29550-13-8

Basic information

• Product Name: 5,6-DIHYDROXY-7-METHOXYFLAVONE
• Synonyms: BAICALEIN-7-METHYL ETHER;BAICALEIN METHYL ETHER;5,6-DIHYDROXY-7-METHOXYFLAVONE;NEGLETEIN;7-O-Methylbaicalein;negletein,Balcalein-7-methyl Ether;Baicalein-7-methylether, 98%, from Scutellaria baicalensis Georgi
• CAS NO: 29550-13-8
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• Product Categories: Tri-substituted Flavones
• Mol File: 29550-13-8.mol
• Article Data: 18

Chemical Properties

• Melting Point: 218-220°C
• Boiling Point: 541.1°Cat760mmHg
• Flash Point: 207.5°C
• Appearance: /
• Density: 1.42g/cm³
• Vapor Pressure: 2.54E-12mmHg at 25°C
• Refractive Index: 1.668
• PKA: 6.15±0.40(Predicted)
• CAS DataBase Reference: 5,6-DIHYDROXY-7-METHOXYFLAVONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIHYDROXY-7-METHOXYFLAVONE(29550-13-8)
• EPA Substance Registry System: 5,6-DIHYDROXY-7-METHOXYFLAVONE(29550-13-8)

Safety Data

• Statements: R36/37/38:Irritating to eyes, respiratory system and skin.
• Safety Statements: S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36:Wear suitable prot
• Hazardous Substances Data: 29550-13-8(Hazardous Substances Data)

Usage

Uses

Negletein is a flavonoid used in different pharmaceutical formulations that also plays bioactive functions.

InChI:InChI=1/C16H12O5/c1-20-13-8-12-14(16(19)15(13)18)10(17)7-11(21-12)9-5-3-2-4-6-9/h2-8,18-19H,1H3

Upstream product

• 742073-28-5 8-amino-5-hydroxy-7-methoxy-2-phenyl-chromen-4-one 
• 7647-01-0 hydrogenchloride 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 
• 74-88-4 methyl iodide 
• 740-33-0 mosloflavone 
• 520-28-5 tectochrysine 
• 6674-40-4 5-hydroxy-7-acetoxyflavone 
• 94465-55-1 7-methoxy-4-oxo-2-phenyl-4H-1-benzopyran-5,6-diyl diacetate 
• 67047-05-6 4-oxo-2-phenyl-4H-1-benzopyran-5,6,7-triyl triacetate 
• 973-67-1 5,6,7-trimethoxyflavone 
• 74-83-9 methyl bromide 
• 67-56-1 methanol 
• 57396-78-8 Oroxin A 
• 82475-03-4 Baicalin methyl ester 

Downstream Products

• 94465-55-1 7-methoxy-4-oxo-2-phenyl-4H-1-benzopyran-5,6-diyl diacetate 
• 491-67-8 5,6,7-trihydroxy-2-phenyl-4H-1-benzopyran-4-one 

Relevant articles and documents

A convenient and efficient approach to synthesize negletein from baicalin

A simple two-step/one-pot and highly efficient strategy for the synthesis of negletein from naturally abundant and inexpensive baicalin has been developed. In this one-pot sequence, esterification of baicalin catalyzed by concentrated H2SO

Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the in Vitro Cytotoxicity of Its Methylated Products

O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions. Substrate preference assays indicated that this recombinant enzyme favored polymethoxylated flavones (PMF)-type substrates in vitro, thereby providing biochemical evidence for the potential role of the enzyme in plants. Additionally, the cytotoxicity of the methylated products from the enzymatic catalytic reaction was evaluated in vitro using human gastric cell lines SGC-7901 and BGC-823. The results showed that the in vitro cytotoxicity of the flavonoids with the unsaturated C2-C3 bond was increased after being methylated at position 3’. These combined results provide biochemical insight regarding CrOMT2 in vitro and indicate the in vitro cytotoxicity of the products methylated by its catalytic reaction.

Crystal structures of the flavonoid Oroxylin A and the regioisomers Negletein and Wogonin

The flavonoid Oroxylin A (6-methoxychrysin or 5,7-dihydroxy-6-methoxy-2- phenyl-4H-chromen-4-one, C16H12O5) and its regioisomers are of increasing interest for a variety of bioactive functions and their pharmaceutical formulation is of importance. Previous difficulties in the separation and misidentification of Oroxylin A from its regioisomers Wogonin (8-methoxychrysin or 5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one) and Negletein (5,6- dihydroxy-7-methoxyflavone or 5,6-dihydroxy-7-methoxy-2-phenyl-4H-chromen- 4-one) render its full structural and powder X-ray characterization highly desirable. The low-temperature (100 K) crystal structures of Oroxylin A, Negletein and Wogonin sesquihydrate are reported for the first time. Wogonin crystallizes in two related but distinct hydrated forms. These have very similar powder diffractograms, indicating that such issues need to be addressed for its pharmaceutical formulation.