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SML0415

Sigma-Aldrich

Alantolactone

≥98% (HPLC)

Synonyme(s) :

(+)-Alantolactone., 3aR,5S,8aR,9aR)-3a,5,6,7,8,8a,9,9a-Octahydro-5,8a-dimethyl-3-methylene-naphtho[2,3-b]furan-2(3H)-one, Alant camphor, Elecampane camphor, Eupatal, Inula camphor, NSC 333843, NSC 93131

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About This Item

Formule empirique (notation de Hill):
C15H20O2
Numéro CAS:
546-43-0
Poids moléculaire :
232.32
Numéro CE :
208-899-3
Numéro MDL:
MFCD00274568
Code UNSPSC :
51111800
ID de substance PubChem :
329825410
Nomenclature NACRES :
NA.77

Pureté

≥98% (HPLC)

Forme

powder

Conditions de stockage

desiccated
protect from light

Couleur

white to beige

Solubilité

DMSO: 15 mg/mL (clear solution)

Température de stockage

−20°C

Chaîne SMILES 

C[C@H]1CCC[C@]2(C)C[C@H]3OC(=O)C(=C)[C@H]3C=C12

InChI

1S/C15H20O2/c1-9-5-4-6-15(3)8-13-11(7-12(9)15)10(2)14(16)17-13/h7,9,11,13H,2,4-6,8H2,1,3H3/t9-,11+,13+,15+/m0/s1

Clé InChI

PXOYOCNNSUAQNS-AGNJHWRGSA-N

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Description générale

Alantolactone is a compound produced by Inula helenium. Alantolactone has antibacterial, antifungal, anti-inflammatory and anticancer properties. It suppresses signal transducer and activator of transcription 3 (STAT3) activation in liver and breast cancer cells. Alantolactone induces apoptosis in A549 lung cancer cells.

Application

Alantolactone has been used:
  • in cell viability assay
  • to examine the percentage of multicentrosomal mitosis in low and high passage human embryonic stem cells (hESC)
  • in assessment of degranulation

Actions biochimiques/physiologiques

Alantolactone is a sesquiterpene lactone disrupts the Cripto-1/ActRII complexes, resulting in an induction of activin/SMAD3 signaling. Alantolactone inhibits proliferation in cancer cells with no affect on normal cells.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H317

Classification des risques

Skin Sens. 1

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Jia-Chuan Lei et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(9), 3313-3319 (2012-06-23)
Alantolactone, a sesquiterpene lactone, possesses anti-inflammatory property. In this study, we provide evidence that it could be developed as a novel agent against human liver cancer. We observed that alantolactone treatment to HepG2, Bel-7402 and SMMC-7721 cells, human liver cancer
Charles L Cantrell et al.
Chemistry & biodiversity, 7(7), 1681-1697 (2010-07-27)
An Aedes aegypti larval toxicity bioassay was performed on compounds representing many classes of natural compounds including polyacetylenes, phytosterols, flavonoids, sesquiterpenoids, and triterpenoids. Among these compounds, two eudesmanolides, alantolactone, and isoalantolactone showed larvicidal activities against Ae. aegypti and, therefore, were
Hadas E Sloin et al.
PloS one, 13(6), e0199777-e0199777 (2018-06-26)
TGF-β signaling is a cellular pathway that functions in most cells and has been shown to play a role in multiple processes, such as the immune response, cell differentiation and proliferation. Recent evidence suggests a possible interaction between TGF-β signaling
J S Ross et al.
Contact dermatitis, 29(2), 84-87 (1993-08-01)
A mix of 3 sesquiterpene lactones (SL) (SL mix 0.1%) was evaluated over a 4-year period. Of 7420 patients with eczema investigated by patch testing, 135 (68 male, 67 female) (1.8%) demonstrated positive reactions, 114 (84%) considered clinically relevant. Females
Muhammad Khan et al.
IUBMB life, 64(9), 783-794 (2012-07-28)
Glioblastoma multiforme (GBM) is the most malignant and aggressive primary brain tumor in adults. Despite concerted efforts to improve current therapies, the prognosis of glioblastoma remains very poor. Alantolactone, a sesquiterpene lactone compound, has been reported to exhibit antifungal, antibacteria
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