DL-3-Methylvaleric acid

Synonym(s):(±)-3-Methylvaleric acid;3-Methylpentanoic acid

CAS NO.：105-43-1
Empirical Formula: C6H12O2
Molecular Weight: 116.16
MDL number: MFCD00002729
EINECS: 203-297-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-11-20 11:41:24

What is DL-3-Methylvaleric acid?

Description

3-Methylpentanoic has a sour, herbaceous, slightly green odor. This is synthesized from the diethylester of sec-butyl-malonic acid.

Chemical properties

clear colorless to slightly yellow liquid

Occurrence

Reported found in the oil from tobacco leaves (d-form), baked potato, parmesan, provolone and romano cheese, goat and sheep cheese, lamb fat, rum, cocoa, black tea and chempedak (Arthocarpus polyphema).

The Uses of DL-3-Methylvaleric acid

3-Methylvaleric acid (3-Methylpentanoic acid) was used in the synthesis of 3-methyl-1-pentanol.

Preparation

From the diethylester of sec-butyl-malonic acid.

Definition

ChEBI: 3-methylvaleric acid is a methyl-branched fatty acid that is pentanoic acid which carries a methyl group at position 3. It has a role as a plant metabolite, an animal metabolite, a fungal metabolite and a flavouring agent. It is a methyl-branched fatty acid, a short-chain fatty acid, a branched-chain saturated fatty acid and a monocarboxylic acid. It is a conjugate acid of a 3-methylvalerate.

Aroma threshold values

Detection: 46 to 280 ppb

Taste threshold values

Taste characteristics at 30 ppm: sour, cheesey, fresh with fruity notes

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 6342, 1953 DOI: 10.1021/ja01120a539
The Journal of Organic Chemistry, 65, p. 397, 2000 DOI: 10.1021/jo991218a
Organic Syntheses, Coll. Vol. 2, p. 416, 1943

Properties of DL-3-Methylvaleric acid

Melting point:	-41 °C
Boiling point:	196-198 °C (lit.)
Density	0.93 g/mL at 25 °C (lit.)
refractive index	n20/D 1.416(lit.)
FEMA	3437 \| 3-METHYLPENTANOIC ACID
Flash point:	185 °F
storage temp.	Sealed in dry,Room Temperature
form	clear liquid
pka	pK1:4.766 (25°C)
Specific Gravity	0.930
color	Colorless to Almost colorless
Odor	at 1.00 % in dipropylene glycol. animal sharp acidic cheesy green fruity sweaty
Water Solubility	insoluble
JECFA Number	262
BRN	1720696
CAS DataBase Reference	105-43-1(CAS DataBase Reference)
NIST Chemistry Reference	Pentanoic acid, 3-methyl-(105-43-1)
EPA Substance Registry System	Pentanoic acid, 3-methyl- (105-43-1)

Safety information for DL-3-Methylvaleric acid

Signal word	Danger
Pictogram(s)	Corrosion Corrosives GHS05
GHS Hazard Statements	H314:Skin corrosion/irritation
Precautionary Statement Codes	P280:Wear protective gloves/protective clothing/eye protection/face protection. P363:Wash contaminated clothing before reuse. P303+P361+P353:IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. P405:Store locked up.