Isoalantolactone

Base Information

• Chemical Name: Isoalantolactone
• CAS No.: 470-17-7
• Molecular Formula: C15H20O2
• Molecular Weight: 232.323
• Hs Code.: 29322090
• European Community (EC) Number: 683-108-6
• NSC Number: 241036
• UNII: BYH07P620U,QTF89ZHT7V
• Nikkaji Number: J12.027H
• Wikidata: Q27089356
• Metabolomics Workbench ID: 50008
• ChEMBL ID: CHEMBL137803
• Mol file: 470-17-7.mol

Synonyms:isoalantolactone

Chemical Property of Isoalantolactone

Chemical Property:

• Vapor Pressure: 1.63E-05mmHg at 25°C
• Melting Point: 115℃
• Refractive Index: 1.527
• Boiling Point: 364.9 °C at 760 mmHg
• Flash Point: 152.7 °C
• PSA: 26.30000
• Density: 1.07 g/cm³
• LogP: 3.24060
• Storage Temp.: 2-8°C
• Solubility.: Soluble in DMSO (up to 50 mg/ml) or ethanol (30 mg/ml)
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 232.146329876
• Heavy Atom Count: 17
• Complexity: 409

Purity/Quality:

≥98% ^*data from raw suppliers

Isoalantolactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCCC(=C)C1CC3C(C2)OC(=O)C3=C
• Isomeric SMILES: C[C@]12CCCC(=C)[C@@H]1C[C@H]3[C@@H](C2)OC(=O)C3=C
• Description: Isohelenin (470-17-7) is a sesquiterpene lactone isolated from Mexican Indian medicinal plants known to have anti-inflammatory properties. A potent inhibitor of NFkB (complete inhibition at 5 μM)1 acting via inhibition of IKK?6. Isohelenin-mediated NFkB inhibition suppresses IL-8 expression2, iNOS expression3 and RANTES biosynthesis4. Displays protective effects in endotoxic shock in rodent models.5 Induces apoptosis in glioma cells.6
• Uses: Isoalantolactone is a sesquiterpene lactone used in the treatment of cancer. It can inhibit tumor cell growth and induce apoptosis.

Technology Process of Isoalantolactone

There total 32 articles about Isoalantolactone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

11β-phenylseleno-5,7,8αH-eudesm-4(15)-en-8,12-olide (123489-82-7) → isoalantolactone (470-17-7)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89024-4

Reference yield: 55.0%

11β-phenylseleno-5,7,8αH-eudesm-4(15)-en-8,12-olide (123489-82-7) → isoalantolactone (470-17-7) + 4-oxo-11-eudesmaen-8,12-olide (74513-15-8)

Guidance literature:

With dihydrogen peroxide; In dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1021/jo00287a024

Reference yield: 19.0%

(3aR,4aS,8aR,9aR)-3-[1-Benzenesulfinyl-meth-(E)-ylidene]-8a-methyl-5-methylene-decahydro-naphtho[2,3-b]furan-2-one (76886-51-6) → isoalantolactone (470-17-7) + 11,13-dihydroisoalantolactone (1856-58-2) + (3aR,4aS,8aR,9aR)-8a-Methyl-5-methylene-3-[1-phenylsulfanyl-meth-(E)-ylidene]-decahydro-naphtho[2,3-b]furan-2-one (69993-39-1)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water-d2; for 0.25h; Ambient temperature;

DOI:10.1021/jo00287a024

upstream raw materials:

11β-phenylseleno-5,7,8αH-eudesm-4(15)-en-8,12-olide

(3aR,4aS,8aR,9aR)-3-[1-Benzenesulfinyl-meth-(E)-ylidene]-8a-methyl-5-methylene-decahydro-naphtho[2,3-b]furan-2-one

11,13-dihydroisoalantolactone

13-(phenylthio)isoalantolactone

Downstream raw materials:

11,13-dihydroisoalantolactone

(3aR,4aR,6R,8aR,9aR)-6-hydroxy-8a-methyl-3,5-dimethylenedecahydronaphtho[2,3-b]furan-2(3H)-one

telekin

13-(phenylthio)isoalantolactone