Sinapine
Chemical compound
From Wikipedia, the free encyclopedia
Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae.[2] It is the choline ester of sinapic acid.
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| Names | |
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| Preferred IUPAC name
2-{[(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-N,N,N-trimethylethan-1-aminium | |
| Other names
Sinapoylcholine; Sinapic acid choline ester | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C16H24NO5 | |
| Molar mass | 310.370 g·mol−1 |
| Melting point | 178 °C (352 °F; 451 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Sinapine was discovered by Étienne-Ossian Henry in 1825.[3]
Occurrence
Sinapine typically occurs in the outer seed coat of oil crops and is plentiful in some types of press cake leftover after vegetable oil extraction.[2] Typical oil seed cake residues high in sinapine include Brassica juncea (1.22% by mass),[4] and rapeseed (0.39-1.06% by mass).[5]
Isolation
The typical protocol for extracting Sinapine from seed cakes entails defatting the cake with hexane via a Soxhlet apparatus followed by extraction with 70% methanol held at 75 °C.[6]
Metabolism
Sinapine esterase is an enzyme whose two substrates are sinapine and H2O and whose two products are sinapic acid and choline.
Sinapoylglucose—choline O-sinapoyltransferase is an enzyme whose two substrates are 1-O-sinapoyl-β-D-glucose and choline, whereas its two products are D-glucose and sinapine.