Glyoxylic acid monohydrate is an organic compound that is both an aldehyde and a carboxylic acid. It is an intermediate in the glyoxalate cycle, which enables certain organisms to convert fatty acids to carbohydrates.2,2-Dihydroxyacetic acid has been found to be associated with primary hyperoxaluria, an inborn error of metabolism. As an aldehyde, glyoxalate is also highly active and can modify proteins to form advanced glycosylation products (AGEs).
| Canonical Smiles | C(=O)C(=O)O.O |
|---|---|
| IUPAC Name | oxaldehydic acid;hydrate |
| InChIKey | MOOYVEVEDVVKGD-UHFFFAOYSA-N |
| INCHI | 1S/C2H2O3.H2O/c3-1-2(4)5;/h1H,(H,4,5);1H2 |
| Isomeric SMILES | C(=O)C(=O)O.O |
| WGK Germany | 1 |
| Alternate CAS | 1152495-30-1 |
| UN Number | 3265 |
| Molecular Weight | 92.05 |
| Beilstein | 969535 |
| Reaxy-Rn | 4190983 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4190983&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic acids and derivatives |
| Class | Carboxylic acids and derivatives |
| Subclass | Carboxylic acids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Carboxylic acids |
| Alternative Parents | Monocarboxylic acids and derivatives Short-chain aldehydes Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Monocarboxylic acid or derivatives - Carboxylic acid - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Short-chain aldehyde - Organooxygen compound - Carbonyl group - Aldehyde - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as carboxylic acids. These are compounds containing a carboxylic acid group with the formula -C(=O)OH. |
| External Descriptors | Not available |
| Sensitivity | Hygroscopic |
|---|---|
| Flash Point(°F) | 230 °F |
| Flash Point(°C) | >110 °C |
| Boil Point(°C) | 100 °C (lit.) |
| Melt Point(°C) | 48-52°C |
| Molecular Weight | 92.050 g/mol |
| XLogP3 | |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 1 |
| Exact Mass | 92.011 Da |
| Monoisotopic Mass | 92.011 Da |
| Topological Polar Surface Area | 55.400 Ų |
| Heavy Atom Count | 6 |
| Formal Charge | 0 |
| Complexity | 55.900 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| 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 | 2 |
| 1. Rongye Li, Yue Zhao, Min Lin, Jing Sun. (2023) Self-assembly Promoted Crystallization of Diblock Copolypeptoids in Solution †. CHINESE JOURNAL OF CHEMISTRY, 41 (18): (2305-2310). [PMID:] [10.1002/cjoc.202300173] |
| 2. Jing Sun, Xutao Ma, Rongye Li, Min Lin, Lilei Shu, Xuesi Chen. (2022) Antimicrobial Nanostructured Assemblies with Extremely Low Toxicity and Potent Activity to Eradicate Staphylococcus Aureus Biofilms. Small, 19 (3): (2204039). [PMID:36412076] [10.1002/smll.202204039] |
| 3. Jinglu Han, Guolong Wu, Yanling Li, Songsong Li, Wuping Liao. (2022) Efficient separation of high-abundance rare earth element yttrium and lanthanides by solvent extraction using 2-(bis((2-ethylhexyl)oxy)phosphoryl)-2-hydroxyacetic acid. SEPARATION AND PURIFICATION TECHNOLOGY, [PMID:] [10.1016/j.seppur.2022.122683] |
| 4. Dan Yang, Xuan Liu, Fei Song, Yihu Dai, Xiaoyue Wan, Chunmei Zhou, Yanhui Yang. (2022) Chemoselective Oxidation of Glycerol over Platinum-Based Catalysts: Toward the Role of Oxide Promoter. ChemCatChem, 14 (10): (e202200011). [PMID:] [10.1002/cctc.202200011] |
| 5. Hehe Qian, Jianzhou Wu, Yongsheng Guo, Wenjun Fang. (2021) Unveiling the Influence of Inherent Parameters of AgPt and AgPtAu Octahedra upon Formic Acid Electrooxidation. Journal of Physical Chemistry C, [PMID:] [10.1021/acs.jpcc.1c03426] |
| 6. Zhiwei Wang, Min Lin, Colin Bonduelle, Rongye Li, Zhekun Shi, Chenhui Zhu, Sébastien Lecommandoux, Zhibo Li, Jing Sun. (2020) Thermoinduced Crystallization-Driven Self-Assembly of Bioinspired Block Copolymers in Aqueous Solution. BIOMACROMOLECULES, [PMID:32786675] [10.1021/acs.biomac.0c00844] |
| 7. Mingwei Wang, Hailiang Nie, Dandan Han, Xiaoqiang Qiao, Hongyuan Yan, Shigang Shen. (2019) Cauliflower-like resin microspheres with tuneable surface roughness as solid-phase extraction adsorbent for efficient extraction and determination of plant growth regulators in cucumbers. FOOD CHEMISTRY, [PMID:31174757] [10.1016/j.foodchem.2019.05.130] |
| 8. Yuze Xie, Mingwei Wang, Xi Chen, Shufen Wang, Dandan Han, Yehong Han, Hongyuan Yan. (2019) 3-Aminophenol-glyoxylic acid resin for the determination of triazine herbicides in tomatoes. ANALYTICA CHIMICA ACTA, [PMID:30926030] [10.1016/j.aca.2019.01.062] |
| 9. Yuhan Wei, Jiliang Tian, Zekun Zhang, Chenhui Zhu, Jing Sun, Zhibo Li. (2019) Supramolecular Nanosheets Assembled from Poly(ethylene glycol)-b-poly(N-(2-phenylethyl)glycine) Diblock Copolymer Containing Crystallizable Hydrophobic Polypeptoid: Crystallization Driven Assembly Transition from Filaments to Nanosheets. MACROMOLECULES, [PMID:] [10.1021/acs.macromol.8b02230] |
| 10. Fengyin Liu, Zijian Chen, Yudong Shen, Yuanming Sun, Jinyi Yang, Hong Wang, Hongtao Lei, Zhenlin Xu. (2018) Hapten synthesis and production of specific antibody against 3-amino-5-morpholinomethyl-2-oxazolidone for immunoassay without derivatisation. FOOD AND AGRICULTURAL IMMUNOLOGY, [PMID:] [10.1080/09540105.2017.1376038] |
| 11. Changlong Dong, Wei Chen, Cheng Liu. (2014) Flocculation of algal cells by amphoteric chitosan-based flocculant. BIORESOURCE TECHNOLOGY, [PMID:25146316] [10.1016/j.biortech.2014.07.108] |
| 12. Yuanming Feng, Yunpeng Bi, Yifei Wang, Fang Yang, Guangxing Yang, Yuguang Jin, Xiaoyue Wan, Yihu Dai, Yanhui Yang, Dan Yang, Chunmei Zhou. (2025) Enhanced Glycerol Oxidation Toward Dihydroxyacetone Over Gold/Palladium Binary Nanocatalysts by Structure Control. CHEMISTRY-A EUROPEAN JOURNAL, [PMID:40067062] [10.1002/chem.202500601] |
| 13. Shengjun Du, Minglong Guo, Guangxing Yang, Qiao Zhang, Zhiting Liu, Feng Peng. (2024) Rational design of carbon materials with tailored pore structure for efficient separation of CH4/N2 mixture. SEPARATION AND PURIFICATION TECHNOLOGY, [PMID:] [10.1016/j.seppur.2024.128096] |
| 14. Di Liu, Kang Yang, Liugen Xu, Xiran Shen, Lei Feng, Yangang Jiang, Amjad Ali, Jianwei Lu, Li Guo. (2024) Self-Assembly Study of Block Copolypeptoids in Response to pH and Temperature Stimulation. Polymers, 16 (8): (1082). [PMID:38675001] [10.3390/polym16081082] |
| 15. Wanyu Li, Jiamin Ye, Zhiwen Jia, Haipeng Yu, Linghao Li, Hong Wang, Enchen Jiang, Yan Sun, Xiwei Xu. (2024) The full utilization of bagasse via deep eutectic solvent pretreatment for low-condensed lignin and cellulose smart indicator film. CHEMICAL ENGINEERING JOURNAL, [PMID:] [10.1016/j.cej.2024.151653] |
| 16. SunHongzheng , HanLongsen , GuoYueshuai , AnHuiqing , WangBing , ZhangXiangzheng , LiJiashuo , JiangYingtong , WangYue , SunGuangyi , ZhuShuai , TangShoubin , GeJuan , ChenMinjian , GuoXuejiang , WangQiang. (2024) The global phosphorylation landscape of mouse oocytes during meiotic maturation. EMBO JOURNAL, [PMID:39256562] [10.1038/s44318-024-00222-1] |
| 17. Dan Yang, Xiang Cui, Zhou Xu, Qian Yan, Yating Wu, Chunmei Zhou, Yihu Dai, Xiaoyue Wan, Yuguang Jin, Leonid M. Kustov, Yanhui Yang. (2025) Efficient electrocatalytic oxidation of glycerol toward formic acid over well-defined nickel nanoclusters capped by ligands. CHINESE JOURNAL OF CATALYSIS, [PMID:] [10.1016/S1872-2067(25)64779-6] |
| 18. Liugen Xu, Junwei Pi, Lei Feng, Junhao Wen, Minghai Zhao, Amjad Ali, Jianwei Lu, Li Guo. (2025) Glycopolypeptoids as Novel Biomimetic Antifreeze Agents: Structural Design, Synthesis, and Antifreeze Properties. Polymers, 17 (12): (1600). [PMID:40574127] [10.3390/polym17121600] |
| 19. Yuan Gan, Shen Shen, Ning Wang, Jie Zhang. (2025) Integrated microfluidic dynamic potential-modulated SERS chip with high sensitivity and self-cleaning. SENSORS AND ACTUATORS B-CHEMICAL, [PMID:] [10.1016/j.snb.2025.138840] |
| 20. Linlin Wang, Yunlong Sun, Lei Song, Lu Li, Yumei Gong, Rui Wang. (2026) Closed-Loop Recyclable Bio-Based Polyesters Featuring a Tricyclic Diglycolicaldehyde Xylose Diol toward High Tg and Excellent Gas Barrier Performance. BIOMACROMOLECULES, [PMID:] [10.1021/acs.biomac.5c02696] |
| 21. Sun Yan, Zhang Xiaoyu, Chen Xiaoyu, Zhao Jiawen, Liu Yunlong, He Weiyang. (2026) Paeoniflorin alleviates nephrolithiasis by targeting serpine1 and inhibiting the NF-κB signaling pathway. Urolithiasis, 54 (1): (62). [PMID:] [10.1007/s00240-026-01963-w] |
| 22. Ruojin Shen, Chao Wang, Keqin Zhang, Changyi Zhu, Lupeng Shao, Kai Zhang, Xianhai Zeng, Feng Xu, Guihua Yang, Jiachuan Chen. (2026) Efficient separation of uncondensed lignin and high-quality cellulose from bamboo using reactive deep eutectic solvents for versatile valorization. GREEN CHEMISTRY, [PMID:] [10.1039/D5GC06709J] |
