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345849

Sigma-Aldrich

Dibenzoyl-L-tartaric acid

98%

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Synonym(s):
L-DBTA, (−)-O,O′-Dibenzoyl-L-tartaric acid
Linear Formula:
[C6H5CO2CH(CO2H)-]2
CAS Number:
Molecular Weight:
358.30
Beilstein/REAXYS Number:
709854
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

98%

optical activity

[α]20/D −116°, c = 9 in ethanol

mp

152-155 °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-/m1/s1

InChI key

YONLFQNRGZXBBF-ZIAGYGMSSA-N

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1 of 4

This Item
T10933622251380
Dibenzoyl-L-tartaric acid 98%

345849

Dibenzoyl-L-tartaric acid

L-(+)-Tartaric acid ≥99.5%

T109

L-(+)-Tartaric acid

L-(+)-Tartaric acid ACS reagent, ≥99.5%

251380

L-(+)-Tartaric acid

mp

152-155 °C (lit.)

mp

170-172 °C (lit.)

mp

88-89 °C (lit.)

mp

170-172 °C (lit.)

optical activity

[α]20/D −116°, c = 9 in ethanol

optical activity

[α]20/D +13.5±0.5°, c = 10% in H2O

optical activity

[α]20/D −110±3°, c = 5% in ethanol

optical activity

[α]20/D +12.4°, c = 20 in H2O

Application

Dibenzoyl-L-tartaric acid may be used as a chiral resolving agent for the resolution of racemic Troger base. It may also be used as a ligand to synthesize chiral transition metal complexes, which have potential utility in organic asymmetric catalysis.

pictograms

CorrosionExclamation mark

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Customers Also Viewed

Slide 1 of 2

1 of 2

Transition metal complexes of dibenzoyl-L-tartaric acid (db-L-tarH2) and L-tartaric acid (L-tarH2); X-ray crystal structure of {[Cu(L-tar)(phen)]?6H2O}n (phen=1,10-phenanthroline).
McCann M, et al.
Polyhedron, 16(20), 3655-3661 (1997)
A convenient method for the synthesis and resolution of Troger base.
Satishkumar S and Periasamy M.
Tetrahedron Asymmetry, 17(7), 1116-1119 (2006)
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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