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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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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
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
Shozo Tomonaga et al.
Animal science journal = Nihon chikusan Gakkaiho, 89(2), 448-455 (2017-11-21)
Exposure to high ambient temperature is detrimental to the poultry industry. To understand the influence from a metabolic perspective, we investigated the effects of exposure to high ambient temperature on plasma low-molecular-weight metabolite levels in chicks using gas chromatography/mass spectrometry-based
P Friden et al.
Molecular and cellular biology, 9(9), 4056-4060 (1989-09-01)
LEU3 of Saccharomyces cerevisiae encodes an 886-amino-acid polypeptide that activates transcription of at least five genes by binding to an upstream decanucleotide sequence. This activation is dependent on the inducer alpha-isopropylmalate, the synthesis of which is repressed by leucine. We
J Y Sze et al.
Science (New York, N.Y.), 258(5085), 1143-1145 (1992-11-13)
In the absence of the leucine biosynthetic precursor alpha-isopropylmalate (alpha-IPM), the yeast LEU3 protein (Leu3p) binds DNA and acts as a transcriptional repressor in an in vitro extract. Addition of alpha-IPM resulted in a dramatic increase in Leu3p-dependent transcription. The
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