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Safety Information

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:
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.

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

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

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

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK5556
MKCH6593
MKBR6486V
SLBH1785V
SLBG8696V

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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)
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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