[(1S,7aR)-1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
Basic information
- CAS
6029-84-1- Standard SMILES
CC(C)[C@@](O)(C(=O)OCC1=CCN2CC[C@H](O)[C@@H]12)C(C)O- InChIKey
SFVVQRJOGUKCEG-LLTIUZATSA-N- Molecular formula
- C15H25NO5
- Average molar mass
- 299.36 g/mol
- Monoisotopic mass
- 299.1732729
Names & identifiers
- Preferred name
- [(1S,7aR)-1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
- IUPAC
- [(7S,8R)-7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl]methyl (2S)-2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoate
- English name
- (7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl 2-hydroxy-2-(1 -hydroxyethyl)-3-methyl-butanoate
- Molecular formula
- C15H25NO5
- Molecular weight
- 299.36
Names & synonyms
[(1S,7aR)-1-Hydroxy-2,3,5,7a-tetrahydro-1H-pyrrolizin-7-yl]methyl (2S)-2-hydroxy-2-(1-hydroxyethyl)-3-methylbutanoateRinderineRinderine-RMRinderine (Standard)(7-hydroxy-5,6,7,8-tetrahydro-3H-pyrrolizin-1-yl)methyl 2-hydroxy-2-(1 -hydroxyethyl)-3-methyl-butanoate(2S,3R)-2,3-Dihydroxy-2-(1-methylethyl)butanoic acid [(1S)-2,3,5,7aβ-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl esterButanoic acid, 2,3-dihydroxy-2-(1-methylethyl)-, [(1S,7aR)-2,3,5,7a-tetrahydro-1-hydroxy-1H-pyrrolizin-7-yl]methyl ester, (2S,3R)-
Database identifiers
- CAS
6029-84-1- PubChem CID
- 6419475
- DTXSID
DTXSID501020159
Properties
Computed structural properties
- XLogP
- -0.4
- Topological polar surface area
- 90.2 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 6
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 436
Physicochemical properties
- Melting point
- 100 · 100-1°C
- Boiling point
- 463.3 · 463.3±45.0 °C(Predicted)
- Density
- 1.26 · 1.26±0.1 g/cm3(Predicted)
- pka
- 12.59 · 12.59±0.29(Predicted)
- FDA UNII
- 17 O052O4FA · 17O052O4FA
- Hazardous Substances Data
- 6029 · 6029-84-1(Hazardous Substances Data)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Hazardous Substances Data
- 6029-84-1(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionAn alkaloid, also belonging to the pyrrolizidine group, this base has been found in Rindera baldshuanica Kusn. It forms colourless crystals from Me2CO and has [α]20D + 24.62° (EtOH). Three non-phenolic hydroxyl groups are present and the alkaloid forms well crystalline salts with mineral acids, e.g. the hydrochloride, m.p. 152-3°C; hydrobromide, m.p. 123-4°C and the hydriodide, m.p. 118- 9°e. The structure may be deduced from the hydrolysis products which are heliotridine and (+ )-trachelanthic acid.
UsesRinderine is a pyrrolizidine alkaloid which are a class of compounds used as defense mechanisms in several plant families. Rinderine may be used by other insects, sequestered from food in use for their own defense and may also be found in some medicinal herb preparations.
Additional notes
DefinitionChEBI: Rinderine is a member of pyrrolizines.
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