42575

Dehydrocostuslacton

analytical standard

• Synonym(e): (−)-Dehydrocostus lactone; Dehydrocostus lactone; Epiligulyl oxide, (3aS,6aR,9aR,9bS)-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one, Dehydro-costus lactone (6CI,7CI), Dehydrocostuslactone, Guaia-4(15),10(14),11(13)-trien-12-oic acid, 6alpha-hydroxy-, gamma-lactone, [3aS-(3aα,6aα,9aα,9bβ)]-Decahydro-3,6,9-tris(methylene)-azuleno[4,5-b]furan-2(3H)-one
• Empirische Formel (Hill-System): C₁₅H₁₈O₂
• CAS-Nummer: 477-43-0
• Molekulargewicht: 230.30
• MDL-Nummer: MFCD00210277
• UNSPSC-Code: 85151701
• PubChem Substanz-ID: 329756240
• NACRES: NA.24

Eigenschaften

• Qualität: analytical standard
• Qualitätsniveau: 100
• Assay: ≥98.0% (GC)
• Optische Aktivität: [α]/D -14.0±3.0°, c = 1 in chloroform
• Haltbarkeit: limited shelf life, expiry date on the label
• Verunreinigungen: ≤2.0% water
• Format: neat
• Lagertemp.: −20°C
• SMILES String: C=C1CC[C@@]2([H])C(CC[C@@H]3[C@H](OC(C3=C)=O)[C@]21[H])=C
• InChI: 1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2/t11-,12-,13-,14-/m0/s1
• InChIKey: NETSQGRTUNRXEO-XUXIUFHCSA-N

Beschreibung

Biochem./physiol. Wirkung

Suppressors of cytokine signaling (SOCS) proteins negatively regulate cytokine receptor signaling. The SOCS family include eight members SOCS-1 to SOCS-7 and CIS. Dehydrocostuslactone (DHE) is a sesquiterpene lactone extracted from Saussurea lappa and Aucklandia lappa. The compound possess antifungal and antimycobacterial activity and exhibit a cytotoxic effect against HepG2, OVCAR-3, and HeLa cell lines. DHE inhibits cell proliferation not only in early-stage breast cancer MCF-7 but also in more advanced stage MDA-MB-231 cancer cells, without significant effect on H184B5F5/M10 normal mammary epithelial cells. The inhibition of breast cancer cells proliferation occurs through cell cycle blockade and apoptosis. DHE inhibits cell cycle progression and cell death through SOCS-1 and SOCS-3.

Sicherheitshinweise

• Piktogramme: GHS07
• Signalwort: Warning
• H-Sätze: H317
• P-Sätze: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Gefahreneinstufungen: Skin Sens. 1
• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable