SML2338
4-Octyl itaconate
≥98% (HPLC), anti-inflammatory , powder
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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A propos de cet article
Formule empirique (notation de Hill) :
C13H22O4
Numéro CAS:
Poids moléculaire :
242.31
UNSPSC Code:
51111800
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Storage condition:
protect from light
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4-Octyl itaconate, ≥98% (HPLC)
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
assay
≥98% (HPLC)
form
powder
storage condition
protect from light
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
Catégories apparentées
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.
Cell-permeable itaconate derivative that decreases cytokine production and is protective against lipopolysaccharide-induced lethality in vivo.
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.
Classe de stockage
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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H John Sharifi et al.
Journal of virology, 96(23), e0118722-e0118722 (2022-11-16)
The cellular protein SAMHD1 is important for DNA repair, suppressing LINE elements, controlling deoxynucleoside triphosphate (dNTP) concentrations, maintaining HIV-1 latency, and preventing excessive type I interferon responses. SAMHD1 is also a potent inhibitor of HIV-1 and other significant viral pathogens.
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.
Valerio Azzimato et al.
Gastroenterology, 161(6), 1982-1997 (2021-08-24)
Oxidative stress plays a key role in the development of metabolic complications associated with obesity, including insulin resistance and the most common chronic liver disease worldwide, nonalcoholic fatty liver disease. We have recently discovered that the microRNA miR-144 regulates protein
Sjors Maassen et al.
Redox biology, 59, 102591-102591 (2022-12-28)
Pathological conditions associated with dysfunctional wound healing are characterized by impaired remodelling of extracellular matrix (ECM), increased macrophage infiltration, and chronic inflammation. Macrophages also play an important role in wound healing as they drive wound closure by secretion of molecules
Xiangyi Kong et al.
Journal of neuroinflammation, 21(1), 104-104 (2024-04-23)
Postoperative cognitive dysfunction (POCD) is a common neurological complication of anesthesia and surgery in aging individuals. Neuroinflammation has been identified as a hallmark of POCD. However, safe and effective treatments of POCD are still lacking. Itaconate is an immunoregulatory metabolite
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