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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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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
D E Chapman et al.
Biochemical pharmacology, 38(22), 3913-3923 (1989-11-15)
The sesquiterpene lactones (STL) helenalin and alantolactone were effective in vitro inhibitors of the mouse hepatic microsomal mixed-function oxidase (MFO) enzymes, aminopyrine demethylase (APD), aniline hydroxylase (ANH) and 7-ethoxyresorufin deethylase (ERD). Helenalin and alantolactone concentrations of 0.5 mM produced a
Xu-Guang Mi et al.
Toxicology letters, 224(3), 349-355 (2013-11-21)
Testes-specific protease 50 (TSP50) is aberrantly expressed in many cancer biopsies and plays a crucial role in tumorigenesis, which make it a potential cancer therapeutic target for drug discovery. Here, we constructed a firefly luciferase reporter driven by the TSP50
S Quirce et al.
Contact dermatitis, 30(2), 73-76 (1994-02-01)
7 subjects, each giving a history of scaly or vesicular dermatitis in light-exposed areas after going for strolls to the park, the forest or the country during warm weather, were evaluated. Patch testing was carried out with Frullania dilatata and
Alantolactone induces apoptosis, promotes STAT3 glutathionylation and enhances chemosensitivity of A549 lung adenocarcinoma cells to doxorubicin via oxidative stress
Maryam A, et al.
Scientific Reports, 7(1), 6242-6242 (2017)
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