SML2338
4-Octyl itaconate
≥98% (HPLC)
Sinónimos:
β-Monooctyl itaconate, 3-[(Octan-4-yloxy)carbonyl]but-3-enoate, 4-Octyl methylenesuccinate, n-Octyl 3-carboxy-3-butenoate
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About This Item
Fórmula empírica (notación de Hill):
C13H22O4
Número de CAS:
Peso molecular:
242.31
UNSPSC Code:
51111800
NACRES:
NA.77
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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
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
Application
4-Octyl itaconate has been used:
- to study its anti-inflammatory effects in macrophages
- to treat bone-marrow-derived macrophages (BMDMs) for BMDM stimulation with nuclear factor-erythroid factor 2-related factor 2 (NRF2)-activating carboxylic acid compounds
- to study its effects on collagen1 expression in systemic Sclerosis (SSc) dermal fibroblasts
Biochem/physiol Actions
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 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.
Storage Class
11 - Combustible Solids
wgk_germany
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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