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Safety Information

SML0953

Sigma-Aldrich

Cirsiliol

≥90% (HPLC)

Synonym(s):

2-(3,4-Dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-1-benzopyran-4-one, 3′,4′,5-Trihydroxy-6,7-dimethoxy-flavone, 5,3′,4′-Trihydroxy-6,7-dimethoxyflavone, 6,7-Dimethoxy-5,3′,4′-trihydroxyflavone, 6-Hydroxyluteolin-6,7-dimethyl ether, 6-Methoxyluteolin 7-methyl ether, Crisiliol

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About This Item

Empirical Formula (Hill Notation):
C17H14O7
CAS Number:
34334-69-5
Molecular Weight:
330.29
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

100

Assay

≥90% (HPLC)

form

powder

storage condition

protect from light

color

white to beige

solubility

DMSO: 10 mg/mL, clear

storage temp.

2-8°C

SMILES string

[o]1c2c([c](cc1c3cc(c(cc3)O)O)=O)c(c(c(c2)OC)OC)O

InChI

1S/C17H14O7/c1-22-14-7-13-15(16(21)17(14)23-2)11(20)6-12(24-13)8-3-4-9(18)10(19)5-8/h3-7,18-19,21H,1-2H3

InChI key

IMEYGBIXGJLUIS-UHFFFAOYSA-N

Biochem/physiol Actions

Cirsiliol is a flavonoid that displays anti-inflammatory, anti-oxidant, anti-proliferative, and anti-bacterial activities. Cirsiliol sensitizes non-small cell lung cancer cell lines (NSCLC) to radiation therapy. Cirsiliol inhibits epithelial-mesenchymal transition likely by induction of tumor-suppressive miR-34a, which suppresses Notch-1 expression NSCLC.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000138101
0000138100
0000138100
0000138101
0000130749

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Mariel Marder et al.
Current topics in medicinal chemistry, 2(8), 853-867 (2002-08-13)
This review describes the new research developments that have established the CNS-activity of some natural flavonoids. The properties of flavone, chrysin, apigenin and cirsiliol are described and a survey of the occurrence of ligands for the benzodiazepine binding site in
T Yoshimoto et al.
Biochemical and biophysical research communications, 116(2), 612-618 (1983-10-31)
Various flavonoids were found to be relatively selective inhibitors of arachidonate 5-lipoxygenase which initiates the biosynthesis of leukotrienes with the activity of slow reacting substance of anaphylaxis. Cirsiliol (3',4',5-trihydroxy-6,7-dimethoxyflavone) was most potent, and the enzyme partially purified from rat basophilic
S Yamamoto et al.
The Journal of allergy and clinical immunology, 74(3 Pt 2), 349-352 (1984-09-01)
The 5-lipoxygenases of guinea pig peritoneal polymorphonuclear leukocytes and of rat basophilic leukemia cells have been solubilized, purified partially by affinity chromatography, and shown to convert arachidonic acid principally to 5-hydroperoxy-6,8,11,14- eicosatetraenoic acid. The activity of both 5-lipoxygenases is calcium
H Blomgren et al.
Anticancer research, 12(3), 981-986 (1992-05-01)
In an attempt to find new methods for the treatment of malignant gliomas a number of tests have been performed to learn whether growth of such cells in vitro may be affected by agents which interfere with the biosynthesis of
E H Mustafa et al.
General pharmacology, 23(3), 555-560 (1992-05-01)
1. In concentrations from 10(-8) M to 3 x 10(-4) M, cirsiliol caused concentration-dependent relaxation of rat isolated ileum. 2. Phentolamine (10(-6) M) or phentolamine and propranolol (10(-6) M) had no significant effects on the concentration-effect curves or on the
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