Sinapine

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title: "Sinapine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["alkaloids", "quaternary-ammonium-compounds", "hydroxycinnamic-acid-esters", "o-methylated-hydroxycinnamic-acids", "resorcinol-ethers"] topic_path: "general/alkaloids" source: "https://en.wikipedia.org/wiki/Sinapine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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={{Chembox Identifiers | CASNo_Ref = | CASNo = 18696-26-9 | UNII_Ref = | UNII = 09211A0HHL | CASNoOther = | PubChem = 5280385 | ChemSpiderID_Ref = | ChemSpiderID = 80576 | SMILES = O=C(/C=C/C1=CC(OC)=C(C(OC)=C1)O)OCCN+(C)C | 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 | InChIKey = HUJXHFRXWWGYQH-IKLDFBCSAX | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = HUJXHFRXWWGYQH-UHFFFAOYSA-O | MeSHName = |Section2={{Chembox Properties | C=16 | H=24 | N=1 | O=5 | Appearance = | Density = | MeltingPtC = 178 | MeltingPt_ref = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = | HPhrases = | PPhrases = | GHS_ref =

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 Étienne-Ossian Henry in 1825.{{Cite journal | last1 = Tzagoloff | first1 = A. | title = Metabolism of Sinapine in Mustard Plants. I. Degradation of Sinapine into Sinapic Acid & Choline | journal = Plant Physiology | volume = 38 | issue = 2 | pages = 202–206 | year = 1963 | pmid = 16655775 | pmc = 549906 | doi=10.1104/pp.38.2.202

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. and rapeseed (0.39-1.06% by mass).

Isolation

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.

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

References

  1. (February 1966). "[Studies on the constituents of various Erysimum varieties: a) identification of the bitter substance erysimupicrone as strophanthidin; b) glucosinolates in the seeds of Erysimum perofskianum Fisch et Mey., E. Allionii hort., E. crepidifolium Rohb. and E. cheiranthoides L].". Arzneimittel-Forschung.
  2. (2014). "Sinapic Acid and Its Derivatives: Natural Sources and Bioactivity". Comprehensive Reviews in Food Science and Food Safety.
  3. (2000). "Variability of specific components in Camelina sativa oilseed cakes". Industrial Crops and Products.
  4. (2005). "Analysis, isolation, and bioactivities of rapeseed phenolics". University of Helsinki.
  5. (2005). "Analysis, isolation, and bioactivities of rapeseed phenolics". University of Helsinki.

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alkaloidsquaternary-ammonium-compoundshydroxycinnamic-acid-esterso-methylated-hydroxycinnamic-acidsresorcinol-ethers