Tartrate

Base Information

• Chemical Name: Tartrate
• CAS No.: 3715-17-1
• Molecular Formula: C4H4O6-2
• Molecular Weight: 148.0721
• UNII: GBG3U2YP5Y
• DSSTox Substance ID: DTXSID901337655
• Nikkaji Number: J209.371E
• Wikipedia: Tartrate
• Wikidata: Q56702301
• Mol file: 3715-17-1.mol

Synonyms:(R*,R*)-(+-)-2,3-dihydroxybutanedioic acid, monoammonium monosodium salt;aluminum tartrate;ammonium tartrate;calcium tartrate;calcium tartrate tetrahydrate;Mn(III) tartrate;potassium tartrate;seignette salt;sodium ammonium tartrate;sodium potassium tartrate;sodium tartrate;stannous tartrate;tartaric acid;tartaric acid, ((R*,R*)-(+-))-isomer;tartaric acid, (R*,S*)-isomer;tartaric acid, (R-(R*,R*))-isomer;tartaric acid, (S-(R*,R*))-isomer;tartaric acid, ammonium sodium salt, (1:1:1) salt, (R*,R*)-(+-)-isomer;tartaric acid, calcium salt, (R-R*,R*)-isomer;tartaric acid, monoammonium salt, (R-(R*,R*))-isomer;tartrate

Chemical Property of Tartrate

Chemical Property:

• Vapor Pressure: 4.93E-08mmHg at 25°C
• Boiling Point: 399.3°Cat760mmHg
• Flash Point: 209.4°C
• Density: g/cm³
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 148.00078784
• Heavy Atom Count: 10
• Complexity: 123

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)[O-])O)(C(=O)[O-])O
• Isomeric SMILES: [C@@H]([C@H](C(=O)[O-])O)(C(=O)[O-])O
• General Description: 2,3-Dihydroxybutanedioate, also known as tartrate, is a dicarboxylic acid derivative with two hydroxyl groups attached to adjacent carbon atoms in its four-carbon backbone. It is commonly found in nature, particularly in fruits like grapes, and plays a role in various biochemical processes, including metabolism and chelation of metal ions. Tartrate and its salts (e.g., potassium bitartrate) are widely used in food, pharmaceutical, and industrial applications due to their acidity, stability, and ability to form complexes. 2,3-dihydroxybutanedioate's stereochemistry (e.g., L-tartrate, D-tartrate, or meso-tartrate) influences its biological activity and applications.

Technology Process of Tartrate

There total 3 articles about Tartrate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

maleic anhydride (108-31-6) → 2,3-dihydroxy-succinic acid; bis-deprotonated form (3715-17-1,5976-86-3,5976-95-4,13997-04-1) + C4H3O9P(4-) + maleate dianion (142-44-9)

Guidance literature:

maleic anhydride; With water; potassium hydroxide; at 25 ℃; for 0.5h;

With sodium tungstate (VI) dihydrate; dihydrogen peroxide; sodium hydroxide; In water; at 60 - 65 ℃; for 3h; pH=5.5 - 6;

With dipotassium hydrogenphosphate; potassium hydroxide; In water; at 92 ℃; for 16.5h; pH=6.8 - 11.7; Reagent/catalyst;

Reference yield:

maleic anhydride (108-31-6) → 2,3-dihydroxy-succinic acid; bis-deprotonated form (3715-17-1,5976-86-3,5976-95-4,13997-04-1) + C4H3O9P(4-)

Guidance literature:

maleic anhydride; With water; potassium hydroxide; at 70 ℃; for 0.75h; Large scale;

With sodium tungstate (VI) dihydrate; dihydrogen peroxide; sodium hydroxide; In water; at 60 - 65 ℃; for 18.5h; pH=5 - 5.6; Large scale;

With dipotassium hydrogenphosphate; potassium hydroxide; sodium hydroxide; In water; at 40 - 90 ℃; for 23h; pH=6.8 - 11.7; Reagent/catalyst; Temperature; Large scale;

Reference yield:

nickel (II) d-tartrate (10471-42-8,10471-47-3,12385-84-1,22438-91-1,41296-05-3,52022-10-3,67952-41-4) → nickel(II) (14701-22-5) + L-tartrate (3715-17-1)

Guidance literature:

In water; equilibrium at 25°C;; not isolated;;

upstream raw materials:

maleic anhydride

nickel (II) d-tartrate

Downstream raw materials:

calcium tartrate tetrahydrate

Refernces

Highly selective total synthesis of enantiomerically pure (-)-anisomycin

10.1021/jo00357a023

The research focuses on the highly selective total synthesis of enantiomerically pure (-)-anisomycin, an antibiotic with significant activity against pathogenic protozoa and fungi, which has been used in the treatment of amebic dysentery and trichomonas vaginitis. The study's purpose was to achieve a chiral total synthesis of optically pure (-)-anisomycin through a series of virtually complete regio- and stereocontrolled reactions, without the need for isomer separation. The synthesis began with 4-O-benzyl-2,3-O-bis(methoxymethyl)-L-threose derived from diethyl L-tartrate as the chiral building block and involved several key steps, including a-chelation-controlled addition of hydride, stereospecific cyclization, and selective introduction of the acetyl group with complete regiochemical control. The process utilized various chemicals such as diethyl L-tartrate, 4-methoxybenzyl chloride, benzyl chloroformate, and protecting groups like tert-butyldimethylsilyl and methoxymethyl groups. The successful synthesis was confirmed by comparing the synthesized (-)-anisomycin with authentic samples through melting point, specific optical rotation, and NMR and mass spectrometry analysis, proving 100% enantiomeric purity. The study concluded with the investigation of the antiprotozoal and antifungal activities of the synthetic (-)-anisomycin.

Intramolecular Michael-type additions to vinyl bissulfoxides: Enantioselective synthesis of chiral aldehydes

10.1055/s-2008-1067176

The research investigates the diastereoselective and enantioselective synthesis of chiral aldehydes through intramolecular Michael-type additions to alkylidene bissulfoxides derived from dithiane and dithiolane. Key chemicals involved include various substrates bearing N- and O-nucleophilic functions, which upon reaction, form cyclic substrates with selectivities ranging from 51:49 to 85:15. The bissulfoxide moiety is subsequently cleaved in a two-step sequence to yield chiral carbaldehydes. Notably, compounds such as tetrahydropyran-2-carbaldehyde and homopipecolic aldehyde, which are difficult to access by other routes, are obtained in enantiomerically pure forms. The stereochemical information is introduced via readily available diethyl D- and L-tartrates, allowing for the synthesis of both enantiomers of the target molecules. The study also explores the optimization of conditions for these additions and the synthesis of the underlying bissulfoxides, utilizing methods like asymmetric oxidation and various synthetic protocols for the preparation of ketene S,S-acetals.

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