Description

Cynaropicrin is a bioactive sesquiterpene lactone primarily isolated from Cynara scolymus (artichoke), Cynara cardunculus, and other plants of the Asteraceae family. BIORLAB offers high-purity cynaropicrin (≥98%) isolated through advanced extraction and purification technologies. This compound has garnered significant scientific interest due to its remarkable pharmacological activities, particularly its potent anti-hepatitis C virus (HCV) effects and diverse therapeutic potential in inflammation, hyperlipidemia, and cancer research.

Technical Specifications

• Appearance: White to off-white crystalline powder
• Purity: ≥98% (HPLC)
• Melting Point: 117-119°C
• Optical Rotation: [α]D20 +71° (c 1.0, CHCl3)
• UV Absorption: λmax at 206 nm in methanol
• Solubility: Soluble in ethanol, methanol, DMSO, ethyl acetate; poorly soluble in water
• LogP: 0.85 (predicted)

IUPAC Name: [(3aR,4S,6aR,8S,9aR,9bR)-8-hydroxy-3,6,9-trimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate

InChI: InChI=1S/C19H22O6/c1-8-5-14(24-18(22)9(2)7-20)16-11(4)19(23)25-17(16)15-10(3)13(21)6-12(8)15/h12-17,20-21H,1-7H2/t12-,13-,14-,15-,16+,17+/m0/s1

InChIKey: KHSCYOFDKADJDJ-NQLMQOPMSA-N

Canonical SMILES: C=C1CC(C2C(C3C1CC(C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO

Isomeric SMILES: C=C1C[C@@H]([C@@H]2[C@@H]([C@@H]3[C@H]1C[C@@H](C3=C)O)OC(=O)C2=C)OC(=O)C(=C)CO

Synonyms: Cynaropicrin; 35730-78-0; Cynaropikrin; 2-Propenoic acid, 2-(hydroxymethyl)-, (3aR,4S,6aR,8S,9aR,9bR)-dodecahydro-8-hydroxy-3,6,9-tris(methylene)-2-oxoazuleno(4,5-b)furan-4-yl ester; CHEBI:4038; CHEMBL374146; M9233789I9; UNII-M9233789I9; …

Botanical Source: Cynara scolymus leaf

Storage and Handling Requirements

• Store at -20°C in airtight containers
• Protect from light and moisture (hygroscopic)
• Allow container to reach room temperature before opening
• Stock solutions can be prepared in DMSO or ethanol (10 mg/ml recommended)
• For maximum stability, store solutions at -20°C protected from light
• Avoid repeated freeze-thaw cycles
• Stable for 24 months when properly stored
• Working solutions should be prepared fresh
• Handle with appropriate protection; may cause skin irritation

Research Applications

Pharmaceutical Research

• Anti-Hepatitis C Virus Studies: Demonstrates outstanding activity against all HCV genotypes, making it a promising lead for HCV drug development
• Anti-inflammatory Investigations: Shows significant inhibition of the pro-inflammatory NF-κB pathway
• Anti-hyperlipidemic Research: Exhibits potent activity in reducing cholesterol and lipid levels
• Anticancer Studies: Shows promising cytotoxic activity against various cancer cell lines
• Antiparasitic Research: Demonstrates potent anti-trypanosomal and anti-malarial properties

Biological Mechanism Research

• NF-κB Pathway Inhibition: Important for investigating inflammatory response mechanisms
• JAK/STAT Signaling Studies: Valuable for studying cytokine signaling pathways
• Bitter Taste Receptor Activation: Critical for understanding TAS2R receptor biology
• Apoptosis Pathway Investigations: Essential for cancer research and cell death mechanisms
• Lipid Metabolism Studies: Important for understanding cholesterol regulation

Traditional Medicine Validation

• Mediterranean Diet Research: Valuable for understanding the health benefits of artichoke consumption
• Ethnopharmacological Studies: Important for validating traditional uses of artichoke and related plants
• Natural Product Chemistry: Essential for standardization of herbal preparations
• Phytochemical Research: Critical for understanding structure-activity relationships of sesquiterpene lactones

Biological Activities

• Anti-HCV Activity: Exhibits potent inhibition against all HCV genotypes with EC50 values in the low micromolar range
• Anti-inflammatory Effects: Suppresses pro-inflammatory cytokine production and NF-κB pathway activation
• Anti-hyperlipidemic Properties: Reduces cholesterol levels through multiple mechanisms
• Anti-trypanosomal Activity: Shows activity against Trypanosoma brucei with IC50 values of 0.3 μM
• Anti-malarial Properties: Demonstrates effectiveness against Plasmodium falciparum
• Antifeedant Activity: Exhibits natural plant defense properties against herbivores
• Antispasmodic Effects: Demonstrates smooth muscle relaxant properties
• Anti-photoaging Activity: Shows protection against UV-induced skin damage
• Anticancer Properties: Exhibits cytotoxicity against various cancer cell lines

Source and Extraction

• Primarily isolated from leaves and flower heads of Cynara scolymus (artichoke)
• Also found in Cynara cardunculus and several other Asteraceae species
• Extracted using environmentally responsible solvent systems
• Purified through multi-stage chromatographic processes
• Structure confirmed through comprehensive spectroscopic analysis
• Standardized extraction protocols ensuring batch consistency

Quality Assurance

BIORLAB’s cynaropicrin undergoes:

• Comprehensive HPLC analysis for purity determination (≥98%)
• Structure verification by 1H and 13C NMR spectroscopy
• Mass spectrometry confirmation
• UV-Vis spectral characterization
• Stereochemical configuration confirmation
• Water content analysis
• Residual solvent screening
• Certificate of Analysis with batch-specific data

Research Value

• Lead Compound: Excellent candidate for anti-HCV drug development with minor hit-to-lead optimization
• Reference Standard: Important for analytical method development and phytochemical profiling
• Pharmacological Tool: Valuable for investigating multiple biological pathways
• Natural Product Scaffold: Essential for structure-activity relationship studies
• Biomarker: Important for quality control of artichoke extracts

Pharmacological Profile

• Lipinski’s Rule of Five: No violations, suggesting favorable drug-like properties
• Water Solubility: Moderate, amenable to pharmaceutical formulation
• Bioavailability: Good absorption profile in preliminary studies
• Safety Profile: Long history of safe consumption as component of edible artichoke
• Structure: Small molecule with multiple functional groups suitable for optimization

Technical Support Services

• Method development assistance
• Analytical reference standard
• Custom purification options
• Bulk quantities available
• Technical consultation

For research use only. Not for human consumption or clinical use. All BIORLAB natural compounds are intended solely for laboratory research applications.

For detailed specifications, bulk quantities, or technical support, please contact BIORLAB’s scientific team.