Itaconic acid 4-octyl ester [4-Octyl itaconate]

CHF 40.00
In stock
AG-CR1-3700-M01010 mgCHF 40.00
AG-CR1-3700-M05050 mgCHF 90.00
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Product Details
Synonyms 4-Octyl ester 2-methylene-butanedioic acid; 4-Octyl methylenesuccinate; β-Monooctyl itaconate
Product Type Chemical
Properties
Formula

C13H22O4

MW 242.3
CAS 3133-16-2
Purity Chemicals ≥98% (mixture of tautomers)
Appearance White powder.
Solubility Soluble in DMSO (30mg/ml), ethanol (30mg/ml) or DMF (30mg/ml).
InChi Key KBASUIDPDITQHT-UHFFFAOYSA-N
Smiles OC(C(CC(OCCCCCCCC)=O)=C)=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Keep cool and dry.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
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Product Specification Sheet
Datasheet Download PDF
  • Derivative of itaconate (AG-CN2-0426) with enhanced cell permeability. Prodrug that is efficiently metabolized to itaconate in cells.
  • Potent anti-inflammatory agent.
  • In vitro it activates the transcription factor nuclear factor erythroid 2-related factor 2 (Nrf2) (also known as NFE2L2) in LPS-induced mouse and human macrophages.
  • Upregulates Nrf2 levels via a newly identified post-translational modification, dicarboxylation of KEAP1. Alkylates cysteine residues 151, 257, 288, 273 and 297 on the protein KEAP1, enabling Nrf2 to increase the expression of downstream gene. Cysteine 151 is uniquely required for inhibiting KEAP1-mediated degradation of Nrf2 and mutating this residue in KEAP1 prevents the stabilization of Nrf2.
  • LPS induces itaconate production, partly via the induction of type I IFNs; this results in Nrf2 stabilization (via itaconate-mediated cysteine alkylation of KEAP1) that promotes an anti-inflammatory response, which is accompanied by the downregulation of itaconate production through reduced IFN expression.
  • In vivo (50 mg/kg) it decreases serum levels of IL-1β and TNF-α, increases Nrf2 protein expression and protects against LPS-induced lethality in wild-type, but not Nrf2 knockout mice.
Product References
  1. Itaconate is an anti-inflammatory metabolite that activates Nrf2 via alkylation of KEAP1: E.L. Mills, et al.; Nature 556, 113 (2018)
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