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Dehydrocostus Lactone (Standard)

CAT: 0804-HY-N0591R-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-N0591R-01Size:5 mg
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Description
Dehydrocostus Lactone (Standard) ((-) -Dehydrocostus lactone (Standard) ) is the analytical standard of Dehydrocostus Lactone. This product is intended for research and analytical applications. Dehydrocostus Lactone is a natural sesquiterpene that can be isolated from Saussurea lappa. Dehydrocostus Lactone has multiple activities such as anti-inflammatory, antibacterial, anti-tumor, and immunomodulatory effects. Dehydrocostus Lactone has an MIC of 2 µg/mL against Mycobacterium tuberculosis. Dehydrocostus Lactone can also inhibit the killing activity of cytotoxic T lymphocytes and induce apoptosis in tumor cells.
CAS Number
477-43-0
Product Name Alternative
(-) -Dehydrocostus lactone (Standard) ; Epiligulyl oxide (Standard)
UNSPSC
12352005
Target
Akt; Apoptosis; Bacterial; Caspase; Interleukin Related; MAPKAPK2 (MK2) ; NF-κB; NO Synthase; p38 MAPK; Reference Standards
Type
Reference Standards
Related Pathways
Anti-infection; Apoptosis; Immunology/Inflammation; MAPK/ERK Pathway; NF-κB; Others; PI3K/Akt/mTOR
Field of Research
Cancer; Infection; Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/dehydrocostus-lactone-standard.html
Smiles
O=C(O[C@@]([C@@]1([H])C(CC[C@@]21[H])=C)([H])[C@@]3([H])CCC2=C)C3=C
Molecular Formula
C15H18O2
Molecular Weight
230.30
References & Citations
[1]Eun Ji Kim, et al. Apoptosis of DU145 human prostate cancer cells induced by dehydrocostus lactone isolated from the root of Saussurea lappa. Food and Chemical Toxicology Volume 46, Issue 12, December 2008, Pages 3651–3658|[2]Lee HJ, et al. A sesquiterpene, dehydrocostus lactone, inhibits the expression of inducible nitric oxide synthase and TNF-alpha in LPS-activated macrophages. Planta Med. 1999 Mar;65 (2) :104-8.|[3]Taniguchi M, et al. COSTUNOLIDE AND DEHYDROCOSTUS LACTONE AS INHIBITORS OF KILLING FUNCTION OF CYTOTOXIC T LYMPHOCYTES. Bioscience, Biotechnology, and Biochemistry, 1995, 59 (11) : 2064-2067|[4]Nie Y, Wang Z, Chai G, et al. Dehydrocostus Lactone Suppresses LPS-induced Acute Lung Injury and Macrophage Activation through NF-κB Signaling Pathway Mediated by p38 MAPK and Akt. Molecules. 2019;24 (8) :1510.
Shipping Conditions
Room temperature
Scientific Category
Reference Standards

Chemical Information

(-)-Dehydrocostus lactone

Dehydrocostus lactone is an organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone. It has a role as a metabolite, an antineoplastic agent, a trypanocidal drug, a cyclooxygenase 2 inhibitor, an antimycobacterial drug and an apoptosis inducer. It is an organic heterotricyclic compound, a guaiane sesquiterpenoid, a gamma-lactone and a sesquiterpene lactone.

CAS Number477-43-0
PubChem CID73174
IUPAC Name(3aS,6aR,9aR,9bS)-3,6,9-trimethylidene-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Molecular FormulaC15H18O2
Molecular Weight230.30
XLogP2.6
Topological Polar Surface Area26.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Heavy Atom Count17
Formal Charge0
Complexity432
SMILES
C=C1CC[C@@H]2[C@@H]([C@@H]3[C@H]1CCC3=C)OC(=O)C2=C
InChI
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
Chemical Structure
2D Structure
2D structure of (-)-Dehydrocostus lactone
CAS: 477-43-0
CID: 73174
Formula: C15H18O2
MW: 230.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight230.30
XLogP32.6
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass230.130679813
Monoisotopic Mass230.130679813
Topological Polar Surface Area26.3 Ų
Heavy Atom Count17
Formal Charge0
Complexity432
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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