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Type HazMat fee for 500 gram (Estimated)
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Chemical Structure| 298-12-4 Chemical Structure| 298-12-4
Chemical Structure| 298-12-4

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Glyoxylic Acid participates in phenylalanine metabolism and the glyoxylate cycle, playing a crucial role as an intermediate in metabolic pathways and potentially involved in antioxidant stress responses in certain plants and microorganisms.

Synonyms: Glyoxalic acid; NSC 27785; Oxalaldehydic acid

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Huddleston, Morgan ;

Abstract: Electrocatalytic valorization of biomass-derived intermediate compounds to value-added products has emerged as a promising approach to mitigate carbon emissions. Capitalizing on renewable electricity as a green energy input for conducting paired electrocatalysis is a promising approach in the field of biorefining. Simultaneous oxidation and reduction of 5-hydroxymethylfurfural (HMF) yields high value products such as 2,5-formylfurancarboxylic acid (FFCA) and 2,5-bishydroxymethylfurfural (BHMF) with applications in the food industry, fuel additives, and pharmaceuticals. Simultaneous upgrading of biomass derived 5-hydroxymethylfurfural (HMF) at both the anode and cathode has been previously explored, however the challenge of tunable selectivity has not been overcome. Traditional electrochemical methods often suffer from energy inefficiencies due to the need for a second conversion at the counter electrode, which can produce non-value-added byproducts. Amino acids are a key example of highly valuable products derived from biomass oxidation followed by reductive amination. Pharmaceutical and food industries will benefit from an alternative strategy to produce amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. HMF can be proven to selectively yield 5-formyl-2-furancarboxylic acid (FFCA) under the same electrochemical conditions as HMF hydrogenation to 2,5-bishydroxymethylfuran (BHMF). With 4-acetamido TEMPO (ACT) as a homogeneous oxidation mediator and silver galvanically displaced copper foam (Ag/Cu) as the cathodic electrocatalyst, both electrochemical conversions can be observed in an H-type cell simultaneously. By employing pH 10 carbonate buffer as the optimized electrolyte, water proves to be an effective proton source for both conversion which demonstrates the extremely mild conditions. HMF anodic conversion of 94% leads to FFCA formation of 83% yield and simultaneous HMF cathodic conversion of 100% yields BHMF at 99%. HMF also oxidizes to 2,5-diformylfuran (DFF) with 75% yield and subsequent amination with ammonium hydroxide followed by reductive hydrogenation yields 2,5-(dimethylamino) furan (DMAF). This paired electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination yield amino acids as the final products. Glycine, Alanine, and Leucine were synthesized with N-hydroxyphthalimide (NHPI) as the oxidation mediator and NH3 as the nitrogen source to yields of 70, 80, and 90%. Phenylalanine required tetramethylpiperidine Noxyl (TEMPO) oxidation mediator with applying the same 2.7 V yielded 100%. Our paired electrolysis improves selectivity and doubles electron efficiency, with the flow electrolyzer demonstrating its potential for large-scale applications. The main challenge for widespread use of our proposed paired electrocatalytic method is the cost of industrial-scale small molecule production. Paired electrocatalysis offers an alternative by using both half-reactions in an electrochemical cell to produce value-added chemicals from biomass feedstocks. The operational principles and benefits of various cell configurations are compared, along with an analysis of electrocatalysts. Heterogeneous and bifunctional catalysts in paired electrocatalysis optimize energy and chemical use, eliminating the need for purification. The future will require further optimization to enhance the benefits of biomass valorization through paired electrocatalysis, while addressing challenges like cost of precursors, large-scale facility expenses, and widespread adoption of sustainably sourced energy.

Purchased from AmBeed: ; ; ; ; ; ; ;

Kaili Yan ; Morgan L. Huddleston ; Brett A. Gerdes ; Yujie Sun ;

Abstract: Electrochemical conversion of biomass-derived intermediate compounds to high-value products has emerged as a promising approach in the field of biorefinery. Biomass upgrading allows for the production of chemicals from non-fossil-based carbon sources and capitalization on electricity as a green energy input. Amino acids, as products of biomass upgrading, have received relatively little attention. Pharmaceutical and food industries will benefit from an alternative strategy for the production of amino acids that does not rely on inefficient fermentation processes. The use of renewable biomass resources as starting materials makes this proposed strategy more desirable. Herein, we report an electrochemical approach for the selective oxidation of biomass-derived α-hydroxyl acids to α-keto acids, followed by electrochemical reductive amination to yield amino acids as the final products. Such a strategy takes advantage of both reactions at the anode and cathode and produces amino acids under ambient conditions with high energy efficiency. A flow electrolyzer was also successfully employed for the conversion of α-hydroxyl acids to amino acids, highlighting its great potential for large-scale application.

Purchased from AmBeed: ; ; ; ; 56-40-6 ; 156-06-9 ; ; ; ; ; ; ; 828-01-3 ;

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Product Details of Glyoxylic Acid

CAS No. :298-12-4
Formula : C2H2O3
M.W : 74.04
SMILES Code : OC(=O)C=O
Synonyms :
Glyoxalic acid; NSC 27785; Oxalaldehydic acid
MDL No. :MFCD00006958
InChI Key :HHLFWLYXYJOTON-UHFFFAOYSA-N
Pubchem ID :760

Safety of Glyoxylic Acid

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H317-H402-H290
Precautionary Statements:P501-P261-P273-P272-P234-P264-P280-P390-P362+P364-P303+P361+P353-P333+P313-P301+P330+P331-P304+P340+P310-P305+P351+P338+P310-P406-P405
Class:8
UN#:3265
Packing Group:

Application In Synthesis of Glyoxylic Acid

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 298-12-4 ]
  • Downstream synthetic route of [ 298-12-4 ]

[ 298-12-4 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 95-83-0 ]
  • [ 298-12-4 ]
  • [ 2427-71-6 ]
References: [1] Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 158 - 175.
[2] Patent: US5541324, 1996, A, .
  • 2
  • [ 107-15-3 ]
  • [ 298-12-4 ]
  • [ 24123-14-6 ]
References: [1] Tetrahedron, 1995, vol. 51, # 44, p. 12069 - 12082.
[2] Journal of Medicinal Chemistry, 2002, vol. 45, # 14, p. 3032 - 3040.
  • 3
  • [ 298-12-4 ]
  • [ 71-36-3 ]
  • [ 105-76-0 ]
  • [ 2050-60-4 ]
  • [ 141-03-7 ]
  • [ 1587-18-4 ]
  • [ 344268-32-2 ]
  • [ 38094-11-0 ]
  • [ 77-94-1 ]
  • [ 105-75-9 ]
  • [ 117538-83-7 ]
  • [ 94086-70-1 ]
References: [1] Chemistry and Biodiversity, 2012, vol. 9, # 4, p. 714 - 726.
  • 4
  • [ 107-15-3 ]
  • [ 298-12-4 ]
  • [ 108-95-2 ]
  • [ 1170-02-1 ]
  • [ 94770-71-5 ]
References: [1] Journal of Agricultural and Food Chemistry, 2006, vol. 54, # 12, p. 4355 - 4363.
  • 5
  • [ 95-47-6 ]
  • [ 96-76-4 ]
  • [ 298-12-4 ]
  • [ 164391-52-0 ]
References: [1] Patent: US6359148, 2002, B1, . Location in patent: Page column 40 - 41.
 

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