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.

InChI

InChI=1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h11-13H,1-2,4-8H2,3H3/t11-,12+,13-,15-/m1/s1

InChIKey

CVUANYCQTOGILD-QVHKTLOISA-N

SMILES

O1C(=O)C(=C)[C@@]2([H])C[C@]3([H])[C@@](C)(C[C@@]12[H])CCCC3=C

LogP

3.420

CAS DataBase Reference

470-17-7(CAS DataBase Reference)

NIST Chemistry Reference

Naphtho(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

Isoalantolactone Usage And Synthesis

Description

Isohelenin (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

Uses

Isoalantolactone is a sesquiterpene lactone used in the treatment of cancer. It can inhibit tumor cell growth and induce apoptosis.

Definition

ChEBI: A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium.

References

Bork 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

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