Isorhamnetin 3-sophoroside-7-rhamnoside 90% Purity CAS 41328-75-0 Research Grade Flavonoid Glycoside Reference Standard for Natural Product Analysis a

Product Overview

Isorhamnetin 3‑sophoroside‑7‑rhamnoside (CAS 41328‑75‑0) is a high‑purity flavonoid glycoside reference standard, featuring isorhamnetin as the aglycone with two sugar moieties attached at different positions of the flavonoid core. The sophoroside group (a disaccharide composed of two glucose units linked via a β‑1→2 glycosidic bond) is attached at the 3‑position, while a rhamnoside moiety is attached at the 7‑position. This complex glycosylation pattern is characteristic of many bioactive flavonoids found in various plant species, including members of the families Fabaceae, Asteraceae, and Polygonaceae. This compound is an important marker for the authentication and quality assessment of flavonoid‑rich botanical extracts and has been studied for its antioxidant and anti‑inflammatory properties. As a reference standard, it is essential for the qualitative and quantitative analysis of complex flavonoid glycosides in plant materials, food products, and pharmaceutical formulations using advanced chromatographic techniques such as HPLC‑DAD and UPLC‑MS/MS.

Synthetic Process / Isolation Method

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

• Extraction: Dried plant material (leaves, fruits, or flowers of species such as Ginkgo biloba, Hippophae rhamnoides, or Sophora japonica) is extracted with aqueous ethanol or methanol.

• Defatting: The crude extract is defatted with non‑polar solvents such as petroleum ether or n‑hexane to remove lipids and chlorophyll.

• Liquid‑Liquid Partitioning: The defatted extract is partitioned between water and ethyl acetate or n‑butanol to concentrate the glycosylated flavonoid fraction.

• Column Chromatography: The glycoside fraction is subjected to repeated column chromatography using polyamide, macroporous resin (such as D101 or HP‑20), or Sephadex LH‑20, eluting with gradient solvent systems (water‑methanol or water‑ethanol).

• Preparative HPLC: Further purification is achieved using preparative HPLC with a C18 column to isolate the target compound with high purity.

• Recrystallization: The purified compound is recrystallized from appropriate solvent systems to achieve ≥90% purity.

• Quality Confirmation: The final product is rigorously characterized by HPLC, NMR (¹H‑NMR, ¹³C‑NMR, 2D‑COSY, HMBC, HSQC), and high‑resolution mass spectrometry to confirm structural identity and purity.

Mechanism of Action

As a flavonoid glycoside, isorhamnetin 3‑sophoroside‑7‑rhamnoside exerts its biological activities through multiple mechanisms:

• Antioxidant Activity: The phenolic hydroxyl groups on the isorhamnetin aglycone effectively scavenge reactive oxygen species (ROS) and reactive nitrogen species (RNS). The sugar moieties may enhance solubility and cellular uptake, potentially increasing the bioavailability of the active aglycone after hydrolysis by intestinal glycosidases.

• Anti‑inflammatory Activity: Modulates inflammatory signaling pathways including NF‑κB and MAPK, reducing the production of pro‑inflammatory mediators such as TNF‑α, IL‑1β, IL‑6, and COX‑2.

• Cardiovascular Protection: Improves endothelial function, reduces oxidative stress, and inhibits platelet aggregation, contributing to the prevention of atherosclerosis.

• Anticancer Potential: Induces apoptosis in cancer cells through the activation of caspase‑dependent pathways and modulation of cell cycle regulatory proteins. The glycosylation pattern may influence the compound‘s affinity for specific molecular targets.

  Packaging & Shipping

  • Packaging: Available in 10mg amber glass vials with PTFE‑lined caps, purged with inert gas (argon or nitrogen) to prevent oxidation.

  • Shipping conditions: This product is not classified as dangerous goods under international transport regulations. It can be shipped at ambient temperature for routine orders.

  • Storage conditions: Store at 2‑8°C, protected from light and moisture for long‑term stability. For extended storage (>6 months), storage at ‑20°C is recommended.

  • Documentation: Each shipment includes a comprehensive Certificate of Analysis (COA), MSDS, and commercial invoice with full customs declarations.

    Parameter	Specification	Details
    Product Name	Isorhamnetin 3‑sophoroside‑7‑rhamnoside	Flavonoid glycoside reference standard
    Synonyms	Isorhamnetin 3‑O‑β‑D‑sophoroside‑7‑O‑α‑L‑rhamnoside	—
    CAS Number	41328‑75‑0	41328‑75‑0
    Molecular Formula	C₃₄H₄₂O₂₁	34 carbons, 42 hydrogens, 21 oxygens
    Molecular Weight	786.69 g/mol	Exact mass: 786.2320
    Appearance	Yellow powder	Visual inspection
    Assay (Purity)	≥90.0%	HPLC area normalization
    Chemical Class	Flavonoid glycoside	Sophoroside‑rhamnoside type
    Glycosyl Type	Sophoroside (3‑position), rhamnoside (7‑position)	Complex glycosylation
    Source	Ginkgo biloba, Hippophae rhamnoides, Sophora spp.	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	10mg/vial	Amber glass vial
    Grade	Research Grade / Reference Standard	For laboratory and analytical use
    Application	Natural product analysis, content determination, pharmacological research	Reference standard for HPLC‑DAD, UPLC‑MS/MS