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Genipin

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Genipin
Skeletal formula of genipin
Ball-and-stick model of the genipin molecule
Names
Preferred IUPAC name Methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopentapyran-4-carboxylate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.164.015 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1Key: AZKVWQKMDGGDSV-BCMRRPTOSA-N
  • InChI=1/C11H14O5/c1-15-10(13)8-5-16-11(14)9-6(4-12)2-3-7(8)9/h2,5,7,9,11-12,14H,3-4H2,1H3/t7-,9-,11-/m1/s1Key: AZKVWQKMDGGDSV-BCMRRPTOBC
SMILES
  • O=C(OC)\C1=C\O(O)2\C(=C/C12)CO
Properties
Chemical formula C11H14O5
Molar mass 226.226 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Genipin is a chemical compound found in Genipa americana fruit extract. It is an aglycone derived from an iridoid glycoside called geniposide which is also present in fruit of Gardenia jasminoides.

Genipin is an excellent natural cross-linker for proteins, collagen, gelatin, and chitosan cross-linking. It has a low acute toxicity, with LD50 i.v. 382 mg/kg in mice, therefore, much less toxic than glutaraldehyde and many other commonly used synthetic cross-linking reagents. Furthermore, genipin can be used as a regulating agent for drug delivery, as the raw material for gardenia blue pigment preparation, and as the intermediate for alkaloid syntheses.

The blue color of genipin is stabilized in milk due to the natural pH of milk

In vitro experiments have shown that genipin blocks the action of the transporter uncoupling protein 2.

References

  1. Ramos-de-la-Peña, A.M.; Renard, C.M.G.C.; Montañez, J.; Reyes-Vega, M.L.; Contreras-Esquivel, J.C. (2014), "A review through recovery, purification and identification of genipin", Phytochemistry Reviews, 15: 37–49, doi:10.1007/s11101-014-9383-z, S2CID 16614004
  2. Brenda Vaandering, Genipin, retrieved 22 December 2019
  3. M.I.L. Neves, A. Valdés, E.K. Silva, M.A.A. Meireles, E. Ibáñez, A. Cifuentes (2022), "Study of the reaction between genipin and amino acids, dairy proteins, and milk to form a blue colorant ingredient", Food Research International, 157: 111240, doi:10.1016/j.foodres.2022.111240, hdl:10261/311292, PMID 35761551, S2CID 248205719, retrieved 9 December 2022{{citation}}: CS1 maint: multiple names: authors list (link)
  4. Zhang, CY; Parton, LE; Ye, CP; Krauss, S; Shen, R; Lin, CT; Porco Jr, JA; Lowell, BB (2006). "Genipin inhibits UCP2-mediated proton leak and acutely reverses obesity- and high glucose-induced beta cell dysfunction in isolated pancreatic islets". Cell Metabolism. 3 (6): 417–27. doi:10.1016/j.cmet.2006.04.010. PMID 16753577.
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