(2S)-2-Hydroxybutanedioic acid

Base Information

• Chemical Name: (2S)-2-Hydroxybutanedioic acid
• CAS No.: 97-67-6
• Deprecated CAS: 124501-05-9,498-37-3,6294-10-6,84781-39-5,6294-10-6,84781-39-5
• Molecular Formula: C4H6O5
• Molecular Weight: 134.089
• Hs Code.: 29181980
• European Community (EC) Number: 202-601-5
• NSC Number: 9232
• UNII: J3TZF807X5
• DSSTox Substance ID: DTXSID30273987
• Nikkaji Number: J74.430A
• Wikidata: Q27104150
• NCI Thesaurus Code: C84394
• Metabolomics Workbench ID: 37105
• ChEMBL ID: CHEMBL1234046
• Mol file: 97-67-6.mol

Synonyms:97-67-6;L-Malic acid;L-(-)-Malic acid;(S)-2-hydroxysuccinic acid;(2S)-2-Hydroxybutanedioic acid;(S)-Malic acid;L(-)-Malic acid;Apple acid;(-)-Malic acid;L-Apple acid;(-)-Hydroxysuccinic acid;L-malate;S-(-)-Malic acid;L-Hydroxybutanedioic acid;S-2-Hydroxybutanedioic acid;Butanedioic acid, hydroxy-, (2S)-;Malic acid, L-;L-2-Hydroxybutanedioic acid;(S)-(-)-Hydroxysuccinic acid;CHEBI:30797;(-)-L-Malic acid;(S)-malate;Malic acid L-(-)-form;Hydroxysuccinnic acid (-);L-Hydroxysuccinic acid;UNII-J3TZF807X5;Hydroxybutanedioic acid, (S)-;J3TZF807X5;CHEMBL1234046;NSC9232;2-Hydroxybutanedioic acid, (S)-;NSC 9232;NSC-9232;EINECS 202-601-5;C4H6O5;MFCD00064213;Butanedioic acid, 2-hydroxy-, (2S)-;BUTANEDIOIC ACID, HYDROXY-, (S)-;(S)-Hydroxybutanedioic acid;MALATE ION;(-)-(S)-Malic acid;Hydroxybutanedioic acid, (-)-;malic-acid;laevo-malic acid;2yfa;4elc;4ipi;4ipj;L-Maleic Acid;L- malic acid;L-Hydroxysuccinate;(S)-(-)-2-Hydroxysuccinic acid;(2s)-malic acid;L-Hydroxybutanedioate;nchembio867-comp7;L-(-) malic acid;(-)-Hydroxysuccinate;L-(-)-Apple Acid;S-(-)-Malate;(S)-Hydroxybutanedioate;S-2-Hydroxybutanedioate;(-)-(S)-Malate;(S)-(-)-malic acid;(S)-hydroxy-Butanedioate;(S)-Hydroxysuccinic acid;L(-)MALIC ACID;(S)-2-hydroxysuccinicacid;bmse000238;MALIC ACID [HSDB];MALIC ACID, (L);(S)-(-)-Hydroxysuccinate;L-MALIC ACID [FHFI];(S)-hydroxy-Butanedioic acid;SCHEMBL256122;L-MALIC ACID [WHO-DD];MALIC ACID, L- [II];(-)-(s)-hydroxybutanedioic acid;DTXSID30273987;(2S)-(-)-hydroxybutanedioic acid;AMY40197;HY-Y1069;BDBM50510127;s6292;AKOS006346693;CS-W020132;MALIC ACID L-(-)-FORM [MI];L-(-)-Malic acid, BioXtra, >=95%;AS-18628;L-(-)-Malic acid, >=95% (titration);(-)-1-Hydroxy-1,2-ethanedicarboxylic acid;M0022;EN300-93424;C00149;L-(-)-Malic acid, purum, >=99.0% (T);L-(-)-Malic acid, ReagentPlus(R), >=99%;M-0850;35F9ECA9-BBE6-463D-BF3F-275FACC5D14E;L-(-)-Malic acid, SAJ special grade, >=99.0%;L-(-)-Malic acid, Vetec(TM) reagent grade, 97%;Q27104150;Z1201618618;(S)-(-)-2-Hydroxysuccinic acid, L-Hydroxybutanedioic acid;L-(-)-Malic acid, 97%, optical purity ee: 99% (GLC);L-(-)-Malic acid, certified reference material, TraceCERT(R);L-(-)-Malic acid, BioReagent, suitable for cell culture, suitable for insect cell culture;26999-59-7

Chemical Property of (2S)-2-Hydroxybutanedioic acid

Chemical Property:

• Appearance/Colour: clear colourless solution
• Vapor Pressure: 7.19E-05mmHg at 25°C
• Melting Point: 101-103 °C(lit.)
• Refractive Index: -6.5 ° (C=10, Acetone)
• Boiling Point: 306.4 °C at 760 mmHg
• PKA: (1) 3.46, (2) 5.10(at 25℃)
• Flash Point: 153.4 °C
• PSA: 94.83000
• Density: 1.641 g/cm³
• LogP: -1.09340
• Storage Temp.: Store at RT.
• Solubility.: H2O: 0.5 M at 20 °C, clear, colorless
• Water Solubility.: soluble
• XLogP3: -1.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 134.02152329
• Heavy Atom Count: 9
• Complexity: 129

Purity/Quality:

99%min ^*data from raw suppliers

L-Malic acid 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Organic Acids
• Canonical SMILES: C(C(C(=O)O)O)C(=O)O
• Isomeric SMILES: C([C@@H](C(=O)O)O)C(=O)O
• Description: L-Malic acid is nearly odorless (sometimes a faint, acrid odor) with a tart, acidic taste. It is nonpungent. May be prepared by hydration of maleic acid; by fermentation from sugars.
• Uses: L-Malic acid is used as a food additive, Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid receptor agonists, 1α,25-dihydroxyvitamin D3 analogue, and phoslactomycin B. Intermediate in chemical synthesis. Chelating and buffering agent. Flavoring agent, flavor enhancer and acidulant in foods.

Technology Process of (2S)-2-Hydroxybutanedioic acid

There total 114 articles about (2S)-2-Hydroxybutanedioic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid (423170-79-0) → D-Malic acid (636-61-3,78644-42-5) + (S)-Malic acid (97-67-6,78644-42-5)

Guidance literature:

2-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxybutanedioic acid; With sodium hydroxide; In water; for 24h;

With hydrogenchloride; In water; pH=1.2;

DOI:10.1002/cbdv.201100341

Reference yield:

bromosuccinic acid (923-06-8,584-98-5) → D-Malic acid (636-61-3,78644-42-5) + (S)-Malic acid (97-67-6,78644-42-5)

Guidance literature:

With alkali; Hydrolysis_.bei der Hydrolyse der Kupfer(II)-salze;

Reference yield:

chlorosuccinic acid (16045-92-4,617-41-4) → D-Malic acid (636-61-3,78644-42-5) + (S)-Malic acid (97-67-6,78644-42-5)

Guidance literature:

With alkali; Hydrolysis_.bei der Hydrolyse der Dinatriumsalze;

upstream raw materials:

propan-1-ol

L-Aspartic acid

Oxalacetic acid

ethanol

Downstream raw materials:

(S)-(-)-di-n-propyl 2-hydroxybutandioate

Oxalacetic acid

2H-pyran-2-one-5-carboxylic acid

3-oxopropanoic acid

Refernces

SYNTHESIS OF THE ENANTIOMERS OF 3-HYDROXY-1,7-DIOXASPIRO<5.5>UNDECANE, A MINOR COMPONENT OF THE OLIVE FLY PHEROMONE

10.1016/S0040-4039(01)81750-0

Kenji Mori and Hidenori Watanabe details the synthesis of the enantiomers of 3-hydroxy-1,7-dioxaspiro[5.5]undecane, a minor component of the olive fly pheromone. The authors synthesized (3R,6R)-(-)-3-hydroxy-1,7-dioxaspiro[5.5]undecane and its antipode from (S)-malic acid. The process involved converting (S)-malic acid to a bromide, followed by alkylation steps and further chemical transformations. The final enantiomers were obtained through a series of reactions, including the Mitsunobu inversion and hydrolysis. The structures of the synthesized compounds were confirmed by NMR spectral data comparison with published data, and the compounds were found to be of 100% enantiomeric excess as verified by HPLC analysis.

Stereoselective total synthesis of stagonolide C and formal total synthesis of modiolide A

10.1055/s-0029-1217556

The study investigates the influence of protecting groups at C4 and C7 on a ring-closing metathesis reaction to achieve the total synthesis of stagonolide C and the formal total synthesis of modiolide A. The key chemicals involved include L-malic acid and butane-1,4-diol as starting materials. Sharpless asymmetric epoxidation, activated zinc dust mediated reductive elimination, and ring-closing metathesis are the crucial reactions. The protecting groups, such as p-methoxybenzyl ethers and TBS ethers, play significant roles in controlling the geometry of the newly formed double bond during the ring-closing metathesis reaction. The successful synthesis of stagonolide C and modiolide A demonstrates the effectiveness of the selected protecting groups and the chosen synthetic strategy.