SML1572

Gentiopicroside

≥98% (HPLC)

• Synonym(s): (3S,4R)-4-ethenyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,6-dihydro-3H-pyrano[3,4-c]pyran-8-one, (5R,6S)-5-Ethenyl-6-(-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-Pyrano[3,4-c]pyran-1-one, (5R-trans)-5-ethenyl-6-(-D-glucopyranosyloxy)-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-one, Gentiopicrin, NSC606402
• Empirical Formula (Hill Notation): C₁₆H₂₀O₉
• CAS Number: 20831-76-9
• Molecular Weight: 356.32
• EC Number: 244-070-2
• MDL number: MFCD00075700
• UNSPSC Code: 12352200
• PubChem Substance ID: 329825970
• NACRES: NA.77

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D -185 to -205°, c = 1 in H₂O
• color: white to beige
• solubility: H₂O: 20 mg/mL, clear
• storage temp.: −20°C
• SMILES string: C=C[C@H]1[C@H](O[C@]2([H])O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)OC=C3C(OCC=C31)=O
• InChI: 1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
• InChI key: DUAGQYUORDTXOR-GPQRQXLASA-N

Description

General description

Gentiopicroside is a natural Iridoid compound, found in Chinese medicinal herbs Gentiana scabra Bge. and Gentiana macrophylla Pall.

Biochem/physiol Actions

Gentiopicroside is an important active component of secoiridoid glycosides from Gentiana macrophylla Pall that exhibit anti-inflammatory, antibacterial and liver protecting activities. Gentiopicroside protects chondrocytes from IL-1β-induced inflammation response.

Gentiopicroside possesses analgesic, anti proliferative, wound healing and antioxidant properties (free radical scavenging activity). Gentiopicroside shows low oral bioavailability, hence it establishes its therapeutic action after metabolism.

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable