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
Beilstein:
1724790
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
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
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
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.
Application
Dihydroxyfumaric acid dihydrate may be used in the preparation of mesoxalic acid semialdehyde and its derivatives.
Storage Class Code
13 - Non Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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The preparation and properties of lithium hydroxypyruvate and hydroxypyruvic acid.
F DICKENS et al.
The Biochemical journal, 68(1), 74-81 (1958-01-01)
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 crystal structure of dihydroxyfumaric acid dihydrate.
Gupta MP and Gupta NP.
Acta Crystallographica Section B, Structural Science, 24(5), 631-636 (1968)
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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