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 fragrant-smelling hydrocarbon called "styrene", which is a derivative of resveratrol. It is found in blueberries and Pterocarpus marsupium (PM) heartwood. It has anti-inflammatory, anti-thrombotic, anti-cancer, anti-cancer, anti-hyperlipidemia and antibacterial effects.

Chemical Properties

Pterostilbene is a white crystalline powder, sensitive to air, soluble in hot methanol, DMSO, insoluble in water. It is a stilbenoid chemically similar to resveratrol and from the leguminous plant Pterocarpus indicus.

Occurrence

Pterostilbene is a natural molecule found in fruits, vegetables and nuts. Blueberries are often quoted as one of the richest sources of pterostilbene. It is also found in almonds,various Vaccinium berries (including blueberries), grape leaves and vines,and Pterocarpus marsupium heartwood.

Uses

Substantial studies demonstrate that pterostilbene has diverse pharmacological activities for the prevention and treatment of diseases including inflammation, cancer, diabetes, and dyslipidemia.Pterostilbene has been used:to investigate its anti-oxidative stress activities and the involvement of the nuclear factor (erythroid-derived 2)-like 2 (Nrf2)-antioxidant response element (ARE) signaling pathwayto determine its effects on transcriptional activation of estrogen receptor-α (ERα) in hormone resistant breast cancer cells)

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%.

Definition

ChEBI: Pterostilbene is a stilbenol that consists of trans-stilbene bearing a hydroxy group at position 4 as well as two methoxy substituents at positions 3' and 5'. It has a role as an antioxidant, an antineoplastic agent, a neurotransmitter, a plant metabolite, an apoptosis inducer, a neuroprotective agent, an anti-inflammatory agent, a radical scavenger and a hypoglycemic agent. It is a stilbenol, a member of methoxybenzenes and a diether. It derives from a hydride of a trans-stilbene.

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

• 7311-34-4 3,5-dimethoxybenzaldehdye 
• 1012-12-0 4-(trimethylsiloxy)benzaldehyde 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 24131-30-4 (3,5-dimethoxybenzyl)triphenylphosphonium bromide 
• 123-08-0 4-hydroxy-benzaldehyde 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 6515-21-5 4-methoxymethoxy-benzaldehyde 
• 120743-99-9 p-[(tert-butyldimethylsilyl)oxy]benzaldehyde 
• 4670-10-4 (3,5-dimethoxyphenyl)acetic acid 
• 501-36-0 (E)-5-[2-4-(hydroxyphenyl)ethenyl]-1,3-benzenediol 
• 74-88-4 methyl iodide 
• 186581-53-3 diazomethane 
• 848487-76-3 (E)-1-(4'-(methoxymethoxy)styryl)-3,5-dimethoxybenzene 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 22255-22-7 3,5,4'-trimethoxy-trans-stilbene 
• 60640-98-4 2,4-Dimethoxy-6-hydroxy-phenanthren 
• 441351-32-2 (Z)-4-hydroxy-3',5'-dimethoxystilbene 
• 1032508-02-3 (E)-S-4-(3,5-dimethoxystyryl)phenyl dimethylcarbamothioate 
• 1032508-00-1 trans-3',5'-dimethoxy-4-mercaptostilbene 
• 1511857-26-3 (E)-4-(3-hydroxy-5-methoxystyryl)phenyl 2-acetoxybenzoate 
• 1511857-25-2 (E)-4-(3,5-dimethoxystyryl)phenyl 2-acetoxybenzoate 

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.