HYDROXY SUCCINIC ACIDS

The other hydroxy di-basic acids which we shall consider are the hydroxyl substitution products of succinic acid. These hydroxy succinic acids are commonly occurring substances and, both from the standpoint of theory and of practical value, are most important compounds. The mono-hydroxy succinic acid is commonly known as malic acid, and the di-hydroxy compound is the common substance, tartaric acid. 

Malic Acid Mono-hydroxy Succinic Acid 

Relation to Succinic Acid.—The constitution of malic acid is fully established by its relation to succinic acid. It may be synthesized from mono-brom succinic acid by treatment with silver hydroxide. 

Mono-hydroxy succinic acid. Malic acid 

The reverse of this reaction takes place when malic acid is heated with hydrobromic acid, malic acid is thus converted into mono-brom succinic acid. 

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On the other hand let us study the case of 2 chloro 3 hydroxy succinic acid which has two asymmetric carbon atoms and which are not identical. This compound exists in four stereoisomeric forms as predicted by 22 formula. The various projection formula are ... 

Pent-2-ene-l,5-diones may be formed in situ (usually by an aldol-type reaction) and subsequently cyclized. Thus, malic acid (i.e. hydroxy succinic acid) with sulfuric acid gives carboxy acetaldehyde (155) which cyclizes spontaneously to coumalic acid (156). 

SYNS BUTANEDIOIC ACID, HYDROXY-(9CI) DEOXYTETRARIC ACID HYDROXYBUTANEDIOIC ACID HYDROXYSUCCINIC ACID tt-HYDROXY-SUCCINIC ACID KYSELINA HYDROXYBUTANDIOVA (CZECH) KYSELINA JABLECNA (CZECH) POMALUS ACID SUCCINIC ACID, HYDROXY-... 

SYNS BUTANEDIOIC ACID, 2,3-DIHYDROXY- 2,3-DIHYDROSUCCINIC ACID 2,3-DIHYDROXY-BUTANEDIOIC ACID KYSEUNA 2,3-DIHYDROXY-BUTANDIOVA KYSEUNA VINNA MALIC ACID, 3-HYDROXY- SUCCINIC ACID, 2,3-DIHYDROXY- 1-(+)-TARTARJC ACID THREARJC ACID... 

Malic Acid Mono-hydroxy Succinic Acid... 

By the introduction of one more hydroxyl group into malic acid we obtain a di-hydroxy succinic acid which, as a di-hydroxy compound, is analogous to mesoxalic acid and bears the same relation to succinic acid and to malic acid that mesoxalic acid bears to malonic acid and to tartronic acid. The acid of this constitution is the commonly occurring substance tartaric acid.. That tartaric acid contains two carboxyl groups and at the same time two alcohol hydroxyl groups and that it is in fact di-hydroxy succinic acid is proven by several syntheses and reactions. 

That tartaric acid is not the unsymmetrical di-hydroxy succinic acid is shown by the fact that an acid of this constitution would, by loss of water, yield a ketone acid, as follows ... 

Such an acid as this ketone acid is known and is called oxal acetic acid, and tartaric acid does not yield this acid on heating nor does it show any properties of a ketone acid. We, thus, have no evidence that tartaric acid is the unsymmetrical di-hydroxy succinic acid. That tartaric acid is, in fact, the symmetrical di-hydroxy succinic acid is proven by its synthesis from glyoxal, and also by its synthesis from succinic acid itself. 

From Succinic Acid.—The synthesis of tartaric acid from succinic acid also proves that it must be the symmetrical di-hydroxy succinic acid. When succinic acid, by means of bromine, yields the symmetrical di-brom succinic acid this, in turn, when treated with silver hydroxide,... 

Isomerism of Tartaric Acid.—Examination of the formula for tartaric acid, which, by the facts given above, has its constitution fully established as symmetrical di-hydroxy succinic acid, shows the interesting fact that there are present two asymmetric carbon atomsy and that each of these has linked to it the same set of four different groups. We should, therefore, expect to find tartaric acid existing in the dextrOy the levo and the inactive forms. The stereo-chemical formulas similar to those of lactic and malic acids we may write as follows. 

Firstly, we consider the SN2 reaction at saturated carbon, which is a one-step process that always proceeds with inversion of configuration. This reaction is shown in Scheme 7.1 with the inversion taking place at C(2) of compound 1. Inversion of configuration in what we now know as Sn2 reactions was first suspected in 1895 by the Latvian-born chemist Walden. He reacted hydroxy succinic acid (2, malic acid) with the acyl chlorides shown in Scheme 7.2, and realized that one of the steps shown in Scheme 7.2 was associated with inversion of configuration, but at that time he was unable to specify which. 

Malic acid (INS No 296 FW 134.09) Chem. name dl malic acid 2-hydroxybutanedioic acid, hydroxy succinic acid. Malic acid is the second most popular general purpose food acid, although only less than one-tenth of the quantity of citric acid is used in food. The functional uses include acidity regulator and as a flavoring agent [46]. The ADI is not limited. The usage of malic acid is similar to that of citric acid. 

Dihydroxysuccinic acid a,p-Dihydroxysuccinic acid 3-Hydroxymalic acid Malic acid, 3-hydroxy- Succinic acid, 2,3-dihydroxy-Tartaric acid (INCI) L-(+)-Tartaric acid Thearic acid... 

The principles set forth above account reasonably well for the course of bifunctional condensations under ordinary conditions and for the relative difficulty of ring formation with units of less than five or more than seven members. They do not explain the formation of cyclic monomers from five-atom units to the total exclusion of linear polymers. Thus 7-hydroxy acids condense exclusively to lactones such as I, 7-amino acids give the lactams II, succinic acid yields the cyclic anhydride III, and ethylene carbonate and ethylene formal occur only in the cyclic forms IV and V. 

Succinic anhydride also may react with protein phenolate side chains of tyrosine residues and the —OH group of aliphatic hydroxy amino acids (Figure 1.82). The phenolate ester derivatives are unstable above pH 5.0, whereas the serine and threonine esters are more stable but may be cleaved by treatment with hydroxylamine at basic pH (Gounaris and Perlman, 1967). 

A group of related siderophores comprises the desferri- or deferriferrioxamines (occasionally abbreviated as desferrioxamines) or proferrioxamines. Originally they were obtained from Actinomycetes, mainly Nocardia and Streptomyces spp. (187) and later found to be produced also by Erwinia spp. (several representatives) (e.g. (30a, 113,115,180)), Arthrobacter simplex (B), Chromobacterium violaceum (E) (246a), and by Pseudomonas stutzeri (several) (229a, 246,398). They consist of three (or in rare cases four) mono-N-hydroxy-l,4-diaminobutane (putrescine), mono-iV-hydroxy-l,5-diaminopentane (cadaverine) or (rarely) mono-N-hydroxy-1,3-diaminopropane units connected by succinic acid links. The hydroxylated terminus carries an acetyl or a succinyl (as in the structural formula heading Table 6)... 

In the MALDI technique a pulsed laser beam strikes a solid sample and heats, vaporizes, and ionizes compounds with little decomposition.201-209 Proteins or other biopolymers are mixed with a "matrix" Fiat absorbs the heat of Fie laser beam. The protein sample together with Fie matrix is dried. Most proteins form crystals and Fie laser beam is directed toward individual protein crystals or aggregates. Various materials are used for the matrix. Compounds as simple as glycerol, succinic acid, or urea can be used with an infrared laser. For proteins an ultraviolet nitrogen laser tuned to 337 nm is usually employed with an ultraviolet light-absorbing matrix such as hydroxy-benzoic acid, 2,5-dihydroxybenzoic acid, a-hydroxy-... 

BA BuE-PA BE-HET BE-HHPA BE-MA BE-PA BE-SA CA CHX DMA DMBA DY 062 GA HEB HHPA HMTA MA MTHPA NMA benzoic acid monobutylester of phthalic acid monobenzylester of hexachloroendomethylenetetrahydrophthalic acid monobenzylester of hexahydrophthalic acid monobenzylester of maleic acid monobenzylester of phthalic acid monobenzylester of succinic acid citraconic anhydride cyclohexanol N,N-dimethylaniline dimethylbenzylamine high boiling tertiary amine (Ciba Geigy AG) gjptaric anhydride 2-hydroxy-4-(2,3-epoxypropoxy)benzophenone hexahydrophthalic anhydride hexamethylenetetramine maleic anhydride methyltetrahydrophthalic anhydride nadic methyl anhydride (methylbicyclo[2.2.1]heptene-2,3-dicarboxylic anhydride isomers)... 

Bittner, B., et al. 2002. Improvement of the bioavailability of colchicine in rats by co-administration of D-alpha-tocopherol polyethylene glycol 1000 succinate and a polyethoxylated derivative of 12-hydroxy-stearic acid. Arzneimittelforschung 52 684. 

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