Sinapine

Sinapine
Names
IUPAC name
2-{[3-(4-Hydroxy-3,5-dimethoxyphenyl)acryloyl]oxy}-N,N,N-trimethylethanaminium
Other names
Sinapoylcholine; Sinapic acid choline ester
Identifiers
ChemSpider 80576 
Jmol-3D images Image
PubChem 5280385
Properties
Molecular formula
C16H24NO5
Molar mass 310.37 g·mol−1
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Sinapine is an alkaloidal amine found in some seeds, particularly oil seeds of plants in the family Brassicaceae.[1] It is the choline ester of sinapic acid.

Sinapine was discovered by Etienne Ossian Henry in 1825.[2]

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.[1] Typical oil seed cake residues high in sinapine include Brassica juncea (12.2% of mass),[3] Brassica napus (9.5% by mass), and Camelina sativa (5.7% by mass).

Isolation

The typical protocol for extracting Sinapine from seed cakes entails deffatting the cake with hexane via a Soxhlet apparatus followed by extraction with 70% methanol held at 75°C.[4]

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.

References

  1. 1.0 1.1 Niciforovic, Neda; Abramovi, Helena (2014). "Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity". Comprehensive Reviews in Food Science and Food Safety 13 (1): 34–51. doi:10.1111/1541-4337.12041.
  2. Tzagoloff, A. (1963). "Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline". Plant physiology 38 (2): 202–206. doi:10.1104/pp.38.2.202. PMC 549906. PMID 16655775.
  3. Matthäus, B .; Zubr, J. (2000). "Variability of specific components in Camelina sativa oilseed cakes". Industrial Crops and Products 12 (1): 9–18. doi:10.1016/S0926-6690(99)00040-0.
  4. Vuorela, Satu (2005). Analysis, isolation, and bioactivities of rapeseed phenolics (PDF). Helsinki, Finland: University of Helsinki. pp. 19–20. ISBN 9789521027215. Retrieved 14 June 2014.