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Merck
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345849

Sigma-Aldrich

Dibenzoyl-L-tartaric acid

98%

Sinónimos:

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

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About This Item

Fórmula lineal:
[C6H5CO2CH(CO2H)-]2
Número de CAS:
2743-38-6
Peso molecular:
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

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sigma-Aldrich

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Sigma-Aldrich

358924

(+)-O,O′-Diacetyl-L-tartaric anhydride

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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