SML2338

Sigma-Aldrich

4-Octyl itaconate

≥98% (HPLC)

Sinónimos:
4-Octyl methylenesuccinate, β-Monooctyl itaconate, 3-(Octan-4-yloxy)carbonylbut-3-enoate, n-Octyl 3-carboxy-3-butenoate
Empirical Formula (Hill Notation):
C13H22O4
Número de CAS:
Peso molecular:
242.31
En este momento no podemos mostrarle ni los precios ni la disponibilidad

assay

≥98% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

−20°C

SMILES string

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

Biochem/physiol Actions

The endogenous metabolite itaconate has recently emerged as a regulator of macrophage function. 4-Octyl itaconate is a cell-permeable itaconate derivative that decreases cytokine production and is protective against lipopolysaccharide-induced lethality in vivo. Esterases in mouse myoblast cells and macrophages hydrolyze it to itaconate, which alkylates cysteine residues on KEAP1, allowing the transcription factor Nrf2 to increase the expression of anti-oxidant and anti-inflammatory downstream genes.

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Forrest Jessop et al.
Infection and immunity, 88(2) (2019-11-20)
The mechanisms by which interferon gamma (IFN-γ) controls the replication of cytosolic pathogens independent of responses, such as the generation of reactive oxygen species/reactive nitrogen species (ROS/RNS), have not been fully elucidated. In the current study, we developed a model...
Michael Riedelberger et al.
Cell host & microbe, 27(3), 454-466 (2020-02-23)
Type I interferons (IFNs-I) fulfil multiple protective functions during pathogenic infections, but they can also cause detrimental effects and enhance immunopathology. Here, we report that IFNs-I promote the dysregulation of iron homeostasis in macrophages during systemic infections with the intracellular...
Evanna L Mills et al.
Nature, 556(7699), 113-117 (2018-03-29)
The endogenous metabolite itaconate has recently emerged as a regulator of macrophage function, but its precise mechanism of action remains poorly understood. Here we show that itaconate is required for the activation of the anti-inflammatory transcription factor Nrf2 (also known...

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