sinapine

Also known as 2-(4-hydroxy-3,5-dimethoxycinnamoyloxy)-N,N,N-trimethylethanaminium, sinapoylcholine, sinapic acid choline ester

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.

In the Vinony graph

Vinony's link graph records 12 inbound references to sinapine, and connects out to (E)-sinapic acid, International Standard Book Number and family.

It is catalogued under topics including Alkaloids, Hydroxycinnamic acid esters and O-methylated hydroxycinnamic acids.

Vinony links it to 12 Wikipedia language editions.

Chemical data

Formula: C16H24NO5+
Molecular weight: 310.36 g/mol
IUPAC name: 2-[(E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxyethyl-trimethylazanium
SMILES: C[N+](C)(C)CCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC
InChIKey: HUJXHFRXWWGYQH-UHFFFAOYSA-O
XLogP: 1.8
Polar surface area: 65 Å²
H-bond donors: 1
H-bond acceptors: 5
Formal charge: 1

via PubChem

Wikidata facts

Mass: 310.165448

Show 5 more facts

isomeric SMILES: C[N+](C)(C)CCOC(=O)/C=C/C1=CC(=C(C(=C1)OC)O)OC
canonical SMILES: C[N+](C)(C)CCOC(=O)C=CC1=CC(=C(C(=C1)OC)O)OC
found in taxon: Brassica nigra
chemical formula: C₁₆H₂₄NO₅⁺
Commons category: Sinapine

Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

5 sections

Contents

Occurrence
Isolation
Metabolism
See also
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 447366952 | Name = Sinapine | ImageFile = Sinapine.svg | ImageName = Chemical structure of sinapine | PIN = 2-{[(2E)-3-(4-Hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]oxy}-N,N,N-trimethylethan-1-aminium | OtherNames = Sinapoylcholine; Sinapic acid choline ester |Section1= |Section2= |Section3= }}

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.

Excerpted from Wikipedia’s “sinapine” article, available under the CC BY-SA 4.0 licence.