90-19-7

Basic information

• Product Name: Rhamnetin
• Synonyms: 3,3,4,5-TETRAHYDROXY-7-METHOXYFLAVONE TECH GRADE;RHAMNETIN WITH HPLC;2-(3,4-Dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4H-1-benzopyran-4-one;7-Methoxyquercetin;4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-;Flavone, 3,3',4',5-tetrahydroxy-7-methoxy-;Nsc19802;2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-y-Methoxy-4H-1-benzopyran-4-one
• CAS NO: 90-19-7
• Molecular Formula: C₁₆H₁₂O₇
• Molecular Weight: 316.26
• EINECS: 201-974-1
• Product Categories: Flavanols;Aromatics;Heterocycles;Inhibitors;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;standard material,plant extracts
• Mol File: 90-19-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 293-296°C (dec.)
• Boiling Point: 375.7°C (rough estimate)
• Appearance: /
• Density: 1.3347 (rough estimate)
• Refractive Index: 1.4790 (estimate)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated)
• Stability: Hygroscopic
• BRN: 47741
• CAS DataBase Reference: Rhamnetin(CAS DataBase Reference)
• NIST Chemistry Reference: Rhamnetin(90-19-7)
• EPA Substance Registry System: Rhamnetin(90-19-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37
• WGK Germany: 3
• RTECS: LK8748000
• F: 3-10
• Hazardous Substances Data: 90-19-7(Hazardous Substances Data)

Usage

Uses

O-Methylated metabolite of the flavanoid Quercertin (Q509500) with antioxidant activity.

Definition

ChEBI: A monomethoxyflavone that is quercetin methylated at position 7.

Purification Methods

Crystallise rhamnetin from EtOH (m 292-293o), aqueous EtOH (m 294-296o) or MeOH (m 290-294o). or Me2CO/MeOH. [Kuhn & Low Chem Ber 77 211 1944, Jurd J Am Chem Soc 80 5531 1958.] The tetra-acetate has m 189-190o (from Me2CO/MeOH). [Beilstein 18 H 245, 18 II 237, 18 III/IV 3474.]

Upstream product

• 2068-02-2 2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one 
• 854693-27-9 3,4-bis-benzoyloxy-benzoic acid-anhydride 
• 857617-58-4 2-benzoyloxy-1-(2,6-dihydroxy-4-methoxy-phenyl)-ethanone 
• 117-39-5 quercetol 
• 20188-83-4 7-O-methylquercetin 3-O-α-L-rhamnopyranoside 
• 186581-53-3 diazomethane 
• 97258-86-1 3,5-Dihydroxy-7-methoxy-3',4'-diphenylmethylendioxy-flavon 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 498548-19-9 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-7-methoxy-4H-chromen-4-one 
• 498548-17-7 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 69789-11-3 3,4-Dibenzoyloxybenzoylchlorid 
• 69789-10-2 3,4-bis(benzoyloxy)benzoic acid 
• 143631-95-2 acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester 

Downstream Products

• 114889-48-4 3-acetoxy-2-(3,4-diacetoxy-phenyl)-5-hydroxy-7-methoxy-chromen-4-one 
• 16280-26-5 Rhamnetin-tetra-O-acetat 
• 1245-15-4 retusin 
• 108-73-6 3,5-dihydroxyphenol 
• 99-50-3 3,4-Dihydroxybenzoic acid 
• 117-39-5 quercetol 
• 2174-64-3 5-methoxyresorcinol 
• 112599-24-3 3-acetoxy-2-(3,4-diacetoxy-phenyl)-5,7-dimethoxy-chromen-4-one 
• 13459-07-9 2-(3,4-dihydroxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-chromen-4-one 
• 552-54-5 rhamnazin 

Relevant articles and documents

Rhamnetin Glycosides from the Genus Spiraea

Rhamnetin (7-O-methylquercetin,1) and its glycosides were found for the first time in the genus Spiraea (Rosaceae) during chromatographic studies of representatives from the subgenus Protospiraea. Leaves of S. salicifolia yielded1, rhamnetin-3-O-β-D-glucopyranoside (2), and two new flavonoids3and4that were identified by UV, IR, and NMR spectroscopy and mass spectrometry as rhamnetin-3-O-(6″-O-p-coumaroyl)-β-D-glucopyranoside (spiraearhamnin A,3) and rhamnetin-3-O-(6″-O-caffeoyl)-β-D-glucopyranoside (spiraearhamnin B,4). Leaves of S. betulifolia and S. betulifolia var. aemiliana afforded1and2and glycosides of kaempferol, quercetin, and isorhamnetin. Species of the subgenus Metaspiraea (S. alpina, S. chamaedryfolia, S. dahurica, S. hypericifolia, and S. media) did not contain1or its derivatives.

Biological evaluation and SAR analysis of O-methylated analogs of quercetin as inhibitors of cancer cell proliferation

Preclinical Research Using a high-throughout screening approach, the anticancer activities of 16 O-methylated (OMe) analogs of quercetin were assessed. The structure-activity relationships showed that OMe moieties at the 4′ and/or 7 positions were important for maintaining inhibitory activities against the 16 cancer cell lines. Furthermore, when the OH groups at the 3′ and 4′ positions were both replaced by OMe moieties, anticancer activity was enhanced.