- 8-Prenylnaringenin
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- $9.80
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2020-01-10
- CAS:53846-50-7
- Min. Order: 1KG
- Purity: ≥98%
- Supply Ability: 20 tons
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| | 8-PRENYLNARINGENIN Basic information |
| Product Name: | 8-PRENYLNARINGENIN | | Synonyms: | Flavaprenin (8-Prenylnaringenin, Sophorafl);(2S)- 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one;Flavaprenin;(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one;4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-buten-1-yl)-, (2S)-;(-)-8-Prenylnaringenin;Phloroglucinol Impurity Y;5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one | | CAS: | 53846-50-7 | | MF: | C20H20O5 | | MW: | 340.37 | | EINECS: | | | Product Categories: | Flavanones;Flavonoids | | Mol File: | 53846-50-7.mol |  |
| | 8-PRENYLNARINGENIN Chemical Properties |
| 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) |
| | 8-PRENYLNARINGENIN Usage And Synthesis |
| Chemical Properties | White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Humulus lupulus. | | 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. | | Synthesis | A method of microbial cell-catalyzed synthesis of 8-isopentenylnaringenin from isoxanthohumol, comprising:
(1) accessing Eupenicillium javanicum CGMCC NO. 3.5706 to a culture solution to obtain a pre-reaction system;
(2) adding isoxanthohumol solution to the pre-reaction system obtained in step (1), and transforming and reacting at 25-30C, preferably 28C, for 5-7 days, preferably 6 days, to obtain the transformed culture solution; wherein the dosage of isoxanthohumol is 0.01-0.1 g in terms of per liter of culture solution, preferably 0.02 g;
(3) The transformed culture broth is post-treated to obtain 8-isopentenylnaringenin. | | 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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