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SML0415

Sigma-Aldrich

Alantolactone

≥98% (HPLC)

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
EC Number:
208-899-3
MDL number:
MFCD00274568
UNSPSC Code:
51111800
PubChem Substance ID:
329825410
NACRES:
NA.77

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

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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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
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
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
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
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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