Sinapine

Sinapine
IUPAC name 2-{[3-(4-Hydroxy-3,5-dimethoxyphenyl)acryloyl]oxy}-N,N,N-trimethylethanaminium
Other names Sinapoylcholine; Sinapic acid choline ester
Identifiers
	PubChem	5280385
ChemSpider	80576 N
Jmol-3D images	{{#if:O=C(OCC[N+](C)(C)C)C=Cc1cc(OC)c(O)c(OC)c1|Image 1
SMILES O=C(OCC[N+](C)(C)C)C=Cc1cc(OC)c(O)c(OC)c1
InChI 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
Properties
Molecular formula	C16H24NO5
Molar mass	310.37 g mol−1
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Sinapine is an alkaloidal amine found in black mustard seeds. It is the choline ester of sinapic acid.

Sinapine was discovered by Etienne Ossian Henry in 1825.^[1]

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