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SML0415

Alantolactone

≥98% (HPLC), activin/SMAD3 signaling inducer, powder

Synonym(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

Empirical Formula (Hill Notation):
C15H20O2
CAS Number:
546-43-0
Molecular Weight:
232.32
NACRES:
NA.77
PubChem Substance ID:
329825410
UNSPSC Code:
51111800
EC Number:
208-899-3
MDL number:
MFCD00274568
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
desiccated, protect from light
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Product Name

Alantolactone, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

storage condition

desiccated, protect from light

color

white to beige

solubility

DMSO: 15 mg/mL (clear solution)

storage temp.

−20°C

SMILES string

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

InChI key

PXOYOCNNSUAQNS-AGNJHWRGSA-N

General description

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

Biochem/physiol Actions

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.
Alantolactone is an inducer of activin/SMAD3 signaling.

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pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H317

Hazard Classifications

Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000487851
0000487851
0000513612
0000513612
0000451513

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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
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
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
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Global Trade Item Number

SKUGTIN
SML0415-25MG04061833222720
SML0415-5MG04061833222737