4-Octyl Itaconate - Moligand™, ≥98% , CAS No.3133-16-2

CAS: 3133-16-2 Cat. No.: O303413 Peso molecular: 242.31 Número EC: 886-904-3

GRADE & PURITY Moligand™, ≥98%

Synonyms

β-Monooctyl itaconate | 3-[(Octan-4-yloxy)carbonyl]but-3-enoate | 4-Octyl methylenesuccinate | n-Octyl 3-carboxy-3-butenoate | 2-Methylene-4-(octyloxy)-4-oxobutanoic Acid

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Descripción general

4-Octyl Itaconate is a cell-permeable Itaconate derivative. Itaconate is an anti-inflammatory metabolite that activates Nrf2 via alkylation of KEAP1

Specifications

Sinónimos

β-Monooctyl itaconate | 3-[(Octan-4-yloxy)carbonyl]but-3-enoate | 4-Octyl methylenesuccinate | n-Octyl 3-carboxy-3-butenoate | 2-Methylene-4-(octyloxy)-4-oxobutanoic Acid

Especificaciones y pureza

Moligand™, ≥98%

Mecanismos bioquímicos y fisiológicos

Activates Nrf2. Inhibits LPS-induced increases in IL-1β mRNA, HIF-1α and IL-10 in macrophages. Decreases cytokine production in response to LPS in mice and prolongs survival. Cell permeable.

Condiciones de almacenamiento de almacenamiento

Protected from light, Store at -20°C

Enviado en

Ice chest + Ice pads

Este producto requiere envío en cadena de frío. Los servicios terrestres y otros servicios económicos no están disponibles.

Grado

Moligand™

Pureza

≥98%

Nombres e identificadores

• Pubchem Sid: 504767600
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504767600
• Sonrisas canónicas: CCCCCCCCOC(=O)CC(=C)C(=O)O
• IUPAC Name: 2-methylidene-4-octoxy-4-oxobutanoic acid
• InChIKey: KBASUIDPDITQHT-UHFFFAOYSA-N
• 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)
• Isómeros SMILES: CCCCCCCCOC(=O)CC(=C)C(=O)O
• Peso molecular: 242.31
• Reaxy-Rn: 2103192
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=2103192&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Clase Fatty Acyls
      • Subclass Fatty acid esters

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Clase: Fatty Acyls
• Subclass: Fatty acid esters
• Intermediate Tree Nodes: Not available
• Direct Parent: Fatty acid esters
• Alternative Parents: Branched fatty acids Unsaturated fatty acids Dicarboxylic acids and derivatives Carboxylic acid esters Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Fatty acid ester - Branched fatty acid - Unsaturated fatty acid - Dicarboxylic acid or derivatives - Carboxylic acid ester - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic acyclic compound
• Descripción: This compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mecanismos de acción

Propiedades químicas y físicas

• Solubilidad: DMSO: 2 mg/mL, clear
• Sensibilidad: light sensitive；heat sensitive
• Punto de fusión (°C): 60 °C
• Peso molecular: 242.310 g/mol
• XLogP3: 3.600
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 242.152 Da
• Monoisotopic Mass: 242.152 Da
• Topological Polar Surface Area: 63.600 Ų
• Heavy Atom Count: 17
• Formal Charge: 0
• Complexity: 258.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Referencias

1. Wenying Li, Dong Chen, Yanmei Zhu, Qiange Ye, Yang Hua, Ping Jiang, Ying Xiang, Yuejie Xu, Yinya Pan, Hua Yang, Yichun Ma, Hang Xu, Cheng Zhao, Chang Zheng, Changrong Chen, Yun Zhu, Guifang Xu.  (2024)  Alleviating Pyroptosis of Intestinal Epithelial Cells to Restore Mucosal Integrity in Ulcerative Colitis by Targeting Delivery of 4-Octyl-Itaconate.  ACS Nano,      [PMID:38907726] [10.1021/acsnano.4c01520]

2. Bao Ronghua, Mao Yifan, Zhang Yuliang, Chai Junlei, Zhang Yuanbin, Luo Cheng, Zhang Kailong, Jiang Guohua, He Xiaodan.  (2024)  Fabrication of injectable alginate hydrogels with sustained release of 4-octyl itaconate for articular anti-inflammatory.  BIO-MEDICAL MATERIALS AND ENGINEERING,  35  (5): (475-485).  [PMID:39150826] [10.3233/BME-240103]

3. Yuying Chang, Yinglan Jin, Xi Chen, Xiaomin Zhang, Yaoyao Tian, Xinyu Gao, Xiushuai Dong, Wei Wang.  (2025)  4-Octyl itaconate ameliorates immune thrombocytopenia by modulating megakaryocyte autophagy and apoptosis.  Hematology,      [PMID:40951941] [10.1080/16078454.2025.2549957]