4-Octyl itaconate | B2171

4-Octyl itaconate is an endogenous metabolite of itaconate that activates the anti-inflammatory transcription factor Nrf2 (also known as NFE2L2) by lipopolysaccharide in mouse and human macrophages. Itaconate alkylates cysteine residues 151, 257, 288, 273 and 297 on the protein KEAP1, enabling Nrf2 to increase the expression of downstream gene. In vivo, 4-octyl itaconate (50 mg/kg) 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.

4-Octyl itaconate is an endogenous metabolite of itaconate that activates the anti-inflammatory transcription factor Nrf2 (also known as NFE2L2) by lipopolysaccharide in mouse and human macrophages. Itaconate alkylates cysteine residues 151, 257, 288, 273 and 297 on the protein KEAP1, enabling Nrf2 to increase the expression of downstream gene. In vivo, 4-octyl itaconate (50 mg/kg) 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.

B2171 | 4-Octyl itaconate DataSheet

Alternate Name/Synonyms: 2-methylene-butanedioic acid, 4-octyl ester

Appearance: Crystalline solid

Formulation: N/A

CAS Number: 3133-16-2

Structure Available?: Yes

Peptide sequence: N/A

Salt Form: No

Molecular Formula: C₁₃H₂₂O₄

Molecular Weight: 242.3

Cell-Permeable?: Yes

Purity: ≥98%

Solubilities: DMSO (~30 mg/ml)

Handling: Protect from air and light

Country of Origin: USA

Tag Line: A Nrf2 activator

MDL Number: N/A

PubChem CID: 71360202

SMILES: CCCCC(CCC)OC(=O)C(=C)CC(=O)[O-]

InChi: InChI=1S/C13H22O4/c1-4-6-8-11(7-5-2)17-13(16)10(3)9-12(14)15/h11H,3-9H2,1-2H3,(H,14,15)/p-1

InChi Key: GIRJEIMINMHXQS-UHFFFAOYSA-M