dihydroxyfumaric acid
fumaric acid, dihydroxy-
Identification
| Name | dihydroxyfumaric acid |
| CAS Number | 133-38-0 |
| EINECS | 205-106-2 |
| FDA UNII | Search |
| Molecular Formula | C4 H4 O6 |
| Molecular Weight | 148.07108000 |
| Nikkaji Number | J69.683H |
| Beilstein | 1724790 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 387.30 °C. @ 760.00 mm Hg (est) |
| Flash Point | 396.00 °F. TCC ( 202.20 °C. ) (est) |
| logP (o/w) | -1.310 (est) |
| Soluble in | water, 2960 mg/L @ 12C (exp) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-rat LD50 6000 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | pharmaceuticals / chemical synthisis |
| Recommendation for dihydroxyfumaric acid usage levels up to | not for fragrance use. |
| Recommendation for dihydroxyfumaric acid flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
2-
butenedioic acid, 2,3-dihydroxy-, (2E)-
2-
butenedioic acid, 2,3-dihydroxy-, (E)- (9CI)
(E)-2,3-
dihydroxy-2-butenedioic acid
(E)-2,3-
dihydroxybut-2-enedioic acid
dihydroxyfumarate
2,3-
dihydroxyfumaric acid
fumaric acid, dihydroxy-
PubMed:
Exploratory experiments on the chemistry of the "glyoxylate scenario": formation of ketosugars from dihydroxyfumarate.
PubMed:
A heme peroxidase with a functional role as an L-tyrosine hydroxylase in the biosynthesis of anthramycin.
PubMed:
VO2+ complexation by bioligands showing keto-enol tautomerism: a potentiometric, spectroscopic, and computational study.
PubMed:
Diastereoselective self-condensation of dihydroxyfumaric acid in water: potential route to sugars.
PubMed:
Heterogeneous solid base nanocatalyst: preparation, characterization and application in biodiesel production.
PubMed:
Potentiometric assessment of iron release during ferritin reduction by exogenous agents.
PubMed:
Facile synthesis of anion dependent versatile Cu(I) and mixed-valent porous Cu(I)/Cu(II) frameworks.
PubMed:
Two- and three-dimensional hydrated coordination polymers of diaqualanthanum(3+) ions with 2-hydroxypropanedioate, oxalate and acetate anions as bridging ligands.
PubMed:
Kinetic study of the hexacyanoferrate (III) oxidation of dihydroxyfumaric acid in acid media.
PubMed:
Endogenous formation of N'-nitrosonornicotine in F344 rats in the presence of some antioxidants and grape seed extract.
PubMed:
Effective attenuation of acute lung injury in vivo and the formyl peptide-induced neutrophil activation in vitro by CYL-26z through the phosphoinositide 3-kinase gamma pathway.
PubMed:
D-propranolol attenuates lysosomal iron accumulation and oxidative injury in endothelial cells.
PubMed:
The vasorelaxing action of labedipinedilol-A involves endothelial cell-derived NO and eNOS expression caused by calcium influx.
PubMed:
Highly symmetric networks derived from cubane-related octametallic complexes of a new oxyanion of carbon, C4O7(4-), each molecule attached to eight neighbors by 24 equivalent hydrogen bonds.
PubMed:
Oxidative stress decreases pHi and Na(+)/H(+) exchange and increases excitability of solitary complex neurons from rat brain slices.
PubMed:
Potent antioxidant properties of 4-hydroxyl-propranolol.
PubMed:
The blockade of formyl peptide-induced respiratory burst by 2',5'-dihydroxy-2-furfurylchalcone involves phospholipase D signaling in neutrophils.
PubMed:
Investigation of the cellular mechanism of inhibition of formyl-methionyl-leucyl-phenylalanine-induced superoxide anion generation in rat neutrophils by 2-benzyloxybenzaldehyde.
PubMed:
Inhibition of formyl-methionyl-leucyl-phenylalanine-stimulated respiratory burst by cirsimaritin involves inhibition of phospholipase D signaling in rat neutrophils.
PubMed:
Inhibition of superoxide anion generation by YC-1 in rat neutrophils through cyclic GMP-dependent and -independent mechanisms.
PubMed:
Cellular mechanisms of inhibition of superoxide anion generation in rat neutrophils by the synthetic isoquinoline DMDI.
PubMed:
Protective mechanisms of Mg-gluconate against oxidative endothelial cytotoxicity.
PubMed:
Inhibition of mitochondrial lipid peroxidation by Bakuchiol, a meroterpene from Psoralea corylifolia.
PubMed:
Kinetic characterisation of ene-diol-based inhibitors of alpha-amylase.
PubMed:
Involvement of peroxynitrite and hydroxyradical generated from nitric oxide in hypoxia/reoxygenation injury in rat cerebrocortical slices.
PubMed:
Scission of polysaccharides by peroxidase-generated hydroxyl radicals.
PubMed:
Protection of mitochondrial functions against oxidative stresses by isoflavans from Glycyrrhiza glabra.
PubMed:
Antioxidant properties of calcium antagonists related to membrane biophysical interactions.
PubMed:
2-Hydroxymethyl-1-naphthol diacetate (TAC) suppresses the superoxide anion generation in rat neutrophils.
PubMed:
Hydroxyl-radical production in physiological reactions. A novel function of peroxidase.
PubMed:
Chloroperoxidase-catalyzed enantioselective oxidation of methyl phenyl sulfide with dihydroxyfumaric acid/oxygen or ascorbic acid/oxygen as oxidants.
PubMed:
Involvement of cyclic AMP generation in the inhibition of respiratory burst by 2-phenyl-4-quinolone (YT-1) in rat neutrophils.
PubMed:
Antioxidant and cytoprotective activities of the calcium channel blocker mibefradil.
PubMed:
Inhibition by Salix- extracts and Phytodolor of copper-catalyzed oxidative destruction.
PubMed:
Protective effect of darodipine, a calcium antagonist, on rat cardiomyocytes against oxygen radical-mediated injury.
PubMed:
Investigation of the inhibition by acetylshikonin of the respiratory burst in rat neutrophils.
PubMed:
Blockade of protein kinase C is involved in the inhibition by cycloheterophyllin of neutrophil superoxide anion generation.
PubMed:
Cellular localization of the inhibitory action of abruquinone A against respiratory burst in rat neutrophils.
PubMed:
Examination of the inhibitory effect of norathyriol in formylmethionyl-leucyl-phenylalanine-induced respiratory burst in rat neutrophils.
PubMed:
Inhibition by HAJ11 of respiratory burst in neutrophils and the involvement of protein tyrosine phosphorylation and phospholipase D activation.
PubMed:
Mechanism of hydroxyl radical-induced modulation of vascular tone.
PubMed:
Antioxidant effects of calcium antagonists on rat myocardial membrane lipid peroxidation.
PubMed:
Microperoxidase/H2O2-catalyzed aromatic hydroxylation proceeds by a cytochrome-P-450-type oxygen-transfer reaction mechanism.
PubMed:
The effect of oxygen free radicals on calcium current and dihydropyridine binding sites in guinea-pig ventricular myocytes.
PubMed:
Kinetic studies of the oscillatory dynamics in the peroxidase-oxidase reaction catalyzed by four different peroxidases.
PubMed:
Protective effects of calcium channel blockers against free radical-impaired endothelial cell proliferation.
PubMed:
Use of brain slices in the study of free-radical actions.
PubMed:
Oxygen-derived free radical stress activates nonselective cation current in guinea pig ventricular myocytes. Role of sulfhydryl groups.
PubMed:
Cellular electrophysiological aspects of myocardial protection.
PubMed:
Inhibition by gomisin C (a lignan from Schizandra chinensis) of the respiratory burst of rat neutrophils.
PubMed:
Role of platelet-activating factor (PAF) in oxygen radical-induced cardiac dysfunction.
PubMed:
Absence of antioxidant effects of nifedipine and diltiazem on myocardial membrane lipid peroxidation in contrast with those of nisoldipine and propranolol.
PubMed:
SB 211475, a metabolite of carvedilol, a novel antihypertensive agent, is a potent antioxidant.
PubMed:
Superoxide-mediated lysis of erythrocytes: the role of colloid-osmotic forces.
PubMed:
Modification by hydroxyl radicals of functional reactivity in rabbit lingual artery.
PubMed:
Alterations in electrical activity and membrane currents induced by intracellular oxygen-derived free radical stress in guinea pig ventricular myocytes.
PubMed:
Inhibition of the iron-catalysed formation of hydroxyl radicals by nitrosouracil derivatives: protection of mitochondrial membranes against lipid peroxidation.
PubMed:
Magnesium deficiency in vitro enhances free radical-induced intracellular oxidation and cytotoxicity in endothelial cells.
PubMed:
Carvedilol, a new vasodilator and beta adrenoceptor antagonist, is an antioxidant and free radical scavenger.
PubMed:
Thianthrene 5-oxide as a probe of the electrophilicity of hemoprotein oxidizing species.
PubMed:
[Effects of oxygen free radicals on cell growth and productions of alpha-fetoprotein (AFP) and albumin (ALB) by human hepatoma cell line (HH2-6)].
PubMed:
Erythrocytes from magnesium-deficient hamsters display an enhanced susceptibility to oxidative stress.
PubMed:
Carvedilol, a new beta-adrenoceptor antagonist and vasodilator antihypertensive drug, inhibits superoxide release from human neutrophils.
PubMed:
Oxygen free radical-mediated selective endothelial dysfunction in isolated coronary artery.
PubMed:
Electrophysiological consequences of exposure of hippocampal slices to dihydroxyfumarate, a generator of superoxide radicals.
PubMed:
Membrane antiperoxidative activities of D-propranolol, L-propranolol and dimethyl quaternary propranolol (UM-272).
PubMed:
Cellular electrophysiological basis for oxygen radical-induced arrhythmias. A patch-clamp study in guinea pig ventricular myocytes.
PubMed:
Thiol and Mn(2+)-mediated oxidation of veratryl alcohol by horseradish peroxidase.
PubMed:
Antioxidative properties of harmane and beta-carboline alkaloids.
PubMed:
Reactive oxygen injury to cultured pulmonary artery endothelial cells: mediation by poly(ADP-ribose) polymerase activation causing NAD depletion and altered energy balance.
PubMed:
Hydroxyl radical participation in the in vitro effects of gram-negative endotoxin on cardiac sarcolemmal Na,K-ATPase activity.
PubMed:
[The effect of ambroxol on peroxidative processes in dog lung mitochondria].
PubMed:
Stimulation of collagen synthesis in fibroblast cultures by superoxide.
PubMed:
Protective effects of sulfhydryl-containing angiotensin converting enzyme inhibitors against free radical injury in endothelial cells.
PubMed:
Lignin peroxidase compounds II and III. Spectral and kinetic characterization of reactions with peroxides.
PubMed:
Oxygen radical-mediated injury of myocytes-protection by propranolol.
PubMed:
Captopril and enalaprilat do not scavenge the superoxide anion.
PubMed:
Reaction of compound III of myeloperoxidase with ascorbic acid.
PubMed:
Inhibition of sarcolemmal carbon-centered free radical formation by propranolol.
PubMed:
Effects of ascorbic acid on the antifungal action of amphotericin B.
PubMed:
Possible mechanism responsible for mechanical dysfunction of ischemic myocardium: a role of oxygen free radicals.
PubMed:
Biochemical test reactions for the evaluation of the potential anticataractic function of iodide.
PubMed:
Abnormal electrical activity induced by free radical generating systems in isolated cardiocytes.
PubMed:
Reductive release of ferritin iron: a kinetic assay.
PubMed:
Lysosomal lipolytic enzymes, lipid peroxidation, and injury.
PubMed:
Protection by beta-blocking agents against free radical-mediated sarcolemmal lipid peroxidation.
PubMed:
Oxygen radical-mediated lipid peroxidation and inhibition of Ca2+-ATPase activity of cardiac sarcoplasmic reticulum.
PubMed:
Myeloperoxidase-oxidase oxidation of cysteamine.
PubMed:
The effects of dihydroxyfumarate on isolated rabbit papillary muscle function: evidence for an iron dependent non-hydroxyl radical mechanism.
PubMed:
Nonenzymatic oxidative cleavage of peptide bonds in apoprotein B-100.
PubMed:
Increased prolyl hydroxylase activity and collagen synthesis in hepatocyte cultures exposed to superoxide.
PubMed:
Horseradish peroxidase catalyzed hydroxylations: mechanistic studies.
PubMed:
Potentiation of free radical-induced lipid peroxidative injury to sarcolemmal membranes by lipid amphiphiles.
PubMed:
Inactivation of glycerol dehydrogenase of Klebsiella pneumoniae and the role of divalent cations.
PubMed:
Differential sensitivity of canine cardiac sarcolemmal and microsomal enzymes to inhibition by free radical-induced lipid peroxidation.
PubMed:
Analysis of the effects of erythrocytes on mitogen-dependent clonal proliferation of murine B lymphocytes.
PubMed:
Hydroxylation by hemoglobin-containing systems: activities and regioselectivities.
PubMed:
Toxicity of oxygen radicals in cultured pulmonary endothelial cells.
PubMed:
Temporal relationship of free radical-induced lipid peroxidation and loss of latent enzyme activity in highly enriched hepatic lysosomes.
PubMed:
Purification and characterization of a bifunctional L-(+)-tartrate dehydrogenase-D-(+)-malate dehydrogenase (decarboxylating) from Rhodopseudomonas sphaeroides Y.
PubMed:
Carbonate anions; effects on the oxidation of luminol, oxidative hemolysis, gamma-irradiation and the reaction of activated oxygen species with enzymes containing various active centres.
PubMed:
A pH-dependent superoxide dismutase activity for zinc-free bovine erythrocuprein. Reexamination of the role of zinc in the holoprotein.
PubMed:
Oxidation of tyrosine to dopachrome by peroxidase isolated from murine melanoma.
PubMed:
The mechanism of cytochrome P-450-dependent oxidation of ethanol in reconstituted membrane vesicles.
PubMed:
Impaired insulin release after exposure of pancreatic islets to autooxidizing dihydroxyfumarate.
PubMed:
Loss of haem and haemoproteins during the generation of superoxide anion and hydrogen peroxide: a pathway not involving production of carbon monoxide.
PubMed:
Effect of the superoxide anion (O2-) on Na+-dependent amino acid transport.
PubMed:
Purification of the agent inducing lipid peroxidation with dihydroxyfumaric acid in rat liver mitochondria.
PubMed:
Dimethylurea: a radical scavenger that protects isolated pancreatic islets from the effects of alloxan and dihydroxyfumarate exposure.
PubMed:
Dihydroxyfumaric acid induced lipid peroxidation in rat liver microsomes.
PubMed:
Generation of hydrogen peroxide, superoxide and hydroxyl radicals during the oxidation of dihydroxyfumaric acid by peroxidase.
PubMed:
Superoxide anion and drug-induced hemolysis.
PubMed:
Hydroxylation of p-coumaric acid by horseradish peroxidase. The role of superoxide and hydroxyl radicals.
PubMed:
A study of the supposed hydroxylation of tyrosine catalysed by peroxidase.
PubMed:
Subcellular demonstration of peroxidatic oxidation of tyrosine to melanin using dihydroxyfumarate as cofactor in mouse melanoma cells.
PubMed:
Inability of murine melanoma "tyrosinase" (dopa ozidase) to oxidize tyrosine in the presence or absence of dopa or dihydroxyfumarate cofactor.
PubMed:
Structural modification of gibberellins by in-vitro hydroxylating systems.
PubMed:
DOPA compared with dihydroxyfumarate as co-factor in peroxidase-mediated oxidation of tyrosine to melanin. Histochemical studies with neutrophils, eosinophils, mast cells, melanoma cells and neurons.
PubMed:
A comparison of horseradish peroxidase and manganese ions as catalysts for the oxidation of dihydroxyfumaric acid.
PubMed:
Tartaric acid metabolism II. Crystalline protein converting meso-tartrate and dihydroxyfumarate to glycerate.
PubMed:
THE DIHYDROXYFUMARIC ACID OXIDASE-PEROXIDASE REACTION. I. THE INHIBITION BY CITRATE.
PubMed:
Peroxidase as oxidase: reaction between 18O2 and dihydroxyfumarate.
PubMed:
Some metabolic pathways of hydroxypyruvate and dihydroxyfumarate leading to the formation of pentose and organic acids in rat liver.
PubMed:
The non-enzymatic decarboxylation of diketosuccinate and oxaloglycolate (dihydroxyfumarate).
PubMed:
The formation of hydroxyaspartic acid from dihydroxyfumaric acid and L-glutamic acid.
PubMed:
Enzymatic oxidation of DPNH by diketosuccinate and dihydroxyfumarate.