A New Method for the Purification of the Alcoholate of the Trimer of Hydroxypyruvic Aldehyde

Evans, William E.; Carr, C. Jelleff; Krantz, John C.

doi:10.1021/ja01274a032

Cited by 16 publications

(5 citation statements)

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“…Better evidence has been obtained for the formation of acetol and reductone (glucic acid) in alkaline sugar solutions. The former may be steam distilled from neutral or alkaline sugar solutions (7) and uniquely identified by conversion to 3-hydroxyquinaldine, while the latter may be precipitated as the lead salt from heated alkaline glucose solutions (6).…”

Section: Thementioning

confidence: 99%

“…Reductone (prepared via the lead salt) and its tautomer, hydroxypyruvaldehyde (7), have identical spectra, with a maximum at 265 µ at pH 2 to 3.5, which is shifted to 290 µ at pH 6.5 to 8. Both peaks disappear rather rapidly when the solutions are allowed to stand at room temperature, since these substances are not stable in solution.…”

Section: Experimental Workmentioning

confidence: 99%

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Sugar Analysis, Ultraviolet Spectra of Sugars in Alkaline Solution

Berl¹,

Feazel²

1954

J. Agric. Food Chem.

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The ultraviolet absorption spectra which are produced in alkaline solutions of some of the simple sugars have been measured. Investigation of these spectra shows that they are not due to the presence of reductone or pyruvaldehyde, as has previously been supposed. The chromogen responsible for the spectra, which was isolated by partition chromatography, is also responsible for the brown color which develops in alkaline sugar solutions. It is suggested that this chromogen is the result of condensation of compounds produced by the fragmentation of sugars in alkaline solution.

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Section: Thementioning

confidence: 99%

Section: Experimental Workmentioning

confidence: 99%

Sugar Analysis, Ultraviolet Spectra of Sugars in Alkaline Solution

Berl¹,

Feazel²

1954

J. Agric. Food Chem.

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“…Hydroxypyruvaldehyde and methyl glyoxylate were synthesized following the synthesis of (Evans et al 1938) and (Kelly et al 1972), respectively.…”

Section: Methodsmentioning

confidence: 99%

Organic residues in astrophysical ice analogues: Thermal processing of hydrogenated glyoxal ices under interstellar conditions

Leroux

Guillemin

Krim

2021

Monthly Notices of the Royal Astronomical Society

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Organic residues are considered as part of the chemical composition of the interstellar dust grains. They are formed under the extreme conditions of the interstellar medium and play an important role in exobiology. They may contain prebiotic organic species such as amino acids, constituents of proteins and building blocks of DNA and RNA, key elements of life. By investigating the formation of organic residues in an astrophysical context, many groups have been focusing in the UV irradiation and subsequent warm-up of astrophysical ice analogs. This aims to suggest that organic residues are mainly formed in regions of molecular clouds exposed to UV light or cosmic rays. The present study shows an organic residues formation involving glyoxal ice and H-atoms. While the hydrogenation of glyoxal at 10 K leads mainly to small molecules such as CO and H2CO and CH3OH, we show that the heating of the hydrogenated ice in the 10–300 K temperature range leads to solid residues which structure is similar to that of glycolaldehyde but they remain stable in solid phase at 300 K and atmospheric pressure. The analysis of the IR data shows that the organic residues formed through the thermal processing of CHOCHO + H reaction would be a mixture of hydroxypyruvaldehyde and methyl glyoxylate, two solid organics which formation starts with an H-abstraction from glyoxal to form CHOCO• radical which recombines to •CH2OH and •OCH3 radicals. These latter may be formed and trapped in glyoxal ice as secondary products from H2CO + H secondary reaction.

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“…Hydroxypyruvic aldehyde was prepared and characterized according to the procedure of Evans et al (1938).…”

Section: Methodsmentioning

confidence: 99%