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498-23-7,MFCD00078086
Catalog No.:AA003HMX
498-23-7 | 2-Methylmaleic acid
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99%(GC)
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99%(GC)
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  • Technical Information
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Technical Information
Catalog Number:
AA003HMX
Chemical Name:
2-Methylmaleic acid
CAS Number:
498-23-7
Molecular Formula:
C5H6O4
Molecular Weight:
130.0987
MDL Number:
MFCD00078086
IUPAC Name:
(Z)-2-methylbut-2-enedioic acid
InChI:
InChI=1S/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2-
InChI Key:
HNEGQIOMVPPMNR-IHWYPQMZSA-N
SMILES:
OC(=O)/C=C(\C(=O)O)/C
UNII:
0RQ6CXO9KD
Properties
Computed Properties
 
Complexity:
168  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
1  
Exact Mass:
130.027g/mol
Formal Charge:
0
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
2  
Isotope Atom Count:
0
Molecular Weight:
130.099g/mol
Monoisotopic Mass:
130.027g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
74.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.1  

Synonyms
 
(E)-2-methyl-2-butenedioic acid 
(Z)-2-methyl-2-butenedioic acid 
monomethylfumarate 
monomethylfumarate 
2-Methylfumaric acid 
D09KCU 
C5H6O4 
Kyselina mesakonova [Czech] 
citraconic acid, sodium salt 
citraconic acid, (E)-isomer 
citraconic acid, calcium salt 
citraconic acid, ammonium salt 
trans-2-Methyl-2-butenedioic acid 
Citraconic acid 
(E)-2-Methyl-2-butenedioic acid 
C5-H6-O4 
(2Z)-2-Methyl-2-butenedioic acid 
c0363 
CID643798 
trans-1-Propene-1,2-dicarboxylic acid 
(2E)-2-METHYLBUT-2-ENEDIOIC ACID 
C073341 
2-methylmaleic acid 
METHYLMALEIC ACID 
498-23-7 
cis-Methylbutenedioic acid 
2-Methyl-2-butenedioic acid 
Citraconate 
(Z)-2-Methyl-2-butenedioic acid 
Maleic acid, methyl- 
citraconic acid 
Citraconsaeure 
Methyl-maleinsaeure 
Kyselina citrakonova 
Kyselina citrakonova [Czech] 
citraconsaure 
UNII-0RQ6CXO9KD 
(2Z)-2-methylbut-2-enedioic acid 
BRN 1722679 
2-Butenedioic acid, 2-methyl-, (Z)- 
2-Methylmaleate 
citraconic acid, (E)-isomer 
alpha-methylmaleic acid 
EINECS 207-858-7 
NSC 32949 
0RQ6CXO9KD 
cis-2-methylbutenedioic acid 
2-methyl-2Z-butenedioic acid 
HNEGQIOMVPPMNR-IHWYPQMZSA-N 
(~{z})-2-Methylbut-2-Enedioic Acid 
2-Butenedioic acid, 2-methyl-, (Z)- (9CI) 
Citronic acid 
citraconic acid, ammonium salt 
W-106003 
methylfumarate 
(E)-Citraconic acid 
MFCD00078086 
(E)-Methylbutendiasure 
Methylmaleate 
(Z)-2-methylbut-2-enedioic acid 
Citronate 
Methyl-maleinsaure 
(E)-Citraconate 
citraconic acid, calcium salt 
7407-59-2 
EINECS 231-014-7 
2-methyl maleic acid 
2-butenedioic acid, 2-methyl-, (2Z)- 
Citraconic acid, 98% 
AC1LD7YR 
Maleic acid, 2-methyl- 
bmse000199 
SCHEMBL5893 
4-02-00-02230 (Beilstein Handbook Reference) 
citraconic acid, sodium salt 
ARONIS23901 
(Z)-2-Methyl-2-butenedioate 
trans-2-Methyl-2-butenedioate 
(2E)-2-Methyl-2-butenedioate 
CHEBI:17626 
BBC/180 
trans-1-Propene-1,2-dicarboxylate 
ZINC3860287 
ZX-AS004397 
(2E)-2-Methyl-2-butenedioic acid 
mesaconic acid 
ACM498237 
LMFA01170099 
SBB065853 
AKOS005111074 
(2Z)-2-Methyl-2-butenedioic acid # 
DB04734 
AJ-45978 
LS-54357 
U619 
AX8121807 
methylfumaric acid 
HY-113298 
CS-0059543 
ST24028105 
ST51038554 
C02226 
45996-EP2269988A2 
45996-EP2270008A1 
45996-EP2275413A1 
45996-EP2287153A1 
45996-EP2287156A1 
methylmaleic acid 
45996-EP2292617A1 
45996-EP2301940A1 
45996-EP2311807A1 
545A0AB4-F752-4DF8-BDB4-845BF57ADC8D 
InChI=1/C5H6O4/c1-3(5(8)9)2-4(6)7/h2H,1H3,(H,6,7)(H,8,9)/b3-2 
CIZ 
mesaconic acid 
mesaconate 
Methylfumaric acid 
2-methylfumarate 
Literature

Title: Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics.

Journal: Scientific reports 20180101

Title: Fumarate Mediates a Chronic Proliferative Signal in Fumarate Hydratase-Inactivated Cancer Cells by Increasing Transcription and Translation of Ferritin Genes.

Journal: Molecular and cellular biology 20170601

Title: Distinct Nrf2 Signaling Mechanisms of Fumaric Acid Esters and Their Role in Neuroprotection against 1-Methyl-4-Phenyl-1,2,3,6-Tetrahydropyridine-Induced Experimental Parkinson's-Like Disease.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20160608

Title: Regulation of proton-coupled folate transporter in retinal Müller cells by the antipsoriatic drug monomethylfumarate.

Journal: Glia 20120301

Title: Downregulation of endothelial adhesion molecules by dimethylfumarate, but not monomethylfumarate, and impairment of dynamic lymphocyte-endothelial cell interactions.

Journal: Experimental dermatology 20111201

Title: Vitamin B12, cognition, and brain MRI measures: a cross-sectional examination.

Journal: Neurology 20110927

Title: Lymphomatosis cerebri presenting as a rapidly progressive dementia with a high methylmalonic acid.

Journal: Journal of neurology 20110801

Title: Clinical characteristics and gene mutation analysis of methylmalonic aciduria.

Journal: Journal of Huazhong University of Science and Technology. Medical sciences = Hua zhong ke ji da xue xue bao. Yi xue Ying De wen ban = Huazhong keji daxue xuebao. Yixue Yingdewen ban 20110601

Title: A methylaspartate cycle in haloarchaea.

Journal: Science (New York, N.Y.) 20110121

Title: Cytokine secretion pattern in treatment of lymphocytes of multiple sclerosis patients with fumaric acid esters.

Journal: Immunological investigations 20110101

Title: Pharmacokinetics of anti-psoriatic fumaric acid esters in psoriasis patients.

Journal: Archives of dermatological research 20100901

Title: Synthesis, characterization and reactivity ratio study of poly(di(tri-n-butyltin) citraconate-co-N-vinylimidazole).

Journal: Molecules (Basel, Switzerland) 20100707

Title: Reduction of fumarate, mesaconate and crotonate by Mfr, a novel oxygen-regulated periplasmic reductase in Campylobacter jejuni.

Journal: Environmental microbiology 20100301

Title: Effects of fumaric acids on cuprizone induced central nervous system de- and remyelination in the mouse.

Journal: PloS one 20100101

Title: Catalytic (transfer) deuterogenation in D2O as deuterium source with H2 and HCO2H as electron sources.

Journal: Dalton transactions (Cambridge, England : 2003) 20090828

Title: Urinary methylmalonic acid in patients with acute myocardial infarction.

Journal: Medical principles and practice : international journal of the Kuwait University, Health Science Centre 20090101

Title: The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist.

Journal: Biochemical and biophysical research communications 20081031

Title: A new antigen retrieval technique for human brain tissue.

Journal: PloS one 20080101

Title: Hyperkalemia after acute metabolic decompensation in two children with vitamin B12-unresponsive methylmalonic acidemia and normal renal function.

Journal: Clinical nephrology 20060701

Title: Fumarate reductase: structural and mechanistic insights from the catalytic reduction of 2-methylfumarate.

Journal: FEBS letters 20060306

Title: Effects of monomethylfumarate on dendritic cell differentiation.

Journal: The British journal of dermatology 20060201

Title: Reversing the effects of formalin fixation with citraconic anhydride and heat: a universal antigen retrieval method.

Journal: The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20050101

Title: Monomethylfumarate affects polarization of monocyte-derived dendritic cells resulting in down-regulated Th1 lymphocyte responses.

Journal: European journal of immunology 20040201

Title: In vitro pharmacokinetics of anti-psoriatic fumaric acid esters.

Journal: BMC pharmacology 20040101

Title: Plausible molecular mechanism for activation by fumarate and electron transfer of the dopamine beta-mono-oxygenase reaction.

Journal: The Biochemical journal 20021001

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