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345849

Sigma-Aldrich

Dibenzoyl-L-tartaric acid

98%

Synonym(s):

L-DBTA, (−)-O,O′-Dibenzoyl-L-tartaric acid

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About This Item

Linear Formula:
[C6H5CO2CH(CO2H)-]2
CAS Number:
2743-38-6
Molecular Weight:
358.30
Beilstein:
709854
EC Number:
241-097-1
MDL number:
MFCD00003074
UNSPSC Code:
12352108
PubChem Substance ID:
24861354
NACRES:
NA.22

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

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
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H317,H318

Hazard Classifications

Eye Dam. 1 - Skin Sens. 1

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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A convenient method for the synthesis and resolution of Troger base.
Satishkumar S and Periasamy M.
Tetrahedron Asymmetry, 17(7), 1116-1119 (2006)
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)
Emily M Jutkiewicz et al.
The Journal of pharmacology and experimental therapeutics, 309(1), 173-181 (2004-01-15)
The diarylpiperazine delta-opioid agonist SNC80 [(+)-4-[(alphaR)-alpha-[(2S,5R)-2,5-dimethyl-4-(2-propenyl)-1-piperazinyl]-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide] produces convulsions, antidepressant-like effects, and locomotor stimulation in rats. The present study compared the behavioral effects in Sprague-Dawley rats of SNC80 with its two derivatives, SNC86 [(+)-4-[alpha(R)-alpha-[(2S,5R)-2,5-dimethyl-4-(2-propenyl)-1-piperazinyl]-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide] and SNC162 [(+)-4-[(alphaR)-alpha-[(2S,5R)-2,5-dimethyl-4-(2-propenyl)-1-piperazinyl]-(3-phenyl)methyl]-N,N-diethylbenzamide], which differ by one
Jin-Lan Zhou et al.
Chemical communications (Cambridge, England), (48)(48), 5200-5202 (2007-12-07)
Chiral calix[4]arenes bearing long tertiary alkyl groups at the upper rim and S-1-phenylethylamine groups at the lower rim can form heat-set gels and egg-like vesicles enantioselectively with d-2,3-dibenzoyltartaric acid in cyclohexane, which is the first example of heat-set gels resulting
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
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