Sinapine

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Sinapine
Chemical structure of sinapine
Chemical structure of sinapine
Names
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)
ChemSpider
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UNII
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  • InChI=1S/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1 ☒N
    Key: HUJXHFRXWWGYQH-UHFFFAOYSA-O ☒N
  • InChI=1/C16H23NO5/c1-17(2,3)8-9-22-15(18)7-6-12-10-13(20-4)16(19)14(11-12)21-5/h6-7,10-11H,8-9H2,1-5H3/p+1
    Key: HUJXHFRXWWGYQH-IKLDFBCSAX
  • O=C(/C=C/C1=CC(OC)=C(C(OC)=C1)O)OCC[N+](C)(C)C
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).

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.

Sinapine was discovered by Étienne-Ossian Henry in 1825.[3]

Occurrence

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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

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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

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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.

See also

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References

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