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ChemicalBook--->CAS DataBase List--->53846-50-7

53846-50-7

53846-50-7 Structure

53846-50-7 Structure
IdentificationBack Directory
[Name]

8-PRENYLNARINGENIN
[CAS]

53846-50-7
[Synonyms]

8-PN
Flavaprenin
(-)-8-Prenylnaringenin
Phloroglucinol Impurity Y
Flavaprenin (8-Prenylnaringenin, Sophorafl)
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
(2S)- 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-, (2S)-
[Molecular Formula]

C20H20O5
[MDL Number]

MFCD21364781
[MOL File]

53846-50-7.mol
[Molecular Weight]

340.37
Chemical PropertiesBack Directory
[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
[form ]

neat
[pka]

7.70±0.40(Predicted)
[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)
Safety DataBack Directory
[WGK Germany ]

3
Hazard InformationBack Directory
[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
[storage]

4°C, protect from light
[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.
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