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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

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

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

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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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
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 Tsukada et al.
Biochemical and biophysical research communications, 140(3), 832-836 (1986-11-14)
Cirsiliol and AA861, specific arachidonate 5-lipoxygenase inhibitors, showed potent antiproliferative effects on human leukemic cell lines K562, Molt4B and HL60. On the other hand, HeLa cells were not affected by these drugs. In the inhibitor treated and growth retarded leukemia
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
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