D-Tartaric acid - CAS 147-71-7

D-Tartaric acid is a chiral resolution reagent to separate racemic compounds into different mirror isomers and is an important tool for the production of optically active drugs.

Product Information

Canonical SMILES
C(C(C(=O)O)O)(C(=O)O)O
InChI
InChI=1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m0/s1
InChI Key
FEWJPZIEWOKRBE-LWMBPPNESA-N
Purity
≥95%
MDL
MFCD00004238
Physical State
Solid
Appearance
white crystals
Storage
Store at RT
Boiling Point
399.3±42.0°C at 760 Torr
Melting Point
166-173°C
Flash Point
210 °C(410 °F)
Density
1.886±0.06 g/cm3
Optical Activity
-12°(c=20 in water)
Solubility
Soluble in Alcohol, Water
TSCA
Yes
WGK Germany
3

Safety Information

Signal Word
Warning
Precautionary Statement
P261 - P305+P351+P338
Hazard Statements
H315 - H319 - H335

Reference Reading

1.Glycine-d-tartaric acid (1/1).
Mohandas T1, Inbaseelan CR, Saravanan S, Sakthivel P. Acta Crystallogr Sect E Struct Rep Online. 2013 Feb 1;69(Pt 2):o236. doi: 10.1107/S1600536813000822. Epub 2013 Jan 16.
In the title co-crystal, C(2)H(5)NO(2)·C(4)H(6)O(6), the gylcine mol-ecule is present in the zwitterion form. In the tartaric acid mol-ecule there is a short intra-molecular O-H⋯O contact. In the crystal, the tartaric acid mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers. These dimers are linked via a number of O-H⋯O and N-H⋯O hydrogen bonds involving the two components, forming a three-dimensional network.
2.Enantiospecific formal total synthesis of iriomoteolide 3a.
Kumar SM1, Prasad KR. Chem Asian J. 2014 Dec;9(12):3431-9. doi: 10.1002/asia.201402593. Epub 2014 Sep 18.
A formal total synthesis of the marine macrolide iriomoteolide 3a is described. Salient features of the synthesis include the elaboration of a β-keto phosphonate derived from D-(-)-tartaric acid and the extension of a chiral butyrolactone derived from L-glutamic acid. Ring-closing metathesis is employed to construct the macrolactone core of the natural product.
3.Ultraviolet radiation induces stress in etiolated Landoltia punctata, as evidenced by the presence of alanine, a universal stress signal: a ¹⁵N NMR study.
Monselise EB1, Levkovitz A, Kost D. Plant Biol (Stuttg). 2015 Jan;17 Suppl 1:101-7. doi: 10.1111/plb.12198. Epub 2014 May 29.
Analysis with (15) N NMR revealed that alanine, a universal cellular stress signal, accumulates in etiolated duckweed plants exposed to 15-min pulsed UV light, but not in the absence of UV irradiation. The addition of 10 mm vitamin C, a radical scavenger, reduced alanine levels to zero, indicating the involvement of free radicals. Free D-alanine was detected in (15) N NMR analysis of the chiral amino acid content, using D-tartaric acid as solvent. The accumulation of D-alanine under stress conditions presents a new perspective on the biochemical processes taking place in prokaryote and eukaryote cells.
4.Enantioselective Extraction System Containing Binary Chiral Selectors and Chromatographic Enantioseparation Method for Determination of the Absolute Configuration of Enantiomers of Cyclopentolate.
Szwed K1, Górecki M, Frelek J, Asztemborska M. Chromatographia. 2013;76:1603-1611. Epub 2013 Aug 23.
The distribution coefficients and enantioseparation of cyclopentolate were studied in an extraction system containing d-tartaric acid ditertbutyl ester in organic phase and 2-hydroxypropyl-β-cyclodextrin (HP-β-CD) in aqueous phase. Various parameters involved in the enantioseparation such as the type and the concentration of chiral selectors, pH value and a wide range of organic solvents were investigated. The maximum enantioselectivity (α = 2.13) and optimum distribution coefficients (K R = 0.85, K S = 0.40) were obtained under the following conditions: 0.10 mol/L HP-β-CD in aqueous phase and 0.20 mol/L d-tartaric acid ditertbutyl ester in decanol as organic phase. Cyclopentolate is present as a racemic mixture to the aqueous phase. The potentially different biological activities of cyclopentolate enantiomers have not been examined yet. Two chiral liquid chromatography methods have been developed for the direct separation of the enantiomers of cyclopentolate.
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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