Home Other Building Blocks Dimethyl itaconate

Dimethyl itaconate

CAS No.:
617-52-7
Catalog Number:
AG0034R4
Molecular Formula:
C7H10O4
Molecular Weight:
158.1519
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
25g
98%
In Stock USA
United States
$25
- +
100g
98%
In Stock USA
United States
$63
- +
500g
98%
In Stock USA
United States
$188
- +
Product Description
Catalog Number:
AG0034R4
Chemical Name:
Dimethyl itaconate
CAS Number:
617-52-7
Molecular Formula:
C7H10O4
Molecular Weight:
158.1519
MDL Number:
MFCD00008446
IUPAC Name:
dimethyl 2-methylidenebutanedioate
InChI:
InChI=1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3
InChI Key:
ZWWQRMFIZFPUAA-UHFFFAOYSA-N
SMILES:
COC(=O)CC(=C)C(=O)OC
EC Number:
210-519-6
UNII:
11JIB0YI93
NSC Number:
9385
Properties
Complexity:
183  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
158.058g/mol
Formal Charge:
0
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
4  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
158.153g/mol
Monoisotopic Mass:
158.058g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
52.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
0.5  
Literature
Title Journal
Electrophilic properties of itaconate and derivatives regulate the IκBζ-ATF3 inflammatory axis. Nature 20180401
Itaconate Links Inhibition of Succinate Dehydrogenase with Macrophage Metabolic Remodeling and Regulation of Inflammation. Cell metabolism 20160712
Phosphine-phosphite ligands: chelate ring size vs. activity and enantioselectivity relationships in asymmetric hydrogenation. Dalton transactions (Cambridge, England : 2003) 20120821
Surface modification of PAMAM dendrimer improves its biocompatibility. Nanomedicine : nanotechnology, biology, and medicine 20120801
Asymmetric Rh-catalyzed hydrogenation using a furanoside phosphite-phosphoroamidite and diphosphoroamidite ligand library. Dalton transactions (Cambridge, England : 2003) 20120314
Synthesis and cytotoxic evaluation of novel paraconic acid analogs. Bioorganic & medicinal chemistry letters 20111201
Synthesis of hybrid transition-metalloproteins via thiol-selective covalent anchoring of Rh-phosphine and Ru-phenanthroline complexes. Dalton transactions (Cambridge, England : 2003) 20100928
Novel, tunable, and efficient chiral bisdihydrobenzooxaphosphole ligands for asymmetric hydrogenation. Organic letters 20100101
Chiral diphosphinites derived from 2,2-biphosphole as a new class of stereodynamic ligands for enantioselective hydrogenation. Dalton transactions (Cambridge, England : 2003) 20090907
Novel contributions to the mechanism of the enantioselective hydrogenation of dimethyl itaconate with rhodium complexes. Chemistry (Weinheim an der Bergstrasse, Germany) 20080101
Stereochemical features making deoxycholic acid derived tropos biphenylphosphites efficient chiral ligands for rhodium: the asymmetric hydrogenation of dimethylitaconate as a case study. The Journal of organic chemistry 20071026
Rigid bis-zinc(II) salphen building blocks for the formation of template-assisted bidentate ligands and their application in catalysis. Dalton transactions (Cambridge, England : 2003) 20070614
Catalytic ability of a cationic Ru(II) monochloro complex for the asymmetric hydrogenation of dimethyl itaconate and enamides. Inorganic chemistry 20060320
The role of Keap1 in cellular protective responses. Chemical research in toxicology 20051201
Rh-catalyzed asymmetric hydrogenation of prochiral olefins with a dynamic library of chiral TROPOS phosphorus ligands. Chemistry (Weinheim an der Bergstrasse, Germany) 20051104
Asymmetric hydrogenation using chiral Rh complexes immobilised with a new ion-exchange strategy. Organic & biomolecular chemistry 20050421
PipPhos and MorfPhos: privileged monodentate phosphoramidite ligands for rhodium-catalyzed asymmetric hydrogenation. The Journal of organic chemistry 20050204
C2-symmetric diphosphinite ligands derived from carbohydrates. The strong influence of remote stereocenters on asymmetric rhodium-catalyzed hydrogenation. The Journal of organic chemistry 20041029
Unsymmetrical hybrid ferrocene-based phosphine-phosphoramidites: a new class of practical ligands for Rh-catalyzed asymmetric hydrogenation. Organic letters 20040930
Rhodium catalysed tandem conjugate addition-protonation: an enantioselective synthesis of 2-substituted succinic esters. Chemical communications (Cambridge, England) 20040907
Molecular mechanism activating Nrf2-Keap1 pathway in regulation of adaptive response to electrophiles. Free radical biology & medicine 20040515
A novel class of P-O monophosphite ligands derived from D-mannitol: broad applications in highly enantioselective Rh-catalyzed hydrogenations. The Journal of organic chemistry 20040402
Protection against electrophile and oxidant stress by induction of the phase 2 response: fate of cysteines of the Keap1 sensor modified by inducers. Proceedings of the National Academy of Sciences of the United States of America 20040217
Chiral monophosphites derived from carbohydrate: conformational effect in catalytic asymmetric hydrogenation. Organic letters 20031030
Synthesis of new chiral monodentate phosphite ligands and their use in catalytic asymmetric hydrogenation. Organic letters 20031016
Construction and probing of multisite chiral catalysts: dendrimer fixation of c2-symmetrical diphosphinerhodium complexes. Chemistry (Weinheim an der Bergstrasse, Germany) 20020916
Properties