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2756-87-8,MFCD00063174
Catalog No.:AA002TZO

2756-87-8 | Monomethyl fumarate

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5g
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25g
98%
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100g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA002TZO
Chemical Name:
Monomethyl fumarate
CAS Number:
2756-87-8
Molecular Formula:
C5H6O4
Molecular Weight:
130.0987
MDL Number:
MFCD00063174
SMILES:
COC(=O)/C=C/C(=O)O
Properties
Properties
 
BP:
250°C at 760 mmHg  
Form:
Solid  
MP:
144-145 °C(lit.);  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
147  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
9  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
0.4  

Downstream Synthesis Route

[1]Pospíšil,Jiří;Potáček,Milan[Tetrahedron,2007,vol.63,#2,p.337-346]

[2]Ma,Yan-Long;Zhou,Ru-Jin;Zeng,Xing-Ye;An,Ya-Xiong;Qiu,Song-Shan;Nie,Li-Jun[JournalofMolecularStructure,2014,vol.1063,#1,p.226-234]

[3]CurrentPatentAssignee:RUTHPSCOTT;GOODYEARTIRE&RUBBERCO-US2414066,1943,A

[4]Jaroszewski,JerzyW.;Grossen,Peter;Mohr,Peter;Tamm,Christoph[HelveticaChimicaActa,1986,vol.69,p.718-725]

[5]CurrentPatentAssignee:AZURITYPHARMACEUTICALSINC-US2014/364604,2014,A1Locationinpatent:Paragraph0205

[6]CurrentPatentAssignee:BIOPHOREINDIAPHARMACEUTICALSPVTLTD-US2017/96384,2017,A1Locationinpatent:Paragraph0027

[7]CurrentPatentAssignee:TEVAPHARMACEUTICALINDUSTRIESLTD.-WO2017/108960,2017,A1Locationinpatent:Page/Pagecolumn60

[1]Grandane,Aiga;Nocentini,Alessio;Supuran,ClaudiuT.;Werner,Thomas;Zalubovskis,Raivis[Bioorganicandmedicinalchemistry,2020]

[2]Pudnika,Linda;Domraceva,Ilona;Werner,Thomas;Zalubovskis,Raivis;Grandane,Aiga[Synthesis,2021,vol.53,#19,p.3545-3554]

[3]CurrentPatentAssignee:ROCHEHOLDINGAG-WO2021/97110,2021,A1Locationinpatent:Paragraph0500;0501;0502

[4]CurrentPatentAssignee:ADITECHPHARMA-WO2007/6308,2007,A1Locationinpatent:Page/Pagecolumn48-49

[5]Erlenmeyer;Schoenauer[HelveticaChimicaActa,1937,vol.20,p.1010]

[6]Katon,J.E.;Chu,Pon-Hsiang[JournalofMolecularStructure,1982,vol.78,p.141-152]

[7]Ishizaki,Miyuki;Takano,Hideaki;Hoshino,Osamu[Heterocycles,1998,vol.49,#1,p.305-314]

[8]Uchida,Takuya;Rodriquez,Manuela;Schreiber,StuartL.[OrganicLetters,2009,vol.11,#7,p.1559-1562]

[9]Wang,Jiangyun;Zhang,Wei;Song,Wenjiao;Wang,Yizhong;Yu,Zhipeng;Li,Jiasong;Wu,Minhao;Wang,Lin;Zang,Jianye;Lin,Qing[JournaloftheAmericanChemicalSociety,2010,vol.132,#42,p.14812-14818]

[10]Luo,Xuelai;Liu,Yongxiang;Kubicek,Stefan;Myllyharju,Johanna;Tumber,Anthony;Ng,Stanley;Che,KaHing;Podoll,Jessica;Heightman,TomD.;Oppermann,Udo;Schreiber,StuartL.;Wang,Xiang[JournaloftheAmericanChemicalSociety,2011,vol.133,#24,p.9451-9456]

[11]CurrentPatentAssignee:CATABASISPHARMACEUTICALS,INC.-US2011/172240,2011,A1Locationinpatent:Page/Pagecolumn34;35-36;36-37

[12]CurrentPatentAssignee:KANDULA,Mahesh-WO2013/179153,2013,A1Locationinpatent:Paragraph0095;00102-00103

[13]Ma,Yan-Long;Zhou,Ru-Jin;Zeng,Xing-Ye;An,Ya-Xiong;Qiu,Song-Shan;Nie,Li-Jun[JournalofMolecularStructure,2014,vol.1063,#1,p.226-234]

[14]Ting,ChiP.;Maimone,ThomasJ.[AngewandteChemie-InternationalEdition,2014,vol.53,#12,p.3115-3119][Angew.Chem.,2014,vol.126,#12,p.3179-3183,5]

[15]Zhou,Zhiwang;Hu,Yu;Wang,Bin;He,Xiaoru;Ren,Gang;Feng,Lihua[JournalofChemicalResearch,2014,vol.38,#6,p.378-380]

[16]Panigrahi,Kaushik;Applegate,GregoryA.;Malik,Guillaume;Berkowitz,DavidB.[JournaloftheAmericanChemicalSociety,2015,vol.137,#10,p.3600-3609]

[17]CurrentPatentAssignee:Kandula,Mahesh-US2015/141513,2015,A1Locationinpatent:Paragraph0106;0113;0114

[18]CurrentPatentAssignee:RIGLPHARMACEUTICAL;RIGELPHARMACEUTICALSINC-WO2016/22434,2016,A1Locationinpatent:Paragraph00379

[19]CurrentPatentAssignee:CELLIXBIOPRIVATELTD-US2016/152553,2016,A1Locationinpatent:Paragraph0168;0169

[20]Yang,Zhantao;Ma,Meiyan;Yang,Chun-Hua;Gao,Yuan;Zhang,Quan;Chen,Yue[JournalofNaturalProducts,2016,vol.79,#9,p.2408-2412]

[21]Duncton,MatthewA.J.;Singh,Rajinder[OrganicandBiomolecularChemistry,2016,vol.14,#39,p.9338-9342]

[22]CurrentPatentAssignee:CELLIXBIOPRIVATELTD-JP2015/518854,2015,ALocationinpatent:Paragraph0117;0118

[23]CurrentPatentAssignee:RIGELPHARMACEUTICALSINC-US2016/213648,2016,A1Locationinpatent:Paragraph0412;0413

[24]CurrentPatentAssignee:ABLIVAAB-WO2017/60420,2017,A1Locationinpatent:Page/Pagecolumn33;34;35;36;37;38

[25]Grandane,Aiga;Longwitz,Lars;Roolf,Catrin;Spannenberg,Anke;Escobar,HugoMurua;Junghanss,Christian;Suna,Edgars;Werner,Thomas[JournalofOrganicChemistry,2019,vol.84,#3,p.1320-1329]

[26]CurrentPatentAssignee:FLAGSHIPPIONEERINGINC-WO2020/118178,2020,A1Locationinpatent:Page/Pagecolumn52;95;96

[27]Cai,LukeL.;Eaton,JohnK.;Furst,Laura;Schreiber,StuartL.;Viswanathan,VasanthiS.[BioorganicandMedicinalChemistryLetters,2020,vol.30,#23]

[28]CurrentPatentAssignee:DRREDDY'SLABORATORIESLIMITED-WO2021/74842,2021,A1Locationinpatent:Page/Pagecolumn22-23

[1]TetrahedronLetters,2005,vol.46,p.5199-5201

[2]JournalofNaturalProducts,2005,vol.68,p.769-772

[3]JournalofOrganicChemistry,2000,vol.65,p.5834-5836

[4]HelveticaChimicaActa,1937,vol.20,p.1010

[5]JournalofHeterocyclicChemistry,1966,vol.3,p.129-136

[1]Lima,MarceloT.;Finelli,FernandaG.;DeOliveira,AllineV.B.;Kartnaller,Vinicius;Cajaiba,JoaõF.;Leaõ,RaquelA.C.;DeSouza,RodrigoO.M.A.[RSCAdvances,2020,vol.10,#5,p.2490-2494]

[2]Hurst,J.K.;Taube,H.[JournaloftheAmericanChemicalSociety,1968,vol.90,#5,p.1178-1186]

[3]CurrentPatentAssignee:HENANNORMALUNIVERSITY-CN104761557,2017,BLocationinpatent:Paragraph0012;0013;0014;0015

[4]CurrentPatentAssignee:GLENMARKPHARMACEUTICALSLTD-WO2021/53476,2021,A1Locationinpatent:Paragraph0143

[1]JournalofMedicinalChemistry,1977,vol.20,p.328-332

Literature

Title: Structure-activity relationships of trans-substituted-propenoic acid derivatives on the nicotinic acid receptor HCA2 (GPR109A).

Journal: Bioorganic & medicinal chemistry letters 20110501

Title: Carbonic anhydrase inhibitors. Identification of selective inhibitors of the human mitochondrial isozymes VA and VB over the cytosolic isozymes I and II from a natural product-based phenolic library.

Journal: Bioorganic & medicinal chemistry 20100101

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

Journal: Biochemical and biophysical research communications 20081031

Title: [Modulatory effect of fumaric acid esters on superoxide-anion generation in human phagocytes].

Journal: Yao xue xue bao = Acta pharmaceutica Sinica 20071101

Title: Dimethylfumarate inhibits nuclear binding of nuclear factor kappaB but not of nuclear factor of activated T cells and CCAAT/enhancer binding protein beta in activated human T cells.

Journal: The British journal of dermatology 20070501

Title: Reactivity of dimethyl fumarate and methylhydrogen fumarate towards glutathione and N-acetyl-L-cysteine--preparation of S-substituted thiosuccinic acid esters.

Journal: Bioorganic & medicinal chemistry 20070101

Title: Fumaric acid esters are effective in chronic experimental autoimmune encephalomyelitis and suppress macrophage infiltration.

Journal: Clinical and experimental immunology 20060701

Title: Enhancement of antibacterial superoxide-anion generation in human monocytes by fumaric acid esters.

Journal: Archives of dermatological research 20051001

Title: Tang H, et al. The psoriasis drug monomethylfumarate is a potent nicotinic acid receptor agonist. Biochem Biophys Res Commun. 2008 Oct 31;375(4):562-5.

Title: Jiang D, et al. Monomethyl Fumarate Protects the Retina From Light-Induced Retinopathy. Invest Ophthalmol Vis Sci. 2019 Mar 1;60(4):1275-1285.

Title: Sghaier R, et al. Dimethyl fumarate and monomethyl fumarate attenuate oxidative stress and mitochondrialalterations leading to oxiapoptophagy in 158N murine oligodendrocytes treated with 7β-hydroxycholesterol. J Steroid Biochem Mol Biol. 2019 Nov;194:105432.

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