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546-43-0,MFCD00274568
Catalog No.:AA00I9OE

546-43-0 | Alantolactone

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1mg
98%
in stock  
$9.00   $7.00
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25mg
98%
in stock  
$34.00   $24.00
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250mg
95%
in stock  
$278.00   $195.00
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1g
95%
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$643.00   $450.00
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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:
AA00I9OE
Chemical Name:
Alantolactone
CAS Number:
546-43-0
Molecular Formula:
C15H20O2
Molecular Weight:
232.3181
MDL Number:
MFCD00274568
SMILES:
C[C@H]1CCC[C@]2(C1=C[C@H]1[C@@H](C2)OC(=O)C1=C)C
NSC Number:
93131
Properties
Computed Properties
 
Complexity:
421  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
2  
XLogP3:
3.7  

Downstream Synthesis Route

[1]HelveticaChimicaActa,1931,vol.14,p.397,405

[2]ComptesRendusHebdomadairesdesSeancesdel'AcademiedesSciences,1958,vol.246,p.1874

[1]EuropeanJournalofMedicinalChemistry,1990,vol.25,p.107-115

[1]ChemistryofNaturalCompounds,2006,vol.42,p.400-406

[2]Patent:CN106491593,2017,A.Locationinpatent:Paragraph0029;0032;0033;0034

[3]Patent:CN106491592,2017,A.Locationinpatent:Paragraph0028;0031;0032;0033

[4]Patent:CN106496169,2017,A.Locationinpatent:Paragraph0033;0034;0035

[5]EuropeanJournalofMedicinalChemistry,2018,vol.157,p.229-247

[6]ChemistryofNaturalCompounds,1996,vol.32,p.869-872

[7]IndianJournalofChemistry-SectionBOrganicandMedicinalChemistry,1985,vol.24,p.835-839

[8]Phytochemistry,1982,vol.21,p.1679-1692

[9]Phytochemistry,1988,vol.27,p.2079-2082

[10]PlantaMedica,1999,vol.65,p.351-355

[11]Chemistryandbiodiversity,2010,vol.7,p.1681-1697

[12]Molecules,2013,vol.18,p.13061-13077

546-43-0    126686-70-2   
alantolactone-Cys(Boc)-Ala(OMe)adduct 

[1]Tetrahedron,1989,vol.45,p.5029-5038

546-43-0    126686-70-2   
alantolactone-Cys(Boc)-Ala(OMe)adduct 

[1]Tetrahedron,1989,vol.45,p.5029-5038

Literature

Title: Alantolactone induces cell apoptosis partially through down-regulation of testes-specific protease 50 expression.

Journal: Toxicology letters 20140130

Title: Alantolactone induces activation of apoptosis in human hepatoma cells.

Journal: Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20120901

Title: Alantolactone induces apoptosis in glioblastoma cells via GSH depletion, ROS generation, and mitochondrial dysfunction.

Journal: IUBMB life 20120901

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: The tibetan uterotonic zhi byed 11: mechanisms of action, efficacy, and historical use for postpartum hemorrhage.

Journal: Evidence-based complementary and alternative medicine : eCAM 20120101

Title: Mechanisms involved in enhancement of the expression and function of aggrecanases by hyaluronan oligosaccharides.

Journal: Arthritis and rheumatism 20120101

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

Journal: International journal of biological sciences 20120101

Title: Evaluation of protective effect of Butea monosperma (lam.) Taub in experimental hepatotoxicity in rats.

Journal: Journal of pharmacology & pharmacotherapeutics 20120101

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

Journal: Pharmacognosy magazine 20120101

Title: Sesquiterpene lactones from Inula falconeri, a plant endemic to the Himalayas, as potential anti-inflammatory agents.

Journal: European journal of medicinal chemistry 20111101

Title: Alantolactone inhibits cell proliferation by interrupting the interaction between Cripto-1 and activin receptor type II A in activin signaling pathway.

Journal: Journal of biomolecular screening 20110601

Title: Screening for Compositae sensitization with pure allergens: implications of molecular structure, strength of reaction, and time of testing.

Journal: Contact dermatitis 20110201

Title: Potent cytotoxic effects of Calomeria amaranthoides on ovarian cancers.

Journal: Journal of experimental & clinical cancer research : CR 20110101

Title: Modeling natural anti-inflammatory compounds by molecular topology.

Journal: International journal of molecular sciences 20110101

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: Protection by Chrysanthemum zawadskii extract from liver damage of mice caused by carbon tetrachloride is maybe mediated by modulation of QR activity.

Journal: Nutrition research and practice 20100401

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: Protective effect of stem bark of Ceiba pentandra linn. against paracetamol-induced hepatotoxicity in rats.

Journal: Pharmacognosy research 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: A rapid identification of Radix inulae and its active component alantolactone in the Tibetan medicine Manuxitang.

Journal: Bioscience trends 20080401

Title: Microbial transformation of alantolactone by Mucor polymorphosporus.

Journal: Journal of Asian natural products research 20080101

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

Journal: Journal of medicinal food 20070901

Title: Sesquiterpene lactones are potent and irreversible inhibitors of the antibacterial target enzyme MurA.

Journal: Bioorganic & medicinal chemistry letters 20061101

Title: Synthesis and anti-viral activity of a series of sesquiterpene lactones and analogues in the subgenomic HCV replicon system.

Journal: Bioorganic & medicinal chemistry 20060101

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: Erythema multiforme due to contact with weeds: a recurrence after patch testing.

Journal: Contact dermatitis 20030101

Title: Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa.

Journal: Phytochemistry 20011201

Title: Antimycobacterial plant terpenoids.

Journal: Planta medica 20011101

Title: Sensitization and cross-reaction patterns in Danish Compositae-allergic patients.

Journal: Contact dermatitis 20011001

Title: Cytotoxic sesquiterpene lactones mediate their death-inducing effect in leukemia T cells by triggering apoptosis.

Journal: Planta medica 20010801

Title: Patch test sensitization to Compositae mix, sesquiterpene-lactone mix, Compositae extracts, laurel leaf, Chlorophorin, Mansonone A, and dimethoxydalbergione.

Journal: American journal of contact dermatitis : official journal of the American Contact Dermatitis Society 20010301

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

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