ChemicalBook CAS DataBase List L-Malic acid

L-Malic acid synthesis

10synthesis methods

Product Name:L-Malic acid
CAS Number:97-67-6
Molecular formula:C4H6O5
Molecular Weight:134.09

By hydration of maleic acid; by fermentation from sugars.

1009815-87-5
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640-68-6
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72-18-4 Synthesis

72-18-4
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97-67-6
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1127229-10-0
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1127229-09-7
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56-40-6 Synthesis

56-40-6
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Yield:-

Reaction Conditions:

Stage #1: largazolewith ozone in dichloromethane at 25; for 0.5 h;
Stage #2: with formic acid;dihydrogen peroxide at 70; for 0.333333 h;
Stage #3: with hydrogenchloride;water at 110; for 24 h;

Steps:

3

Example 3: Determination of Absolute Configuration. A sample of compound 21 (~100 μg) was dissolved in 4 mL Of CH₂Cl₂ and subjected to ozonolysis at room temperature for 30 min. The solvent was evaporated and the residue was treated with 0.6 mL Of H₂O₂-HCO₂H (1 :2) at 70 ⁰C for 20 min. The solvent was evaporated and the resulting oxidation product was hydrolyzed with 0.5 mL of 6 N HCl at 1 10 ⁰C for 24 h. The hydrolyzed product was dried and analyzed by chiral HPLC (column, Phenomenex Chirex phase 3126 N.S-dioctyl-φ)- pencillamine, 4.60 x 250 mm, 5 μm; solvent 1, 2 mM CuSO₄ in 95:5 H₂O/MeCν, pH 4.50; solvent 2, 0.5 mM Cu(OAc)₂/0.1 M NH₄OAc in 85:15 H₂O/MeCN, pH 4.6; flow rate 1.0 mL/min; detection at 254 nm). The absolute configuration of the amino acids in the hydrolyzate was determined by direct comparison with the retention times of authentic standards. The retention times (t_R, min) for solvent 1 were as follows: GIy (5.3), L-VaI (12.6), D-VaI (16.4), (S)-2-Me-cysteic acid (20.0), and (λ)-2-Me- cysteic acid (23.9). The retention times (J_R, min) of the hydrolyzate components were 5.3, 12.6, 23.9, indicating the presence of GIy, L-VaI and (/?)-2-Me-cysteic acid in the product mixture. Solvent 2 was used to detect malic acid. Standard L-malic acid eluted at f? 7.6 min and D-malic acid at t_R 20.4 min. Malic acid in the hydrolyzate eluted after 7.6 min, indicating the presence of the L isomer. GIy, L-VaI, and (R)-2- Me-cysteic acid eluted after 4.0, 5.8 and 6.5 min, respectively.