SML2338
4-Octyl itaconate
≥98% (HPLC)
Synonyme(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
Formule empirique (notation de Hill):
C13H22O4
Numéro CAS:
Poids moléculaire :
242.31
Code UNSPSC :
51111800
Nomenclature NACRES :
NA.77
Produits recommandés
Pureté
≥98% (HPLC)
Forme
powder
Conditions de stockage
protect from light
Couleur
white to beige
Solubilité
DMSO: 2 mg/mL, clear
Température de stockage
−20°C
Chaîne SMILES
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
Clé InChI
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
Actions biochimiques/physiologiques
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.
Code de la classe de stockage
11 - Combustible Solids
Classe de danger pour l'eau (WGK)
WGK 3
Point d'éclair (°F)
Not applicable
Point d'éclair (°C)
Not applicable
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4-Octyl itaconate inhibits aerobic glycolysis by targeting GAPDH to exert anti-inflammatory effects.
Shan-Ting Liao et al.
Nature communications, 10(1), 5091-5091 (2019-11-11)
Activated macrophages switch from oxidative phosphorylation to aerobic glycolysis, similar to the Warburg effect, presenting a potential therapeutic target in inflammatory disease. The endogenous metabolite itaconate has been reported to regulate macrophage function, but its precise mechanism is not clear.
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Annexin A1 is a key anti-inflammatory effector protein that is involved in the anti-inflammatory effects of glucocorticoids. 4-Octyl itaconate (4-OI), a derivative of the endogenous metabolite itaconate, which is abundantly produced by LPS-activated macrophages, has recently been identified as a
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