Glyoxylic acid solution - 50% aqueous solution , CAS No.298-12-4

CAS: 298-12-4 Cat. No.: G169372 Molecular Weight: 74.04 Beilstein Registry Number: 741891 EC Number: 206-058-5

GRADE & PURITY 50% aqueous solution

Synonyms

dioxymethylene formaldehyde | Oxalaldehydic acid

Storage

Room temperature

Shipped In

Normal

Specifications

Synonyms

dioxymethylene formaldehyde | Oxalaldehydic acid

Specifications & Purity

50% aqueous solution

Storage

Room temperature

Shipped In

Normal

Names and Identifiers

• Pubchem Sid: 504750412
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504750412
• Canonical Smiles: C(=O)C(=O)O
• IUPAC Name: oxaldehydic acid
• InChIKey: HHLFWLYXYJOTON-UHFFFAOYSA-N
• INCHI: 1S/C2H2O3/c3-1-2(4)5/h1H,(H,4,5)
• Isomeric SMILES: C(=O)C(=O)O
• WGK Germany: 1
• RTECS: MD4550000
• UN Number: 3265
• Packing Group: I
• Molecular Weight: 74.04
• Beilstein: 741891
• Reaxy-Rn: 741891
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=741891&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Carboxylic acids

• 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: 2-oxo monocarboxylic acid - aldehydic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

SLC16A3 Tchem Monocarboxylate transporter 4 (196 Activities)

Discover Target: SLC16A3

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

dapA Dihydrodipicolinate synthase (65 Activities)

Discover Target: dapA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Miscible with ethanol. Slightly miscible with ether and benzene. Immiscible with esters
• Refractive Index: n20/D 1.4149
• Boil Point(°C): 111 °C
• Melt Point(°C): -93 °C
• Molecular Weight: 74.040 g/mol
• XLogP3: -0.300
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 74.0004 Da
• Monoisotopic Mass: 74.0004 Da
• Topological Polar Surface Area: 54.400 Ų
• Heavy Atom Count: 5
• 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: 1

References

1. Xiaomei Ning, Liang Zhan, Xiaosong Zhou, Jin Luo, Yanli Wang.  (2023)  In-situ Bi-modified Pt towards glycerol and formic acid electro-oxidation: Effects of catalyst structure and surface microenvironment on activity and selectivity.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:37979297] [10.1016/j.jcis.2023.11.075]

2. Ju Yun, Zhang Hong, Jiang Yanxiao, Wang Wenxin, Kan Guangfeng, Yu Kai, Wang Xiaofei, Liu Jilin, Jiang Jie.  (2023)  Aqueous microdroplets promote C–C bond formation and sequences in the reverse tricarboxylic acid cycle.  Nature Ecology & Evolution,  7  (11): (1892-1902).  [PMID:37679455] [10.1038/s41559-023-02193-8]

3. Pingping Wan, Chen Yang, Aolin Wang, Liping Yu, Shixun Lian, Wenli Zhou.  (2023)  Surface lattice enhancement of red-emitting fluorides enabled by embedding small cations.  Inorganic Chemistry Frontiers,  10  (17): (5089-5097).  [PMID:] [10.1039/D3QI01088K]

4. Zhi Li, Shuangying Li, Yanhui Li, Menghua Liu, Liushan Jiang, Jinwen Niu, Yue Zhang, Qingxiang Zhou.  (2023)  Highly selective and sensitive determination of doxycycline integrating enrichment with thermosensitive magnetic molecular imprinting nanomaterial and carbon dots based fluorescence probe.  SCIENCE OF THE TOTAL ENVIRONMENT,      [PMID:37414165] [10.1016/j.scitotenv.2023.165257]

5. An-Ni Zheng, Zhao-Yun Wang, Jia-Qiang Yang, Lei Jin, Fang-Zu Yang, Dong-Ping Zhan.  (2023)  Advanced Ag nanoparticles for the catalyzation of glyoxylic acid oxidation in through-holes electroless copper metallization.  JOURNAL OF COLLOID AND INTERFACE SCIENCE,      [PMID:37301151] [10.1016/j.jcis.2023.05.177]

6. Zhang Guoxing, Sun Huixuan, Gong Qirui, Xie Yisi, Fei Fan, Fan Lihong.  (2023)  Preparation and modification of antibacterial polyurethane foam for oil–water separation.  JOURNAL OF MATERIALS RESEARCH,  38  (10): (2701-2712).  [PMID:] [10.1557/s43578-023-00993-z]

7. Juanjuan Ding, Wenyan Ba, Shengping You, Wei Qi, Rongxin Su.  (2023)  Development of an oil-sealed anaerobic fermentation process for high production of γ-aminobutyric acid with Lactobacillus brevis isolated by directional colorimetric screening.  BIOCHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.bej.2023.108893]

8. Gui-Hua Wei, Ting Lu, Hai-Yan Liu, Jiao-Xuan Bai, Qian Wang, Guang-Yue Li, Ying-Hua Liang.  (2023)  Exploring the continuous cleavage-oxidation mechanism of the catalytic oxidation of cellulose to formic acid: A combined experimental and theoretical study.  FUEL,      [PMID:] [10.1016/j.fuel.2023.127667]

9. Yongfang Zhou, Thomas J.A. Slater, Xuanli Luo, Yi Shen.  (2022)  A versatile single-copper-atom electrocatalyst for biomass valorization.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2022.122218]

10. Ming Shaoxiong, Tian Jia, Ma Ke, Pei Chengbin, Li Ling, Wang Zeyu, Fang Ziyu, Liu Min, Dong Hao, Li Weijian, Zeng Jianwen, Peng Yonghan, Gao Xiaofeng.  (2022)  Oxalate-induced apoptosis through ERS-ROS–NF-κB signalling pathway in renal tubular epithelial cell.  MOLECULAR MEDICINE,  28  (1): (1-20).  [PMID:35922749] [10.1186/s10020-022-00494-5]

11. Jing Yang, Peilan Luo, Pingping Wan, Menglin Ye, Zhongxian Qiu, Jilin Zhang, Shixun Lian, Chengzhi Li, Wenli Zhou.  (2021)  Surface engineered environment-stable red-emitting fluorides for white light emitting diodes.  CERAMICS INTERNATIONAL,      [PMID:] [10.1016/j.ceramint.2021.11.038]

12. Liu Jun-bo, Chang Hanqi, Zhao Wensi, Liang Dadong, Tang Shanshan, Jin Ruifa.  (2021)  Theoretical design and preparation of molecularly imprinted polymers of formaldehyde and acrylamide.  JOURNAL OF POLYMER RESEARCH,  28  (11): (1-10).  [PMID:] [10.1007/s10965-021-02724-6]

13. Shaoyu Tang, Lei Xu, Xiaolong Yu, Shuona Chen, Huanyong Li, Ying Huang, Junfeng Niu.  (2020)  Degradation of anticancer drug capecitabine in aquatic media by three advanced oxidation processes: Mechanisms, toxicity changes and energy cost evaluation.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2020.127489]

14. Qingna Lin, Lipeng Han, Guoqin Liu, Weiwei Cheng, Liqing Wang.  (2018)  A preliminary study on the formation pathways of glycated phosphatidylethanolamine of food rich in phospholipid during the heat-processing.  RSC Advances,  8  (21): (11280-11288).  [PMID:35542782] [10.1039/C8RA01072B]

15. Ting Lu, Yucui Hou, Weize Wu, Muge Niu, Wei Li, Shuhang Ren.  (2018)  Catalytic oxidation of cellulose to formic acid in V(V)-Fe(III)-H2SO4 aqueous solution with O2.  FUEL PROCESSING TECHNOLOGY,      [PMID:] [10.1016/j.fuproc.2018.02.001]

16. Yunxia Ni, Jing Sun, Yuhan Wei, Xiaohui Fu, Chenhui Zhu, Zhibo Li.  (2017)  Two-Dimensional Supramolecular Assemblies from pH-Responsive Poly(ethyl glycol)-b-poly(l-glutamic acid)-b-poly(N-octylglycine) Triblock Copolymer.  BIOMACROMOLECULES,      [PMID:28956910] [10.1021/acs.biomac.7b01014]

17. Shenyu Lan, Ya Xiong, Shuanghong Tian, Lianpeng Sun, Tianyao Xie, Xin Wang, Lingjun Kong.  (2014)  Simultaneous Determination of Cu-EDTA and Its Degradation Intermediates by Capillary Electrophoresis with a Capacitively Coupled Contactless Conductivity Detector.  ELECTROANALYSIS,  26  (11): (2534-2540).  [PMID:] [10.1002/elan.201400335]

18. Min Zhou, Wei Wu, Hong Pu, Feng Chen, Chaofan Yi, Yuande Long.  (2024)  A drug–excipient interaction impurity of bromhexine hydrochloride injection: Structure and formation mechanism elucidation.  JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS,      [PMID:38850847] [10.1016/j.jpba.2024.116256]

19. Liu Yan, Wei Jie, Yang Zhengwu, Zheng Lirong, Zhao Jiankang, Song Zhimin, Zhou Yuhan, Cheng Jiajie, Meng Junyang, Geng Zhigang, Zeng Jie.  (2024)  Efficient tandem electroreduction of nitrate into ammonia through coupling Cu single atoms with adjacent Co3O4.  Nature Communications,  15  (1): (1-11).  [PMID:38684692] [10.1038/s41467-024-48035-4]

20. Xiran Shen, Tiantian Wei, Di Liu, Kang Yang, Yangang Jiang, Jianwei Lu, Li Guo.  (2024)  Self-assembled polypeptoid micelles from amphiphilic polypeptoid copolymers for drug delivery.  POLYMER INTERNATIONAL,      [PMID:] [10.1002/pi.6635]

21. Xiaoyuan Liu, Yu Zou, Jiang Jiang.  (2024)  Sunlight-driven selective oxidation of glycerol on formate oxidase mimicking AuPt/TiO2.  APPLIED CATALYSIS B-ENVIRONMENTAL,      [PMID:] [10.1016/j.apcatb.2024.123927]

22. Kong Xiangdong, Ni Jie, Song Zhimin, Yang Zhengwu, Zheng Jiana, Xu Zifan, Qin Lang, Li Hongliang, Geng Zhigang, Zeng Jie.  (2024)  Synthesis of hydroxylamine from air and water via a plasma-electrochemical cascade pathway.  Nature Sustainability,      [PMID:] [10.1038/s41893-024-01330-w]

23. Haichao Li, Deqiang Li, Yuan He, Chaobing Luo, Wu Lan, Arthur J. Ragauskas, Tingting You, Feng Xu.  (2025)  Unleashing the potential of lignin with innovative trifunctional binary deep eutectic solvent strategy: Isolation of uncondensed lignin.  Science Advances,  11  (27):   [PMID:40614203] [10.1126/sciadv.adv7299]

24. Jie Ni, Jie Wei, Yeqi Yu, Ming-Hui Fan, Wanting Liu, Kwun Nam Hui, Yan Yan, Yan Liu, Yanqiang Huang, Jie Zeng.  (2025)  Revealing the Role of Interfacial Water in pH-Dependent Hydroxylamine Electrosynthesis over Bi-Based Catalysts.  ACS Catalysis,      [PMID:] [10.1021/acscatal.5c04422]

25. Pengfei Li, Yanke Lu, Jiangxue Cao, Mengyuan Li, Chunliu Yang, Hongyuan Yan.  (2020)  Imidazolium ionic-liquid-modified phenolic resin for solid-phase extraction of thidiazuron and forchlorfenuron from cucumbers.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:32505285] [10.1016/j.chroma.2020.461192]

26. 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]

27. Zizhao Ding, Shenglong Huang, Yiting Zhu, Yilun Chen, Dou Zhang, Zixiang Zhao, Chao Jiang.  (2025)  Multi-scenario application of non-volatile smart invisible textiles based on copper-ion modulated MoS2.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2025.169649]

28. Yuping Liu, Zhipeng Li, Ke Shen, Hua Huang, Xinshuai Zhang.  (2025)  In vitro reconstitution of the pantothenic acid catabolic pathway in Geobacillus thermodenitrificans NG80-2.  BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS,      [PMID:41183400] [10.1016/j.bbrc.2025.152876]

29. Zhenjun Liu, Tianpei Yang, Yi Shen.  (2025)  Enhancing the selectivity of glycerol electrooxidation toward C3 products through the synergistic effect of Au and Pt.  INTERNATIONAL JOURNAL OF HYDROGEN ENERGY,      [PMID:] [10.1016/j.ijhydene.2025.152668]

30. Jing Su, Tan Li, Xin Liu, Qihui Song, Jianmeng Cen, Zhongyang Luo, Kaige Wang.  (2026)  Electronic structure tailoring via P-ligation in CoP nanoflowers drives bifunctional electrocatalysis for plastic waste valorization and hydrogen evolution.  CHEMICAL ENGINEERING JOURNAL,      [PMID:] [10.1016/j.cej.2026.172721]

31. Ya Zongyang, Li Mei, Fu Donglong, Zheng Yu, Wei Ruhan, Wang Hao, Zhang Kangning, Xu Dong, Zhang Zixuan, Zhang Xue, Yan Shen, Wang Hua, Zhang Shengbo, Gong Jinlong.  (2026)  Glycine photosynthesis via C−N coupling of waste plastic and nitrate over diatomic Pd−B catalyst.  Nature Communications,      [PMID:41559096] [10.1038/s41467-026-68666-z]

32. Hongyang Jiang, Xiaoyu Zhu, Weizhen Pan, Wenchao Xu, Hanlin Tao, Yiduo Jia, Yang Xun, Zhuo Liu, Jihong Liu, Zhiping Zhang, Songwei Tan.  (2026)  Iterative-Designed Multifunctional Carbon Dots Nanodrug for Celastrol Loading, Targeting Delivery, and Combination Therapy of Kidney Stones.  ADVANCED FUNCTIONAL MATERIALS,      [PMID:] [10.1002/adfm.202523181]