Pterostilbene
[CAS# 537-42-8]

Identification

• Classification: Biochemical >> Plant extracts
• Name: Pterostilbene
• Synonyms: 3',5'-Dimethoxy-4-stilbenol; 4-[(1E)-2-(3,5-Dimethoxyphenyl)ethenyl]phenol
• Molecular Formula: C₁₆H₁₆O₃
• Molecular Weight: 256.30
• CAS Registry Number: 537-42-8
• EC Number: 611-041-4
• SMILES: COC1=CC(=CC(=C1)/C=C/C2=CC=C(C=C2)O)OC

Properties

• Solubility: 21.24 mg/L (25 °C water)
• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.640, Calc.^*
• Melting point: 137.45 °C
• Boiling Point: 420.5±35.0 °C (760 mmHg), Calc.^*, 379.57 °C
• Flash Point: 208.1±25.9 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS05;GHS09 Danger
• Risk Statements: H318-H411
• Safety Statements: P264+P265-P273-P280-P305+P354+P338-P317-P391-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	2	H411
Serious eye damage	Eye Dam.	1	H318

• Transport Information: UN 3077

Discovery and Applications

Pterostilbene is a natural stilbene compound that belongs to the same chemical family as resveratrol. It was first discovered in plants such as blueberries, grapes, and rosewood (a tree native to India). Scientists discovered that pterostilbene is a phytochemical with potent antioxidant and anti-inflammatory properties, leading to further research into its potential therapeutic applications. The chemical structure of pterostilbene consists of two methoxy groups (-OCH3) attached to the stilbene backbone, which enhances its bioavailability and bioactivity compared to resveratrol.

Pterostilbene has strong antioxidant activity and can effectively fight oxidative stress and neutralize free radicals in the body. It scavenges reactive oxygen species (ROS) and inhibits lipid peroxidation, thereby protecting cells and tissues from oxidative damage. Research suggests that pterostilbene may have cardioprotective effects, including lowering cholesterol levels, lowering blood pressure and preventing plaque buildup in the arteries. Pterostilbene can regulate lipid metabolism by inhibiting cholesterol synthesis and promoting the clearance of low-density lipoprotein (LDL) cholesterol. Pterostilbene has potential neuroprotective effects and the ability to support cognitive function. It crosses the blood-brain barrier and exerts antioxidant and anti-inflammatory effects in the brain, which may help prevent age-related cognitive decline and neurodegenerative diseases such as Alzheimer's and Parkinson's disease. Pterostilbene exhibits anti-inflammatory properties by inhibiting the production of pro-inflammatory cytokines and mediators such as tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6). By reducing inflammation, pterostilbene may reduce symptoms associated with inflammation, such as arthritis, inflammatory bowel disease, and asthma. Preliminary research suggests that pterostilbene may have anti-cancer properties by inhibiting cancer cell proliferation, inducing apoptosis (programmed cell death) and inhibiting tumor growth. The antioxidant and anti-inflammatory effects of pterostilbene may help prevent DNA damage and inhibit the formation and progression of various types of cancer, including breast, colon, prostate, and skin cancers. By neutralizing free radicals and reducing inflammation, pterostilbene helps prevent UV-induced skin damage, oxidative stress, and signs of premature aging such as wrinkles, fine lines, and age spots.

References

2021. Resveratrol-zinc nanoparticles or pterostilbene-zinc: Potential COVID-19 mono and adjuvant therapy. Biomedicine & Pharmacotherapy, 139.
DOI: 10.1016/j.biopha.2021.111626

2020. Pterostilbene Enhances Cytotoxicity and Chemosensitivity in Human Pancreatic Cancer Cells. Biomolecules, 10(5).
DOI: 10.3390/biom10050709

2019. Delivery of natural phenolic compounds for the potential treatment of lung cancer. Daru, 27(1).
DOI: 10.1007/s40199-019-00267-2