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
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
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMSO |
30.0 |
123.80 |
| Ethanol |
30.0 |
123.80 |
| DMF |
30.0 |
123.80 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
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.
| 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 |
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.
