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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/REAXYS Number:
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

Related Categories

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

signalword

Danger

hcodes

H317,H318

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

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)
C Q Cao et al.
European journal of pharmacology, 418(1-2), 79-87 (2001-05-04)
Due to low central nervous system (CNS) bioavailability of delta-opioid peptides, little is known about the effect of systemic administration of delta-opioid receptor ligands. The present study examined the effect of non-peptidergic delta-opioid receptor agonists, (+)-4-[(alphaR)-alpha-((2R,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N-diethylbenzamide (SNC80) and (-)dibenzoyl-L-tartaric acid
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
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
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