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68255

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:
Molecular Weight:
130.14
Beilstein:
1701823
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

Pricing and availability is not currently available.

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.)

functional group

carboxylic acid
ketone

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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1494217P0250000P1918
manufacturer/tradename

BP

manufacturer/tradename

USP

manufacturer/tradename

EDQM

manufacturer/tradename

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application(s)

pharmaceutical
pharmaceutical small molecule

application(s)

pharmaceutical (small molecule)

application(s)

pharmaceutical (small molecule)

application(s)

-

form

powder

form

-

form

-

form

powder

format

neat

format

neat

format

neat

format

-

shelf life

limited shelf life, expiry date on the label

shelf life

-

shelf life

-

shelf life

-

General description

4-Methyl-2-oxovaleric acid, also known as α-ketoisocaproic acid (KIC), is a metabolite of leucine. [1]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.[2] Additionally, KIC serves as an intermediate in the formation of Strecker aldehydes.[3]

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

Signal Word

Danger

Hazard Statements

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

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    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
    W E Mitch et al.
    The Journal of clinical investigation, 67(2), 553-562 (1981-02-01)
    We measured the effects of seven consecutive daily infusions of alpha-ketoisocaproate (the alpha-keto analogue of leucine) or leucine itself on urinary urea and total nitrogen excretion during fasting. Two study protocols were undertaken. In protocol I, subjects underwent three separate
    Yulan Wang et al.
    Proceedings of the National Academy of Sciences of the United States of America, 101(34), 12676-12681 (2004-08-18)
    Schistosomiasis, a chronic and debilitating parasitic disease, affects approximately 200 million people in the developing world and imposes a substantial public health and economic impact. Accurately diagnosing at the individual level, monitoring disease progression, and assessing the impact of pharmacological
    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

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