SML2338
4-Octyl itaconate
≥98% (HPLC)
Synonym(s):
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
Empirical Formula (Hill Notation):
C13H22O4
CAS Number:
Molecular Weight:
242.31
UNSPSC Code:
51111800
NACRES:
NA.77
Recommended Products
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 Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Certificates of Analysis (COA)
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4-Octyl itaconate inhibits aerobic glycolysis by targeting GAPDH to exert anti-inflammatory effects.
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