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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.)

functional group

carboxylic acid
ester
phenyl

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBL1161
STBJ9074
STBG6917
STBH3742
STBG9917

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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)
Jianghong An et al.
Journal of medicinal chemistry, 52(9), 2667-2672 (2009-05-08)
Computational molecular docking provides an efficient and innovative approach to examine small molecule and protein interactions. We have utilized this method to identify potential inhibitors of the H5N1 neuraminidase protein. Of the 20 compounds tested, 4-(4-((3-(2-amino-4-hydroxy-6-methyl-5-pyrimidinyl)propyl)amino)phenyl)-1-chloro-3-buten-2-one (1) (NSC89853) demonstrated the
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
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