The concentration of this product can be determined using the lot-specific purity reported in the Certificate of Analysis, the density, and the compound molecular weight. This product has a density of 1.124 g/mL and a molecular weight of 158.15 g/mol. The minimum purity is 96.5%, thus the molarity will vary slightly from lot to lot. The molarity can range from 6.86M (96.5%) to 7.11M (100%).
109533
Dimethyl itaconate
97%
Synonym(s):
2-(Methylene)butanedioic dimethyl ester
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About This Item
Linear Formula:
CH3O2CCH2C(=CH2)CO2CH3
CAS Number:
Molecular Weight:
158.15
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
210-519-6
Beilstein/REAXYS Number:
386674
MDL number:
Assay:
97%
Form:
solid
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InChI key
ZWWQRMFIZFPUAA-UHFFFAOYSA-N
InChI
1S/C7H10O4/c1-5(7(9)11-3)4-6(8)10-2/h1,4H2,2-3H3
SMILES string
COC(=O)CC(=C)C(=O)OC
assay
97%
form
solid
bp
208 °C (lit.)
mp
37-41 °C (lit.)
density
1.124 g/mL at 25 °C (lit.)
functional group
ester
Quality Level
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Related Categories
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This Item | 163228 | 592498 | 476196 |
|---|---|---|---|
| assay 97% | assay 98% | assay 99% | assay 96% |
| Quality Level 100 | Quality Level 100 | Quality Level - | Quality Level 100 |
| mp 37-41 °C (lit.) | mp - | mp 37-41 °C (lit.) | mp - |
| form solid | form liquid | form solid | form - |
| bp 208 °C (lit.) | bp 127-131 °C/12 mmHg (lit.) | bp 208 °C (lit.) | bp 284 °C (lit.) |
| density 1.124 g/mL at 25 °C (lit.) | density 1.057 g/mL at 25 °C (lit.) | density 1.124 g/mL at 25 °C (lit.) | density 0.985 g/mL at 25 °C (lit.) |
Application
General description
Dimethyl itaconate undergoes enantioselective Rh(I)-catalyzed hydrogenation which can be enhanced by appropriate choice of substituents on aromatic ring of (1,2-diarylphosphinoxy)cyclohexane[3].
signalword
Warning
hcodes
Hazard Classifications
Skin Irrit. 2 - Skin Sens. 1B
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
212.0 °F - closed cup
flash_point_c
100 °C - closed cup
ppe
Eyeshields, Gloves, type N95 (US)
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M Sendra et al.
Fish & shellfish immunology, 106, 645-655 (2020-08-18)
Immune-responsive gene 1 (irg1) is a gene that is well-conserved among different taxa and is highly expressed in the mussel Mytilus galloprovincialis at the constitutive level. The expression of this gene increases after a bacterial infection, primarily in haemocytes. irg1
Modification of poly (propylene) through grafting with dimethyl itaconate in solution.
Yazdani-Pedram M, et al.
Macromolecular Chemistry and Physics, 199(11), 2495-2500 (1998)
Polymers with shape memory effect from renewable resources: crosslinking of polyesters based on isosorbide, itaconic acid and succinic acid.
Goerz O and Ritter H.
Polymer International, 62(5), 709-712 (2013)
T. V. RajanBabu et al.
The Journal of organic chemistry, 64(10), 3429-3447 (2001-10-25)
Enantioselectivity of Rh(I)-catalyzed asymmetric hydrogenation of dehydroamino acid derivatives and dimethyl itaconate can be enhanced by the appropriate choice of substituents on the aromatic rings of vicinal diarylphosphinites derived from carbohydrates as well as trans-cyclohexane-1,2-diol. For example, the use of
Thekla Cordes et al.
Metabolites, 11(2) (2021-03-07)
Itaconate is a small molecule metabolite that is endogenously produced by cis-aconitate decarboxylase-1 (ACOD1) in mammalian cells and influences numerous cellular processes. The metabolic consequences of itaconate in cells are diverse and contribute to its regulatory function. Here, we have
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