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Sigma-Aldrich

4-Methyl-2-oxovaleric acid

≥98.0% (T)

Synonyme(s) :

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

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About This Item

Formule linéaire :
(CH3)2CHCH2COCOOH
Numéro CAS:
816-66-0
Poids moléculaire :
130.14
Numéro Beilstein :
1701823
Numéro CE :
212-435-5
Numéro MDL:
MFCD00066204
Code UNSPSC :
12352100
ID de substance PubChem :
57652142
Nomenclature NACRES :
NA.22

Pureté

≥98.0% (T)

Indice de réfraction

n20/D 1.431

Point d'ébullition

82-83 °C/11 mmHg (lit.)

Pf

8-10 °C

Densité

1.055 g/mL at 20 °C (lit.)

Température de stockage

2-8°C

Chaîne SMILES 

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)

Clé InChI

BKAJNAXTPSGJCU-UHFFFAOYSA-N

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Catégories apparentées

Description générale

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).

Pictogrammes

Corrosion
GHS05

Mention d'avertissement

Danger

Mentions de danger

H314

Classification des risques

Skin Corr. 1B

Code de la classe de stockage

8A - Combustible corrosive hazardous materials

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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
D L Hachey et al.
Analytical chemistry, 63(9), 919-923 (1991-05-01)
A rapid, single-step procedure for the extraction and derivatization of organic alpha-keto acids from microliter quantities of human plasma has been developed. The keto acids were analyzed as the pentafluorobenzyl (PFB) ester by methane negative chemical ionization gas chromatography/mass spectrometry.
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
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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