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Sigma-Aldrich

4-Methyl-2-oxovaleric acid

≥98.0% (T)

Synonym(s):

α-Ketoisocaproic acid, 2-Oxoisocaproic acid, 4-Methyl-2-oxopentanoic acid, Ketoleucine

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About This Item

Linear Formula:
(CH3)2CHCH2COCOOH
CAS Number:
816-66-0
Molecular Weight:
130.14
Beilstein:
1701823
EC Number:
212-435-5
MDL number:
MFCD00066204
UNSPSC Code:
12352100
PubChem Substance ID:
57652142
NACRES:
NA.22

Assay

≥98.0% (T)

refractive index

n20/D 1.431

bp

82-83 °C/11 mmHg (lit.)

mp

8-10 °C

density

1.055 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)CC(=O)C(O)=O

InChI

1S/C6H10O3/c1-4(2)3-5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)

InChI key

BKAJNAXTPSGJCU-UHFFFAOYSA-N

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General description

4-Methyl-2-oxovaleric acid, also known as α-ketoisocaproic acid (KIC), is a metabolite of leucine. It is commonly used as a building block in the synthesis of leucine and its derivatives, and it plays a role in amination reactions and asymmetric synthesis. Additionally, KIC serves as an intermediate in the formation of Strecker aldehydes.

Application

  • Role in Human Brain Ketometabolism: 4-Methyl-2-oxovaleric acid has been implicated in the temporal patterns of ketometabolism in cerebral microdialysis fluids of patients with traumatic brain injury, underscoring its significance in biochemical pathways within the brain (Eiden et al., 2019).

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Lisa S Chow et al.
American journal of physiology. Endocrinology and metabolism, 291(4), E729-E736 (2006-05-18)
Despite being an anabolic hormone in skeletal muscle, insulin's anticatabolic mechanism in humans remains controversial, with contradictory reports showing either stimulation of protein synthesis (PS) or inhibition of protein breakdown (PB) by insulin. Earlier measurements of muscle PS and PB
The First Highly Enantioselective Homogeneously Catalyzed Asymmetric Reductive Amination:? Synthesis of ?-N-Benzylamino Acids
Kadyrov et al.
The Journal of Organic Chemistry, 68, 4067-4070 (2003)
Intermediate role of ?-keto acids in the formation of Strecker aldehydes
Hidalgo et al.
Basic Food Chemistry, 141, 1140-1146 (2013)
Direct Analysis of Leucine and Its Metabolites ??Hydroxy-?-methylbutyric Acid, ??Ketoisocaproic Acid, and ??HydroxyisocaproicAcid in Human Breast Milk by Liquid Chromatography?MassSpectrometry
Ehling et al.
Journal of Agricultural and Food Chemistry, 63, 7567-7573 (2015)
Eiji Yoshihara et al.
Nature communications, 1, 127-127 (2010-12-02)
Type 2 diabetes mellitus (T2DM) is characterized by defects in both insulin sensitivity and glucose-stimulated insulin secretion (GSIS) and is often accompanied by obesity. In this study, we show that disruption of thioredoxin binding protein-2 (TBP-2, also called Txnip) in
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