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163449

Sigma-Aldrich

(+)-2,3-Dibenzoyl-D-tartaric acid

≥98%, made from synthetic tartaric acid

Synonym(s):

(+)-O,O′-Dibenzoyl-D-tartaric acid, D-Tartaric acid 2,3-dibenzoate

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About This Item

Linear Formula:
[C6H5CO2CH(CO2H)]2
CAS Number:
17026-42-5
Molecular Weight:
358.30
Beilstein:
2227343
EC Number:
241-097-1
MDL number:
MFCD00063222
UNSPSC Code:
12352106
PubChem Substance ID:
24849748
NACRES:
NA.22

Assay

≥98%

optical activity

[α]28/D +116°, c = 9 in ethanol

mp

154-156 °C (lit.)

SMILES string

OC(=O)[C@@H](OC(=O)c1ccccc1)[C@H](OC(=O)c2ccccc2)C(O)=O

InChI

1S/C18H14O8/c19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12/h1-10,13-14H,(H,19,20)(H,21,22)/t13-,14-/m0/s1

InChI key

YONLFQNRGZXBBF-KBPBESRZSA-N

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General description

(+)-2,3-Dibenzoyl-D-tartaric acid is commonly used as an optically active resolving agent in the chiral resolution process such as diastereomeric salt resolution technique.

Application

Reagent for chiral resolution of amino compounds.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tetrahedron Asymmetry, 2, 989-989 (1991)
Analysis and Comparison of Commonly Used Acidic Resolving Agents in Diastereomeric Salt Resolution-Examples for dl-Serine.
Sistla VS, et al.
Crystal Growth & Design, 11(9), 3761-3768 (2011)
Stanley I Goldberg
Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life, 43(1), 31-37 (2013-01-25)
Construction and operation of a laboratory model, which combines the lately discovered enantioenrichment method of the author (2007) with the sun-powered evaporative pumping process of Hsu and Siegenthaler (Sedimentology 12:11-25 1969), is described. The model operated continuously for 120 days
Christian Zimmer et al.
Applied microbiology and biotechnology, 73(1), 132-140 (2006-07-19)
In a screening procedure a pink-colored yeast was isolated from enrichment cultures with (2R,3R)-(-)-di-O-benzoyl-tartrate (benzoyl-tartrate) as the sole carbon source. The organism saar1 was identified by morphological, physiological, and 18S ribosomal DNA/internal transcribed spacer analysis as Rhodotorula mucilaginosa, a basidiomycetous
Yan-Song Zheng et al.
Organic letters, 6(8), 1189-1192 (2004-04-09)
Calixarenes bearing optically pure alpha,beta-amino alcohol groups at their lower rim exhibit exceptional and efficient chiral recognition ability in discrimination of racemic mandelic acid, 2,3-dibenzoyltartaric acid and 2-hydroxy-3-methylbutyric acid. [structure: see text]
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