CAS 1178-24-1 | 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxy- | CAS Number 1178-24-1

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1178-24-1 | 4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-

CAS No: 1178-24-1 Catalog No: AG000HUC MDL No:MFCD00210513

Product Description

Catalog Number:

AG000HUC

Chemical Name:

4H-1-Benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxy-

CAS Number:

1178-24-1

Molecular Formula:

C22H24O9

Molecular Weight:

432.4206

MDL Number:

MFCD00210513

IUPAC Name:

2-(3,4-dimethoxyphenyl)-3,5,6,7,8-pentamethoxychromen-4-one

InChI:

InChI=1S/C22H24O9/c1-24-12-9-8-11(10-13(12)25-2)16-19(27-4)15(23)14-17(26-3)20(28-5)22(30-7)21(29-6)18(14)31-16/h8-10H,1-7H3

InChI Key:

SSXJHQZOHUYEGD-UHFFFAOYSA-N

SMILES:

COc1cc(ccc1OC)c1oc2c(OC)c(OC)c(c(c2c(=O)c1OC)OC)OC

UNII:

288R4CAV1V

NSC Number:

618928

Properties

Complexity:

651

Compound Is Canonicalized:

Yes

Covalently-Bonded Unit Count:

Defined Atom Stereocenter Count:

Defined Bond Stereocenter Count:

Exact Mass:

432.142g/mol

Formal Charge:

Heavy Atom Count:

Hydrogen Bond Acceptor Count:

Hydrogen Bond Donor Count:

Isotope Atom Count:

Molecular Weight:

432.425g/mol

Monoisotopic Mass:

432.142g/mol

Rotatable Bond Count:

Topological Polar Surface Area:

90.9A^2

Undefined Atom Stereocenter Count:

Undefined Bond Stereocenter Count:

XLogP3:

3.2

Literature

Title	Journal
Heptamethoxyflavone, a citrus flavonoid, enhances brain-derived neurotrophic factor production and neurogenesis in the hippocampus following cerebral global ischemia in mice.	Neuroscience letters 20121024
Isolation and characterization of activators of ERK/MAPK from citrus plants.	International journal of molecular sciences 20120101
Neurotrophic effect of citrus auraptene: neuritogenic activity in PC12 cells.	International journal of molecular sciences 20120101
Isolation of six new flavonoids from Melicope triphylla.	Chemical & pharmaceutical bulletin 20120101
Inhibition of nitric oxide production and inducible nitric oxide synthase expression by a polymethoxyflavone from young fruits of Citrus unshiu in rat primary astrocytes.	Bioscience, biotechnology, and biochemistry 20120101
Structure-activity relationships of flavonoids as inhibitors of breast cancer resistance protein (BCRP).	Bioorganic & medicinal chemistry 20110315
Isolation and identification of polymethoxyflavones from the hybrid Citrus, hallabong.	Journal of agricultural and food chemistry 20100908
Flavonoids from the stems of Croton caudatus Geisel. var. tomentosus Hook.	Molecules (Basel, Switzerland) 20100226
Simultaneous determination of five bioactive flavonoids in pericarpium Citri reticulatae from china by high-performance liquid chromatography with dual wavelength detection.	Journal of agricultural and food chemistry 20090812
Polymethoxyflavones activate Ca2+-dependent apoptotic targets in adipocytes.	Journal of agricultural and food chemistry 20090708
Monodemethylated polymethoxyflavones from sweet orange (Citrus sinensis) peel inhibit growth of human lung cancer cells by apoptosis.	Molecular nutrition & food research 20090301
Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer.	Bioorganic & medicinal chemistry 20090101
Anti-inflammatory activity of an orange peel polymethoxylated flavone, 3',4',3,5,6,7,8-heptamethoxyflavone, in the rat carrageenan/paw edema and mouse lipopolysaccharide-challenge assays.	Journal of agricultural and food chemistry 20081022
A citrus polymethoxyflavonoid, nobiletin, is a novel MEK inhibitor that exhibits antitumor metastasis in human fibrosarcoma HT-1080 cells.	Biochemical and biophysical research communications 20080201
Validated reversed phase LC method for quantitative analysis of polymethoxyflavones in citrus peel extracts.	Journal of separation science 20080101
Effects of various methoxyflavones on vincristine uptake and multidrug resistance to vincristine in P-gp-overexpressing K562/ADM cells.	Pharmaceutical research 20071001
Isolation and syntheses of polymethoxyflavones and hydroxylated polymethoxyflavones as inhibitors of HL-60 cell lines.	Bioorganic & medicinal chemistry 20070515
Efficient and scalable method in isolation of polymethoxyflavones from orange peel extract by supercritical fluid chromatography.	Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20070201
Preparative isolation and purification of polymethoxylated flavones from Tangerine peel using high-speed counter-current chromatography.	Journal of chromatography. A 20051007
Effect of flavones on rat brain and lung matrix metalloproteinase activity measured by film in-situ zymography.	The Journal of pharmacy and pharmacology 20050401
[Chemical study of citrus plants in the search for cancer chemopreventive agents].	Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20050301
Topochemical model for prediction of anti-HIV activity of HEPT analogs.	Bioorganic & medicinal chemistry letters 20050117
Fungicidal potential of methoxylated flavones from citrus for in vitro control of Colletotrichum gloeosporioides, causal agent of anthracnose disease in tropical fruits.	Pest management science 20031101
Identification of epoxybergamottin as a CYP3A4 inhibitor in grapefruit peel.	European journal of clinical pharmacology 20030201
Increasing resistance against Phytophthora citrophthora in tangelo Nova fruits by modulating polymethoxyflavones levels.	Journal of agricultural and food chemistry 20020508
Genetic toxicity of a standardized mixture of citrus polymethoxylated flavones.	Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20020501
Immunotoxicity of a standardized citrus polymethoxylated flavone extract.	Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 20011101
Cancer chemopreventive activity of 3,5,6,7,8,3',4'-heptamethoxyflavone from the peel of citrus plants.	Cancer letters 20010210