≥99% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Room temperature Ships Normal Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 3 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
(+)-Diethyl L-tartrate is used as a chiral auxiliary in the Sharpless enantioselective epoxidation of allylic alcohols, for Sharpless-type enantioselective oxidation of sulfides to sulfoxides and as a chiral auxiliary in the enantioselective construction of cyclopropanes from allylic alcohols by an asymmetric Simmons-Smith reaction. It is also used as a chiral reagent in a host of chemical reactions, such as the synthesis of isoquinoline alkaloids and arundic acid, which has been used in acute ischemic stroke therapy.
| Pubchem Sid | 504764451 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504764451 |
| Canonical Smiles | CCOC(=O)C(C(C(=O)OCC)O)O |
| IUPAC Name | diethyl (2R,3R)-2,3-dihydroxybutanedioate |
| InChIKey | YSAVZVORKRDODB-PHDIDXHHSA-N |
| 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 |
| Isomeric SMILES | CCOC(=O)[C@@H]([C@H](C(=O)OCC)O)O |
| WGK Germany | 3 |
| Molecular Weight | 206.19 |
| Beilstein | 1727145 |
| Reaxy-Rn | 1727142 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1727142&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Hydroxy acids and derivatives |
| Subclass | Beta hydroxy acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Beta hydroxy acids and derivatives |
| Alternative Parents | Fatty acid esters Monosaccharides Dicarboxylic acids and derivatives Secondary alcohols Carboxylic acid esters 1,2-diols Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Beta-hydroxy acid - Fatty acid ester - Dicarboxylic acid or derivatives - Monosaccharide - Fatty acyl - 1,2-diol - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Organooxygen compound - Alcohol - Organic oxide - Carbonyl group - Organic oxygen compound - Hydrocarbon derivative - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. |
| External Descriptors | Not available |
Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Date | Item |
|---|---|---|---|
 H2205142 | Certificate of Analysis | May 18, 2026 | D120026 |
| H2205143 | Certificate of Analysis | May 18, 2026 | D120026 |
| H2205150 | Certificate of Analysis | May 18, 2026 | D120026 |
| L2129213 | Certificate of Analysis | Oct 11, 2025 | D120026 |
| L2129214 | Certificate of Analysis | Oct 11, 2025 | D120026 |
| L2129215 | Certificate of Analysis | Oct 11, 2025 | D120026 |
| F2129299 | Certificate of Analysis | Apr 08, 2025 | D120026 |
| H1715015 | Certificate of Analysis | Mar 04, 2025 | D120026 |
| K2504311 | Certificate of Analysis | Jul 10, 2024 | D120026 |
| K2504323 | Certificate of Analysis | Jul 10, 2024 | D120026 |
| K2504322 | Certificate of Analysis | Jul 10, 2024 | D120026 |
| A1519012 | Certificate of Analysis | Oct 24, 2022 | D120026 |
| F2316923 | Certificate of Analysis | Jul 06, 2022 | D120026 |
| F2316924 | Certificate of Analysis | Jul 06, 2022 | D120026 |
| G2412053 | Certificate of Analysis | Jul 06, 2022 | D120026 |
| Solubility | Fully miscible in water. |
|---|---|
| Refractive Index | 1.446 |
| Specific Rotation[α] | +27 (c=1 in water) |
| Flash Point(°F) | 199.4 °F |
| Flash Point(°C) | 93°(199°F) |
| Boil Point(°C) | 280°C |
| Melt Point(°C) | 17°C |
| Molecular Weight | 206.190 g/mol |
| XLogP3 | -0.300 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Exact Mass | 206.079 Da |
| Monoisotopic Mass | 206.079 Da |
| Topological Polar Surface Area | 93.100 Ų |
| Heavy Atom Count | 14 |
| Formal Charge | 0 |
| Complexity | 180.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
| 1. Lv Jianhua, Ou Xiaoyu, Fang Yaru, Wu Mi, Zheng Fanghao, Shang Lei, Lei Kaijun, Liu Yunen, Zhao Yan. (2022) The Study of Deep Eutectic Solvent Based on Choline Chloride and l-(+)-Tartaric Acid Diethyl Ester for Transdermal Delivery System. AAPS PHARMSCITECH, 23 (7): (1-10). [PMID:36076112] [10.1208/s12249-022-02342-5] |
| 2. Shaoping Ma, Fenfang Li, Zhijian Tan. (2021) Enantioselective liquid-liquid extraction of tryptophan enantiomers by a recyclable aqueous biphasic system based on stimuli-responsive polymers. JOURNAL OF CHROMATOGRAPHY A, [PMID:34525428] [10.1016/j.chroma.2021.462532] |
| 3. Dongfang Li, Shang Ma, Abdelatif Laroui, Yixian Zhang, Jie Wang, Ping Lu, Jian Dong. (2020) Controlling water dynamics for kinetic inhibition of clathrate hydrate. FUEL, [PMID:] [10.1016/j.fuel.2020.117588] |
