4-Octyl Itaconate
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MedKoo CAT#: 565253

CAS#: 3133-16-2

Description: 4-Octyl Itaconate is a cell permeable activator of Nrf2 which inhibits LPS-induced increases in IL-1β mRNA, HIF-1α, and IL-10 in macrophages.


Chemical Structure

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4-Octyl Itaconate
CAS# 3133-16-2

Theoretical Analysis

MedKoo Cat#: 565253
Name: 4-Octyl Itaconate
CAS#: 3133-16-2
Chemical Formula: C13H22O4
Exact Mass: 242.1518
Molecular Weight: 242.32
Elemental Analysis: C, 64.44; H, 9.15; O, 26.41

Price and Availability

Size Price Availability Quantity
50.0mg USD 450.0 2 Weeks
100.0mg USD 750.0 2 Weeks
200.0mg USD 1250.0 2 Weeks
500.0mg USD 1950.0 2 Weeks
1.0g USD 2850.0 2 Weeks
2.0g USD 4850.0 2 Weeks
5.0g USD 6950.0 2 Weeks
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Synonym: 4-Octyl Itaconate; 4 Octyl Itaconate; 4-Octyl-Itaconate

IUPAC/Chemical Name: 2-Methylene-4-(octyloxy)-4-oxobutanoic acid

InChi Key: KBASUIDPDITQHT-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H22O4/c1-3-4-5-6-7-8-9-17-12(14)10-11(2)13(15)16/h2-10H2,1H3,(H,15,16)

SMILES Code: O=C(O)C(CC(OCCCCCCCC)=O)=C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 30.0 123.8
Ethanol 30.0 123.8
DMF 30.0 123.8

Preparing Stock Solutions

The following data is based on the product molecular weight 242.32 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Tang C, Tan S, Zhang Y, Dong L, Xu Y. Activation of Keap1-Nrf2 signaling by 4-octyl itaconate protects human umbilical vein endothelial cells from high glucose. Biochem Biophys Res Commun. 2019 Jan 15;508(3):921-927. doi: 10.1016/j.bbrc.2018.12.032. Epub 2018 Dec 10. PubMed PMID: 30545629.

2: Tang C, Wang X, Xie Y, Cai X, Yu N, Hu Y, Zheng Z. 4-Octyl Itaconate Activates Nrf2 Signaling to Inhibit Pro-Inflammatory Cytokine Production in Peripheral Blood Mononuclear Cells of Systemic Lupus Erythematosus Patients. Cell Physiol Biochem. 2018;51(2):979-990. doi: 10.1159/000495400. Epub 2018 Nov 22. PubMed PMID: 30466076.

3: Mills EL, Ryan DG, Prag HA, Dikovskaya D, Menon D, Zaslona Z, Jedrychowski MP, Costa ASH, Higgins M, Hams E, Szpyt J, Runtsch MC, King MS, McGouran JF, Fischer R, Kessler BM, McGettrick AF, Hughes MM, Carroll RG, Booty LM, Knatko EV, Meakin PJ, Ashford MLJ, Modis LK, Brunori G, Sévin DC, Fallon PG, Caldwell ST, Kunji ERS, Chouchani ET, Frezza C, Dinkova-Kostova AT, Hartley RC, Murphy MP, O'Neill LA. Itaconate is an anti-inflammatory metabolite that activates Nrf2 via alkylation of KEAP1. Nature. 2018 Apr 5;556(7699):113-117. doi: 10.1038/nature25986. Epub 2018 Mar 28. PubMed PMID: 29590092; PubMed Central PMCID: PMC6047741.