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Merck

68255

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
57652142
EC Number:
212-435-5
Beilstein/REAXYS Number:
1701823
MDL number:
MFCD00066204

Key Documents

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Product Name

4-Methyl-2-oxovaleric acid, ≥98.0% (T)

InChI key

BKAJNAXTPSGJCU-UHFFFAOYSA-N

InChI

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

SMILES string

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

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

Quality Level

200

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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).

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.

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

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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Certificates of Analysis (COA)

Lot/Batch Number
0000326663
0000326656
0000326656
0000326663
0000243785

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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)
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
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)
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