Pterostilbene

Pterostilbene 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:537-42-8
MF:C16H16O3
MW:256.3
EINECS:611-041-4
Product Categories:chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;natural product;Health supplements;Herb extract;Inhibitors;API;537-42-8
Mol File:537-42-8.mol
Pterostilbene Structure
Pterostilbene Chemical Properties
Melting point 89-92 ºC
Boiling point 420.4±35.0 °C(Predicted)
density 1.169±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility DMSO: >20mg/mL
pka9.96±0.26(Predicted)
form solid
color White or off-white
OdorCharacteristic
λmax321nm(MeOH)(lit.)
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.
InChIInChI=1S/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+
InChIKeyVLEUZFDZJKSGMX-ONEGZZNKSA-N
SMILESC1(O)=CC=C(/C=C/C2=CC(OC)=CC(OC)=C2)C=C1
LogP4.056 (est)
Safety Information
Hazard Codes Xi,N
Risk Statements 41-51/53
Safety Statements 26-39-61
RIDADR 3077
WGK Germany 3
HazardClass IRRITANT
PackingGroup 
HS Code 29095000
MSDS Information
Pterostilbene Usage And Synthesis
DescriptionPterostilbene 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 PropertiesPterostilbene 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.
OccurrencePterostilbene 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.
UsesSubstantial 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 pathway
to determine its effects on transcriptional activation of estrogen receptor-α (ERα) in hormone resistant breast cancer cells)
PreparationPterostilbene 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%.
synthesis of Pterostilbene
DefinitionChEBI: 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.
benefitsPterostilbene 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 ActivityA 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.
Pterostilbene Preparation Products And Raw materials
Raw materials4-Nitrobenzaldehyde-->3,5-DIMETHOXYBENZYL BROMIDE
3,4-Dimethylenedioxypterocarpan PTEROSTILBENE Diphenyldimethoxysilane ANGOLENSIN (+)-Medicarpin Dimethyldimethoxysilane Phenol Red Phenol Pterostilbene4%-5% 1,1-Dimethoxyethane Pterocarpus santalinus, ext. 1,2-Diphenylethylenediamine PHENOL ON POLYSTYRENE PTEROSTILBENE(P),PTEROSTILBENE(RG) 9,10-Dimethoxy-pterocarpane-3-O-β-D-glucoside Pterostilbene 3-Aminophenol 4-hydrostyrene

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