Synonym: (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
CAS Number: 20831-76-9
Empirical Formula (Hill Notation): C16H20O9
Molecular Weight: 356.32
EC Number: 244-070-2
MDL Number: MFCD00075700
Linear Formula: C16H20O9
Product Type: Chemical
| assay |
≥98% (HPLC) |
| color |
white to beige |
| form |
powder |
| 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 |
| optical activity |
[α]/D -185 to -205°, c = 1 in H2O |
| Quality Level |
100  |
| 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 |
| solubility |
H2O: 20 mg/mL, clear |
| storage temp. |
−20°C |
| 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. |
| Biochem/physiol Actions: |
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. |
| General description: |
Gentiopicroside is a natural Iridoid compound, found in Chinese medicinal herbs Gentiana scabra Bge. and Gentiana macrophylla Pall. |
| Packaging: |
5, 25 mg in glass bottle |
| RIDADR |
NONH for all modes of transport |
| WGK Germany |
WGK 3 |
| Flash Point(F) |
Not applicable |
| Flash Point(C) |
Not applicable |
| Purity |
≥98% (HPLC) |
| Storage Temp. |
−20°C |
| UNSPSC |
12352200 |
