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68255

Sigma-Aldrich

4-Methyl-2-oxovaleric acid

≥98.0% (T)

Sinónimos:

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

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About This Item

Fórmula lineal:
(CH3)2CHCH2COCOOH
Número de CAS:
816-66-0
Peso molecular:
130.14
Beilstein/REAXYS Number:
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.)

functional group

carboxylic acid

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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
BGBC2940V
BCBJ2629V
1432183V
1432183
039857/1

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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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