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Merck
CN

D2696

Dehydrocostus lactone

≥98% (HPLC)

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

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About This Item

Empirical Formula (Hill Notation):
C15H18O2
CAS Number:
477-43-0
Molecular Weight:
230.30
NACRES:
NA.77
PubChem Substance ID:
329798749
UNSPSC Code:
12352200
MDL number:
MFCD00210277

Key Documents

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InChI key

NETSQGRTUNRXEO-XUXIUFHCSA-N

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

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: ≥20 mg/mL

storage temp.

room temp

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Biochem/physiol Actions

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.
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.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
119K4710

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Zhi Li et al.
Journal of AOAC International, 93(5), 1390-1398 (2010-12-15)
Due to their complexity, multicomponent herbal drugs pose enormous analytical challenges for quality control (QC). Although they may have traditionally been used for hundreds of years, the information about their chemical composition is often still limited. Selecting suitable markers to
Eun Mi Choi et al.
Toxicology in vitro : an international journal published in association with BIBRA, 23(5), 862-867 (2009-05-22)
Oxidative stress regulates cellular functions in multiple pathological conditions, including bone formation by osteoblasic cells. To elucidate the protective effects of dehydrocostus lactone on the response of osteoblast to oxidative stress, osteoblastic MC3T3-E1 cells were incubated with 0.3mM hydrogen peroxide
Cheng Peng et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 34(8), 1007-1008 (2009-07-31)
To study the chemical constituents of Oxytropis microphylla. The compounds were isolated and purified by various column chromatographic techniques and their structures were elucidated on the basis of spectral analysis (EI-MS, 1H-NMR, 13C-NMR). Eight compounds were isolated and identified as
Xiao-ping Zhao et al.
Zhejiang da xue xue bao. Yi xue ban = Journal of Zhejiang University. Medical sciences, 41(1), 43-46 (2012-03-16)
To screen the potential hepatotoxic components in Chinese herb medicine Aucklandiae Radix. The potential hepatotoxic components were screened using HepG2 cells labeled with fluorescein diacetate from 25 fractions of Aucklandiae Radix, in which the hepatotoxic compounds were further identified with
Dan Wang et al.
Journal of Asian natural products research, 11(12), 991-996 (2010-02-26)
Aspergillus versicolor D-1 was employed to convert dehydrocostuslactone (1) and 3-hydroxy-1(10),3,11(13)-guaiatriene-12,6-olide-2-one (5) stereoselectively. The reactions occurring were specific hydrogenation on the exocyclic alpha,beta-double bond of sesquiterpene lactones with excellent conversion. Products were identified by the analysis of their spectra such
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