Genipin
| Genipin | |
|---|---|
 | |
| IUPAC name Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate | |
| Identifiers | |
| CAS number | 6902-77-8  |
| PubChem | 442424 |
| ChemSpider | 390864 |
| KEGG | C09780 |
| ChEMBL | CHEMBL459016 |
| Jmol-3D images | {{#if:O=C(OC)\C1=C\O[C@@H](O)[C@@H]2\C(=C/C[C@H]12)CO|Image 1 |
| |
| |
| Properties | |
| Molecular formula | C11H14O5 |
| Molar mass | 226.226 g/mol |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| 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
- ↑ 1.0 1.1 CBC Genipin
- ↑ Introduction of genipin
- ↑ 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.