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53653

Supelco

(−)-α-Santonin

analytical standard

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:
85151701
PubChem Substance ID:
329757965
NACRES:
NA.24

grade

analytical standard

Quality Level

100

Assay

≥95.0% (HPLC)

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable
gas chromatography (GC): suitable

impurities

≤5.0% water

mp

172-173 °C (lit.)

application(s)

cleaning products
cosmetics
food and beverages
personal care

format

neat

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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Application

Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

53653-BULK:
53653-VAR:
53653-10MG:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCJ5098
BCCF8112
BCCC9958
BCCC7959
BCCC2284

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Ryuichi Tamura et al.
Bioscience, biotechnology, and biochemistry, 76(12), 2360-2363 (2012-12-12)
(11S)-2α-Bromo-3-oxoeudesmano-12,6α-lactone, designated santonin-related compound 2 (SRC2), only weakly affected IκBα degradation after tumor necrosis factor-α (TNF-α) stimulation, but strongly blocked the nuclear translocation of nuclear factor κB (NF-κB) subunit p65. Replacement of Cys-38 of p65 with serine abolished the inhibitory
James K Harper et al.
Journal of magnetic resonance (San Diego, Calif. : 1997), 189(1), 20-31 (2007-09-18)
The (1)H-(13)C solid-state NMR heteronuclear correlation (HETCOR) experiment is demonstrated to provide shift assignments in certain powders that have two or more structurally independent molecules in the unit cell (i.e. multiple molecules per asymmetric unit). Although this class of solids
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
Sin Ho Kweon et al.
Archives of pharmacal research, 34(2), 191-198 (2011-03-08)
Induction of differentiation is a new and promising approach to leukemia therapy, well illustrated by the treatment of acute promyelocytic leukemia with 1,25-dihydroxyvitamin D(3) [1,25-(OH)(2)D(3)] or all-trans retinoic acid (ATRA). Using combination of either 1,25-(OH)(2)D(3) or ATRA and chemotherapy, adverse
Francisco F P Arantes et al.
European journal of medicinal chemistry, 44(9), 3739-3745 (2009-05-02)
Ten alpha-santonin derivatives were synthesized in moderate to high yields. Four derivatives namely 10alpha-acetoxy-3-oxo-1,7alphaH,6,11betaH-guai-4-en-6,12-olide (2), isofotosantonic acid (3), 10alpha-hydroxy-3-oxo-1,7alphaH,6,11betaH-guai-4-en-6,12-olide (4), and lumisantonin (5), were prepared by different photochemical reactions using alpha-santonin (1) as starting material. These transformations were carried out
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