117047-35-5

Basic information

• Product Name: 4-geranyl-3,5,4'-trihydroxy-trans-stilbene
• Synonyms: 4-geranyl-3,5,4'-trihydroxy-trans-stilbene
• CAS NO: 117047-35-5
• Molecular Weight: 364.485
• Mol File: 117047-35-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 4-geranyl-3,5,4'-trihydroxy-trans-stilbene(CAS DataBase Reference)
• NIST Chemistry Reference: 4-geranyl-3,5,4'-trihydroxy-trans-stilbene(117047-35-5)
• EPA Substance Registry System: 4-geranyl-3,5,4'-trihydroxy-trans-stilbene(117047-35-5)

Safety Data

• Hazardous Substances Data: 117047-35-5(Hazardous Substances Data)

Upstream product

• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 763-10-0 geranyl diphosphate 
• 252679-37-1 4-((2E)-3,7-dimethyl-2,6-octadienyl)-3,5-bis(methoxymethoxy)benzyl alcohol 
• 76280-59-6 methyl 3,5-bis(methoxymethoxy)benzoate 
• 2150-44-9 1-carbomethoxy-3,5-dihydroxybenzene 
• 1381781-06-1 C₂₂H₃₁BrO₄ 
• 1381781-05-0 C₂₂H₃₀Br₂O₄ 
• 495412-19-6 4-(3,7-dimethyl-octa-2,6-dienyl)-3,5-bis-methoxymethoxy-benzaldehyde 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 123-11-5 4-methoxy-benzaldehyde 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 106-24-1 Geraniol 

Relevant articles and documents

Heterologous biosynthesis of prenylated resveratrol and evaluation of antioxidant activity

Prenylated stilbenoids are good candidates of nutraceuticals presented in food resources. The levels of natural prenylated stilbenoids are usually low. Biotransformation is a promising synthesis strategy to produce novel bioactive compounds. However, information regarding biosynthesis of prenylated stilbenoids is rare. In this work, prenyltransferase and geranyl diphosphate biosynthesis pathway were overexpressed in E. coli. Multiple prenyltransferase genes were tested and Ambp1 was found to be effective on resveratrol geranylation. The products were identified by mass spectrometry and nuclear magnetic resonance spectroscopy as 4-C-geranyl resveratrol (1) and 3-O-geranyl resveratrol (2, novel chemical). By optimization of culture conditions, a yield of 36.9% was achieved for the conversion to geranylated resveratrol from resveratrol. These two compounds demonstrated good antioxidant activities with IC50 values of 28.09 μM for 4-C-geranyl resveratrol and 403.88 μM for 3-O-geranyl resveratrol. The results were helpful for developing novel technique to produce prenylated phenolics.

Total synthesis and dual PPARα/γ agonist effects of Amorphastilbol and its synthetic derivatives

Amorphastilbol (APH-1), isolated from a Robinia pseudoacacia var. umbraculifer seed extract, is a biologically interesting natural trans-stilbene compound with dual peroxisome proliferator-activated receptor (PPAR) α/γ agonist activity. After total synthesis of APH-1 and its derivatives by Pd-catalyzed Suzuki-Miyaura cross-coupling of a common (E)-styryl bromide intermediate and various aromatic trifluoroborate compounds, we biologically evaluated APH-2-APH-12 for PPAR agonist activity. APH-4 and APH-11 were effective PPARα/γ transcriptional activators, compared with APH-1. Therefore, we suggest that APH-4 and APH-11 are novel dual PPARα/γ agonists and are potentially useful for treating type 2 diabetes by enhancing glucose and lipid metabolism.

METABOLITES FROM CHLOROPHORA EXCELSA: POSSIBLE INTERMEDIATES IN THE BIOGENESIS OF A PENTASUBSTITUTED STILBENE

Key Word Index-Chlorophora excelsa; Moraceae; 2,4-dihydroxybenzaldehyde; 3,5-dihydroxybenzaldehyde; 3,5-dihydroxy-4-geranylbenzaldehyde; 3',4,5'-trihydroxy-4'-geranylstilbene; 2,3',4,5'-tetrahydroxy-4'-geranylstilbene; 2,3',4,5'-tetrahydroxystilbene; 3,4'-7-tri-O-methylquercitin; 2'-methoxy-3,4',7-tri-O-methylquercitin.Abstract-A series comprising substituted hydroxyl-geranylstilbenes, substituted benzenoid compounds and quercitin-type flavones were isolated and characterized from the acetone extract of the heartwood of Chlorophora excelsa.