42575

Dehydrocostus lactone

analytical standard

• Synonym(s): (−)-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
• Empirical Formula (Hill Notation): C₁₅H₁₈O₂
• CAS Number: 477-43-0
• Molecular Weight: 230.30
• MDL number: MFCD00210277
• UNSPSC Code: 85151701
• PubChem Substance ID: 329756240
• NACRES: NA.24

Properties

• grade: analytical standard
• Quality Level: 100
• assay: ≥98.0% (GC)
• optical activity: [α]/D -14.0±3.0°, c = 1 in chloroform
• shelf life: limited shelf life, expiry date on the label
• impurities: ≤2.0% water
• format: neat
• storage temp.: −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
• InChI key: NETSQGRTUNRXEO-XUXIUFHCSA-N

Description

Biochem/physiol Actions

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H317
• pcodes: P261 - P272 - P280 - P302 + P352 - P333 + P313 - P362 + P364
• Hazard Classifications: Skin Sens. 1
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable