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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:
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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
Lin Yang et al.
Yao xue xue bao = Acta pharmaceutica Sinica, 40(9), 834-837 (2005-12-14)
To obtain more valuable derivatives for the further structural modification of 6beta-santonin (1) via biotransformation by using cell suspension cultures of Phytolacca acinosa. The substrate 1 was incubated with cell suspension cultures of P. acinosa, the products were obtained by
Xing Chen et al.
The journal of physical chemistry. A, 115(26), 7815-7822 (2011-06-02)
The CASSCF and CASPT2 methodologies have been used to explore the potential energy surfaces of lumisantonin in the ground and low-lying triplet states along the photoisomerization pathways. Calculations indicate that the (1)(nπ*) state is the accessible low-lying singlet state with
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