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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:
481-06-1
Molecular Weight:
246.30
Beilstein/REAXYS Number:
89489
EC Number:
207-560-7
MDL number:
MFCD00135865
UNSPSC Code:
12352204
PubChem Substance ID:
24899466
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
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_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK5556
MKCH6593
MKBR6486V
SLBH1785V
SLBG8696V

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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)
Chapter 3 - Natural Products
Sharma S and Anand N
Pharmacognosy Journal , 25(7), 71-123 (1997)
Fungal hydroxylation of (-)-alpha-santonin
Bustos D A
Report Intl Narcotics Control Brd 03, 2, 1-6 (2012)
Athar Ata et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 59(3-4), 209-214 (2004-07-10)
Fungal biotransformations of alpha-santonin (1) were conducted with Mucor plumbeus (ATCC 4740), Cunninghamella bainieri (ATCC 9244), Cunninghamella echinulata (ATCC 9245), Curvularia lunata (ATCC 12017) and Rhizopus stolonifer (ATCC 10404). Rhizopus stolonifer (ATCC 10404) metabolized compound 1 to afford 3,4-epoxy-alpha-santonin (2)
Francisco F P Arantes et al.
European journal of medicinal chemistry, 45(12), 6045-6051 (2010-10-26)
Ten novel α-santonin derivatives have been synthesized as cytotoxic agents. The in vitro antitumor activity of these compounds has been evaluated against cancer cells lines. Structure-activity relationships indicate that α-methylene-γ-lactone and endoperoxide functionalities play important roles in conferring cytotoxicity. The
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