Cirsiliol

Modify Date: 2024-01-06 21:18:56

Cirsiliol Structure
Cirsiliol structure
 Common Name Cirsiliol
CAS Number 34334-69-5 Molecular Weight 330.289
Density 1.5±0.1 g/cm3 Boiling Point 616.1±55.0 °C at 760 mmHg
Molecular Formula C17H14O7 Melting Point 280-281.5℃ (methanol )
MSDS Chinese USA Flash Point 230.8±25.0 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Cirsiliol


Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.

 Names

Name cirsiliol
Synonym More Synonyms

 Cirsiliol Biological Activity

Description Cirsiliol is a potent and selective 5-lipoxygenase inhibitor and a competitive low affinity benzodiazepine receptor ligand.
Related Catalog
Target

Target: 5-lipoxygenase[1]

In Vitro In concentrations from 0.01 to 300 μM, cirsiliol causes concentration-dependent relaxation of rat isolated ileum. Cirsiliol may inhibit Ca2+ influx but stimulates Ca2+ release from intracellular stores[1]. Treatment with rhamnetin or cirsiliol reduces the proliferation of NSCLC cells through the suppression of radiation-induced Notch-1 expression[2].
In Vivo In xenograft mouse model, tumor volume is significantly reduced by combinational treatment with irradiation and rhamnetin or cirsiliol compared with irradiation alone[2].
Cell Assay NSCLC, NCI-H1299, NCI-H460, WI-26 VA4 and MRC-5 cell lines are exposed to a single dose of γ-rays. Cells are then treated with rhamnetin and cirsiliol (5, 10, 15, 20, 25 μM) dissolved in DMSO for 4 h[2].
Animal Admin Mice[1] BALB/c athymic nude mice are injected with 2×106 NCI-H1299 cells. When the tumor has acquired a minimal volume of 200 mm3, DMSO or Cirsiliol (200 μg/kg body weight) is administered intraperitoneally every day for 25 days. The animals are also irradiated with 10 Gy once a week for 3 weeks. On day 25, the tumors are excised and subjected to further analyses[1].
References

[1]. Mustafa EH, et al. Effects of cirsiliol, a flavone isolated from Achillea fragrantissima, on rat isolated ileum. Gen Pharmacol. 1992 May;23(3):555-60.

[2]. Kang J, et al. Rhamnetin and cirsiliol induce radiosensitization and inhibition of epithelial-mesenchymal transition (EMT) by miR-34a-mediated suppression of Notch-1 expression in non-small cell lung cancer cell lines. J Biol Chem. 2013 Sep 20;288(38):27343-57.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 616.1±55.0 °C at 760 mmHg
Melting Point 280-281.5℃ (methanol )
Molecular Formula C17H14O7
Molecular Weight 330.289
Flash Point 230.8±25.0 °C
Exact Mass 330.073944
PSA 109.36000
LogP 2.27
Vapour Pressure 0.0±1.8 mmHg at 25°C
Index of Refraction 1.671
Storage condition 2-8℃

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Hazard Codes Xi
RIDADR NONH for all modes of transport
RTECS DJ3011100
HS Code 2914509090

 Synthetic Route

2-(3,4-bis-benzyloxy-phenyl)-5,6,7-trimethoxy-chromen-4-one structure

2-(3,4-bis-benz...

CAS#:51145-78-9

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Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
2,3,4-trimethoxy-6-hydroxyacetophenone structure

2,3,4-trimethox...

CAS#:22248-14-2

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Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
N/A structure

N/A

CAS#:55274-37-8

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Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
Ethanone,1-(3,6-dihydroxy-2,4-dimethoxyphenyl)- structure

Ethanone,1-(3,6...

CAS#:6962-57-8

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Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
3,4-bis(phenylmethoxy)benzoyl chloride structure

3,4-bis(phenylm...

CAS#:1486-54-0

~%

Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
2-(3,4-dibenzyloxybenzoyloxy) 4,5,6-trimethoxy acetophenone structure

2-(3,4-dibenzyl...

CAS#:55274-36-7

~%

Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
3',4'-diacetoxy-5-hydroxy-3,6,7-trimethoxyflavone structure

3',4'-diacetoxy...

CAS#:97389-87-2

~%

Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
2-(3,4-dihydroxyphenyl)-5,6,7-trimethoxychromen-4-one structure

2-(3,4-dihydrox...

CAS#:51145-79-0

~%

Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262
4-(5,6,7-trimethoxy-4-oxo-4H-chromen-2-yl)-1,2-phenylene diacetate structure

4-(5,6,7-trimet...

CAS#:97389-88-3

~%

Cirsiliol Structure

Cirsiliol

CAS#:34334-69-5

Literature: Horie, Tokunaru; Tsukayama, Masao; Kourai, Hiroki; Yokoyama, Chieko; Furukawa, Masayuki; et al. Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2256 - 2262

 Customs

HS Code 2914509090
Summary HS:2914509090 other ketones with other oxygen function VAT:17.0% Tax rebate rate:9.0% Supervision conditions:none MFN tariff:5.5% General tariff:30.0%

 Articles12

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[Chemical constituents of Eupatorium lindleyanum].

Zhongguo Zhong Yao Za Zhi 37(7) , 937-40, (2012)

To study chemical constituents of Eupatorium lindleyanum. Ethyl acetate extractive fractions were separated with silica gel and Sephadex LH-20 by column chromatography, and their structures were ident...

[Determination of flavonoids in buds of Herba Artemisiae Scopariae by HPLC].

Zhongguo Zhong Yao Za Zhi 30(8) , 591-4, (2005)

To develop a quantitative method for the determination of four flavonoids in buds of Herba Artemisiae Scopariae.The sample was extracted by ultrasonic with ethyl acetate for 30 minutes and separated o...

Potent and selective 5-lipoxygenase inhibitors: cirsiliol and AA-861.

Adv. Prostaglandin. Thromboxane. Leukot. Res. 15 , 217-9, (1985)

 Synonyms

5,3',4'-Trihydroxy-6,7-dimethoxyflavone
2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxychromen-4-one
6,7-dimethoxy-5,3',4'-trihydroxyflavone
4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-
3',4',5-Trihydoxy-6,7-dimethoxyflavone
2-(3,4-Dihydroxyphenyl)-5-hydroxy-6,7-dimethoxy-4H-chromen-4-one
6-Hydroxyluteolin-6,7-dimethyl ether
3',4',5-Trihydroxy-6,7-dimethoxyflavone
Cirsiliol
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Related Compounds: More...
Cirsiliol 4′-glucoside
41087-98-3
Chemsrc provides Cirsiliol(CAS#:34334-69-5) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Cirsiliol are included as well.>> amp version: Cirsiliol

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