Genipin

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Genipin
Skeletal formula of genipin
Ball-and-stick model of the genipin molecule
Names
IUPAC name
Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.164.015
KEGG
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 gardenia fruit extract. It is an aglycone derived from an iridoid glycoside called geniposide present in fruit of Gardenia jasminoides.

Genipin is an excellent natural cross-linker for proteins, collagen, gelatin, and chitosan cross-linking.[1] 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.[1] 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]

In vitro experiments have shown that genipin blocks the action of the enzyme uncoupling protein 2.[3]

References[edit]

  1. ^ a b CBC Genipin
  2. ^ Introduction of genipin
  3. ^ 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. PMID 16753577. doi:10.1016/j.cmet.2006.04.010.