Verbenalin
Basic information
- CAS
548-37-8- Standard SMILES
COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@H]2[C@@H]1C(=O)C[C@@H]2C- InChIKey
HLXRWTJXGMHOFN-XJSNKYLASA-N- Molecular formula
- C17H24O10
- Average molar mass
- 388.4 g/mol
- Monoisotopic mass
- 388.13694696
Overview
Verbenalin is a terpene glycoside.
Names & identifiers
- Preferred name
- Verbenalin
- IUPAC
- methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylate
- English name
- VERBENALIN
- Molecular formula
- C17H24O10
- Molecular weight
- 388.37
Names & synonyms
Verbenalin548-37-8VerbenalosideCornin (glycoside)cornin iridoid71B68181Z6NSC-118055methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylatemethyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta(c)pyran-4-carboxylateRefChem:193972CorninC17H24O10
Show more names
VerbenalinpVerbenalineVerbenalin-RMcornin(glycosidecornin(glycoside)CORNIN (VERBENALIN)
MFCD00017414Methyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-1,4a,5,6,7,7a-hexahydrocyclopenta[c]pyran-4-carboxylatemethyl (1S,4aS,7S,7aR)-7-methyl-5-oxo-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-4a,6,7,7a-tetrahydro-1H-cyclopenta[c]pyran-4-carboxylateVerbenalol, beta-D-glucopyranosideGlucopyranoside, verbenalol, beta-D-NSC 118055NSC118055Verbenalin CRS
Properties
Computed structural properties
- XLogP
- -1.5
- Topological polar surface area
- 152 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 5
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 619
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C10 isoprenoids (monoterpenes) [PR0102]
Physicochemical properties
- Melting point
- 180 · 180-182°C
- alpha
- 25 · D25 -173° (water)
- Boiling point
- 610.1 · 610.1±55.0 °C(Predicted)
- Density
- 1.5 · 1.50±0.1 g/cm3(Predicted)
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 250 mg/mL · DMSO : 250 mg/mL (643.72 mM; Need ultrasonic)
- pka
- 12.79 · 12.79±0.70(Predicted)
- form
- powder
- color
- White
- Merck
- 13 · 13,10021
- BRN
- 57895 · 57895
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
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 ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- F
- 10-21
- wgk
- 3
- rtecs
- GY5826000
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesVerbenalin is an iridoid glucoside isolated found in Verbena officinalis and other herb plants.
Usescell growth inhibitor, coagulant
Additional notes
DefinitionChEBI: Verbenalin is a terpene glycoside.
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Related reactions
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Compound notes
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