Gentiopicroside
Basic information
- CAS
20831-76-9- Standard SMILES
C=C[C@@H]1C2=CCOC(=O)C2=CO[C@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
DUAGQYUORDTXOR-GPQRQXLASA-N- Molecular formula
- C16H20O9
- Average molar mass
- 356.32 g/mol
- Monoisotopic mass
- 356.11073221
Overview
Gentiopicrin is a glycoside.
Names & identifiers
- Preferred name
- Gentiopicroside
- IUPAC
- (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
- English name
- Gentiopicroside
- Molecular formula
- C16H20O9
- Molecular weight
- 356.33
Names & synonyms
GentiopicrosideGentiopicrin20831-76-90WE09Z21RCDTXSID40878043NSC-606402(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-one1H,3H-Pyrano(3,4-c)pyran-1-one, 5-ethenyl-6-(beta-D-glucopyranosyloxy)-5,6-dihydro-, (5R-trans)-(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-oneRefChem:37451DTXCID501016106244-070-2
Show more names
gentiamarinNSC 606402Gentiop icroinGentiopicrosidumChinese Gentian ExtractGentiopicroside standardGentiana manshurica KitagGentiopicroside 20831-76-9
MFCD00075700C16H20O9(5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydro-1H,3H-pyrano[3,4-c]pyran-1-oneQ27106718Gentiopicroside, >=98% (HPLC)(5R,6S)-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-5,6-dihydropyrano[3,4-c]pyran-1(3H)-onegentiopicorsideGentiopicroside?
Properties
Computed structural properties
- XLogP
- -1.2
- Topological polar surface area
- 135 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 4
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 598
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Physicochemical properties
- Melting point
- 191 °C · 191°C
- alpha
- -200 · -200 º (c=2, H2O)
- Boiling point
- 667.8 · 667.8±55.0 °C(Predicted)
- Density
- 1.52 · 1.52±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- DMSO (Slightly), Ethanol (Slightly, Sonicated)
- form
- Solid
- pka
- 12.79 · 12.79±0.70(Predicted)
- color
- Pale Beige
- biological source
- plant (Gentiana macrophylla Pall)
- optical activity
- -185 to · [α]/D -185 to -205°, c =1 in H2O
- Water Solubility
- 2 O: · H2O: 20mg/mL, clear
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS02
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319-H226
- Precautionary statements
- P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P303+P361+P353-P332+P313-P403+P235
Chemistry & industry
Applications
UsesGentiopicroside is an anticonvulsant agent present in plant extracts.
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: Gentiopicrin is a glycoside.
Suppliers
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Related reactions
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Compound notes
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