475231-21-1

Basic information

• Product Name: 3'-Hydroxypterostilbene
• Synonyms: 3'-Hydroxypterostilbene;3'-H518-82-1ydroxypterostilbene;4-[(E)-2-(3,5-Dimethoxyphenyl)ethenyl]benzene-1,2-diol;4-[(E)-2-(3,5-Dimethoxyphenyl)vinyl]benzene-1,2-diol;4-[(1E)-2-(3,5-Dimethoxyphenyl)vinyl]benzene-1,2-diol
• CAS NO: 475231-21-1
• Molecular Formula: C16H16O4
• Molecular Weight: 272.298
• EINECS: 1312995-182-4
• Product Categories: reference substance
• Mol File: 475231-21-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 469.67 °C at 760 mmHg
• Flash Point: 237.848 °C
• Appearance: /
• Density: 1.252 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3'-Hydroxypterostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: 3'-Hydroxypterostilbene(475231-21-1)
• EPA Substance Registry System: 3'-Hydroxypterostilbene(475231-21-1)

Safety Data

• Hazardous Substances Data: 475231-21-1(Hazardous Substances Data)

Usage

Description

3'-Hydroxypterostilbene, also known as (E)-4-(3,5-dimethoxystyryl)benzene-1,2-diol, is a naturally occurring compound with potential applications in various fields. It is characterized by its unique chemical structure, which includes a stilbene backbone with hydroxyl and methoxy groups attached.

Uses

Used in Pharmaceutical and Toxicological Research:
3'-Hydroxypterostilbene is used as a subject for biological studies, specifically for evaluating its 90-day repeated dose oral toxicity and reproductive/developmental toxicity in experimental animals. This application is crucial for understanding the safety and potential side effects of the compound before considering its use in pharmaceutical or therapeutic applications.
Used in Chemical and Material Science:
3'-Hydroxypterostilbene may also have potential applications in the chemical and material science industries due to its unique chemical structure. It could be used as a building block for the synthesis of new compounds or materials with specific properties, such as optical, electronic, or mechanical characteristics.

Upstream product

• 99815-16-4 3,4-bis(tert-butyldimethylsilanyloxy)benzaldehyde 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 17345-77-6 1-bromo-3,4-dihydroxybenzene 
• 1073354-86-5 2-[(E)-2-(3,5-dimethoxyphenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 537-42-8 3,5-dimethoxy-4'-hydroxy-trans-stilbene 
• 150258-69-8 1,2-bis(benzyloxy)-4-(bromomethyl)benzene 
• 1699-58-7 3,4-bis(benzyloxy)benzyl alcohol 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 

Downstream Products

• 1235867-72-7 C₁₆H₁₆O₇S 

Relevant articles and documents

Enzymatic synthesis of a catecholic polyphenol product with excellent antioxidant activity

Polyphenols, especially catecholic stilbene derivatives, have attracted much attention due to the huge pharmacological effects and promising health benefits. However, their chemical synthesis via regioselective ortho-hydroxylation on aromatic rings is highly challenging. In this study, 3′-hydroxypterostilbene (HPS) is taken as a model product due to its strong potential as an antitumor agent. One-step enzymatic synthesis of HPS from pterostilbene (PS) was explored, with immobilised tyrosinase as catalyst. The impact of solvent, pH, temperature, oxygen and reductant concentration on the reaction was investigated, and the conversion was optimised by employing the response surface methodology (RSM). Finally, a high yield of 77.9% was obtained in 2.7 h. This study demonstrates the first successful use of a biotechnological strategy to synthesise HPS. The antioxidant activities of both PS and HPS were evaluated by using the DPPH assay, demonstrating that HPS is more potent than PS as a radical scavenger.

Protective effect of piceatannol and bioactive stilbene derivatives against hypoxia-induced toxicity in H9c2 cardiomyocytes and structural elucidation as 5-LOX inhibitors

Stilbenes with well-known antioxidant and antiradical properties are beneficial in different pathologies including cardiovascular diseases. The present research was performed to investigate the potential protective effect of resveratrol (1) and piceatannol (2), against hypoxia-induced oxidative stress in the H9c2 cardiomyoblast cell line, and the underlying mechanisms. Compounds 1 and 2 significantly inhibited the release of peroxynitrite and thiobarbituric acid levels at na no- or submicromolar concentrations, and this effect was more evident in piceatannol-treated cells, that significantly increased MnSOD protein level in a concentration dependent manner. Furthermore, since piceatannol, which is far less abundant in natural sources, displayed a higher bioactivity than the parent compound, we hereby report on a very fast synthesis and detailed structure-based design of a focused stilbene library. Finally, taking into account that hypoxia-induced ROS accumulation also increases expression and activity of 5-lipoxygenase (5-LOX) with production of leukotrienes, we have disclosed structural key factors crucial for 5-LOX activity. Among the synthesized analogues (3–7), compound 7 was the most effective in improving cardiomyocytes viability and in 5-LOX inhibition. In conclusion, modeling and experimental studies provided the basis for further optimization of stilbene analogues as multi-target inhibitors of the inflammatory and oxidative pathway.

Process for the manufacture of 3′-hydroxy pterostilbene

The invention discloses high yielding synthetic process for 3′-hydroxy pterostilbene.