Glyoxylic acid is a reagent for sulfinylmaleate synthesis. It is one of the chemicals used in the Hopkins Cole reaction. It is involved to check the presence of tryptophan in proteins. It is condensed with urea and 1,2-diaminobenzene to form heterocycles. It also undergoes Friedel-Crafts and cyclocondensation reactions to form bis(pentamethylphenyl) acetic acid and a beta-carboline respectively. It is employed in the synthesis of a sulfinylmaleate, which serves as an efficient dienophile for enantioselective Diels-Alder cycloadditions.
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Applications
Glyoxylic acid is a reagent for sulfinylmaleate synthesis. It is one of the chemicals used in the Hopkins Cole reaction. It is involved to check the presence of tryptophan in proteins. It is condensed with urea and 1,2-diaminobenzene to form heterocycles. It also undergoes Friedel-Crafts and cyclocondensation reactions to form bis(pentamethylphenyl) acetic acid and a beta-carboline respectively. It is employed in the synthesis of a sulfinylmaleate, which serves as an efficient dienophile for enantioselective Diels-Alder cycloadditions.
Solubility
Soluble in water, dimethyl sulfoxide and alcohol. Insoluble in diethyl ether and hydrocarbons.
Notes
Hygroscopic. Keep the container tightly closed in a dry and well-ventilated place. Incompatible withbases, oxidizing agents and reducing agents.
RUO – Research Use Only
General References:
- For reaction with tryptamine hydrochloride, followed by cyclization to give 1,2,3,4-tetrahydro-ß-carboline, see: Org. Synth. Coll., 6, 965 (1988).
- Reagent for transthioacetalization of dithioacetal groups from protected aldehydes and ketones in acetic acid catalyzed by mineral acid: Synthesis, 694 (1976); for alternative methods of dithioacetal cleavage, see 1,3-Dithiane, A10505.
- Lundell, J.; Olbert-Majkut, A. Isolated glyoxylic acid-water 1: 1 complexes in low temperature argon matrices. Spectrochim. Acta. A Mol. Biomol. Spectrosc. 2015, 136, 113-121.
- Ghimbeu, C. M.; Vidal, L.; Delmotte, L.; Le Meins, J. M.; Vix-Guterl, C. Catalyst-free soft-template synthesis of ordered mesoporous carbon tailored using phloroglucinol/glyoxylic acid environmentally friendly precursors. Green Chem. 2014, 16 (6), 3079-3088.
- Lundell, J.; Olbert-Majkut, A. Isolated glyoxylic acid-water 1: 1 complexes in low temperature argon matrices. Spectrochim. Acta. A Mol. Biomol. Spectrosc. 2015, 136, 113-121.