537-42-8

Basic information

• Product Name: Pterostilbene
• Synonyms: AKOS 236-80;3,5-DIMETHOXY-4'-HYDROXYSTILBENE;3',5'-DIMETHOXY-4-STILBENOL;4-[(1E)-2-(3,5-DIMETHOXYPHENYL)ETHENYL]PHENOL;PTEROSTILBENE;PTEROCARPUS MARSUPIUM;TRANS-3,5-DIMETHOXY-4'-HYDROXYSTILBENE;(E)-3,5-Dimethoxy-4'-hydroxystilbene
• CAS NO: 537-42-8
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.3
• EINECS: 1308068-626-2
• Product Categories: Inhibitors;Health supplements;Herb extract;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product
• Mol File: 537-42-8.mol
• Article Data: 55

Chemical Properties

• Melting Point: 89-92 ºC
• Boiling Point: 420.4 °C at 760 mmHg
• Flash Point: 208.1 °C
• Appearance: off-white crystalline powder
• Density: 1.169 g/cm³
• Vapor Pressure: 1.15E-07mmHg at 25°C
• Refractive Index: 1.639
• Storage Temp.: 2-8°C
• Solubility: DMSO: >20mg/mL
• PKA: 9.96±0.26(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 week.
• CAS DataBase Reference: Pterostilbene(CAS DataBase Reference)
• NIST Chemistry Reference: Pterostilbene(537-42-8)
• EPA Substance Registry System: Pterostilbene(537-42-8)

Safety Data

• Hazard Codes: Xi,N
• Statements: 41-51/53
• Safety Statements: 26-39-61
• RIDADR: 3077
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 537-42-8(Hazardous Substances Data)

Usage

Description

Pterostilbene is a stilbenol derivative of resveratrol, characterized by its fragrant smell and hydrocarbon structure. It is a white crystalline powder that is sensitive to air and soluble in hot methanol and DMSO, but insoluble in water. Pterostilbene exhibits a range of pharmacological activities, including anti-inflammatory, anti-thrombotic, anti-cancer, anti-hyperlipidemia, and antibacterial effects. It is a natural molecule found in various fruits, vegetables, and nuts, with blueberries being one of its richest sources.

Uses

1. Used in Pharmaceutical Applications:
Pterostilbene is used as a therapeutic agent for the prevention and treatment of various diseases, including inflammation, cancer, diabetes, and dyslipidemia. Its diverse pharmacological activities make it a promising candidate for pharmaceutical research and development.
2. Used in Antioxidant Research:
Pterostilbene is used as a subject of investigation to study its anti-oxidative stress activities and the involvement of the nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-antioxidant response element (ARE) signaling pathway.
3. Used in Hormone-Resistant Breast Cancer Research:
Pterostilbene is used to determine its effects on the transcriptional activation of estrogen receptor-α (ERα) in hormone-resistant breast cancer cells, potentially offering insights into novel treatment strategies for this type of cancer.
4. Used in Functional Foods and Supplements:
Given its health-promoting properties, pterostilbene can be used as an additive or ingredient in the development of functional foods and dietary supplements aimed at promoting overall health and well-being.
5. Used in Cosmetics:
Due to its antioxidant and anti-inflammatory properties, pterostilbene can be utilized in the cosmetics industry for the development of skincare products that target inflammation, aging, and other skin conditions.

Preparation

Pterostilbene was synthesized from 3,5-dimethoxybenzyl bromide and p-nitrobenzaldehyde by Witting-Hornor reaction, reduction, diazotization and hydrolysis, with a total yield of 53.9%.

benefits

Pterostilbene is a naturally-derived stilbenoid structurally related to resveratrol, with potential antioxidant, anti-inflammatory, pro-apoptotic, antineoplastic and cytoprotective activities. Pterostilbene is known to have many pharmacological benefits for the prevention and treatment of a wide variety of diseases, including ( cancer (McCormack and McFadden 2012), dyslipidaemia (Rimando et al. 2005), diabetes (Amarnath Satheesh and Pari 2006), cardiovascular degeneration (Amarnath Satheesh and Pari 2008) and pain (Hougee et al. 2005).

Biological Activity

A cell-permeable methoxylated analog of Resveratrol that displays antioxidant, anti-proliferative, and hypoglycemic properties. Appears to be a better free radical scavenger than Trolox. Moderately inhibits COX-1 & COX-2 activities (IC50 = 19.8 μM & 83.9 μM, respectively) and induces apoptosis in HL60 cells (IC50 = 70 μM). Also prevents DMBA-induced pre-neoplastic lesions (ED50 = 4.8 μM). Reported to decrease plasma glucose levels in streptozotocin-induced diabetic rats comparable to that of Metformin.

InChI:InChI=1/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+

Upstream product

• 441351-31-1 trans-3,5-dimethoxy-4'-tert-butyldimethylsilyloxystilbene 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 77-78-1 dimethyl sulfate 
• 848487-76-3 (E)-1-(4'-(methoxymethoxy)styryl)-3,5-dimethoxybenzene 
• 186581-53-3 diazomethane 
• 74-88-4 methyl iodide 
• 4670-10-4 (3,5-dimethoxyphenyl)acetic acid 
• 123-08-0 4-hydroxy-benzaldehyde 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 108957-75-1 diethyl 3,5-dimethoxybenzylphosphonate 
• 705-76-0 3,5-dimethoxybenzyl alcohol 

Downstream Products

• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 1132-21-4 3,5-dimethoxybenzoic acid 
• 1028098-06-7 (E)-dibenzyl 4-(3,5-dimethoxystyryl)phenyl phosphate 
• 116518-94-6 3,5-di-O-methyldihydroresveratrol 
• 1032508-01-2 (E)-O-4-(3,5-dimethoxystyryl)phenyl dimethylcarbamothioate 
• 42438-89-1 pinostilbene 
• 1094101-40-2 4-(3,5-dimethoxystyryl)phenyl-2-(4-(4-chlorobenzoyl)phenoxy)-2-methyl propanoate 
• 1224713-66-9 1-(E)-2-[4-(allyloxy)phenyl]ethen-1-yl-3,5-dimethoxybenzene 
• 1224713-70-5 4-[(E)-2-(3,5-dimethoxyphenyl)ethen-1-yl]phenylmethanesulfonate 
• 1224713-69-2 4-[(E)-2-(3,5-dimethoxyphenyl)ethen-1-yl]phenyl-4-methyl-1-benzenesulfonate 
• 1224713-67-0 4-[(E)-2-(3,5-dimethoxyphenyl)ethen-1-yl]phenylbenzenesulfonate 
• 1224713-71-6 ethyl (E)-2-(4-(3,5-dimethoxystyryl)phenoxy)acetate 
• 1224713-65-8 2-{4-[(E)-2-(3,5-dimethoxyphenyl)ethen-1-yl]phenoxyethyl}-N,N-dimethylamine 
• 936318-66-0 4-(2-[4-(E)-2-(3,5-dimethoxyphenyl)ethen-1-yl]phenoxyethyl)morpholine 

Relevant articles and documents

Synthesis and evaluation of resveratrol derivatives as fetal hemoglobin inducers

Resveratrol (RVT) derivatives (10a-i) were designed, synthesized, and evaluated for their potential as gamma-globin inducers in treating Sickle Cell Disease (SCD) symptoms. All compounds were able to release NO at different levels ranging from 0 to 26.3percent, while RVT did not demonstrate this effect. In vivo, the antinociceptive effect was characterized using an acetic acid-induced abdominal contortion model. All compounds exhibited different levels of protection, ranging from 5.9 to 37.3percent; the compound 10a was the most potent among the series. At concentrations between 3.13 and 12.5 μM, the derivative 10a resulted in a reduction of 41.1–64.3percent in the TNF-α levels in the supernatants of macrophages that were previously LPS-stimulated. This inhibitory effect was higher than that of RVT used as the control. In addition, the compound 10a and RVT induced double the production of the gamma-globin chains (γG + γA), compared to the vehicle, using CD34+ cells. Compound 10a also did not induce membrane perturbation and it was not mutagenic in the in vivo assay. Thus, compound 10a emerged as a new prototype of the gamma-globin-inducer group with additional analgesic and anti-inflammatory activities and proving to be a useful alternative to treat SCD symptoms.

Preparation method of resveratrol compound

The invention provides a preparation method of a resveratrol compound, and belongs to the technical field of organic synthesis. The preparation method comprises the following steps: firstly, carryingout oxidation addition and reduction elimination reaction on alkoxy-substituted benzyl halide, alkoxy-substituted benzaldehyde and a metal catalyst to obtain alkoxy-substituted diacetophenone; then carrying out reduction, reverse elimination and selective debenzylation reaction on the alkoxy-substituted diacetophenone and the metal catalyst in a hydrogen atmosphere to obtain the resveratrol compound. In the preparation method, hydrogenation reduction, reverse elimination and selective debenzylation reaction can be achieved through a one-pot method, trans-olefin is directly obtained through thereaction, and the generation of isomers is avoided; the Lewis acid is removed from the source through the selective catalytic debenzylation of the reaction, so that the method has the advantage of high yield, and is an environment-friendly process. Experimental results show that the products obtained by the preparation method are trans-olefins, the purity can reach more than 99.5%, and the yieldis more than 80%.

Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage

C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.