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Documentos

333115

Sigma-Aldrich

2-Isopropylmalic acid

98%

Sinónimos:

2-Hydroxy-2-isopropylsuccinic acid

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About This Item

Fórmula lineal:
HO2CCH2C[CH(CH3)2](OH)CO2H
Número de CAS:
3237-44-3
Peso molecular:
176.17
MDL number:
MFCD00075003
UNSPSC Code:
12352100
PubChem Substance ID:
24860103
NACRES:
NA.22

Quality Level

100

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «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
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
Satoshi Takemoto et al.
Animal science journal = Nihon chikusan Gakkaiho, 88(12), 1970-1978 (2017-07-20)
Long-distance transportation is sometimes inevitable in the beef industry because of the geographic separation of major breeding and fattening areas. Long-distance transportation negatively impacts production and health of cattle, which may, at least partly, result from the disturbance of metabolism
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
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