66178-02-7

Basic information

• Product Name: Malic acid 4-Me ester
• Synonyms: Malic acid 4-Me ester;(S)-2-Hydroxybutanedioic acid 4-methyl ester;Malic acid 4-methyl ester
• CAS NO: 66178-02-7
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.11402
• Product Categories: Miscellaneous
• Mol File: 66178-02-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 357.7±27.0 °C(Predicted)
• Appearance: /
• Density: 1.383±0.06 g/cm3(Predicted)
• PKA: 3.49±0.23(Predicted)
• CAS DataBase Reference: Malic acid 4-Me ester(CAS DataBase Reference)
• NIST Chemistry Reference: Malic acid 4-Me ester(66178-02-7)
• EPA Substance Registry System: Malic acid 4-Me ester(66178-02-7)

Safety Data

• Hazardous Substances Data: 66178-02-7(Hazardous Substances Data)

Usage

General Description

Malic acid 4-Me ester, also known as 4-methyl malic acid, is an organic compound that is commonly used as a food additive and flavoring agent. It is a derivative of malic acid, a naturally occurring acid found in many fruits and vegetables. Malic acid 4-Me ester is often used to enhance the sourness and tartness of food products, and it is commonly found in sour candies, fruit-flavored beverages, and other sour-tasting foods. It is also used in the production of fragrances and as a component in cosmetic and personal care products. In addition to its use in the food and cosmetic industries, malic acid 4-Me ester has also been studied for its potential medicinal properties, including its antioxidant and anti-inflammatory effects.

Upstream product

• 186581-53-3 diazomethane 
• 97-67-6 (S)-Malic acid 
• 38115-87-6 malic acid dimethyl ester 

Downstream Products

• 95422-24-5 methyl (3S)-3,4-O-isopropylidene-3,4-dihydroxybutanoate 
• 162584-13-6 methyl (2R,3S)-3-benzyloxymethoxy-4-(tert-butyldimethylsilyloxy)-2-methylbutanoate 

Relevant articles and documents

Biologically active macrolides, compositions, and uses thereof

The present invention provides a compound of the formula (I) or (II), wherein R1 is H, alkyl, alkenyl or aryl, R2 is H, alkyl or aryl, R3 is H, a alkyl, alkenyl or aryl, R4 and R4-R8 are independently R10, C(O)R10 or SO2R10, wherein R10 is H, alkyl, alkenyl or aryl, and R9 is R9a, C(O)R9a or SO2R9a, wherein R9a is H, alkyl, alkenyl or aryl. R9a can be unsubstituted or substituted with one or more oxo(═O), OR9b, OC(O)R9b, OSO2R9b, NHR9b, NHC(O)R9b and NHSO2R9b groups. R9b is H, alkyl, alkenyl, or aryl. R9b can be unsubstituted or substituted with one or more groups such as oxo(═O), OR9c, CO2R9c, CO2R9c and OC(O)R9c. R9c is H, or a unsubstituted or substituted alkyl, alkenyl or aryl. The present invention further provides a composition comprising at least one compound of the present invention and a pharmaceutically acceptable carrier, alone or in combination with at least one additional active agent. The present invention further provides a method of treating a condition treatable by the inhibition of vacuolar-type (H+)-ATPase and a method of treating cancer.

A Biocatalytic Approach to the Enantioselective Synthesis of (R)- and (S)-Malic Acid

(S)-Diethyl malate 1a was prepared (70-80percent yield; >98percent optical purity) by an enantioselective reduction of sodium diethyl oxalacetate 2 by fermenting baker's yeast (Saccharomyces cerevisiae).Other microorganisms were tested for their capability of reducing 2.Most of them afforded (S)-1a with ee from 8 to 94percent and only Candida utilis, Aspergillus niger and Lactobacillus fermentum ILC G18D preferentially reduced compound 2 to (R)-1a. (R)-Dimethyl malate 1b was obtained from (R,S)-malate 1b by hydrolysis with pig liver esterase (PLE), the highest ee (93percent) being realized at 0 deg C in 20percent aqueous methanol.Enzymatic hydrolyses of protected malates 1d and 1e did not lead to improvement of the ee.