| Identification | Back Directory | [Name]
Butanedioic acid, methylene-, 4-octyl ester | [CAS]
3133-16-2 | [Synonyms]
Itaconate
4-Octyl itaconate
Monooctyl Itaconate
itaconate(CTK1B2911)
4-Octyl itaconate(CTK1B2911)
4-Octyl itaconate >=98% (HPLC)
2-Methylenebutanedioic acid 4-octyl ester
Butanedioic acid, methylene-, 4-octyl ester
Butanedioic acid, 2-methylene-, 4-octyl ester | [EINECS(EC#)]
681-695-3 | [Molecular Formula]
C13H22O4 | [MDL Number]
MFCD31706409 | [MOL File]
3133-16-2.mol | [Molecular Weight]
242.32 |
| Chemical Properties | Back Directory | [Boiling point ]
377.2±25.0 °C(Predicted) | [density ]
1.026±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,Store in freezer, under -20°C | [solubility ]
DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml | [form ]
A crystalline solid | [pka]
3.84±0.11(Predicted) | [color ]
White to off-white | [Cosmetics Ingredients Functions]
ANTIOXIDANT | [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 | [InChIKey]
GIRJEIMINMHXQS-UHFFFAOYSA-M | [SMILES]
OC(C(CC(OCCCCCCCC)=O)=C)=O |
| Hazard Information | Back Directory | [Uses]
4-Octyl Itaconate increases nuclear factor erythroid 2-related factor 2 (Nrf2) protein levels and expression of Nrf2 target genes and enhances LPS-induced Nrf2 stabilization in mouse macrophages. 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. | [Biological Activity]
4-Octyl itaconate (4-OI) possesses anti-inflammatory effects. It can obstruct glyceraldehyde 3-phosphate dehydrogenase (GAPDH) and glycolysis in macrophages. It can be a good substitute to itaconate due to its thiol reactivity. The electrophilic α and β-unsaturated moieties of 4-OI might help to alkylate the thiol in cysteine residues of proteins through Michael reaction.''The endogenous metabolite itaconate has recently emerged as a regulator of macrophage function. 4-Octyl itaconate is a cell-permeable itaconate derivative th at decreases cytokine production and is protective against lipopolysaccharide-induced lethality in vivo. Esterases in mouse myoblast cells and macrophages hydrolyze it to itaconatewhich alkylates cysteine residues on KEAP1allowing the transcription factor Nrf2 to increase the expression of anti-oxidant and anti-inflammatory downstream genes. | [in vivo]
4-Octyl Itaconate (OI) is a cell-permeable itaconate derivative. 4-Octyl Itaconate is protective against lipopolysaccharide-induced lethality in vivo and decreases cytokine production[1]. | [storage]
Store at -20°C |
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