Brevilin A CAS 16503-32-5

Introduction：Basic information about Brevilin A CAS 16503-32-5, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Brevilin A Basic information

• Product Name: Brevilin A
• Synonyms: Brevilin A;6-O-Angeloylplenolin;2-Butenoic acid,2-methyl-,(3S,3aR,4S,4aR,7aR,8R,9aR)-2,3,3a,4,4a,5,7a,8,9,9a-decahydro-3,4a,8-trimethyl-2,5-dioxoazuleno[6,5-b]furan-4-ylester, (2Z)-;(3S,3aR,4S,4aR,7aR,8R,9aR)-3,4a,8-Trimethyl-2,5-dioxo-2,3,3a,4,4a ,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl (2Z)-2-methyl-2-bu tenoate;brevillin A;Brevelin A;6-OAP;(3S,3aR,4S,4aR,7aR,8R,9aR)-3,4a,8-Trimethyl-2,5-dioxo-2,3,3a,4,4a,5,7a,8,9,9a-decahydroazuleno[6,5-b]furan-4-yl (Z)-2-methylbut-2-enoate
• CAS: 16503-32-5
• MF: C20H26O5
• MW: 346.42
• Mol File: 16503-32-5.mol

Brevilin A Chemical Properties

• Boiling point: 494.0±45.0 °C(Predicted)
• density: 1.17±0.1 g/cm3(Predicted)
• storage temp.: 2-8°C
• solubility: DMSO:100.0(Max Conc. mg/mL);288.67(Max Conc. mM)
• form: A solid
• color: White to off-white
• InChI: 1S/C20H26O5/c1-6-10(2)18(22)25-17-16-12(4)19(23)24-14(16)9-11(3)13-7-8-15(21)20(13,17)5/h6-8,11-14,16-17H,9H2,1-5H3/b10-6-/t11-,12+,13+,14-,16-,17+,20+/m1/s1
• InChIKey: KUPPZVXLWANEJJ-UXPPPGSFSA-N
• SMILES: C(O[C@H]1[C@]2([H])[C@H](C)C(=O)O[C@]2([H])C[C@@H](C)[C@@]2([H])[C@@]1(C)C(=O)C=C2)(=O)/C(/C)=C\C

Safety Information

• WGK Germany: WGK 3
• Storage Class: 11 - Combustible Solids
• Hazard Classifications: Skin Sens. 1

Brevilin A Usage And Synthesis

Uses

Brevilin A can be used using a selective extraction method to obtain natural substances, and can also be applied to prepare derivatives to use for anti-cancer activity.

General Description

This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG

Enzyme inhibitor

This naturally occurring sesquiterpenoid (FW = 346.40 g/mol; CAS 16503- 32-5) from the volatile oils of the plant Centipeda minima inhibits (IC50 = 10 μg/mL) STAT3 phosphorylation in the Jak/STAT signal transduction pathway of A549R cells. Brevilin A showed high specificity on Janus Kinase activity and following STAT3 signaling without directly affecting some other signals, including p65, AKT and GSK-3β phosphorylation, as well as Src kinase activity. Brevilin A is also an antibiotic with activity against Giardia (IC50 = 16 μM) and Entamoeba histolitica (IC50 = 4–9 μM).

in vivo

Brevilin A (oral gavage; 10 and 20 mg/kg; once daily; 16 d) inhibits CNE-2 xenograft tumor growth, and inhibits PI3K/AKT and STAT3 signaling in vivo^[2].

• Animal Model: Male BALB/c nude mice injected with CNE-2 cells^[2]
• Dosage: 10 and 20 mg/kg
• Administration: Oral gavage; 10 and 20 mg/kg; once daily; 16 days
• Result: Decreased average tumor volumes and weights treated with 20 mg/kg by 36.3% and 46.0%, respectively, compared to vehicle control. Inhibited the protein expression of p-AKT and p-STAT3 at both low and high doses.

IC 50

STAT3: 10.6 μM (IC₅₀)