53846-50-7

Basic information

• Product Name: 8-PRENYLNARINGENIN
• Synonyms: Flavaprenin;Flavaprenin (8-Prenylnaringenin, Sophorafl);(2S)- 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one
• CAS NO: 53846-50-7
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.37
• Product Categories: Flavanones;Flavonoids
• Mol File: 53846-50-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 597.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.314±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• Solubility: Soluble in DMSO
• PKA: 7.70±0.40(Predicted)
• BRN: 5611472
• CAS DataBase Reference: 8-PRENYLNARINGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: 8-PRENYLNARINGENIN(53846-50-7)
• EPA Substance Registry System: 8-PRENYLNARINGENIN(53846-50-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 53846-50-7(Hazardous Substances Data)

Usage

Description

8-PRENYLNARINGENIN, also known as (-)-8-Prenylnaringin, is a prenylflavonoid, a class of non-steroidal phytoestrogen that mimics and/or modulates endogenous estrogens via estrogen receptor binding. It is derived from natural plant sources and exhibits a range of biological activities, making it a promising candidate for various applications.

Uses

Used in Pharmaceutical Industry:
8-PRENYLNARINGENIN is used as a pharmaceutical agent for its potential estrogenic effects. It can be employed in the development of treatments for conditions related to hormonal imbalances, such as menopause symptoms, osteoporosis, and certain types of cancer.
Used in Nutraceutical Industry:
8-PRENYLNARINGENIN is used as a nutraceutical ingredient for its potential health benefits. It can be incorporated into dietary supplements and functional foods to support hormonal balance and promote overall well-being.
Used in Cosmetic Industry:
8-PRENYLNARINGENIN is used as an active ingredient in cosmetic products for its potential skin health benefits. It can be formulated into creams, lotions, and serums to help improve skin elasticity, reduce wrinkles, and maintain a youthful appearance.
Used in Agricultural Industry:
8-PRENYLNARINGENIN can be used as a natural plant growth regulator in the agricultural industry. It may help improve crop yield, enhance resistance to diseases, and promote overall plant health.

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.

Upstream product

• 569-83-5 xanthohumol 
• 68682-02-0 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-8-(3-methyl-but-2-enyl)-chroman-4-one 
• 70872-29-6 Isoxanthohumol 
• 334701-04-1 2-(4-acetoxyphenyl)-5-hydroxy-8-(3-methylbut-2-enyloxy)-4-oxochroman-7-yl acetate 
• 358-72-5 dimethylallyl diphosphate 
• 480-41-1 naringenin 
• 3682-04-0 (S)-2-(4-acetoxyphenyl)-4-oxochromane-5,7-diyl diacetate 
• 1141487-32-2 2-(4-acetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-5,7-diyl diacetate 
• 780724-90-5 dimethylallyl diphosphate 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 152464-78-3 8-dimethylallylsteppogenin 

Relevant articles and documents

Prenylflavonoids: A new class of non-steroidal phytoestrogen (Part 1). Isolation of 8-isopentenylnaringenin and an initial study on its structure- activity relationship

Bioassay-guided fractionation of a methanolic extract of a Thai crude drug, derived from heartwood of Anaxagorea luzonensis A. Gray (Annonaceae), resulted in the isolation of 8-isopentenylnaringenin (1) as an estrogen agonist with an activity of about an order of magnitude greater than genistein. Various flavonoids possessing isopentenyl side chains in the A- ring have been prepared and evaluated for their ability to bind estrogen receptor. In addition, enantiomers of 1 were separated and the respective enantiomers were assayed. These studies have demonstrated that the presence of an 8-isopentenyl group is an important factor for binding. Flavones, flavanones and flavonols having an isopentenyl substituent at C-8 exhibited an appreciable affinity for estrogen receptor. Conversely, isoflavones possessing an 8-isopentenyl substituent at C-8 did not show this activity. Movement of the isopentenyl group from position 8 to 6 resulted in loss of the activity. No significant difference was observed between 2(S)- and 2(R)- enantiomers of 1 in their binding affinity. Prenylflavonoids are reported to possess a wide range of biological activities; however, estrogenic activity has not been described.

Formation of (2 R)- And (2 S)-8-Prenylnaringenin Glucuronides by Human UDP-Glucuronosyltransferases

Occurring in hops (Humulus lupulus) and beer as a racemic mixture, (2R,2S)-8-prenylnaringenin (8-PN) is a potent phytoestrogen in hop dietary supplements used by women as alternatives to conventional hormone therapy. With a half-life exceeding 20 h, 8-PN is excreted primarily as 8-PN-7-O-glucuronide or 8-PN-4′-O-glucuronide. Human liver microsomes and 11 recombinant human UDP-glucuronosyltransferases (UGTs) were used to catalyze the formation of the two oxygen-linked glucuronides of purified (2R)-8-PN and (2S)-8-PN, which were subsequently identified using mass spectrometry and nuclear magnetic resonance spectroscopy. Formation of (2R)- and (2S)-8-PN-7-O-glucuronides predominated over the 8-PN-4′-O-glucuronides except for intestinal UGT1A10, which formed more (2S)-8-PN-4′-O-glucuronide. (2R)-8-PN was a better substrate for all 11 UGTs except for UGT1A1, which formed more of both (2S)-8-PN glucuronides than (2R)-8-PN glucuronides. Although several UGTs conjugated both enantiomers of 8-PN, some conjugated just one enantiomer, suggesting that human phenotypic variation might affect the routes of metabolism of this chiral estrogenic constituent of hops.

A practical access to highly enantiomerically pure flavanones by catalytic asymmetric transfer hydrogenation

A surprisingly selective, non-enzymatic kinetic resolution of readily available, racemic β-chiral ketones enabled the title process, which was applied to a rapid synthesis of several bioactive flavanones in virtually enantiopure form (see scheme; MOM=methoxymethyl, Ts=p-toluenesulfonyl). Copyright