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-tetrahydrocyclopenta[c]pyran-4-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.164.015
KEGG
UNII
  • 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/s1 checkY
    Key: AZKVWQKMDGGDSV-BCMRRPTOSA-N checkY
  • 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/s1
    Key: AZKVWQKMDGGDSV-BCMRRPTOBC
  • O=C(OC)\C1=C\O[C@@H](O)[C@@H]2\C(=C/C[C@H]12)CO
Properties
C11H14O5
Molar mass 226.226 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

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.[1]

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.[2]

The blue color of genipin is stabilized in milk due to the natural pH of milk [3]

In vitro experiments have shown that genipin blocks the action of the transporter uncoupling protein 2.[4]

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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