Synonyms: dimethylitaconate | itaconic acid dimethyl ester
Compound class:
Synthetic organic
Comment: Dimethyl itaconate is a membrane-permeable derivative of the immunoregulatory metabolite itaconate. Itaconate is one of the most highly induced metabolites produced when activated macrophages undergo metabolic remodeling. Itaconate acts as a major physiological regulator of metabolic switching and effector functions of inflammatory macrophages. Itaconate and dimethyl itaconate inhibit production of IL-6 and IL-12 (secondary transcriptional response), but not TNF (a primary transcriptional response) following Toll-like receptor stimulation [4].
Itaconate has been found to promote an electrophilic stress response (i.e. a rapid adaptive defense response) [1]. An electrophilic stress response involves various mechanisms, including the nuclear translocation of the redox-sensitive transcription factor Nrf2 (nuclear factor E2-related factor 2), which senses electrophilic and oxidative stresses and protects against cellular damage via Kelch-like ECH-associated protein 1 (Keap1) [2-3,5]. Both itaconate and dimethyl itaconate induce Nrf2-dependent and -independent responses, the Nrf2-independent response being that which involves regulation of IκBζ [1]. |
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Classification ![]() |
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Compound class | Synthetic organic |
IUPAC Name ![]() |
dimethyl 2-methylidenebutanedioate |
Synonyms ![]() |
dimethylitaconate | itaconic acid dimethyl ester |
Database Links ![]() |
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CAS Registry No. | 617-52-7 (source: PubChem) |
GtoPdb PubChem SID | 363894233 |
PubChem CID | 69240 |
Search Google for chemical match using the InChIKey | ZWWQRMFIZFPUAA-UHFFFAOYSA-N |
Search Google for chemicals with the same backbone | ZWWQRMFIZFPUAA |
UniChem Compound Search for chemical match using the InChIKey | ZWWQRMFIZFPUAA-UHFFFAOYSA-N |
UniChem Connectivity Search for chemical match using the InChIKey | ZWWQRMFIZFPUAA-UHFFFAOYSA-N |