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G10601

Sigma-Aldrich

Glyoxylic acid monohydrate

98%

Synonym(s):

Formylformic acid, Oxoethanoic acid

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About This Item

Linear Formula:
HCOCO2H · H2O
CAS Number:
563-96-2
Molecular Weight:
92.05
Beilstein:
969535
EC Number:
206-058-5
MDL number:
MFCD00149497
UNSPSC Code:
12352100
PubChem Substance ID:
24895036
NACRES:
NA.22

Quality Level

200

Assay

98%

bp

100 °C (lit.)

mp

49-52 °C (lit.)

SMILES string

[H]O[H].[H]C(=O)C(O)=O

InChI

1S/C2H2O3.H2O/c3-1-2(4)5;/h1H,(H,4,5);1H2

InChI key

MOOYVEVEDVVKGD-UHFFFAOYSA-N

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Application

Employed in the synthesis of a sulfinylmaleate, which serves as an efficient dienophile for enantioselective Diels-Alder cycloadditions. Undergoes Friedel-Crafts and cyclocondensation reactions to form bis(pentamethylphenyl)acetic acid and a β-carboline, respectively.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H290,H315,H317,H318

Hazard Classifications

Eye Dam. 1 - Met. Corr. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 1

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Journal of the American Chemical Society, 109, 3378-3378 (1987)
The Journal of Organic Chemistry, 58, 3231-3231 (1993)
The Journal of Organic Chemistry, 57, 362-362 (1992)
Paris Grant-Preece et al.
Food chemistry, 215, 292-300 (2016-08-21)
Glyoxylic acid is a tartaric acid degradation product formed in model wine solutions containing iron and its production is greatly increased by exposure to UV-visible light. In this study, the combined effect of sulfur dioxide, caffeic acid, pH and temperature
Paris Grant-Preece et al.
Food chemistry, 243, 239-248 (2017-11-18)
Model wine solutions containing organic acids, individually or combined, and iron(III), were exposed to light from fluorescent lamps or stored in darkness for four hours. (-)-Epicatechin was then added, and the solutions incubated in darkness for 10days. Browning was monitored
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