37690
Dihydroxyfumaric acid dihydrate
technical, ≥90% (T)
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About This Item
Empirical Formula (Hill Notation):
C4H4O6 · 2H2O
CAS Number:
Molecular Weight:
184.10
PubChem Substance ID:
UNSPSC Code:
12352100
Beilstein/REAXYS Number:
1724790
MDL number:
Assay:
≥90% (T)
Form:
powder
Product Name
Dihydroxyfumaric acid dihydrate, technical, ≥90% (T)
SMILES string
O.O.OC(=O)\C(O)=C(/O)C(O)=O
InChI
1S/C4H4O6.2H2O/c5-1(3(7)8)2(6)4(9)10;;/h5-6H,(H,7,8)(H,9,10);2*1H2/b2-1+;;
InChI key
LDRMCGGUXOJSDA-SEPHDYHBSA-N
grade
technical
assay
≥90% (T)
form
powder
mp
~155 °C (dec.)
solubility
methanol: soluble 1 g/10 mL, clear, colorless (hot)
storage temp.
2-8°C
Application
Dihydroxyfumaric acid dihydrate may be used in the preparation of mesoxalic acid semialdehyde and its derivatives.
General description
Crystal structure of dihydroxyfumaric acid dihydrate has been reported. Homogeneous reaction of dihydroxyfumarate (DHF) with glyoxylic acid monohydrate has been reported. It is also reported to react with glyoxylate, glycolaldehyde and glyceraldehyde, via α-keto acid intermediates, to afford triose, tetrulose and pentuloses.
Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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The crystal structure of dihydroxyfumaric acid dihydrate.
Gupta MP and Gupta NP.
Acta Crystallographica Section B, Structural Science, 24(5), 631-636 (1968)
Christopher Butch et al.
Journal of the American Chemical Society, 135(36), 13440-13445 (2013-08-07)
An abiotic formation of meso- and DL-tartrates in 80% yield via the cyanide-catalyzed dimerization of glyoxylate under alkaline conditions is demonstrated. A detailed mechanism for this conversion is proposed, supported by NMR evidence and (13)C-labeled reactions. Simple dehydration of tartrates
The preparation and properties of lithium hydroxypyruvate and hydroxypyruvic acid.
F DICKENS et al.
The Biochemical journal, 68(1), 74-81 (1958-01-01)
Vasudeva Naidu Sagi et al.
Journal of the American Chemical Society, 134(7), 3577-3589 (2012-01-28)
In the context of a "glyoxylate scenario" of primordial metabolism, the reactions of dihydroxyfumarate (DHF) with reactive small molecule aldehydes (e.g., glyoxylate, formaldehyde, glycolaldehyde, and glyceraldehyde) in water were investigated and shown to form dihydroxyacetone, tetrulose, and the two pentuloses
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