Isorhamnetin

Base Information

• Chemical Name: Isorhamnetin
• CAS No.: 480-19-3
• Molecular Formula: C16H12O7
• Molecular Weight: 316.267
• Hs Code.: 29329990
• Mol file: 480-19-3.mol

Synonyms:3-Methoxy-3,4,5,7-tetrahydroxyflavone;3,5,7-trihydroxy-2-(4-hydroxy-3-methoxy-phenyl)chromen-4-one;4H-1-Benzopyran-4-one,3,5,7-trihydroxy-2- (4-hydroxy-3-methoxyphenyl)-;3-Methoxyquercetin;3-Methylquercetine;4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-;4H-1-Benzopyran-4-one, 2-(3-methoxy-4-hydroxyphenyl)-3,5,7-trihydroxy-;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-benzopyrone;Flavone, 3-methoxy-3,4,5,7-tetrahydroxy-;C.I. 75680;4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxy-3-methoxyphenyl)- (9CI);3-Methylquercetin;Flavonoid;3,5,7-Trihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one;

Chemical Property of Isorhamnetin

Chemical Property:

• Appearance/Colour: powder
• Vapor Pressure: 5.79E-15mmHg at 25°C
• Melting Point: 307 °C
• Refractive Index: 1.74
• Boiling Point: 599.429 °C at 760 mmHg
• PKA: 6.31±0.40(Predicted)
• Flash Point: 227.827 °C
• PSA: 120.36000
• Density: 1.634 g/cm³
• LogP: 2.29100
• Storage Temp.: 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

Isorhamnetin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-40
• Safety Statements: 22-36-26-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Isorhamnetin is a flavonoid, which occurs naturally in plants and it is also a metabolite of quercetin. Isorhamnetin has anti-inflammatory effect as it can reduce the formation of large amounts of nitric oxide by the inhibition the activation of nuclear factor-κB (NF-κB), which is a significant transcription factor for inducible nitric oxide synthase.? Isorhamnetin is also reported to have effect in inducing the expression of neurofilaments, and it potentiated the NGF-induced neurite outgrowth and neurofilament expression, which could be a new direction in searching potential candidates as new drugs or food supplements for neurodegenerative diseases.
• Uses: A metabolite of the flavanoid Quercetin (Q509500) with antioxidant properties. It helps to protect H9c2 cardiomyoblasts against H2O2-induced oxidative stress via the modulation of PI3K/Akt and ERK1/2 signaling pathways. Isorhamnetin is a natural flavonol aglycone that is the 3-methyl metabolite of quercetin . It has antioxidant activity and inhibits xanthine oxidase (IC50 = 0.40 μM). Isorhamnetin also competitively inhibits the human multidrug and toxic compounds extrusion transporter 1 (Ki = 0.32 μM), which has an important role in the excretion of xenobiotics at the kidney and liver. It has also been reported to potentiate the neurological actions of nerve growth factor, diminish the cardiotoxic impact of doxorubicin, and have beneficial anti-cancer effects. Reference Standard in the analysis of herbal medicinal products

Technology Process of Isorhamnetin

There total 67 articles about Isorhamnetin 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: 96.7%

4.2'.4'.6'-tetrahydroxy-3-methoxy-trans-chalcone (25515-47-3) → isorhamnetin (480-19-3)

Guidance literature:

With potassium hydrogensulfate; sodium hydrogencarbonate; sodium carbonate; In dichloromethane; water; acetone; at 20 ℃; for 42h; pH=9;

Reference yield: 92.0%

3,7-bis(benzyloxy)-2-(4-(benzyloxy)-3-methoxyphenyl)-5-hydroxy-4H-chromen-4-one → isorhamnetin (480-19-3)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In ethyl acetate; at 20 ℃; for 4h;

DOI:10.1021/acs.jnatprod.6b00274

Reference yield: 63.0%

isorhamnetin-3-O-glucoside (6743-92-6,50306-07-5,5041-82-7) → D-Glucose (2280-44-6) + isorhamnetin (480-19-3)

Guidance literature:

With hydrogen cation;

DOI:10.1007/BF00575723

upstream raw materials:

2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone

3,5,7,4′-tetrahydroxy-8,3′-dimethoxyflavone-3-O-β-D-glucopyranoside

isorhamnetin-3-O-glucoside

Quercetin-7-O-monoglucoside

Downstream raw materials:

3,5-dihydroxyphenol

3-methoxy-4-hydroxybenzoic acid

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-(((2R,3S,4S,5R)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4 -one

isorhamnetin 3-β-D-galactopyranoside

Refernces

• 1、 Ahmad, Saeed,Riaz, Naheed,Saleem, Muhammad,Jabbar, Abdul,Nisar-Ur-Rehman,Ashraf, Mohammad. "Antioxidant flavonoids from Alhagi maurorum". . p. 138 - 143. Retrieved 2010.
• 2、 Yokozawa, Takako,Kim, Hyun Young,Cho, Eun Ju,Choi, Jae Sue,Chung, Hae Young. "Antioxidant effects of isorhamnetin 3,7-di-O-β-D-glucopyranoside isolated from mustard leaf (Brassica juncea) in rats with streptozotocin-induced diabetes". . p. 5490 - 5495. Retrieved 2002.
• 3、 Wang, Dong-Mei,Pu, Wen-Jun,Wang, Yong-Hong,Zhang, Yu-Juan,Wang, Shan-Shan. "A new isorhamnetin glycoside and other phenolic compounds from Callianthemum taipaicum". . p. 4595 - 4603. Retrieved 2012.
• 4、 Abd El-Wahab, Mohammed F.,Abdalla, Ashraf N.,Mohammed, Abd El-Salam I.,Mohammed, Hamdoon A.,Ragab, Ehab A.,Shaheen, Usama. "Isolation, characterization, complete structural assignment, and anticancer activities of the methoxylated flavonoids from rhamnus disperma roots". . . Retrieved 2021/10/01.
• 5、 Xiong, Wei,Wang, Xiaohong,Shen, Xianyan,Hu, Cuifang,Wang, Xin,Wang, Fei,Zhang, Guolin,Wang, Chun. "Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone". . p. 13160 - 13176. Retrieved 2020/11/23.