552-59-0

Basic information

• Product Name: Prunetin
• Synonyms: 4’,5-dihydroxy-7-methoxy-isoflavon;5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4h-1-benzopyran-4-on;5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4h-1-benzopyran-4-one;5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4-benzopyrone;PRUNETIN(RG);5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-chromen-4-one;5-Hydroxy-3-(4-hydroxyphenyl)-7-methoxychromen-4-one;3-(p-Hydroxyphenyl)-5-hydroxy-7-methoxychromone
• CAS NO: 552-59-0
• Molecular Formula: C₁₆H₁₂O₅
• Molecular Weight: 284.26
• EINECS: 209-018-5
• Product Categories: Iso-Flavones
• Mol File: 552-59-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 240-242°C
• Boiling Point: 346.76°C (rough estimate)
• Flash Point: 209.7 °C
• Appearance: /
• Density: 1.2160 (rough estimate)
• Vapor Pressure: 1.49E-12mmHg at 25°C
• Refractive Index: 1.6200 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 6.35±0.20(Predicted)
• BRN: 292155
• CAS DataBase Reference: Prunetin(CAS DataBase Reference)
• NIST Chemistry Reference: Prunetin(552-59-0)
• EPA Substance Registry System: Prunetin(552-59-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• RTECS: DJ3100050
• F: 10
• Hazardous Substances Data: 552-59-0(Hazardous Substances Data)

Usage

Uses

Prunetin is isoflavone with diverse biological activities. Prunetin is an antagonist of the progesterone receptor when used at concentrations of 25 and 50 μM.

Definition

ChEBI: A hydroxyisoflavone that is genistein in which the hydroxy group at position 7 is replaced by a methoxy group.

Enzyme inhibitor

This Prunus species isoflavone (FW = 284.27 g/mol; CAS 552-59-0; melting point = 240°C), also known as 4’,5-dihydroxy-7- methoxyisoflavone and 5-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-4H-1- benzopyran-4-one, inhibits alcohol dehydrogenase, aldehyde dehydrogenase, 3’,5’-cyclic-nucleotide phosphodiesterase, phosphodiesterase 4, and protein-tyrosine kinase. Its 4’-glucoside is prunitrin. Methylated isoflavones, such as prunetin, are rapidly converted by CYP1A2 to more active genistein and daidzein, which inhibit.formation of acetaminophen from phenacetin with an IC50 value of 16 μM.

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

Upstream product

• 446-72-0 5,7-Dihydroxy-3-(4-hydroxy-phenyl)-chromen-4-on 
• 77-78-1 dimethyl sulfate 
• 853925-91-4 5-hydroxy-3-(4-hydroxy-phenyl)-7-methoxy-4-oxo-4H-chromene-2-carboxylic acid 
• 69127-80-6 3-(4-hydroxyphenyl)-5,7-dimethoxychromen-4-one 
• 333-27-7 methyl trifluoromethanesulfonate 
• 15485-65-1 2,4,4',6-tetrahydroxydeoxybenzoin 
• 485-80-3 S-adenosyl-L-methionine 
• 56982-36-6 2-hydroxy-4,6-dimethoxy-4'-nitro-deoxybenzoin 
• 98029-76-6 5,7-dimethoxy-3-(4-nitro-phenyl)-chromen-4-one 
• 855829-21-9 3-(4-amino-phenyl)-5,7-dimethoxy-chromen-4-one 
• 69127-79-3 2,4'-dihydroxy-4,6-dimethoxy-deoxybenzoin 
• 89595-66-4 prunetin 5‐O‐glucoside 
• 1162-82-9 4',5,7-trimethoxyisoflavone 
• 855938-33-9 4-(cyanomethyl)phenyl benzoate 

Downstream Products

• 34086-51-6 4',7-dimethoxy-5-hydroxyisoflavone 
• 23626-98-4 5,4'-diacetoxy-7-methoxyisoflavone 
• 156-38-7 4-hydroxyphenylacetate 
• 1179998-24-3 2-(2,6-dihydroxy-4-methoxyphenyl)-3-(4-hydroxyphenyl)-pyrimido[1,2-a]benzimidazole 
• 115123-86-9 4,5-diacetoxy-3-(4-acetoxy-phenyl)-7-methoxy-coumarin 
• 101094-12-6 2,6,4'-trihydroxy-4-methoxy-deoxybenzoin 
• 1162-82-9 4',5,7-trimethoxyisoflavone 
• 109570-89-0 3-(4-acetoxy-phenyl)-5-hydroxy-7-methoxy-chromen-4-one 

Relevant articles and documents

PRUNETIN 5-O-β-D-GLUCOPYRANOSIDE, AN ISOFLAVONE FROM THE PEDUNCLE OF PRUNUS AVIUM AND P. CERASUS

Prunetin 5-glucoside was isolated from cherry peduncle Prunus avium and P. cerasus.The structure was fully assigned on the basis of NMR evidence.It is the second 5-O-glycosylated isoflavonoid to be reported. Key Word Index-Prunus avium; P. ceraus; Rosaceae; cherry; peduncle; prunetin 5-glucoside; isoflavone.

Free-radical-scavenging, antityrosinase, and cellular melanogenesis inhibitory activities of synthetic isoflavones

In this study, we examined the potential of synthetic isoflavones for application in cosmeceuticals. Twenty-five isoflavones were synthesized and their capacities of free-radical-scavenging and mushroom tyrosinase inhibition, as well as their impact on cell viability of B16F10 murine melanoma cells and HaCaT human keratinocytes were evaluated. Isoflavones that showed significant mushroom tyrosinase inhibitory activities were further studied on reduction of cellular melanin formation and antityrosinase activities in B16F10 melanocytes in vitro. Among the isoflavones tested, 6-hydroxydaidzein (2) was the strongest scavenger of both ABTS.+ and DPPH. radicals with SC50 values of 11.3±0.3 and 9.4±0.1 μM, respectively. Texasin (20) exhibited the most potent inhibition of mushroom tyrosinase (IC50 14.9±4.5 μM), whereas retusin (17) showed the most efficient inhibition both of cellular melanin formation and antityrosinase activity in B16F10 melanocytes, respectively. In summary, both retusin (17) and texasin (20) exhibited potent free-radical-scavenging capacities as well as efficient inhibition of cellular melanogenesis, suggesting that they are valuable hit compounds with potential for advanced cosmeceutical development.

Unsaturated genistein disaccharide glycoside as a novel agent affecting microtubules

Genistein, due to its recognized chemopreventive and antitumor potential, is a molecule of interest as a lead compound in drug design. While multiple molecular targets for genistein have been identified, so far neither for this isoflavonoid nor for its na