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MilliporeSigma

T206

Sigma-Aldrich

D-(−)-Tartaric acid

ReagentPlus®, 99%

Synonym(s):

(2S,3S)-(−)-Tartaric acid, D-Threaric acid

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1 ML
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About This Item

Linear Formula:
HO2CCH(OH)CH(OH)CO2H
CAS Number:
Molecular Weight:
150.09
Beilstein/REAXYS Number:
1725145
EC Number:
MDL number:
UNSPSC Code:
12352300
PubChem Substance ID:
NACRES:
NA.22

CA$339.00


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description

synthetic

Quality Level

product line

ReagentPlus®

assay

99%

optical activity

[α]20/D −12°, c = 20 in H2O

optical purity

ee: 99% (GLC)

mp

172-174 °C (lit.)

solubility

water: soluble 100 mg/mL, clear, colorless

SMILES string

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

InChI

1S/C4H6O6/c5-1(3(7)8)2(6)4(9)10/h1-2,5-6H,(H,7,8)(H,9,10)/t1-,2-/m0/s1

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This Item
95320T180727506
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

solubility

water: soluble 100 mg/mL, clear, colorless

solubility

-

solubility

H2O: 1 M at 20 °C, clear, colorless

solubility

water: soluble 150 g/L at 20 °C

mp

172-174 °C (lit.)

mp

167-171 °C, 172-174 °C (lit.)

mp

170-172 °C (lit.)

mp

168-170 °C, 170-172 °C (lit.)

description

synthetic

description

synthetic

description

-

description

-

product line

ReagentPlus®

product line

-

product line

BioXtra

product line

-

General description

D-(-)-Tartaric acid is a polycrystalline solid, widely used as food additive.[1] It has been reported to exhibit piezoelectric effect.[2]
D-(−)-Tartaric acid is a polyhydroxy acid. Oxidation of d-tartaric acid has been reported.[3] Crystal structure of D-(−)-tartaric acid has been studied by X-ray and neutron diffraction.[4] Tartaric acid is reported to be one of the constituents of soy bean Lipositol.[5] Tartaric acid assists in the generation Y2O3:Eu3+ nanoparticles by sol–gel method.[6] Tartaric acid is the main acid present in grapes and red wine.[7]

Application

D-(-)-Tartaric acid has been used in the near-field, terahertz time-domain spectroscopic (THz-TDS) analysis of waveguides filled with polycrystalline D-tartaric acid, and with polyethylene and silicon powders.[1]
D-(−)-Tartaric acid may be used in the synthesis of the HIV-protease inhibitor nelfinavir.[8] It may be used in the synthesis of chiral aziridine derivative, a common intermediate for the synthesis of hydroxyethylamine class HIV protease inhibitors such as saquinavir, amprenavir, or nelfinavir.[9]

Other Notes

Unnatural isomer

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

pictograms

Corrosion

signalword

Danger

hcodes

Hazard Classifications

Eye Dam. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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A synthesis of the HIV-protease inhibitor nelfinavir from D-tartaric acid.
Albizati KF, et al.
Tetrahedron Letters, 42(37), 6481-6485 (2001)
Refinement of the structure of D-tartaric acid by x-ray and neutron diffraction.
Okaya Y, et al.
Acta Crystallographica, 21(2), 237-242 (1966)
On oxidative decarboxylations with periodic acid.
D B SPRINSON et al.
The Journal of biological chemistry, 164, 433-449 (1946-07-01)
Isolation and partial determination of structure of soy bean lipositol, a new inositol-containing phospholipid.
Woolley DW.
The Journal of Biological Chemistry, 147(3), 581-591 (1943)
Tartaric acid-assisted sol-gel synthesis of Y 2 O 3: Eu 3+ nanoparticles.
Taxak VB, et al.
J. Alloy Compounds, 469(1), 224-228 (2009)

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