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

pka

9.96±0.26(Predicted)

form 

solid

color 

White or off-white

Odor

Characteristic

λmax

321nm(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.

InChI

InChI=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+

InChIKey

VLEUZFDZJKSGMX-ONEGZZNKSA-N

SMILES

C1(O)=CC=C(/C=C/C2=CC(OC)=CC(OC)=C2)C=C1

LogP

4.056 (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 

Ⅲ

HS Code 

29095000

Pterostilbene Usage And Synthesis

Description

Pterostilbene (PTS) is a fragrant-smelling hydrocarbon called "styrene", which is a derivative of resveratrol. It is found in blueberries and Pterocarpus marsupium (PM) heartwood. Similar to resveratrol, PTS 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 pathway
to 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.

Side effects

The side effects of pterostilbene are relatively minor, but you still need to pay attention to the dosage. Low-dose pterostilbene supplementation improves cholesterol metabolism and reduces triglyceride levels. Side effects include mild weight loss and muscle pain, but dose adjustment is usually not necessary.

References

[1] ESTRELAJOSé M. Pterostilbene: Biomedical applications.[J]. Critical reviews in clinical laboratory sciences, 2013. DOI:10.3109/10408363.2013.805182.
[2] HYUNSOOK KIM  Wallace Y  Kun Ho Seo. Chemistry of Pterostilbene and Its Metabolic Effects[J]. Journal of Agricultural and Food Chemistry, 2020. DOI:10.1021/acs.jafc.0c00070.
[3] MACICKOVATATIANA. In vivo effect of pinosylvin and pterostilbene in the animal model of adjuvant arthritis.[J]. Neuro endocrinology letters, 2010.
[4] WASAMON NUTAKUL. Inhibitory Effects of Resveratrol and Pterostilbene on Human Colon Cancer Cells: A Side-by-Side Comparison[J]. Journal of Agricultural and Food Chemistry, 2011. DOI:10.1021/jf202846b.

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