Isorhamnetin 3-glucoside-7-rhamnoside 98% Purity CAS 17331-71-4 Research Grade Flavonoid Diglycoside Reference Standard for HPLC Analysis

Product Overview

Isorhamnetin 3‑glucoside‑7‑rhamnoside (CAS 17331‑71‑4) is a high‑purity flavonoid diglycoside reference standard, featuring isorhamnetin as the aglycone with a glucose moiety at the 3‑position and a rhamnose moiety at the 7‑position. This compound is naturally distributed in various medicinal plants, including sea buckthorn (Hippophae rhamnoides), Ginkgo biloba, and several species of the Polygonaceae family. As a major flavonoid component in many botanical extracts, it has been extensively studied for its antioxidant, anti‑inflammatory, and cardioprotective activities. The glycosylation at both the 3‑ and 7‑positions enhances the compound‘s water solubility and stability compared to the aglycone, while potentially affecting its biological activity profile through modulation of cellular uptake and metabolism. As a high‑purity reference standard, it is essential for the validation of analytical methods, quality control of botanical products, and quantitative analysis of isorhamnetin diglycosides in complex samples.

Synthetic Process / Isolation Method

Isorhamnetin 3‑glucoside‑7‑rhamnoside is typically isolated from natural plant sources:

• Extraction: Dried plant materials (such as sea buckthorn berries or ginkgo leaves) are extracted with hydroalcoholic solvents (ethanol‑water or methanol‑water mixtures).

• Enzymatic Hydrolysis (Optional): In some cases, enzymatic hydrolysis is used to release specific glycosides from complex flavonoid mixtures.

• Chromatographic Purification: The crude extract undergoes sequential purification using macroporous adsorption resin, silica gel column chromatography, and preparative HPLC with C18 columns.

• Recrystallization: The isolated compound is recrystallized from methanol, ethanol, or aqueous solvent systems to achieve ≥98% purity.

• Quality Confirmation: The product is rigorously characterized by HPLC‑DAD, ¹H‑NMR, ¹³C‑NMR, and high‑resolution MS.

Mechanism of Action

As a flavonoid diglycoside, isorhamnetin 3‑glucoside‑7‑rhamnoside exerts its biological activities through:

• Antioxidant Activity: Scavenges free radicals, reduces oxidative stress biomarkers, and protects cellular membranes from lipid peroxidation.

• Cardioprotective Effects: Improves vascular endothelial function, reduces blood lipid levels, and protects against ischemia‑reperfusion injury.

• Anti‑inflammatory Activity: Modulates cytokine production and inflammatory cell infiltration in various tissue injury models.

• Potential Bioavailability Enhancement: The diglycoside structure may be hydrolyzed by intestinal microbiota, releasing isorhamnetin as the active metabolite.

  Parameter	Specification	Details
  Product Name	Isorhamnetin 3‑glucoside‑7‑rhamnoside	Flavonoid diglycoside reference standard
  Synonyms	Isorhamnetin 3‑O‑β‑D‑glucoside‑7‑O‑α‑L‑rhamnoside	—
  CAS Number	17331‑71‑4	17331‑71‑4
  Molecular Formula	C₂₈H₃₂O₁₆	28 carbons, 32 hydrogens, 16 oxygens
  Molecular Weight	624.55 g/mol	—
  Appearance	Yellow powder	Visual inspection
  Assay (Purity)	≥98.0%	HPLC area normalization
  Chemical Class	Flavonoid diglycoside	Glucoside‑rhamnoside type
  Source	Hippophae rhamnoides, Ginkgo biloba	Natural product isolation
  Storage Condition	2‑8°C, protected from light, sealed, dry	Store in a cool, dry place
  Shelf Life	24 months	From date of manufacture
  Packaging	5mg/vial	Amber glass vial
  Grade	Research Grade / Reference Standard	For laboratory and analytical use