIGITOXIGENIN
• RUBRATOXIN B
• CYMARIN
• CYTOCHALASIN A
• LANATOSIDE A
• Methyl trans-2-nonenoate
• G-STROPHANTHIN
• METHYL NONENOATE
• METHYL TRANS-3-NONENOATE
• METHYL TRANS-3-NONENOATE
• Aliskiren inter-7