51225-30-0 Usage
Description
3-(4-Hydroxyphenyl)-5,7-dihydroxy-6-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, also known as Wighteone, is a natural product derivative of Genistein (G350000). It is a member of the class of 7-hydroxyisoflavones, characterized by the presence of hydroxy groups at positions 5, 7, and 4', and a prenyl group at position 6. Wighteone has been isolated from Ficus mucuso and exhibits various biological activities, making it a promising compound for pharmaceutical and industrial applications.
Uses
Used in Pharmaceutical Applications:
Wighteone is used as a bioactive compound for its inhibitory activity against tyrosine kinases, including the autophosphorylation of epidermal growth factor receptor kinase (IC50 2.6uM). It also inhibits other protein kinases through competitive inhibition of ATP. Wighteone has demonstrated the ability to inhibit tumor cell proliferation, induce tumor cell differentiation, and produce cell-cycle arrest and apoptosis in Jurkat T-leukemia cells. Additionally, it prevents anti-CD3 monoclonal antibody-induced thymic apoptosis. Wighteone also inhibits topoisomerase II activity in vitro, which contributes to its potential as a therapeutic agent.
Used in Drug Delivery Systems:
In the field of drug delivery, Wighteone can be employed as a component in the development of novel drug delivery systems. Its biological activities and chemical properties make it a suitable candidate for improving the delivery, bioavailability, and therapeutic outcomes of various drugs. Researchers can explore the use of Wighteone in the formulation of organic and metallic nanoparticles, liposomes, or other advanced drug delivery platforms to enhance the efficacy of existing treatments and develop new therapies.
Used in Chemical Research:
Wighteone's unique chemical structure and biological activities make it an interesting subject for chemical research. Scientists can study its interactions with various biological targets, such as enzymes, receptors, and cellular pathways, to gain a deeper understanding of its mechanisms of action. This knowledge can be applied to the design and synthesis of new compounds with improved pharmacological properties, potentially leading to the development of more effective drugs for various diseases.
Used in Analytical Chemistry:
Wighteone's UV absorption properties, with a maximum absorption at 262.5 nm (ε = 138), make it a useful compound for analytical chemistry applications. It can be employed as a reference compound or a chromophore in the development of new analytical methods, such as high-performance liquid chromatography (HPLC) or spectrophotometric assays, for the detection and quantification of related compounds in biological samples or pharmaceutical formulations.
Check Digit Verification of cas no
The CAS Registry Mumber 51225-30-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,2,2 and 5 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 51225-30:
(7*5)+(6*1)+(5*2)+(4*2)+(3*5)+(2*3)+(1*0)=80
80 % 10 = 0
So 51225-30-0 is a valid CAS Registry Number.
InChI:InChI=1/C20H18O5/c1-11(2)3-8-14-16(22)9-17-18(19(14)23)20(24)15(10-25-17)12-4-6-13(21)7-5-12/h3-7,9-10,21-23H,8H2,1-2H3
51225-30-0Relevant articles and documents
Complementary Flavonoid Prenylations by Fungal Indole Prenyltransferases
Zhou, Kang,Yu, Xia,Xie, Xiulan,Li, Shu-Ming
supporting information, p. 2229 - 2235 (2015/10/12)
Flavonoids are found mainly in plants and exhibit diverse biological and pharmacological activities, which can often be enhanced by prenylations. In plants, such reactions are catalyzed by membrane-bound prenyltransferases. In this study, the prenylation of nine flavonoids from different classes by a soluble fungal prenyltransferase (AnaPT) involved in the biosynthesis of the prenylated indole alkaloid acetylaszonalenin is demonstrated. The behavior of AnaPT toward flavonoids regarding substrate acceptance and prenylation positions clearly differs from that of the indole prenyltransferase 7-DMATS. The two enzymes are therefore complementary in flavonoid prenylations.
Selective C-6 prenylation of flavonoids via europium(III)-catalyzed claisen rearrangement and cross-metathesis
Tischer, Sandra,Metz, Peter
, p. 147 - 151 (2008/02/03)
Starting from the readily available parent flavonoids, the flavanone 6-prenylnaringenin, the isoflavone 6-prenylgenistein (wighteone, erythrinin B) and a protected derivative of the flavonol 6-prenylquercetin (gancaonin P) have been synthesized in short reaction sequences featuring the title processes as key steps.
Regioselective synthesis of 6-prenylpolyhydroxyisoflavone (wighteone) and wighteone hydrate with hypervalent iodine
Hossain, Mohammad M.,Tokuoka, Takanori,Yamashita, Kazuyo,Kawamura, Yasuhiko,Tsukayama, Masao
, p. 1201 - 1211 (2007/10/03)
The oxidative rearrangement of 3′-iodotetraalkoxychalcone with [hydroxyl(tosyloxy)iodo]benzene, followed by cyclization of the resultant acetal gave 6-iodotrialkoxyisoflavone. The coupling reaction of the isoflavone with 2-methyl-3-butyn-2-ol gave 6-alkynylisoflavone, whose hydrogenation gave wighteone hydrate. Wighteone was synthesized by dehydration of wighteone hydrate. Copyright Taylor & Francis Group, LLC.
