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SMB00174

Sigma-Aldrich

Cirsimaritin

≥90% (LC/MS-ELSD)

Synonym(s):

4′,5-Dihydroxy-6,7-dimethoxyflavone, Skrofulein

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About This Item

Empirical Formula (Hill Notation):
C17H14O6
CAS Number:
6601-62-3
Molecular Weight:
314.29
MDL number:
MFCD00238561
UNSPSC Code:
12352200
PubChem Substance ID:
329824840
NACRES:
NA.25

Assay

≥90% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1cc2OC(=CC(=O)c2c(O)c1OC)c3ccc(O)cc3

InChI

1S/C17H14O6/c1-21-14-8-13-15(16(20)17(14)22-2)11(19)7-12(23-13)9-3-5-10(18)6-4-9/h3-8,18,20H,1-2H3

InChI key

ZIIAJIWLQUVGHB-UHFFFAOYSA-N

Related Categories

General description

Natural product derived from plant source.

Biochem/physiol Actions

Cirsimaritin has been shown to inhibit tumor cell growth and induce mitochondrial apoptosis in GBC-SD cells. It was proposed that cirsimaritin-induced reactive oxygen species is the trigger for ER stress and down-regulate the phosphorylation of Akt.

Pictograms

Skull and crossbonesEnvironment
GHS06,GHS09

Signal Word

Danger

Hazard Statements

H301,H410

Precautionary Statements

P273 - P301 + P310 + P330

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1

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

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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Effects of cirsimaritin, a flavone isolated from Artemisia judaica, on isolated guinea-pig ileum.
S S Abdalla et al.
Planta medica, 53(4), 322-324 (1987-08-01)
Zheng-wen Yu et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 30(17), 1335-1338 (2005-12-06)
To study chemical constituents of Incarvillea arguta and their accelerating PC-12 cell differentiation. The constituents were isolated and repeatedly purified on silica gel column chromatography, and were identified on the basis of physicochemical and spectroscopic analysis. The neurotrophic activity of
Mohamed Ben Sghaier et al.
Environmental toxicology and pharmacology, 32(3), 336-348 (2011-10-19)
Fractionation of the chloroformic extracts from Teucrium ramosissimum leaves resulted in the isolation of three flavonoids: genkwanin (1), cirsimaritin (2) and 4',7-dimethoxy apigenin (4) and one sesquiterpene: β-eudesmol (3). The structures were determined using data obtained from (1)H and (13)C
Jih-Pyang Wang et al.
Naunyn-Schmiedeberg's archives of pharmacology, 366(4), 307-314 (2002-09-19)
In this study, the cellular localization of the inhibitory effect of a natural flavonoid cirsimaritin against formyl-methionyl-leucyl-phenylalanine (fMLP)-induced respiratory burst in rat neutrophils was investigated. Cirsimaritin concentration-dependently inhibited the superoxide anion (O(*-)(2))generation and O(2) consumption (IC(50) 11.5+/-2.2 micro M and
J A Hasrat et al.
The Journal of pharmacy and pharmacology, 49(11), 1150-1156 (1997-12-24)
In traditional medicine Microtea debilis is used against proteinuria. In ligand-binding studies extracts of Microtea debilis have been shown to inhibit the binding of [3H]1,3-dipropyl-8-cyclopentylxanthine ([3H]DPCPX) to adenosine-A1 receptors in rat forebrain membranes. Subsequently, cirsimarin, a flavonoid, was isolated as
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