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S1250

Sigma-Aldrich

(−)-α-Santonin

≥99%

Synonym(s):

(3S,5aS,9bS)-3a,5,5a,9b-Tetrahydro-3,5a,9-trimethylnaphtho[1,2-b]furan-2,8(3H,4H)dione, Semenen

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About This Item

Empirical Formula (Hill Notation):
C15H18O3
CAS Number:
Molecular Weight:
246.30
Beilstein:
89489
EC Number:
MDL number:
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.83

Assay

≥99%

mp

172-173 °C (lit.)

storage temp.

2-8°C

SMILES string

C[C@H]1[C@@H]2CC[C@@]3(C)C=CC(=O)C(C)=C3[C@H]2OC1=O

InChI

1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10-,13-,15-/m0/s1

InChI key

XJHDMGJURBVLLE-BOCCBSBMSA-N

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General description

(−)-α-Santonin is a sesquiterpene lactone. It is found in the genus Artemisia.[1]

Application

(−)-α-Santonin has been used as a eudesmane-type sesquiterpene to study its effects on impairment of 231MFP breast cancer cell survival.[2]

Biochem/physiol Actions

(−)-α-Santonin exhibits anti-helminthic properteis.[1] It exhibits therapeutic effects against intestinal round worms.[3]

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Parthenolide Covalently targets and inhibits focal adhesion kinase in breast cancer cells
Berdan C A, et al.
Cell Chemical Biology, 26(7), 1027-1035 (2019)
Fungal hydroxylation of (-)-alpha-santonin
Bustos D A
Report Intl Narcotics Control Brd 03, 2, 1-6 (2012)
Chapter 3 - Natural Products
Sharma S and Anand N
Pharmacognosy Journal , 25(7), 71-123 (1997)
Yao Shen et al.
Molecules (Basel, Switzerland), 26(1) (2020-12-31)
Induced phase separation extraction (IPSE) is an efficient sample clean-up technique that can replace liquid-liquid extraction (LLE). The purpose of this study was to miniaturize IPSE by carrying it out in a microfluidic chip. An IPSE chip was designed and
Ryuichi Tamura et al.
Bioscience, biotechnology, and biochemistry, 76(12), 2360-2363 (2012-12-12)
(11S)-2α-Bromo-3-oxoeudesmano-12,6α-lactone, designated santonin-related compound 2 (SRC2), only weakly affected IκBα degradation after tumor necrosis factor-α (TNF-α) stimulation, but strongly blocked the nuclear translocation of nuclear factor κB (NF-κB) subunit p65. Replacement of Cys-38 of p65 with serine abolished the inhibitory

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