97-67-6 | L-(-)-Malic acid

Packsize	Purity	Availability	Price	Discounted Price
25g	98%	in stock	$13.00	$9.00
100g	98%	in stock	$26.00	$18.00
500g	98%	in stock	$35.00	$24.00
1000g	98%	in stock	$62.00	$43.00
25kg	98%	in stock	$1,473.00	$1,031.00

Description

• Catalog Number: AB74993
• Chemical Name: L-(-)-Malic acid
• CAS Number: 97-67-6
• Molecular Formula: C4H6O5
• Molecular Weight: 134.0874
• MDL Number: MFCD00064213
• SMILES: OC(=O)C[C@@H](C(=O)O)O
• NSC Number: 9232

Computed Properties

• Complexity: 129
• Covalently-Bonded Unit Count: 1
• Defined Atom Stereocenter Count: 1
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 5
• Hydrogen Bond Donor Count: 3
• Rotatable Bond Count: 3
• XLogP3: -1.3

Upstream Synthesis Route

(S)-2-hydroxysuccinic acid, also known as L-malic acid, is a versatile compound in chemical synthesis due to its unique stereochemistry and reactivity. As an optically pure organic acid with a hydroxyl group, (S)-2-hydroxysuccinic acid finds various applications in the production of pharmaceuticals, food additives, and fine chemicals.In chemical synthesis, (S)-2-hydroxysuccinic acid serves as a chiral building block for the preparation of enantiopure compounds. Its stereochemistry allows for precise control over the configuration of the final product, making it ideal for synthesizing chiral intermediates and pharmaceuticals with specific biological activities. Additionally, the hydroxyl group in (S)-2-hydroxysuccinic acid can be functionalized to introduce additional chemical functionalities, expanding its synthetic versatility.One notable application of (S)-2-hydroxysuccinic acid is in the synthesis of chiral pharmaceuticals. By incorporating (S)-2-hydroxysuccinic acid into the molecular structure of drug candidates, chemists can enhance the pharmacological properties and biological interactions of the resulting compounds. The chiral purity of (S)-2-hydroxysuccinic acid enables the preparation of enantioenriched drugs with improved efficacy and reduced side effects.In summary, (S)-2-hydroxysuccinic acid plays a crucial role in chemical synthesis as a chiral building block for the production of enantiopure compounds, particularly in the pharmaceutical industry. Its stereochemistry and reactivity make it a valuable tool for the development of novel drugs and fine chemicals with enhanced properties.

Literature

• Structural framework for covalent inhibition of Clostridium botulinum neurotoxin A by targeting Cys165.

  The Journal of biological chemistry 20120928

• Activity-guided discovery of (S)-malic acid 1'-O-β-gentiobioside as an angiotensin I-converting enzyme inhibitor in lettuce (Lactuca sativa).

  Journal of agricultural and food chemistry 20120725

• Asymmetric hydrovinylation of vinylindoles. A facile route to cyclopenta[g]indole natural products (+)-cis-trikentrin A and (+)-cis-trikentrin B.

  Journal of the American Chemical Society 20120328

• Salmonella enterica: a surprisingly well-adapted intracellular lifestyle.

  Frontiers in microbiology 20120101

• Fumarate hydratase isoforms of Leishmania major: subcellular localization, structural and kinetic properties.

  International journal of biological macromolecules 20120101

• Nutritional programming in the rat is linked to long-lasting changes in nutrient sensing and energy homeostasis in the hypothalamus.

  PloS one 20100101

• Refolding, characterization and crystal structure of (S)-malate dehydrogenase from the hyperthermophilic archaeon Aeropyrum pernix.

  Biochimica et biophysica acta 20091001

• Bacillithiol is an antioxidant thiol produced in Bacilli.

  Nature chemical biology 20090901

• Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli.

  Nature chemical biology 20090801

• Brucella microti: the genome sequence of an emerging pathogen.

  BMC genomics 20090101

• Proteome analysis of Aspergillus niger: lactate added in starch-containing medium can increase production of the mycotoxin fumonisin B2 by modifying acetyl-CoA metabolism.

  BMC microbiology 20090101

• A simple helical macrocyclic polyazapyridinophane as a stereoselective receptor of biologically important dicarboxylates under physiological conditions.

  The Journal of organic chemistry 20080118

• The first synthesis of the ABC-ring system of 'upenamide.

  Organic letters 20070927

• Discovery of a natural thiamine adenine nucleotide.

  Nature chemical biology 20070401

• Quantifying the metabolic capabilities of engineered Zymomonas mobilis using linear programming analysis.

  Microbial cell factories 20070101

• Production of L-carnitine by secondary metabolism of bacteria.

  Microbial cell factories 20070101

• Quantitative studies, taste reconstitution, and omission experiments on the key taste compounds in morel mushrooms (Morchella deliciosa Fr.).

  Journal of agricultural and food chemistry 20060405

• GEM System: automatic prototyping of cell-wide metabolic pathway models from genomes.

  BMC bioinformatics 20060101

• Activity-guided identification of (S)-malic acid 1-O-D-glucopyranoside (morelid) and gamma-aminobutyric acid as contributors to umami taste and mouth-drying oral sensation of morel mushrooms (Morchella deliciosa Fr.).

  Journal of agricultural and food chemistry 20050518

• Synthesis and stereochemistry of musacins isolated from Streptomyces griseoviridis(FH-S 1832).

  Organic & biomolecular chemistry 20050121

• Synthesis of optically active constrained 2-substituted norstatines: a straightforward application of Seebach's 'SRS' synthetic principle.

  The Journal of organic chemistry 20041224

• Stereoselective synthesis and structure of butalactin and lactone II isolated from Streptomyces species.

  Organic & biomolecular chemistry 20041007

• A concise asymmetric synthesis of (2S,3S,7S)-3,7-dimethylpentadecan-2-yl Acetate and propionate, the sex pheromones of pine sawflies.

  The Journal of organic chemistry 20040528

• Peroxomolybdate(VI)-citrate and -malate complex interconversions by pH-dependence. Synthetic, structural and spectroscopic studies.

  Dalton transactions (Cambridge, England : 2003) 20040507

• Concise formal synthesis of (-)-peduncularine via ring-closing metathesis.

  Organic letters 20030918

• A stereoselective and short total synthesis of the polyhydroxylated gamma-amino acid (-)-detoxinine, based on stereoselective preparation of dihydropyrrole derivatives from lithiated alkoxyallenes.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20030317

• X-ray crystallographic and kinetic correlation of a clinically observed human fumarase mutation.

  Protein science : a publication of the Protein Society 20020601

• Chiral versus racemic building blocks in supramolecular chemistry: malate salts of organic diamines.

  Acta crystallographica. Section B, Structural science 20020601

• A new approach for asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids from (S)-malic acid.

  Natural product letters 20020201

• RIO: analyzing proteomes by automated phylogenomics using resampled inference of orthologs.

  BMC bioinformatics 20020101

• Synthesis and absolute configuration of lactone II isolated from Streptomyces sp. Go 40/10.

  Chemical communications (Cambridge, England) 20010921

• Enantiospecific synthesis of the (9S,18R)-diastereomer of the leukocyte adhesion inhibitor cyclamenol A.

  Chemistry (Weinheim an der Bergstrasse, Germany) 20010803

• Total synthesis of the marine alkaloids (-)-lepadins a, b, and c based on stereocontrolled intramolecular acylnitroso-Diels-Alder reaction.

  The Journal of organic chemistry 20010518

• Total synthesis of (-)-rosmarinecine by intramolecular cycloaddition of (S)-malic acid derived pyrroline N-oxide.

  Organic letters 20010503