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Chemical Structure| 79-14-1 Chemical Structure| 79-14-1
Chemical Structure| 79-14-1

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Glycolic acid (or hydroxyacetic acid) is the smallest alpha-hydroxy acid. Due to its excellent capability to penetrate skin, glycolic acid is often used in skin care products, most often as a chemical peel.

Synonyms: Hydroxyethanoic acid; dicarbonous acid; Glycollic acid

4.5 *For Research Use Only !

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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: ; ; ; ; ; ; ;

Hassan, Sara A ; Zaater, Marwa A ; Abdel-Rahman, Islam M ; Ibrahim, Elsayed A ; El Kerdawy, Ahmed M ; Abouelmagd, Sara A

Abstract: The development of new forms of existing APIs with enhanced physicochemical properties is critical for improving their therapeutic potential. In this context, ionic liquids (ILs) and deep eutectic solvents (DESs) have gained significant attention in recent years due to their unique properties and potential for solubility enhancement. In this study, we explore the role of different counterparts in the formation of IL/DESs with piperine (PI), a poorly water-soluble drug. After screening a library of fourteen counterpart molecules, ten liquid PI-counterpart systems were developed and investigated. Thermal analysis confirmed the formation of IL/DES, while computational and spectroscopic studies revealed that hydrogen bonding played a crucial role in the interaction between PI and the counterparts, confirming DES formation. The solubility enhancement of PI in these systems ranged from ∼ 36 % to 294 %, with PI-Oxalic acid (OA) exhibiting the highest saturation solubility (49.71 μg/mL) and PI-Ibuprofen (IB) the lowest (17.23 μg/mL). The presence of hydrogen bonding groups in counterparts was key to successful DES formation. A negative correlation was observed between solubility and logP (r =  − 0.75, p* = 0.0129), while a positive correlation was found between solubility and normalized polar surface area (PSA) (r = 0.68, p* = 0.029). PI-OA and PI-IB were located at the extreme ends of these regression lines, further validating the relationship between these properties and solubility enhancement. These findings highlight essential aspects of rational IL/DES design, optimizing their properties for broader applications.

Purchased from AmBeed: ;

Bednarczyk, Paulina ; Nowak, Anna ; Duchnik, Wiktoria ; Kucharski, Lukasz ; Ossowicz-Rupniewska, Paula ;

Abstract: This study investigated the impact of various enhancers on permeation through the skin and accumulation in the skin from acrylic pressure-sensitive adhesive-based drug-in-adhesives matrix-type transdermal patches. Eleven patches, each containing a 5% enhancer of permeation, encompassing compounds such as salicylic acid, menthol, urea, glycolic acid, allantoin, oleic acid, Tween 80, linolenic acid, camphor, N-dodecylcaprolactam, and glycerin, were developed. Ibuprofen (IBU) was the model active substance, a widely-used non-steroidal anti-inflammatory drug. The results were compared to patches without enhancers and commercial preparations. The study aimed to assess the effect of enhancers on IBU permeability. The adhesive properties of the patches were characterised, and active substance permeability was tested. The findings revealed that patches with 5% allantoin exhibited the highest IBU permeability, approximately 2.8 times greater than patches without enhancers after 24 h. These patches present a potential alternative to commercial preparations, highlighting the significant impact of enhancers on transdermal drug delivery efficiency.

Keywords: acrylic pressure-sensitive adhesives ; adhesion ; enhancers ; ibuprofen ; shear strength ; tack ; transdermal patch

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 Glycolic Acid

CAS No. :79-14-1
Formula : C2H4O3
M.W : 76.05
SMILES Code : O=C(O)CO
Synonyms :
Hydroxyethanoic acid; dicarbonous acid; Glycollic acid
MDL No. :MFCD00004312
InChI Key :AEMRFAOFKBGASW-UHFFFAOYSA-N
Pubchem ID :757

Safety of Glycolic Acid

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314-H332
Precautionary Statements:P264-P271-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P403+P233-P501
Class:8
UN#:3261
Packing Group:

Application In Synthesis of Glycolic 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 [ 79-14-1 ]
  • Downstream synthetic route of [ 79-14-1 ]

[ 79-14-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 79-14-1 ]
  • [ 99-56-9 ]
  • [ 20034-00-8 ]
YieldReaction ConditionsOperation in experiment
87% at 130℃; for 3 h; General procedure: To a mixture of 1a–1c (10 mmol) with glycolic acid (2.28 g, 30 mmol) was added concentrated H3PO4(20 mL). The reaction mixture was refluxed at 130°C for 3 h, then quenched with 20percent NaOH. The respective solid product was collected by filtration.
References: [1] Russian Journal of General Chemistry, 2017, vol. 87, # 12, p. 3006 - 3016.
[2] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 4, p. 1272 - 1274.
[3] Molecules, 2015, vol. 20, # 8, p. 15206 - 15223.
[4] Journal of the American Chemical Society, 1952, vol. 74, p. 3689.
[5] Journal of the American Chemical Society, 1957, vol. 79, p. 4391,4393.
[6] Patent: US2004/209865, 2004, A1, .
[7] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 933 - 936.
  • 2
  • [ 79-14-1 ]
  • [ 95-55-6 ]
  • [ 77186-95-9 ]
References: [1] Patent: US2932649, 1958, , .
[2] Patent: US2877155, 1957, , .
[3] Patent: US2508324, 1946, , .
 

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