Genipin

Last updated
Genipin
Genipin.svg
Genipin 3D ball.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 Yes check.svgY
    Key: AZKVWQKMDGGDSV-BCMRRPTOSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Related Research Articles

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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.