Rhamnetin

Base Information

• Chemical Name: Rhamnetin
• CAS No.: 90-19-7
• Molecular Formula: C16H12 O7
• Molecular Weight: 316.267
• Mol file: 90-19-7.mol

Synonyms:Flavone,3,3',4',5-tetrahydroxy-7-methoxy- (7CI,8CI); Rhamnetin (6CI);3,3',4',5-Tetrahydroxy-7-methoxyflavone;3,5,3',4'-Tetrahydroxy-7-methoxyflavone; 7-Methoxyquercetin; 7-Methylquercetin;7-O-Methylquercetin; C.I. 75690; LY 805921; NSC 19802; Quercetin 7-methylether; b-Rhamnocitrin

Chemical Property of Rhamnetin

Chemical Property:

• Melting Point: 293-296°C (dec.)
• Refractive Index: 1.4790 (estimate)
• Boiling Point: 375.7°C (rough estimate)
• Flash Point: 238.9oC
• PSA: 120.36000
• Density: 1.3347 (rough estimate)
• LogP: 2.29100
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

98%,99%, ^*data from raw suppliers

7-O-Methyl quercetin ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Rhamnetin

There total 25 articles about Rhamnetin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-7-methoxy-4H-chromen-4-one (498548-19-9) → rhamnetin (90-19-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; ethanol; for 12h; under 760.051 Torr;

DOI:10.1016/j.ejmech.2012.04.044

Reference yield: 67.0%

acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester (143631-95-2) + methyl iodide (74-88-4) → rhamnetin (90-19-7)

Guidance literature:

acetic acid 2-acetoxy-4-(3,5-diacetoxy-7-hydroxy-4-oxo-4H-chromen-2-yl)-phenyl ester; methyl iodide; With potassium carbonate; In N,N-dimethyl-formamide; at -78 - 20 ℃;

With hydrogenchloride; In water; acetonitrile; for 1.5h; Reflux;

DOI:10.3390/molecules15074722

Reference yield: 53.0%

quercetol (117-39-5,74893-81-5) + dimethyl sulfate (77-78-1) → rhamnetin (90-19-7)

Guidance literature:

quercetol; With borax; sodium hydrogencarbonate; In water; acetone; at 70 ℃; for 0.5h;

dimethyl sulfate; With sodium hydrogencarbonate; In water; acetone; at 50 ℃; for 6h;

DOI:10.1055/s-0030-1258310

upstream raw materials:

2-(3,4-dihydroxyphenyl)-5-hydroxy-3,7-dimethoxychromen-4-one

3,4-bis-benzoyloxy-benzoic acid-anhydride

2-benzoyloxy-1-(2,6-dihydroxy-4-methoxy-phenyl)-ethanone

quercetol

Downstream raw materials:

3-acetoxy-2-(3,4-diacetoxy-phenyl)-5-hydroxy-7-methoxy-chromen-4-one

Rhamnetin-tetra-O-acetat

retusin

3,5-dihydroxyphenol

Refernces

• 1、 Pabuprapap, Wachirachai,Wassanatip, Yanisa,Khetkam, Pichit,Chaichompoo, Waraluck,Kunkaewom, Sukanya,Senabud, Pongpan,Hata, Janejira,Chokchaisiri, Ratchanaporn,Svasti, Saovaros,Suksamrarn, Apichart. "Quercetin analogs with high fetal hemoglobin-inducing activity". . p. 1755 - 1765. Retrieved 2019/08/02.
• 2、 Ryu, Byeol,Kim, Hye Mi,Lee, Jin Su,Lee, Chan Kyu,Sezirahiga, Jurdas,Woo, Jeong-Hwa,Choi, Jung-Hye,Jang, Dae Sik. "New Flavonol Glucuronides from the Flower Buds of Syzygium aromaticum (Clove)". . p. 3048 - 3053. Retrieved 2016/05/19.