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
CAS Number	18696-26-9 N
3D model (Jmol)	Interactive image
ChemSpider	80576 N
PubChem CID	5280385
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 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
SMILES O=C(/C=C/C1=CC(OC)=C(C(OC)=C1)O)OCC[N+](C)(C)C
Properties
Chemical formula	C16H24NO5
Molar mass	310.37 g·mol−1
Melting point	178 °C (352 °F; 451 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

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

Sinapine was discovered by Etienne Ossian Henry in 1825.

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

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.

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.