Cyanidin-3-O-rhamnoside chloride 98% Purity Natural Product Reference Standard CAS 38533-30-1 Research Grade Anthocyanin

Product Overview

Cyanidin-3-O-rhamnoside chloride is a naturally occurring anthocyanin pigment belonging to the flavonoid class of compounds . It consists of the cyanidin aglycone (2-(3,4-dihydroxyphenyl)chromenylium core) glycosylated with an α-L-rhamnopyranosyl moiety at the 3-position . The chloride salt form ensures the compound remains in the stable red flavylium cation state under acidic conditions.

With the molecular formula C₂₁H₂₁ClO₁₀ and a molecular weight of 468.84 g/mol , this compound appears as a dark red to purple-red crystalline powder . It exhibits characteristic UV-Vis absorption with λmax at 518–525 nm in methanol containing 0.1% HCl . The compound is a high-purity reference standard (>98% by HPLC) suitable for content determination, identification, pharmacological research, and bioactivity screening .

Natural Sources

Cyanidin-3-O-rhamnoside chloride is primarily isolated from plant sources rich in anthocyanins, including:

• Fruits of Vaccinium myrtillus (bilberry/European blueberry) 

• Fruits of Nitraria tangutorum (Chinese sea buckthorn) 

• Fruits of Prunus spinosa (blackthorn/sloe) 

• Other sources: red cabbage, Chamaecyparis species, and Plumbago rosea 

Biosynthetic Pathway

The biosynthesis of cyanidin-3-O-rhamnoside involves the phenylpropanoid pathway, with a critical divergence point being the utilization of UDP-rhamnose by 3-O-rhamnosyltransferase (3RT) . Unlike the common UDP-glucose flavonoid glucosyltransferase (UFGT), this enzyme exhibits high specificity for UDP-rhamnose as the sugar donor .

Extraction and Purification Protocol

For isolation of Cyanidin-3-O-rhamnoside Chloride with >95% purity, a standard solid-liquid extraction followed by chromatographic purification is typically employed :

1. Biomass Preparation: Lyophilize (freeze-dry) fruit pulp to prevent enzymatic degradation; grind to fine powder (mesh 40-60)

2. Acidified Extraction: Use Methanol:Water:HCl (80:19:1 v/v/v). The 1% HCl is essential to maintain pH < 2.0, keeping anthocyanins in the flavylium cation form

3. Solid Phase Extraction: Enrichment using Amberlite XAD-7 or C18 Sep-Pak; elute with acidified methanol

4. Purification: Semi-preparative HPLC on C18 reverse phase column; detection at 520 nm 

Mechanism of Action & Biological Activities

• CYP3A4 Inhibition: Cyanidin-3-O-rhamnoside chloride significantly inhibits cytochrome P450 3A4 (CYP3A4) activity . At 100 μM concentration, it inhibits CYP3A4 by >75% with an IC₅₀ of 44 μM. Among 21 anthocyanins tested, only cyanidin-3-O-rhamnoside and two delphinidin glycosides demonstrated significant inhibition of cytochromes P450 .

• Antioxidant Activity: As an anthocyanin, it scavenges free radicals through electron donation by multiple hydroxyl groups, preventing oxidative damage to cells .

• Gene Regulation: May influence gene expression related to antioxidant defense mechanisms .

Physicochemical Properties

• Solubility: Optimal solubility in DMSO at approximately 5 mg/mL; moderate solubility in methanol and ethanol; PBS (pH 7.2) solubility approximately 1 mg/mL; aqueous solubility is pH-dependent and enhanced under acidic conditions .

• pH Sensitivity: Color changes with pH variations - red in acidic conditions, blue-green in alkaline environments .

• Photostability: UV-B radiation (280-315 nm) induces the most severe photodegradation; UV-A produces moderate to high degradation; visible light exposure typically causes 50-75% loss over extended periods .

• Thermal Stability: Thermal degradation follows first-order reaction kinetics. At 50°C, half-life ranges from 138.66 to 433.12 hours; at 70°C, half-life decreases to 10.5-42 hours. Activation energy ranges from 22.54 to 93.38 kJ/mol .

Research Applications

• Pharmacokinetic and Drug Metabolism Studies: As a selective CYP3A4 inhibitor, used in studies examining herb-drug interactions and drug metabolism 

• Food Chemistry: Serves as a reference standard for anthocyanin analysis in food products and beverages

• Antioxidant Research: Evaluated for radical scavenging activity and potential health benefits 

• Quality Control: Acts as a marker compound for anthocyanin-rich botanical extracts (bilberry, berries)

• Natural Colorant Research: Used in the development of natural food colorants 

Quality Specifications

• Purity: ≥98.0% determined by HPLC (area normalization) 

• Appearance: Dark red to purple-red crystalline powder 

• Identification: Confirmed by UV-Vis (λmax ~518-525 nm), HPLC retention time, and MS spectral matching 

• Molecular Formula: C₂₁H₂₁ClO₁₀ 

• Molecular Weight: 468.84 g/mol 

• Source: Vaccinium myrtillus (bilberry) fruits and other anthocyanin-rich sources

• Each batch accompanied by comprehensive Certificate of Analysis (COA) with HPLC, Mass, and NMR spectra 

• Stability: ≥2 years under proper storage conditions 

Packaging & Storage

Packaging Options:

• 2mg, 5mg, 10mg, 20mg, 50mg, 100mg amber glass vials 

• 200mg, 500mg, 1g available upon request 

• Custom packaging available

Storage Conditions :

• Short-term: 2-8°C, sealed containers, protected from light and moisture (stable for up to 24 months)

• Long-term: -20°C, in sealed containers (stable for up to 3 years)

• Equilibration: Allow product to equilibrate to room temperature for at least 1 hour before opening

• Solution storage: Prepare stock solutions as aliquots; store at -20°C for up to two weeks

Shipping:

• Routine orders: ambient temperature with blue ice for stability

• International shipping available with proper documentation

Safety Information

This product is intended exclusively for research purposes, including content determination, identification, pharmacological experiments, and bioactivity screening . It is not for human use, clinical diagnosis, or therapeutic applications. Standard laboratory safety practices, including appropriate personal protective equipment, should be followed when handling this compound.

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