Description

High-purity Amarogentin, a secoiridoid glycoside isolated from Swertia chirata and Gentiana lutea, known as one of the most bitter natural compounds, with significant pharmacological properties.

Technical Specifications

• Molecular Formula: C₂₉H₃₀O₁₃
• Molecular Weight: 586.5 g/mol
• Purity: ≥98% (HPLC)
• Appearance: White to off-white crystalline powder
• Solubility: Soluble in methanol, DMSO; slightly soluble in water

IUPAC Name: [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate

InChI: InChI=1S/C29H30O13/c1-2-16-17-6-7-38-26(36)19(17)12-39-28(16)42-29-25(24(35)23(34)21(11-30)40-29)41-27(37)22-18(9-15(32)10-20(22)33)13-4-3-5-14(31)8-13/h2-5,8-10,12,16-17,21,23-25,28-35H,1,6-7,11H2/t16-,17+,21-,23-,24+,25-,28+,29+/m1/s1

InChIKey: DBOVHQOUSDWAPQ-WTONXPSSSA-N

Canonical SMILES: C=CC1C2CCOC(=O)C2=COC1OC3C(C(C(C(O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O)C5=CC(=CC=C5)O

Isomeric SMILES: C=C[C@@H]1[C@@H]2CCOC(=O)C2=CO[C@H]1O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC(=O)C4=C(C=C(C=C4O)O)C5=CC(=CC=C5)O

Synonyms: Amarogentin; 21018-84-8; 5L82GT5I0W; [(2S,3R,4S,5S,6R)-2-[[(3S,4R,4aS)-4-ethenyl-8-oxo-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl] 2,4-dihydroxy-6-(3-hydroxyphenyl)benzoate; sweroside-2′-(3”,5”,3”’-trihydroxydiphenyl)-2”-carboxylic acid ester; (2S,3R,4S,5S,6R)-4,5-Dihydroxy-6-(hydroxymethyl)-2-(((3S,4R,4aS)-8-oxo-4-vinyl-3,4,4a,5,6,8-hexahydropyrano[3,4-c]pyran-3-yl)oxy)tetrahydro-2H-pyran-3-yl 3,3′,5-trihydroxy-[1,1′-biphenyl]-2-carboxylate; (4aR)-5t-ethenyl-6c-[O(2)-(3,5,3′-trihydroxybiphenyl-2-ylcarbonyl)-beta-D-glucopyranosyloxy]-4,4ar,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-1-one; (4aS,5R,6S)-5-ethenyl-1-oxo-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-6-yl- 2-O-[(3,3′,5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranoside; …

Botanical Source: Gentianae radix et rhizoma

Key Features & Benefits

• A most bitter natural compound known
• DNA topoisomerase I inhibitor
• Hepatoprotective properties
• Anti-inflammatory activity
• Complete analytical documentation

Research Applications

1. Bitter Taste Research

   • Taste receptor studies
   • Sensory evaluation
   • Food science research
   • Taste masking studies

2. Cancer Research

   • DNA topoisomerase I inhibition
   • Anti-proliferative studies
   • Cancer cell mechanisms
   • Drug development

3. Hepatic Research

   • Liver protection studies
   • Hepatitis research
   • Liver enzyme modulation
   • Hepatoprotective mechanisms

Storage & Handling

• Store at -20°C
• Protect from light and moisture
• Avoid repeated freeze-thaw cycles
• Stock solution guidelines provided
• 24-month stability under recommended conditions

Quality Assurance

• GMP-compliant manufacturing
• Rigorous quality control
• Full spectroscopic characterization
• Traceable lot numbers
• Stability monitoring program

Package Sizes

• 5mg
• 10mg
• 25mg
• 100mg
• Bulk quantities available

Biological Activities

1. Molecular Mechanisms

   • Topoisomerase I inhibition
   • Anti-inflammatory pathways
   • Hepatoprotective actions
   • Bitter taste receptor activation

2. Therapeutic Potential

   • Cancer treatment
   • Liver protection
   • Anti-inflammatory effects
   • Antimicrobial activity

Research Support

BIORLAB provides:

• Technical consultation
• Analytical method support
• Stability data
• Custom synthesis options
• Application Guidance

Quality Control

• Identity confirmed by NMR/MS
• Purity verified by HPLC
• Structure confirmation
• Stability testing

For research and development purposes only. Not for human consumption or clinical use.