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| Other Sizes |
| Targets |
(2R,3R)-Diethyl 2,3-dihydroxysuccinate does not have a specific biological target or mechanism of action as a drug. Its "activity" is purely chemical. It functions as a chiral auxiliary or ligand in transition metal-catalyzed reactions, such as the Sharpless asymmetric epoxidation. In this context, it targets the metal center (e.g., titanium) of a catalyst, creating an asymmetric environment that induces chirality in the product. In biological assays, it has been evaluated for its ability to inhibit the enzyme dihydroorotase from mouse Ehrlich ascites cells, showing an IC50 of 1.00 x 10⁶ nM at pH 7.37, though this activity is very weak.
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| ln Vitro |
The primary in vitro activity of (2R,3R)-Diethyl 2,3-dihydroxysuccinate is not biological but catalytic. In the Sharpless epoxidation, it is used to form a titanium complex with titanium tetraisopropoxide. This complex then catalyzes the enantioselective epoxidation of allylic alcohols. The reaction proceeds with high yield and excellent enantioselectivity (often >90% enantiomeric excess). The compound demonstrates poor biological activity as a direct therapeutic agent, but its derivatives are essential in the synthesis of numerous bioactive molecules. Its weak dihydroorotase inhibition activity at high concentrations is not considered physiologically relevant for therapeutic applications.
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| ln Vivo |
There are no reports of direct in vivo activity for (2R,3R)-Diethyl 2,3-dihydroxysuccinate itself, as it is not a therapeutic agent. Its relevance to in vivo systems is indirect, through the synthesis of drugs and other biologically active compounds. For example, it is used in the synthesis of d-alpha-Vitamin E (tocopherol) and other chiral pharmaceutical intermediates. The in vivo activity of the final drugs synthesized using this compound would be well-documented, but the activity of the parent diester is not studied in animal models. Its metabolic fate would be hydrolysis to tartaric acid and ethanol.
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| Enzyme Assay |
Non-cellular assays for this compound are primarily chemical in nature, used to verify its function as a chiral ligand. A standard protocol for the Sharpless Asymmetric Epoxidation is performed in anhydrous dichloromethane (DCM) at -20degC. The reaction involves a mixture of titanium tetraisopropoxide (Ti(OiPr)4) and (2R,3R)-Diethyl 2,3-dihydroxysuccinate. An allylic alcohol and tert-butyl hydroperoxide (TBHP) are then added as the substrate and oxidant, respectively. The reaction is stirred for several hours at -20degC. The product's enantiomeric purity is determined via chiral HPLC or GC, demonstrating the ligand's effectiveness by comparing it to a racemic control.
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| Cell Assay |
As a chemical reagent, (2R,3R)-Diethyl 2,3-dihydroxysuccinate is not used in standard cell culture experiments. It has no known biological effects that would warrant its use in such studies. If a cell-based assay were to be performed, it would likely be to test its cytotoxic potential as a possible impurity in drug synthesis. A standard MTT assay on a hepatocyte cell line (e.g., HepG2) could be performed. Cells are seeded in 96-well plates, treated with increasing concentrations of the compound (1-1000 uM) for 24-48 hours. Cell viability is measured by absorbance at 570 nm, but no significant cytotoxicity is expected at physiologically relevant concentrations, as it is considered safe for human consumption as a food additive.
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| Animal Protocol |
(2R,3R)-Diethyl 2,3-dihydroxysuccinate is not used directly in animal experiments for efficacy. However, it is used in the synthesis of drug candidates that are then studied in vivo. An in vivo protocol for a drug synthesized using this building block would follow standard pharmacodynamic models. For example, if used to synthesize an anti-cancer drug, a xenograft model would be employed. In this case, mice bearing human tumor xenografts are administered the synthesized drug (e.g., intravenously, 1-10 mg/kg). Tumor volume and body weight are measured 2-3 times per week for several weeks to evaluate efficacy and toxicity. The parent diester is not administered, making its own in vivo profile irrelevant.
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| ADME/Pharmacokinetics |
As an ester, (2R,3R)-Diethyl 2,3-dihydroxysuccinate is highly lipophilic (logP ~1.3) and rapidly absorbed if ingested. It has a molecular weight of 206.19 g/mol. In the body, it is expected to be quickly hydrolyzed by non-specific esterases in the gastrointestinal tract, blood, and liver. The hydrolysis products are tartaric acid and ethanol. Tartaric acid is a naturally occurring compound in many fruits, which is either excreted unchanged in the urine or further metabolized by the Krebs cycle. Ethanol is rapidly metabolized by alcohol dehydrogenase. Therefore, the pharmacokinetic profile of the parent compound is characterized by a very short half-life due to rapid first-pass metabolism.
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| Toxicity/Toxicokinetics |
(2R,3R)-Diethyl 2,3-dihydroxysuccinate is recognized as safe (GRAS) for its intended use as a food additive at low concentrations. In animal studies, the acute oral toxicity is very low, with an LD50 estimated to be greater than 5,000 mg/kg in rats. The primary toxicological concern would be related to its hydrolysis product, ethanol, though the amount produced from normal use is negligible. It is not considered a carcinogen, mutagenic, or a reproductive toxin. However, as a concentrated chemical, it can be an irritant to the eyes, skin, and respiratory tract. Due to its low toxicity profile, it is widely used in the food and pharmaceutical industries, and its handling only requires standard laboratory safety practices to avoid prolonged contact.
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| References | |
| Additional Infomation |
Diethyl tartrate is a metabolite of Saccharomyces cerevisiae. The reference number (RN) given here refers to the R-(R*,R*)- isomer; for compounds without isomer names, reference number (RN) is not applicable (7/90).
This compound is a prototypical chiral auxiliary, and its most celebrated application is in the Nobel Prize-winning Sharpless Asymmetric Epoxidation reaction, which was a major breakthrough in asymmetric synthesis. This reaction allows chemists to produce enantiomerically pure epoxides, which are critical building blocks for many pharmaceuticals, agrochemicals, and natural products. Its industrial applications are equally significant; it is used in the flavor and fragrance industry to enhance the taste and aroma of various products, particularly in winemaking. As a tool in academic research, it continues to be essential for the development of new asymmetric catalytic methods, enabling the production of single-enantiomer compounds. |
| Molecular Formula |
C8H14O6
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|---|---|
| Molecular Weight |
206.19
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| Exact Mass |
206.079
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| CAS # |
87-91-2
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| PubChem CID |
6993580
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| Appearance |
Liquid
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| Density |
1.204
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| Boiling Point |
280 ºC
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| Melting Point |
17 °C
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| Flash Point |
93 ºC
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
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| Index of Refraction |
1.445-1.447
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| LogP |
-0.29
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
14
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| Complexity |
180
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| Defined Atom Stereocenter Count |
2
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| SMILES |
[C@H](O)(C(=O)OCC)[C@@H](O)C(=O)OCC
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| InChi Key |
YSAVZVORKRDODB-PHDIDXHHSA-N
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| InChi Code |
InChI=1S/C8H14O6/c1-3-13-7(11)5(9)6(10)8(12)14-4-2/h5-6,9-10H,3-4H2,1-2H3/t5-,6-/m1/s1
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| Chemical Name |
diethyl (2R,3R)-2,3-dihydroxybutanedioate
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| Synonyms |
Diethyl tartrate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.8499 mL | 24.2495 mL | 48.4990 mL | |
| 5 mM | 0.9700 mL | 4.8499 mL | 9.6998 mL | |
| 10 mM | 0.4850 mL | 2.4249 mL | 4.8499 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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