552-59-0 Usage
Description
Prunetin, also known as a hydroxyisoflavone, is a compound derived from genistein with a methoxy group replacing the hydroxy group at position 7. It exhibits a wide range of biological activities and has potential applications in various fields due to its unique chemical structure and properties.
Uses
Used in Pharmaceutical Applications:
Prunetin is used as a progesterone receptor antagonist, particularly at concentrations of 25 and 50 μM. This application is significant in the development of treatments for conditions related to hormonal imbalances or disorders influenced by progesterone receptor activity.
Used in Research and Development:
As a compound with diverse biological activities, Prunetin is utilized in research and development for the discovery of new drugs and therapies. Its unique structure and properties make it a valuable tool for studying various biological processes and identifying potential targets for intervention.
Used in Nutraceutical and Dietary Supplements:
Due to its potential health benefits and biological activities, Prunetin may be used as an ingredient in nutraceutical and dietary supplements. It could be incorporated into products aimed at promoting hormonal balance, supporting reproductive health, or providing antioxidant and anti-inflammatory benefits.
Used in Cosmetics and Personal Care:
Prunetin's potential antioxidant and anti-inflammatory properties may also make it a valuable ingredient in the cosmetics and personal care industry. It could be used in products designed to improve skin health, reduce signs of aging, or provide protection against environmental stressors.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 552-59-0 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,5 and 2 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 552-59:
(5*5)+(4*5)+(3*2)+(2*5)+(1*9)=70
70 % 10 = 0
So 552-59-0 is a valid CAS Registry Number.
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
552-59-0Relevant articles and documents
PRUNETIN 5-O-β-D-GLUCOPYRANOSIDE, AN ISOFLAVONE FROM THE PEDUNCLE OF PRUNUS AVIUM AND P. CERASUS
Khalid, S. A.,Gellert, M.,Szendrei, K.,Duddeck, Helmut
, p. 1560 - 1561 (1989)
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
Lu, Tzy-Ming,Ko, Horng-Huey,Ng, Lean-Teik,Hsieh, Yen-Pin
, p. 963 - 979 (2015/06/25)
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
Rusin, Aleksandra,Gogler, Agnieszka,Glowala-Kosinska, Magdalena,Bochenek, Daria,Gruca, Aleksandra,Grynkiewicz, Grzegorz,Zawisza, Jadwiga,Szeja, Wieslaw,Krawczyk, Zdzislaw
body text, p. 4939 - 4943 (2010/03/02)
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