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8-PRENYLNARINGENIN

8-PRENYLNARINGENIN Structure
8-PRENYLNARINGENIN
  • CAS No.53846-50-7
  • Chemical Name:8-PRENYLNARINGENIN
  • CBNumber:CB31484307
  • Molecular Formula:C20H20O5
  • Formula Weight:340.37
  • MOL File:53846-50-7.mol
8-PRENYLNARINGENIN Property
  • Boiling point 597.6±50.0 °C(Predicted)
  • Density 1.314±0.06 g/cm3(Predicted)
  • storage temp. 2-8°C
  • solubility Soluble in DMSO
  • pka 7.70±0.40(Predicted)
  • form Solid
  • color White to off-white
  • BRN 5611472
  • InChI InChI=1S/C20H20O5/c1-11(2)3-8-14-15(22)9-16(23)19-17(24)10-18(25-20(14)19)12-4-6-13(21)7-5-12/h3-7,9,18,21-23H,8,10H2,1-2H3/t18-/m0/s1
  • InChIKey LPEPZZAVFJPLNZ-SFHVURJKSA-N
  • SMILES [C@H]1(C2=CC=C(O)C=C2)OC2=C(C/C=C(/C)\C)C(O)=CC(O)=C2C(=O)C1
  • LogP 4.037 (est)
  • FDA UNII 5L872SZR8X
Safety
  • WGK Germany  :3
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordWarning
  • Hazard statements H315-H319
  • Precautionary statements P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

8-PRENYLNARINGENIN Chemical Properties,Usage,Production

  • Uses (-)-8-Prenylnaringin is a prenylflavonoid, a class on non-steroidal phytoestrogen that mimicks and/or modulating endogenous estrogens via estrogen receptor binding.
  • Definition ChEBI: Sophoraflavanone B is a trihydroxyflavanone that is (S)-naringenin having a prenyl group at position 8. It has a role as a platelet aggregation inhibitor and a plant metabolite. It is a trihydroxyflavanone, a member of 4'-hydroxyflavanones and a (2S)-flavan-4-one. It is functionally related to a (S)-naringenin. It is a conjugate acid of a sophoraflavanone B(1-).
  • Biological Activity 8-prenylnaringenin is an estrogen receptor inhibitor.the two estrogen receptors erα and erβ belong to the nuclear receptor superfamily and are ligand-regulated transcription factors accounting for mediating the physiological effects of the steroid hormone 17α-estradiol. er is an established target for the development of synthetic ligands for therapeutic applications.
  • in vitro previous study identified 8-prenylnaringenin as a potent phytoestrogen in hops, which had an activity greater than other known plant estrogens. the estrogenic activity of 8-prenylnaringenin was reflected in its relative binding affinity to estrogen receptors from rat uteri. in addition, the presence of 8-prenylnaringenin in hops might explane the accounts of menstrual disturbances in female hop workers [1].
  • in vivo previous animal data demonstrated that 8-prenylnaringenin treatment could result in ampk signaling pathway activation, therefore suppressing lipogenesis. the consumption of 8-prenylnaringenin was able to prevent body weight gain and improve plasma lipid profile, with significant improvement of insulin resistance and glucose tolerance. moreove, it was found that 8-prenylnaringenin-enriched diet could ameliorate diabetic-associated metabolic disturbances via regulating glucose and lipid pathways [2].
  • IC 50 57 and 68 nm for erα and erβ, respectively
  • References [1] milligan sr, kalita jc, heyerick a, rong h, de cooman l, de keukeleire d. identification of a potent phytoestrogen in hops (humulus lupulus l.) and beer. j clin endocrinol metab. 1999 jun;84(6):2249-52.
    [2] costa r et al. xanthohumol and 8-prenylnaringenin ameliorate diabetic-related metabolic dysfunctions in mice. j nutr biochem. 2017 apr 6;45:39-47.
8-PRENYLNARINGENIN Preparation Products And Raw materials
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8-PRENYLNARINGENIN Spectrum
53846-50-7, 8-PRENYLNARINGENINRelated Search:
  • Flavonoids
  • Flavanones
  • 黄酮类
  • 抑制剂
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  • 植物提取物
  • 8-异戊烯基柚皮素,10 MM DMSO 溶液
  • 8-PRENYLNARINGENIN|||8-异戊烯基柚皮素
  • 8-苯基纳林格宁
  • (S)-5,7-二羟基-2-(4-羟基苯基)-8-(3-甲基丁-2-烯-1-基)苯并二氢吡喃-4-酮
  • 8-异戊烯基柚皮素/8PN
  • 间苯三酚杂质Y
  • 8-异戊烯基柚皮素
  • 53846-50-7
  • 8-Prenylnaringenin, 10 mM in DMSO
  • inhibit,Apoptosis,8?Prenylnaringenin,8-?Prenylnaringenin,Inhibitor,8 ?Prenylnaringenin
  • 5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
  • 8-PN
  • Phloroglucinol Impurity Y
  • (-)-8-Prenylnaringenin
  • 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-, (2S)-
  • (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
  • (S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-en-1-yl)chroman-4-one
  • Flavaprenin
  • (2S)- 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
  • Flavaprenin (8-Prenylnaringenin, Sophorafl)

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