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333115

Sigma-Aldrich

2-Isopropylmalic acid

98%

Synonym(s):

2-Hydroxy-2-isopropylsuccinic acid

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About This Item

Linear Formula:
HO2CCH2C[CH(CH3)2](OH)CO2H
CAS Number:
3237-44-3
Molecular Weight:
176.17
MDL number:
MFCD00075003
UNSPSC Code:
12352100
PubChem Substance ID:
24860103
NACRES:
NA.22

Assay

98%

mp

144-146 °C (lit.)

SMILES string

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

InChI

1S/C7H12O5/c1-4(2)7(12,6(10)11)3-5(8)9/h4,12H,3H2,1-2H3,(H,8,9)(H,10,11)

InChI key

BITYXLXUCSKTJS-UHFFFAOYSA-N

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General description

2-Isopropylmalic acid is an intermediate formed during leucine biosynthesis. Budding yeast Saccharomyces cerevisiae secrets 2-isopropylmalic acid and helps in reduction of aluminum toxicity by forming chelate with Al ions, thereby preventing them from entering the cells.

Application

2-Isopropylmalic acid was employed as an internal standard in diagnostic model for pancreatic cancer using GC/MS-based human serum metabolomics.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Carlo M T Marobbio et al.
The Journal of biological chemistry, 283(42), 28445-28453 (2008-08-07)
In Saccharomyces cerevisiae, alpha-isopropylmalate (alpha-IPM), which is produced in mitochondria, must be exported to the cytosol where it is required for leucine biosynthesis. Recombinant and reconstituted mitochondrial oxalacetate carrier (Oac1p) efficiently transported alpha-IPM in addition to its known substrates oxalacetate
Taisuke Suzuki et al.
Biological trace element research, 120(1-3), 257-263 (2007-10-06)
The budding yeast Saccharomyces cerevisiae secretes 2-isopropylmalic acid (2-iPMA), an intermediate in leucine biosynthesis. Because 2-iPMA binds Al(III) in the culture medium, it is thought to reduce toxicity by Al(III). The effects of 2-iPMA and malic acid (MA) on Al
Y Hu et al.
Molecular and cellular biology, 15(1), 52-57 (1995-01-01)
The Leu3 protein of Saccharomyces cerevisiae has been shown to be a transcriptional regulator of genes encoding enzymes of the branched-chain amino acid biosynthetic pathways. Leu3 binds to upstream activating sequences (UASLEU) found in the promoters of LEU1, LEU2, LEU4
Anna Mizusawa et al.
Nutrients, 12(8) (2020-08-06)
Branched-chain amino acid (BCAA) catabolism is regulated by its rate-limiting enzyme, branched-chain α-keto acid dehydrogenase (BCKDH), which is negatively regulated by BCKDH kinase (BDK). Loss of BDK function in mice and humans leads to dysregulated BCAA catabolism accompanied by neurological
Gaelen Burke et al.
The ISME journal, 4(2), 242-252 (2009-11-13)
We examined metabolite pools of pea aphids with different facultative symbiont infections, and characterized their effects on aphid metabolism in baseline and heat stress conditions. The bacterial symbiont Serratia symbiotica protects aphid hosts from the detrimental results of heat stress
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