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95352

Sigma-Aldrich

(−)-Dibenzyl D-tartrate

≥98.0% (sum of enantiomers, HPLC)

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Empirical Formula (Hill Notation):
C18H18O6
CAS Number:
4136-22-5
Molecular Weight:
330.33
Beilstein:
4787873
MDL number:
MFCD01863133
UNSPSC Code:
12352108
PubChem Substance ID:
57653674
NACRES:
NA.22

Quality Level

100

Assay

≥98.0% (sum of enantiomers, HPLC)

form

powder

optical activity

[α]20/D −12.5±1°, c = 1.1% in acetone

mp

66-70 °C

SMILES string

O[C@@H]([C@H](O)C(=O)OCc1ccccc1)C(=O)OCc2ccccc2

InChI

1S/C18H18O6/c19-15(17(21)23-11-13-7-3-1-4-8-13)16(20)18(22)24-12-14-9-5-2-6-10-14/h1-10,15-16,19-20H,11-12H2/t15-,16-/m0/s1

InChI key

LCKIPSGLXMCAOF-HOTGVXAUSA-N

Related Categories

Application

(-)-Dibenzyl D-tartrate can be employed as a reactant to synthesize:
  • 2,3-bis(8-Methoxyoctanoyl) dibenzyl tartrate (DBT) by reacting with 8-methoxyoctanoic acid in the presence of 1-ethyl-3-(3-(dimethylamino)propyl)carbodiimide (EDCI) as a coupling reagent.
  • (-)-Chicoric acid (2,3-bis{[3-(3,4-dihydroxyphenyl)-1-oxoprop-2-enyl]oxy}butanedioic acid), as a potent inhibitor.
  • Diesters of aziridine-2,3-dicarboxylic acid derivatives.

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)

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A Convenient Synthesis of the Echinacea-Derived Immunostimulator and HIV-1 Integrase Inhibitor (-)-(2R, 3R)-Chicoric Acid
Lamidey A-M, et al.
Helvetica Chimica Acta, 85(8), 2328-2334 (2002)
An improved synthesis of aziridine-2, 3-dicarboxylates via azido alcohols?epimerization studies
Breuning A, et al.
Tetrahedron Asymmetry, 14(21), 3301-3312 (2003)
Allison Faig et al.
Biomacromolecules, 15(9), 3328-3337 (2014-07-30)
Amphiphilic macromolecules (AMs) composed of sugar backbones modified with branched aliphatic chains and a poly(ethylene glycol) (PEG) tail can inhibit macrophage uptake of oxidized low-density lipoproteins (oxLDL), a major event underlying atherosclerosis development. Previous studies indicate that AM hydrophobic domains

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