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SML0953

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
Assay:
≥90% (HPLC)
Form:
powder
Quality level:
100
Storage condition:
protect from light
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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 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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

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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Articles

Discover Bioactive Small Molecules for Cell Cycle

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

Bioactive Molecules for Apoptosis

Apoptosis regulation involves multiple pathways and molecules for cellular homeostasis.

Potent and selective 5-lipoxygenase inhibitors: cirsiliol and AA-861.
S W Kohno et al.
Advances in prostaglandin, thromboxane, and leukotriene research, 15, 217-219 (1985-01-01)
T Horie et al.
Journal of medicinal chemistry, 29(11), 2256-2262 (1986-11-01)
Arachidonate 5-lipoxygenase plays a pivotal role in the biosynthesis of leukotrienes. Cirsiliol (3',4',5-trihydroxy-6,7-dimethoxyflavone), a selective inhibitor of the enzyme, was derivatized by introducing alkyl groups of various chain lengths at positions 5, 6, 7, and 8 of the A ring
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
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Global Trade Item Number

SKUGTIN
SML0953-25MG04061832926032
SML0953-5MG04061832926049