68682-02-0

Basic information

• Product Name: (+/-)-8-PRENYLNARINGENIN
• Synonyms: (±)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-butenyl)-4H-1-benzopyran-4-one;2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-8-(3-Methyl-2-buten-1-yl)-4H-1-benzopyran-4-one;rac 8-Prenylnaringenin
• CAS NO: 68682-02-0
• Molecular Formula: C₂₀H₂₀O₅
• Molecular Weight: 340.37
• EINECS: 245-096-7
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 68682-02-0.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• Storage Temp.: −20°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: (+/-)-8-PRENYLNARINGENIN(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-8-PRENYLNARINGENIN(68682-02-0)
• EPA Substance Registry System: (+/-)-8-PRENYLNARINGENIN(68682-02-0)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 68682-02-0(Hazardous Substances Data)

Usage

Description

(±)-8-Prenylnaringenin ((±)-8-PN) is a prenylflavonoid with potent estrogenic activity that can be isolated from hops. It inhibits both isoforms of the human estrogen receptor (ER; IC50s = 57 and 68 nM for ERα and ERβ, respectively). (±)-8-PN is effective in vivo, suppressing loss of bone mineral density in ovariectomized rats and blocking changes in tail skin temperature in a rat model of postmenopausal hot flashes.

Uses

8-Prenylnaringenin is a prenylflavonoid, a class on non-steroidal phytoestrogen that mimicks and/or modulating endogenous estrogens via estrogen receptor binding.

Upstream product

• 480-41-1 5,7-Dihydroxy-2-(4-hydroxy-phenyl)-chroman-4-on 
• 870-63-3 prenyl bromide 
• 84092-47-7 5,7,4'-trimethoxymethoxy-8-(3,3-dimethylallyl)-flavanone 
• 115063-39-3 desmethylxanthohumol 
• 115-18-4 2-methyl-3-buten-2-ol 
• 334701-03-0 4-(7-acetoxy-5-((3-methylbut-2-en-1-yl)oxy)-4-oxochroman-2-yl)phenyl acetate 
• 906368-85-2 7,4'-di-triisopropylsilyloxy-8-prenylnaringenin 
• 521-48-2 isoxanthohumol 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 27364-71-2 2',4',6'-trihydroxy-3'-(3-methyl-2-butenyl)acetophenone 
• 84092-45-5 2',4'-bis(methoxymethoxy)-5'-(3,3-dimethylallyl)-6'-hydroxyacetophenone 
• 906368-84-1 7,4'-di-triisopropylsilyloxy-isoxanthohumol 
• 569-83-5 xanthohumol 
• 3162-03-6 2-(4-acetoxyphenyl)-5-hydroxy-4-oxochroman-7-yl acetate 

Downstream Products

• 70872-27-4 5-hydroxy-2-(4-hydroxyphenyl)-8,8-dimethyl-3,4-dihydro-2H,8H-benzo-<1,2;3,4-b'>dipyran-4-one 
• 68634-20-8 4',5-dihydroxy-6'',6''-dimethyl-5'',6''-dihydro-4''H-pyrano[2'',3'':7,8]flavanone 
• 53846-50-7 sophoraflavanone B 
• 152464-78-3 8-dimethylallylsteppogenin 
• 72357-31-4 4',5,7-trihydroxy-8-prenylflavone 
• 851776-94-8 (2S)-(-)-4-[5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-7-yloxy]butyric acid 
• 851776-96-0 (2R)-(+)-4-[5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-7-yloxy]butyric acid 
• 851776-92-6 (2S)-(-)-7-[5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-7-yloxy]heptanoic acid 
• 851776-95-9 (2R)-(+)-7-[5-hydroxy-2-(4-hydroxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-7-yloxy]heptanoic acid 
• 1141487-32-2 2-(4-acetoxyphenyl)-8-(3-methylbut-2-enyl)-4-oxochroman-5,7-diyl diacetate 

Relevant articles and documents

Transformation of 8-prenylnaringenin by Absidia coerulea and Beauveria bassiana

Beauveria bassiana AM278 and Absidia coerulea AM93 converted 8-prenylnaringenin (1) into two glycoside derivatives (7-O-β-d- glucopyranoside) (2) and 7-O-β-d-4?-O-methylglucopyranoside) (3) in high yields in processes conducted in Saboraud medium. 8-Prenylnaringenin 7-O-β-d-4?-O-methylglucopyranoside (3) is a new compound. 8-Prenylnaringenin-7-sulfate (4) was obtained in transformation of 1 by Absidia coerulea AM93 in a buffer. Formation of conjugated products in this study proceeds in a manner analogous to mammalian systems which indicates the potential use of microbes to mimic mammalian metabolism.

Neuroregenerative Potential of Prenyl- And Pyranochalcones: A Structure-Activity Study

Loss of neuronal tissue is a hallmark of age-related neurodegenerative diseases. Since adult neurogenesis has been confirmed in the human brain, great interest has arisen in substances stimulating the endogenous neuronal regeneration mechanism based on ad

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.