D-malate

Base Information

• Chemical Name: D-malate
• CAS No.: 636-61-3
• Deprecated CAS: 1245537-07-8,15856-21-0
• Molecular Formula: C4H6O5
• Molecular Weight: 134.089
• Hs Code.: 29181980
• European Community (EC) Number: 211-262-2
• UNII: P750Y95K96
• DSSTox Substance ID: DTXSID90892496
• Nikkaji Number: J14.674I
• Wikidata: Q27104149
• Metabolomics Workbench ID: 44921
• ChEMBL ID: CHEMBL225986
• Mol file: 636-61-3.mol

Synonyms:D-(+)-malic acid;636-61-3;D-malic acid;D(+)-Malic acid;(R)-2-Hydroxysuccinic acid;(R)-malic acid;D-malate;(2R)-2-hydroxybutanedioic acid;Malic acid, D-;Malic acid D-(+)-form;L(+)-Malic acid;(+)-D-malic acid;D-Hydroxybutanedioic acid;Butanedioic acid, hydroxy-, (2R)-;MFCD00004245;R-Malic acid;Malic acid, L(+)-;(R)-malate;EINECS 211-262-2;MLS000069520;(r)-(+)-hydroxysuccinic acid;UNII-P750Y95K96;CHEBI:30796;C4H6O5;P750Y95K96;SMR000058580;D-(+)-Apple Acid;(R)-Hydroxybutanedioic acid;MALATE ION;(R)-(+)-2-Hydroxysuccinic acid;ApfelsA currencyure;(+)-Malic acid;Opera_ID_1814;(R)-2-Hydroxysuccinicacid;SCHEMBL98496;Hydroxy-(R)-Butanedioic acid;(R)-2-hydroxybutanedioic acid;CHEMBL225986;DTXSID90892496;D-Malic acid, analytical standard;HMS2234D08;Butanedioic acid, hydroxy-, (R)-;CS-B0824;AKOS016842807;AC-1885;DB03499;MALIC ACID D-(+)-FORM [MI];AS-14126;HY-20558;LS-88710;M0021;EN300-96989;BUTANEDIOIC ACID, 2-HYDROXY-, (2R)-;C00497;M-0800;AAF7D69B-7713-4E35-92ED-EA50BA0FCDCE;D-(+)-Malic acid, unnatural form, >=97.0% (T);Q27104149;Z1205493568;(2R)-2-HYDROXYBUTANEDIOIC ACID;2-HYDROXY-SUCCINIC ACID

Chemical Property of D-malate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 7.19E-05mmHg at 25°C
• Melting Point: 98-102 °C(lit.)
• Refractive Index: 6.5 ° (C=10, Acetone)
• Boiling Point: 306.4 °C at 760 mmHg
• PKA: 3.61±0.23(Predicted)
• Flash Point: 153.4 °C
• PSA: 94.83000
• Density: 1.641 g/cm³
• LogP: -1.09340
• Storage Temp.: Store below +30°C.
• Solubility.: Soluble in methanol, ethanol, acetone, ether.
• 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% ^*data from raw suppliers

D-Malic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 37/38-41-36/37/38
• 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
• Uses: The naturally occuring isomer is the L-form which has been found in apples and many other fruits and plants. Selective α-amino protecting reagent for amino acid derivatives. Versatile synthon for the preparation of chiral compounds including κ-opioid rece D-(+)-Malic acid used as an acidulant and flavoring agent, food additive. And it is also used in the place of the less sour citric acid in sour sweets. D-(+)-Malic acid can be used: As a starting material for the enantioselective total synthesis of (?)-erinapyrone B.As a chiral organocatalyst in the synthesis of α-aminophosphonates from various aldehydes, aniline, and diethyl phosphite.

Technology Process of D-malate

There total 73 articles about D-malate 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: 86.0%

L-Aspartic acid (56-84-8,25608-40-6,27881-03-4,32505-46-7,52526-39-3) → D-Malic acid (636-61-3,78644-42-5) + (2S)-chlorobutanedioic acid (4198-33-8,617-41-4) + 2-butenedioic acid (6915-18-0,26099-09-2)

Guidance literature:

With hydrogenchloride; sodium nitrite; In water; at -15 - 0 ℃; for 8h;

Reference yield: 79.0%

(R)-4,4,4-trichloro-3-hydroxybutanoic acid (80513-23-1) → D-Malic acid (636-61-3,78644-42-5) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 24h;

DOI:10.1021/ja00365a030

Reference yield: 75.0%

maleic acid (110-16-7,26099-09-2) → D-Malic acid (636-61-3,78644-42-5)

Guidance literature:

With TETRACYCLINE; In water; at 37 ℃; for 18h; Clostridium formicoaceticum, phosphate buffer;

DOI:10.1016/S0040-4020(01)85678-7

upstream raw materials:

malic acid-4-methylamide

(R)-Asparagine

L-asparagine

malic acid

Downstream raw materials:

diethyl (R)-malate

(R)-dimethyl malate

(R)-1,2,4-butanetriol

(2R)-diisopropyl 2-hydroxybutanedioate

Refernces

• 1、 Davies-Coleman, Michael T.,Rivett, Douglas E. A.. "STEREOCHEMICAL STUDIES ON BORONOLIDE, AN α-PYRONE FROM TETRADENIA BARBERAE". . p. 3047 - 3050. Retrieved 1987.
• 2、 Jun, Chanha,Sa, Young Seung,Gu, Sol-A,Joo, Jeong Chan,Kim, Seil,Kim, Kyung-Jin,Kim, Yong Hwan. "Discovery and characterization of a thermostable D-lactate dehydrogenase from Lactobacillus jensenii through genome mining". . p. 109 - 117. Retrieved 2013/04/10.
• 3、 Jeyakanthan, Jeyaraman,Drevland, Randy M.,Gayathri, Dasara Raju,Velmurugan, Devadasan,Shinkai, Akeo,Kuramitsu, Seiki,Yokoyama, Shigeyuki,Graham, David E.. "Substrate specificity determinants of the methanogen homoaconitase enzyme: Structure and function of the small subunit". scheme or table. p. 2687 - 2696. Retrieved 2011/03/20.