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

4-octyl Itaconate; 4-Octyl ester 2-methylene-butanedioic acid; 4-Octyl methylenesuccinate; beta-Monooctyl itaconate

White powder.

3133-16-2

32160000

liquid

Keep cool and dry.

InChI=1S/C13H22O4/c1-3-4-5-6-7-8-9-17-12(14)10-11(2)13(15)16/h2-10H2,1H3,(H,15,16)

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Chemical. CAS: 3133-16-2. Formula: C13H22O4. MW: 242.3. Derivative of itaconate (AG-CN2-0426 https://adipogen.com/ag-cn2-0426-itaconic-acid.html ) 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-1beta and TNF-alpha, increases Nrf2 protein expression and protects against LPS-induced lethality in wild-type, but not Nrf2 knockout mice.

MFCD31706409

C13H22O4

242.3

Vial

Derivative of itaconate (AG-CN2-0426 https://adipogen.com/ag-cn2-0426-itaconic-acid.html ) 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-1beta and TNF-alpha, increases Nrf2 protein expression and protects against LPS-induced lethality in wild-type, but not Nrf2 knockout mice.

>98% (mixture of tautomers)

Warning

OC(C(CC(OCCCCCCCC)=O)=C)=O

Soluble in DMSO (30mg/ml), ethanol (30mg/ml) or DMF (30mg/ml).

Non-hazardous

Biochemical Reagents

12352200

Stable for at least 2 years after receipt when stored at -20°C.