≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice 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 1 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
| Pubchem Sid | 504765950 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504765950 |
| Canonical Smiles | COC(=O)CC(C(=O)OC)O |
| IUPAC Name | dimethyl (2R)-2-hydroxybutanedioate |
| InChIKey | YSEKNCXYRGKTBJ-SCSAIBSYSA-N |
| INCHI | 1S/C6H10O5/c1-10-5(8)3-4(7)6(9)11-2/h4,7H,3H2,1-2H3/t4-/m1/s1 |
| Isomeric SMILES | COC(=O)C[C@H](C(=O)OC)O |
| WGK Germany | 3 |
| Molecular Weight | 162.14 |
| Beilstein | 1908705 |
| Reaxy-Rn | 1724362 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1724362&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 methyl esters Dicarboxylic acids and derivatives Methyl esters Secondary alcohols Organic oxides Hydrocarbon derivatives Carbonyl compounds |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Beta-hydroxy acid - Fatty acid methyl ester - Fatty acid ester - Dicarboxylic acid or derivatives - Fatty acyl - Methyl ester - Carboxylic acid ester - Secondary alcohol - Carboxylic acid derivative - Hydrocarbon derivative - Organic oxide - Alcohol - Carbonyl group - Organic oxygen compound - Organooxygen compound - 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 |
| Refractive Index | 1.44 |
|---|---|
| Specific Rotation[α] | 7 ° (neat) |
| Flash Point(°F) | 235.4 °F |
| Flash Point(°C) | 113 °C |
| Boil Point(°C) | 104-108 °C/1 mmHg |
| Molecular Weight | 162.140 g/mol |
| XLogP3 | -0.700 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Exact Mass | 162.053 Da |
| Monoisotopic Mass | 162.053 Da |
| Topological Polar Surface Area | 72.800 Ų |
| Heavy Atom Count | 11 |
| Formal Charge | 0 |
| Complexity | 153.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| 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. Zhao Cui, Jiameng Li, Caifeng Li, Shiwen Deng, Wei Liu, Tong Lei, Junxian Cao, Ziyi Wang, Xiaoxu Wang, Shuhua Ma, Yinhua Zhu, Hongjun Yang, Peng Chen. (2025) Identifying the target, mechanism, and agonist of α-ketoglutaric acid in delaying mesenchymal stem cell senescence. Cell Reports, [PMID:40570373] [10.1016/j.celrep.2025.115917] |
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