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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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Product Name

(−)-α-Santonin, ≥99%

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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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.

General description

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

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)
Oliver Schwarz et al.
Journal of combinatorial chemistry, 9(6), 1104-1113 (2007-09-14)
Recently, we developed a concept known as biology-oriented synthesis (BIOS), which targets the design and synthesis of small- to medium-sized compound libraries on the basis of genuine natural product templates to provide screening compounds with high biological relevance. We herein
Seung Hyun Kim et al.
Archives of pharmacal research, 29(1), 40-45 (2006-02-24)
Several diacetoxy acetal analogues have been synthesized from santonin and assessed for their ability of inducing or enhancing the differentiation of human HL-60 leukemia cells. The compounds themselves had little effect on HL-60 cell differentiation. However, three analogues, 2a, 3a
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