Skip to Content
Merck
CN

68255

4-Methyl-2-oxovaleric acid

≥98.0% (T)

Synonym(s):

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

Sign In to View Organizational & Contract Pricing

Select a Size

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

Key Documents

View All Documentation
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

Quality Level

200

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
0000326663
0000326656
0000326656
0000326663
0000243785

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service