Isoalantolactone

Isoalantolactone Basic information
Product Name:Isoalantolactone
Synonyms:11(13)-dien-12-oicacid,8-beta-hydroxy-eudesma-4(14gamma-lactone;ISOALANTOACTONE;ISOALANTOLACTONE;ISOHELENIN;(3ar,4as,8ar,9ar)-8a-methyl-3,5-dimethylene-decahydro-naphtho[2,3-b]furan-2-one;methyl-3,5-bis(methylene)-,(3aR,4aS,8aR,9aR)-;Naphtho[2,3-b]furan-2(3H)-one,decahydro-8a-;(3aR)-3aα,4,4aα,5,6,7,8,8a,9,9aα-Decahydro-3,5-bismethylene-8aβ-methylnaphtho[2,3-b]furan-2(3H)-one
CAS:470-17-7
MF:C15H20O2
MW:232.32
EINECS:
Product Categories:Inhibitors;Miscellaneous Natural Products;chiral;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
Mol File:470-17-7.mol
Isoalantolactone Structure
Isoalantolactone Chemical Properties
Melting point 115℃
Boiling point 364.9±42.0 °C(Predicted)
density 1.07±0.1 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in DMSO (up to 50 mg/ml) or ethanol (30 mg/ml)
form solid
color White
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
LogP3.420
CAS DataBase Reference470-17-7(CAS DataBase Reference)
NIST Chemistry ReferenceNaphtho(2,3-b)furan-2(3h)-one, decahydro-8a-methyl-3,5-bis(methylene)-, (3ar-(3a«alpha»,4a«alpha»,8a«beta»,9a«alpha»))-(470-17-7)
Safety Information
Hazard Codes Xn
Risk Statements 40
Safety Statements 22-36
HS Code 29322090
MSDS Information
Isoalantolactone Usage And Synthesis
DescriptionIsohelenin (470-17-7) is a sesquiterpene lactone isolated from Mexican Indian medicinal plants known to have anti-inflammatory properties. A potent inhibitor of NFkB (complete inhibition at 5 μM)1 acting via inhibition of IKK?6. Isohelenin-mediated NFkB inhibition suppresses IL-8 expression2, iNOS expression3 and RANTES biosynthesis4. Displays protective effects in endotoxic shock in rodent models.5 Induces apoptosis in glioma cells.6
UsesIsoalantolactone is a sesquiterpene lactone used in the treatment of cancer. It can inhibit tumor cell growth and induce apoptosis.
DefinitionChEBI: A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium.
ReferencesBork et al. (1997), Sesquiterpene lactone containing Mexican Indian medicinal plants and pure sesquiterpene lactones as potent inhibitors of transcription factor NK-kappaB; FEBS Lett., 402 85 Mazor et al. (2000), Sesquiterpene lactones are potent inhibitors of interleukin 8 gene expression in cultured human respiratory epithelium; Cytokine, 12 239 Wong and Menendez (1999), Sesquiterpene lactones inhibit inducible nitric oxide synthase gene expression in cultured rat aortic smooth muscle cells; Biochem. Biophys. Res. Commun., 262 375 Li et al. (2001), Induction of RANTES chemokine expression in human astrocytic cells is dependent upon activation of NK-kappaB transcription factor; Int. J. Mol. Med., 7 527 Sheehan et al. (2002), Protective effects of isohelenin, an inhibitor of nuclear factor KappaB in endotoxic shock in rats; Endotoxin Res, 8 99 Xing et al. (2019), Isoalantolactone inhibits IKK? kinase activity to interrupt the NF-kB/COX-2-mediated signaling cascade and induces apoptosis regulated by the mitochondrial translocation of cofilin in glioblastoma; Cancer Med., 8 1655
Methylparaben Alantolactone Methyl ε-Caprolactone Bensulfuron methyl Parathion-methyl D-(+)-Glucono-1,5-lactone Kresoxim-methyl ivalin DECAHYDRO-2-NAPHTHOL ACETATE Thiophanate-methyl Inula racemosa Extract Methyl acrylate Methyl bromide Isoalantolactone METHYL THIOPHENE-2-CARBOXYLATE Spironolactone Furan

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