Malic

Colourless prisms m.p. 130 C. Manufactured by treating maleic anhydride with water. It is converted to the anhydride by heating at By prolonged heating at 150 "C or by heating with water under pressure at 200 C, it is converted to the isomeric (trans) fumaric acid. Reduced by hydrogen to succinic acid. Oxidized by alkaline solutions of potassium permanganate to mesotartaric acid. When heated with solutions of sodium hydroxide at 100 C, sodium( )-malate is formed. Used in the preparation of ( )-malic acid and in some polymer formulations. 

Malic acid crystallizes in colourless needles m.p. lOO C. It o- curs in many acid fruits, such as grapes, apples and gooseberries. It can be prepared by microbiological processes using various moulds or from ( + )-bromosuccinic acid by the action of NaOH. 

Acetophenone similarly gives an oxime, CHjCCgHjlCtNOH, of m.p. 59° owing to its lower m.p. and its greater solubility in most liquids, it is not as suitable as the phenylhydrazone for characterising the ketone. Its chief use is for the preparation of 1-phenyl-ethylamine, CHjCCgHslCHNHj, which can be readily obtained by the reduction of the oxime or by the Leuckart reaction (p. 223), and which can then be resolved by d-tartaric acid and /-malic acid into optically active forms. The optically active amine is frequently used in turn for the resolution of racemic acids. 

Oxalic (Hibdrate) Malonio Sttooinio Qluiaric Adipic Pimclic Suberic Aiclaic Scbacic Malic Mocic Fumaric Maleic Meaaoonic Citraconic Itaoonio Camphoric roC Tartaric mcco Tartaric d.Tartahc. Citric (hydrated) Aconitic... 

Maleic acid may be prepared by warming malic acid with acetyl chloride, distilling the mixture under atmospheric pressure to isolate maleic anhydride, and hydrolysing the latter by boding with water. 

A. Maleic acid. Assemble the apparatus shown in Fig. Ill, 28, 1. Place 45 g. of dry mahc acid in the 200-250 ml. distilling flask and cautiously add 63 g. (57 ml.) of pure acetyl chloride. Warm the flask gently on a water bath to start the reaction, which then proceeds exothermically. Hydrogen chloride is evolved and the malic acid passes into solution. When the evolution of gas subsides, heat the flask on a water bath for 1-2 hours. Rearrange the apparatus and distil. A fraction of low boiling point passes over first and the temperature rises rapidly to 190° at this point run out the water from the condenser. Continue the distillation and collect the maleic anhydride at 195-200°. Recrystallise the crude maleic anhydride from chloroform (compare Section 111,93) 22 g. of pure maleic anhydride, m.p. 54°, are obtained. 

Optically inactive starting materials can give optically active products only if they are treated with an optically active reagent or if the reaction is catalyzed by an optically active substance The best examples are found m biochemical processes Most bio chemical reactions are catalyzed by enzymes Enzymes are chiral and enantiomerically homogeneous they provide an asymmetric environment m which chemical reaction can take place Ordinarily enzyme catalyzed reactions occur with such a high level of stereo selectivity that one enantiomer of a substance is formed exclusively even when the sub strate is achiral The enzyme fumarase for example catalyzes hydration of the double bond of fumaric acid to malic acid m apples and other fruits Only the S enantiomer of malic acid is formed m this reaction... 

The reaction is reversible and its stereochemical requirements are so pronounced that neither the cis isomer of fumaric acid (maleic acid) nor the R enantiomer of malic acid can serve as a substrate for the fumarase catalyzed hydration-dehydration equilibrium... 

In the resolution of 1 phenylethylamine using (-) malic acid the compound obtained by recrystallization of the mixture of diastereomeric salts is (/ )... 

Malic acid [97-d7-d] Malnutrition Malodor evaluation Malolacticfermentation Malonate [1797-75-7] Malonate esters Malonates... 

Acid content calculated as tartaric acid is about 6—7 g/L for best flavor and stabiUty. It is higher for tart low Brix musts and less important for sweet high Brix musts. High acid levels coiacide with a higher level of the second acid of grapes, malic acid. 

In addition to alcohoHc fermentation, a malolactic fermentation by certain desirable strains of lactic acid bacteria needs to be considered. Occasionally, wild strains produce off-flavors. Malolactic fermentation is desirable in many red table wines for increased stabiUty, more complex flavor, and sometimes for decreased acidity. Selected strains are often added toward the end of alcohoHc fermentation. AH the malic acid present is converted into lactic acid, with the resultant decrease of acidity and Hberation of carbon dioxide. Obviously this has more effect on the acidity the more malic acid is present, and this is the case in wine from underripe, too-tart grapes. Once malolactic fermentation has occurred, it does not recur unless another susceptible wine is blended. 

Ergonovine (100, R = NHCH(CH3)CH2 0H) was found to yield lysergic acid (100, R = OH) and (+)-2-aminopropanol on alkaline hydrolysis during the early analysis of its stmcture (66) and these two components can be recombined to regenerate the alkaloid. Salts of ergonovine with, for example, malic acid are apparently the dmgs of choice in the control and treatment of postpartum hemorrhage. 

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