Resveratrol

Resveratrol (3,5,4′-trihydroxy-trans-stilbene) is a naturally occurring polyphenol most famously found in the skin of red grapes, berries, and peanuts. In humans, it is taken as a dietary supplement primarily for its antioxidant and anti-inflammatory actions, which have been linked to cardiovascular, metabolic, and neuro-protective effects in pre-clinical and early-clinical studies.

• Compound Type: Resveratrol is a stilbene polyphenol.
• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24 g/mol
• IUPAC Name: 5-(4-hydroxyphenyl)-1-(2-hydroxyphenyl)-2-propene (or trans-3-(4-hydroxyphenyl)-2-propene-5-ol).
• Structure: It consists of two phenolic rings linked by an ethylene bridge (C=C), existing mainly as the trans isomer (more biologically active than the cis form).
• Key Features: Key structural features include three hydroxyl groups (positions 3, 4′, and 5) conferring antioxidant activity, and a planar, conjugated double-bond system that enables free-radical scavenging.
• Solubility: Solubility is low in water (<0.05 mg/mL) but higher in ethanol and oily matrices; the compound is stable under acidic conditions but degrades with light and high pH.

• Natural Sources: Natural resveratrol is extracted from Vitis vinifera (red grape skins, red wine), Polygonum cuspidatum (Japanese knotweed), Arachis hypogaea (peanuts), and Vaccinium species (blueberries).
• Extraction Methods:
  • Commercially, high-pressure liquid chromatography (HPLC) isolates the trans-isomer from plant extracts.
  • Alternatively, synthetic chemical routes (Wittig or Heck coupling) produce >99 % pure trans-resveratrol for pharmaceutical-grade products.
• Quality Considerations:
  • % trans-isomer purity
  • Absence of heavy-metal contamination
  • Verification by LC-MS or HPLC-UV
• Manufacturing Practices: Good Manufacturing Practice (GMP) facilities often use supercritical CO₂ extraction to minimize solvent residues.
• Product Verification: Look for third-party testing (e.g., USP, NSF) and an NRF (non-reactive filler) matrix to ensure stability and bioavailability.