4-METHYLNONANOIC ACID Chemical Properties

Boiling point:

292-293 °C (lit.)

Density 

0.871 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.4355(lit.)

FEMA 

3574 | 4-METHYLNONANOIC ACID

Flash point:

>230 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly)

pka

4.80±0.10(Predicted)

Odor

at 1.00 % in propylene glycol. meaty pork lamb chicken

Appearance

Colorless to light yellow Liquid

biological source

synthetic

Odor Type

meaty

JECFA Number

274

BRN 

1758201

LogP

3.78

CAS DataBase Reference

45019-28-1(CAS DataBase Reference)

EPA Substance Registry System

Nonanoic acid, 4-methyl- (45019-28-1)

Safety Information

Hazard Codes 

C

Risk Statements 

34-43-52/53

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3265 8/PG 2

WGK Germany 

2

TSCA 

Yes

HS Code 

2915.90.1800

HazardClass 

8

PackingGroup 

III

MSDS

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

4-METHYLNONANOIC ACID Usage And Synthesis

Chemical Properties

4-Methylnonanoic acid has a costus, animal odor.

Occurrence

Reported found in cooked mutton fat, romano cheese, sheep and goat cheese and raw and cooked mutton

Uses

flavors and fragrances

Definition

ChEBI: 4-Methylnonanoic acid is a medium-chain fatty acid.

Synthesis

Reaction of hept-1-ene with EtMgCl in THF in the presence of TaCl5-(i-OPr)3P catalyst [EtMgCl-hept-1-ene-TaCl5-(i-OPr)3P, 24:20:1]; TaCl5-(i-OPr)3P, 1:1; EtMgCl in THF at a concentration of 0.5 mM; 20 °C; at room temperature The reaction was carried out at room temperature for 3 h to form organomagnesium compound 2. The procedure was as follows: to a solution of EtMgCl (12 mmol) in THF (24 mL) was added hept-1-ene (10 mmol, 1.4 mL), TaCl5 (0.2 g, 0.5 mmol) and (i-OPr)3P (0.1 g, 0.5 mmol). CO2 was slowly passed into the resulting mixture for 3 h at 0°C. After completion of the reaction, the mixture was treated with 10% HCl solution (15 mL) to afford carboxylic acid 3 (1.7 g, 97%, boiling point 272 °C, 750 mmHg). The product was analyzed by IR spectroscopy (1710 cm-1 ), PMR spectroscopy (0.88-0.92 ppm, 2H, m; 1.16-1.52 ppm, 10H, m; 1.56-1.80 ppm, 1H, m; 2.28-2.38 ppm, 2H, m; 11.40 ppm, 1H, s), and 13C NMR spectroscopy (14.03, 19.75, 23.19, 28.30, 31.83, 31.97, 32.27, 33.10, 37.10, 179.37 ppm) for characterization. Finally, the reaction mixture was extracted with Et2O (3 × 50 mL) and the extract was dried with anhydrous MgSO4 and evaporated.

References

[1] Chemistry of Natural Compounds, 2018, vol. 54, # 1, p. 218 - 219
[2] Khim. Prir. Soedin., 2018, # 1, p. 181,1

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