68682-01-9

Basic information

• Product Name: 5,7,4'-trihydroxy-6-prenylflavanone
• Synonyms: 5,7,4'-trihydroxy-6-prenylflavanone
• CAS NO: 68682-01-9
• Molecular Weight: 340.376
• Mol File: 68682-01-9.mol
• Article Data: 18

Chemical Properties

• CAS DataBase Reference: 5,7,4'-trihydroxy-6-prenylflavanone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,4'-trihydroxy-6-prenylflavanone(68682-01-9)
• EPA Substance Registry System: 5,7,4'-trihydroxy-6-prenylflavanone(68682-01-9)

Safety Data

• Hazardous Substances Data: 68682-01-9(Hazardous Substances Data)

Usage

Description

5,7,4'-trihydroxy-6-prenylflavanone is a naturally occurring flavanone compound characterized by its unique structure featuring three hydroxyl groups at positions 5, 7, and 4', along with a prenyl group at the 6 position. 5,7,4'-trihydroxy-6-prenylflavanone is derived from various plant sources and exhibits a range of biological activities, making it a potential candidate for pharmaceutical and industrial applications.

Uses

Used in Pharmaceutical Industry:
5,7,4'-trihydroxy-6-prenylflavanone is used as a bioactive compound for its antimicrobial properties. It demonstrates growth inhibition against various bacterial strains, such as Escherichia coli, Staphylococcus aureus, and Klebsiella pneumoniae, making it a promising candidate for the development of new antimicrobial agents to combat drug-resistant infections.
Used in Cosmetic Industry:
5,7,4'-trihydroxy-6-prenylflavanone can be used as an active ingredient in the cosmetic industry due to its potential antioxidant and anti-inflammatory properties. These characteristics may contribute to the development of skincare products aimed at promoting skin health and addressing various skin conditions.
Used in Food Industry:
As a natural product with antimicrobial properties, 5,7,4'-trihydroxy-6-prenylflavanone can be utilized in the food industry as a preservative to extend the shelf life of perishable products and maintain their quality. Its potential antioxidant activity may also be beneficial in the development of functional foods with added health benefits.
Used in Agricultural Industry:
The antimicrobial properties of 5,7,4'-trihydroxy-6-prenylflavanone can be harnessed in the agricultural industry for the development of natural pesticides or fungicides. These could be used to protect crops from various pathogens, reducing the reliance on synthetic chemicals and promoting sustainable agricultural practices.

Upstream product

• 115-18-4 2-methyl-3-buten-2-ol 
• 480-41-1 naringenin 
• 569-83-5 xanthohumol 
• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 870-63-3 prenyl bromide 
• 115063-39-3 desmethylxanthohumol 
• 1026476-67-4 7,4’-O,O-diacetoxy-6-prenylnaringenin 
• 65490-09-7 2'-hydroxy-4',6'-bis(methoxymethoxy)acetophenone 
• 556-82-1 3-methyl-2-buten-1-ol 
• 1186-30-7 3,3-dimethylallyl diphosphate triammonium salt 
• 3162-03-6 2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate 
• 1026010-63-8 acetic acid 4-(7-acetoxy-6-allyl-5-hydroxy-4-oxochroman-2-yl)phenyl ester 
• 1026270-90-5 C₂₂H₂₀O₇ 
• 521-48-2 isoxanthohumol 

Downstream Products

• 70872-26-3 5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H,8H-benzo-<1,2-b;5,4-b'>dipyran-4-one 
• 68634-19-5 (+/-)-3,4,8,9-Tetrahydro-5-hydroxy-8-(4-hydroxyphenyl)-2,2-dimethyl-2H,10H-benzo<1,2-b:3,4-b'>dipyran-10-on 
• 68634-18-4 (+/-)-2,3,7,8-Tetrahydro-5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-4H,6H-benzo<1,2-b:5,4-b'>dipyran-4-on 
• 68682-02-0 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one 
• 115063-39-3 desmethylxanthohumol 

Relevant articles and documents

Resolution of diastereomeric flavonoid (1S)-(-)-camphanic acid esters via reversed-phase HPLC

Prenylflavonoids are an unique class of phytochemicals found in the inflorescences of the hop plant (Humulus lupulus). These flavonoids have demonstrated a wide range of biological activities, which may be influenced by their stereochemical configuration.

Prenylated flavonoids with potential antimicrobial activity: Synthesis, biological activity, and in silico study

Prenylated flavonoids are an important class of naturally occurring flavonoids with important biological activity, but their low abundance in nature limits their application in medicines. Here, we showed the hemisynthesis and the determination of various biological activities of seven prenylated flavonoids, named 7–13, with an emphasis on antimicrobial ones. Compounds 9, 11, and 12 showed inhibitory activity against human pathogenic fungi. Compounds 11, 12 (flavanones) and 13 (isoflavone) were the most active against clinical isolated Staphylococcus aureus MRSA, showing that structural requirements as prenylation at position C-6 or C-8 and OH at positions C-5, 7, and 4′ are key to the antibacterial activity. The combination of 11 or 12 with commercial antibiotics synergistically enhanced the antibacterial activity of vancomycin, ciprofloxacin, and methicillin in a factor of 10 to 100 times against drug-resistant bacteria. Compound 11 combined with ciprofloxacin was able to decrease the levels of ROS generated by ciprofloxacin. According to docking results of S enantiomer of 11 with ATP-binding cassette transporter showed the most favorable binding energy; however, more studies are needed to support this result.

PROCESSES FOR THE PREPARATION OF ORTHO-ALLYLATED HYDROXY ARYL COMPOUNDS

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

Design and synthesis of novel anti-hyperalgesic agents based on 6-prenylnaringenin as the T-type calcium channel blockers

Since 6-prenylnaringenin (6-PNG) was recently identified as a novel T-type calcium channel blocker with the IC50 value around 1 μM, a series of flavanone derivatives were designed, synthesized and subsequently evaluated for T-channel-blocking a