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470-17-7,MFCD08689940
Catalog No.:AA003ANG

470-17-7 | Isoalantolactone

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1mg
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5mg
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10mg
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250mg
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1g
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA003ANG
Chemical Name:
Isoalantolactone
CAS Number:
470-17-7
Molecular Formula:
C15H20O2
Molecular Weight:
232.3181
MDL Number:
MFCD08689940
SMILES:
O=C1O[C@H]2[C@@H](C1=C)C[C@@H]1[C@](C2)(C)CCCC1=C
NSC Number:
241036
Properties
Computed Properties
 
Complexity:
409  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
2  
XLogP3:
3.4  

Downstream Synthesis Route

[1]ChemischeBerichte,1931,vol.64,p.67,69    JournalfuerPraktischeChemie(Leipzig),1933,vol.<2>136,p.176,185

470-17-7   
(11Ξ)-8β-hydroxy-13-nor-eudesm-4(15)-ene-11,12-dicarboxylicacid-11-lactone 

[1]JournalfurpraktischeChemie(Leipzig1954),1933,vol.<2>136,p.176,179,187

110-91-8    470-17-7   
(11Ξ)-8β-hydroxy-13-morpholin-4-yl-eudesm-3-en-12-oicacidlactone 
  67416-70-0 

[1]IndianJournalofChemistry-SectionBOrganicandMedicinalChemistry,1978,vol.16,p.191-195

[1]IndianJournalofChemistry-SectionBOrganicandMedicinalChemistry,1978,vol.16,p.191-195

[1]LiebigsAnnalenderChemie,1987,p.455-458

Literature

Title: Isoalantolactone induces apoptosis through reactive oxygen species-dependent upregulation of death receptor 5 in human esophageal cancer cells.

Journal: Toxicology and applied pharmacology 20180801

Title: Antistaphylococcal activity of Inula helenium L. root essential oil: eudesmane sesquiterpene lactones induce cell membrane damage.

Journal: European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 20120601

Title: Chemical composition of essential oils from a multiple shoot culture of Telekia speciosa and different plant organs.

Journal: Natural product communications 20120501

Title: Isoalantolactone induces reactive oxygen species mediated apoptosis in pancreatic carcinoma PANC-1 cells.

Journal: International journal of biological sciences 20120101

Title: Ultrasound-assisted extraction of total flavonoids from Inula helenium.

Journal: Pharmacognosy magazine 20120101

Title: Antitumour activities of sesquiterpene lactones from Inula helenium and Inula japonica.

Journal: Zeitschrift fur Naturforschung. C, Journal of biosciences 20120101

Title: Isoalantolactone protects against Staphylococcus aureus pneumonia.

Journal: FEMS microbiology letters 20111101

Title: Activation of caspases and poly (ADP-ribose) polymerase cleavage to induce apoptosis in leukemia HL-60 cells by Inula racemosa.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20100901

Title: Structure-activity relationship studies on derivatives of eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults.

Journal: Chemistry & biodiversity 20100701

Title: HPLC determination and NMR structural elucidation of sesquiterpene lactones in Inula helenium.

Journal: Journal of pharmaceutical and biomedical analysis 20100311

Title: Ultrasound-assisted extraction of alantolactone and isoalantolactone from Inula helenium roots.

Journal: Pharmacognosy magazine 20100101

Title: Isoalantolactone from Inula helenium caused Nrf2-mediated induction of detoxifying enzymes.

Journal: Journal of medicinal food 20091001

Title: Nrf2-mediated induction of detoxifying enzymes by alantolactone present in Inula helenium.

Journal: Phytotherapy research : PTR 20081101

Title: Neural networks as valuable tools to differentiate between sesquiterpene lactones' inhibitory activity on serotonin release and on NF-kappaB.

Journal: Journal of medicinal chemistry 20080313

Title: Induction of detoxifying enzyme by sesquiterpenes present in Inula helenium.

Journal: Journal of medicinal food 20070901

Title: Simultaneous quantification of eudesmanolides and thymol derivatives from tissues of Inula helenium and I. royleana by reversed-phase high-performance liquid chromatography.

Journal: Phytochemical analysis : PCA 20060101

Title: Separation and determination of two sesquiterpene lactones in Radix inulae and Liuwei Anxian San by microemulsion electrokinetic chromatography.

Journal: Biomedical chromatography : BMC 20041201

Title: Constituents of two Flourensia species.

Journal: Phytochemistry 20040701

Title: Antiproliferative sesquiterpene lactones from the roots of Inula helenium.

Journal: Biological & pharmaceutical bulletin 20021001

Title: Anti-trypanosomal activity of helenalin and some structurally related sesquiterpene lactones.

Journal: Planta medica 20020801

Title: Antimycobacterial plant terpenoids.

Journal: Planta medica 20011101

Title: Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone.

Journal: Bioorganic & medicinal chemistry letters 20010212

Title: Antimycobacterial eudesmanolides from Inula helenium and Rudbeckia subtomentosa.

Journal: Planta medica 19990501

Title: A murine in vitro model of allergic contact dermatitis to sesquiterpene alpha-methylene-gamma-butyrolactones.

Journal: Archives of dermatological research 19920101

Title: Lawrence NJ, et al. Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone. Bioorg Med Chem Lett. 2001 Feb 12;11(3):429-31.

Title: Khan M, et al. Isoalantolactone induces reactive oxygen species mediated apoptosis in pancreatic carcinoma PANC-1 cells. Int J Biol Sci. 2012;8(4):533-47.

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