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242926

Sigma-Aldrich

Dimethyl fumarate

97%

Synonyme(s) :

(2E)-2-Butenedioic acid dimethyl ester, (E)-But-2-enedioic acid dimethyl ester, Allomaleic acid dimethyl ester, Boletic acid dimethyl ester, Dimethyl trans-ethylenedicarboxylate, Methyl fumarate, trans-1,2-Ethylenedicarboxylic acid dimethyl ester, trans-Butenedioic acid dimethyl ester

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About This Item

Formule linéaire :
CH3OCOCH=CHCOOCH3
Numéro CAS:
624-49-7
Poids moléculaire :
144.13
Beilstein:
774590
Numéro CE :
210-849-0
Numéro MDL:
MFCD00064438
Code UNSPSC :
12352100
ID de substance PubChem :
24854591
Nomenclature NACRES :
NA.22
Le tarif et la disponibilité ne sont pas disponibles actuellement.

Niveau de qualité

200

Essai

97%

Forme

solid

pb

192-193 °C (lit.)

Pf

102-106 °C (lit.)

Groupe fonctionnel

ester

Chaîne SMILES 

[H]\C(=C(\[H])C(=O)OC)C(=O)OC

InChI

1S/C6H8O4/c1-9-5(7)3-4-6(8)10-2/h3-4H,1-2H3/b4-3+

Clé InChI

LDCRTTXIJACKKU-ONEGZZNKSA-N

Informations sur le gène

human ... KEAP1(9817)

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Catégories apparentées

Application

Dimethyl fumarate can be used:
  • In the preparation of an adduct [dimethyl-(+)-(11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylate].[1]
  • As a ligand in the synthesis of Ni(II)-based catalytic system applicable in the Negishi alkylations of N-sulfonyl aziridines with organozinc reagents.[2]
  • As a ligand to synthesize zerovalent ruthenium metal complex namely Ru(η6-1,3,5-cyclooctatriene)(η2-dimethyl fumarate)2.[3]

Pictogrammes

Exclamation markEnvironment
GHS07,GHS09

Mention d'avertissement

Warning

Mentions de danger

H312,H315,H317,H335,H411

Classification des risques

Acute Tox. 4 Dermal - Aquatic Chronic 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Organes cibles

Respiratory system

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 1

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

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Certificats d'analyse (COA)

Lot/Batch Number
BCBR2626V
BCBN9637V
BCBK1522V
BCBM0793V
BCBL8279V

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DIMETHYL 4-CYCLOHEXENE-1,2-DICARBOXYLATE AldrichCPR

S544612

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Importance of c*--h based modes and large amplitude motion effects in vibrational circular dichroism spectra: the case of the chiral adduct of dimethyl fumarate and anthracene
Passarello M, et al.
The Journal of Physical Chemistry A, 118, 4339-4350 (2014)
Marco Passarello et al.
The journal of physical chemistry. A, 118(24), 4339-4350 (2014-05-21)
The role played by the C*-H based modes (C* being the chiral carbon atom) and the large amplitude motions in the vibrational absorption (VA) and vibrational circular dichroism (VCD) spectra is investigated. The example of an adduct of dimethyl fumarate
Ru (η6-1, 3, 5-cyclooctatriene)(η2-dimethyl fumarate) 2: a novel, versatile zerovalent ruthenium complex with electron-deficient olefinic ligands
Mitsudo T, et al.
Journal of Organometallic Chemistry, 689, 4530-4539 (2004)
Yanwen Chen et al.
Redox biology, 32, 101485-101485 (2020-03-17)
NRF2 is a master regulator of cellular anti-oxidant and anti-inflammatory responses, and strategies to augment NRF2-dependent responses may beneficial in many diseases. Basal NRF2 protein level is constrained by constitutive KEAP1-mediated degradation, but in the presence of electrophiles, NRF2 ubiquitination
Giovanna Casili et al.
Journal of neurotrauma, 35(13), 1437-1451 (2018-01-25)
Traumatic brain injury (TBI) is a serious neuropathology that causes secondary injury mechanisms, including dynamic interplay between ischemic, inflammatory, and cytotoxic processes. Fumaric acid esters (FAEs) showed beneficial effects in pre-clinical models of neuroinflammation and toxic oxidative stress, so the
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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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