Chloro malic acid

Results of stereochemical studies with various halohydrins confirm that the oxy-anion attacks the carbon from the opposite side, causing Walden inversion the erythro forms of 3-bromo-2-butanol, stilbene bromohydrin, and chloro malic acid give the trans oxide, and the corresponding threo forms lead to the cis oxides [146]. Furthermore, the frans-halohydrin of cyclohexene reacts 150 times as fast with OH- as the cis compound. Only the reaction of the trans compound yields an epoxide [147] in the reaction of the cis compound, an enol is formed first which then rearranges to the corresponding ketone [148, 149]. 

MACB=5-chloro-2-(methylamino)benzo-phenone la 227 Macrolide antibiotics la 195 Magnesium cations lal44,145,311,312 Malachite green la 45 Malathion lb 83, 304, 305,338,340,341 Maleic acid la 44,61,171,230,249,250 Malic acid la 45,175,230,233,250,258, 259,308... 

D (-) malic acid L (+) chloro succinic acid L (+) malic acid... 

Figure 4.7 Anion exchange separation of carboxylic acids in red wine. Column, Shodex C811, 100 cm x 7.6 mm i.d. eluent, 3 mM perchloric acid flow rate, 0.9 ml min-1 temperature, 60 °C detection, reaction detection using chloro-phenol red at 430 nm. Peaks 1, citric acid 2, tartaric acid 3, malic acid 4, succinic acid 5, lactic acid 6, formic acid and 1, acetic acid.

These compounds are L-dopa (13-tyrosinase) D-p-hydroxyphenylglycine, D-phenylglycine (hydantoinase) ethyl (R)-4-chloro-3-hydroxybutanoate (aldehyde reductase) acrylamide, nicotinamide (nitrile hydratase) acrylic acid, nicotinic acid (nitrilase) 6-hydroxynicotinic acid (hydroxylase) D-malic acid (maleate hydratase) D-pantoic acid (aldonolactonase) and theobromine (oxygenase). 

---