dihydroxyfumaric acid
fumaric acid, dihydroxy-
 
Notes:
Dihydroxyfumaric acid is a known generator of superoxide anions and by hydroxyl free radicals. Dihydroxyfumarate exposure can cause insulin inhibitory effects. It can spontaneously convert to hydroxypyruvate or to oxaloglycolate. [HMDB]
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CAS Number: 133-38-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 205-106-2
Nikkaji Web: J69.683H
Beilstein Number: 1724790
XlogP3-AA: 0.40 (est)
Molecular Weight: 148.07108000
Formula: C4 H4 O6
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: pharmaceuticals / chemical synthisis
 
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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)
 water, 7.425e+005 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
Carbosynth
For experimental / research use only.
Dihydroxyfumaric acid hydrate
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
oral-rat LD50  6000 mg/kg
Bollettino Chimico Farmaceutico. Vol. 101, Pg. 903, 1962.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
AIDS Citations: Search
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 54678503
National Institute of Allergy and Infectious Diseases: Data
 (E)-2,3-dihydroxybut-2-enedioic acid
Chemidplus: 0000133380
RTECS: LT1500000 for cas# 133-38-0
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References:
 (E)-2,3-dihydroxybut-2-enedioic acid
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 54678503
Pubchem (sid): 134974587
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C00975
HMDB (The Human Metabolome Database): HMDB02050
FooDB: FDB022816
Export Tariff Code: 2918.19.9000
ChemSpider: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 not found in nature
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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-
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Articles:
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.
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