Idaric acid

Deamination of 2-amino-2-deoxy-D-idonolactone (27) with nitrous acid led, after oxidation with nitric acid, to 2,5-anhydro-D-glucaric acid39,42 (28). As deamination of 2-amino-2-deoxy-D-idonic acid, followed by oxidation, gave 2,5-anhydro-D-idaric acid, the different behavior of the lactone 27 must be due to an attack on the incipient carbonium-ion at C-2 by a favorably disposed hydroxyl group in the molecule, such as at C-5. 

Diacetals of mannitol with the groups disposed 2,3,4,5 present several problems. The structure of only one has been established beyond doubt 2,4 3,5-di-O-methylene-D-mannitoF has been converted to 2,4 3,5-di-0-methylene-L-idaric acid by oxidation and epimerization. Two conformations for this diacetal are possible, the H-iriside with two equatorial, terminal groups (LVI) or 0-inside with two axial groups (LVII). It is... 

The optically inactive carbohydrate bio-inonose, QH10O5, reduces Benedict s solution, but does not react with bromine water. It is reduced to R and S, of formula C6H12O6. Compounds R and S are oxidized by HIO4 to six moles of HCOOH, and react with acetic anhydride to yield products of formula CigH240i2. Vigorous oxidation of bio-inonose yields DL-idaric acid (the dicarboxylic acid from idose) as the only six-carbon fragment. 

A meso -compd., certain derivs. induce asymmetry. For stereoisomers see Glucaric acid, G-241, Allaric acid, A-74, Mannaric acid, M-23, Galactaric acid, G-2 and Idaric acid, I-l. Isol. from sporophylls of brown algae, various fruits and fungi. Used as 2% aq. soln. to form colour complexes with Fe, Co, Cr(/J7), Mn, U(F/). (pH 3-10). Cryst. Sol. alkalis spar. sol. H2O. 

Diamino-2,4,5,6-tetradeoxy-/Fx o-heptaric add, D-467 Dibenzoyltartaric add, T-12 2,4 3,5-Di-0-benzylidene-D-idaric acid, I-l... 

Di-0-methylene-L-idaric acid, I-l A A -Dimethyl-D-glucaranide, G-241 2,5-Di- O -methyl-D-1,4 6,3-glucarodilactone, G-242 Diphenyl tartrate, T-12 FEMA 2655, M-6 Feruloyltartaric acid, T-12... 

Postemak, on the other hand, applied the alkaline permanganate oxidation to scyllo-myo-inosose (bioinosose) and obtained DL-idaric acid (4 ). This evidence simultaneously establishes the configurations of the inosose, m o-inositol, and scj/Zto-inositol. The only configuration compatible with the recovery of DL-idaric acid from the inosose is ... 

This oxidation, as employed by Posternak, was very useful in elucidating the configuration of the inositols (see above). From mj/o-inositol, S. and T. Posternak obtained DL-talaric and DL-glucaric acids. From myo-inosose-2, T. Posternak obtained DL-idaric acid. In these instances, the ring was opened to form dibasic acids. d-Quercitol was oxidized by Posternak (6S) to 3-deoxy-D-galactaric acid. In all these oxidations, it was necessary to maintain low temperatures. 

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