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Merck
CN

S1250

(−)-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:
481-06-1
Molecular Weight:
246.30
UNSPSC Code:
12352204
NACRES:
NA.83
PubChem Substance ID:
24899466
EC Number:
207-560-7
Beilstein/REAXYS Number:
89489
MDL number:
MFCD00135865

Key Documents

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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

SMILES string

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

assay

≥99%

mp

172-173 °C (lit.)

storage temp.

2-8°C

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General description

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

Application

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

Biochem/physiol Actions

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

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

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

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK5556
MKCH6593
MKBR6486V
SLBH1785V
SLBG8696V

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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)
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)
Gonzalo Blay et al.
The Journal of organic chemistry, 69(21), 7294-7302 (2004-10-09)
The synthesis of the spirovetivane sesquiterpenes (+)-anhydro-beta-rotunol and all the diastereomers of 6,11-spirovetivadiene in enantiomerically pure form has been achieved starting from santonin. The key step is the silicon-guided acid-promoted rearrangement of a 1-trimethylsilyl-4,5-epoxyeudesmane prepared from santonin in several steps
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
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