Genipin
From Infogalactic: the planetary knowledge core
| Skeletal formula of genipin | |
| Ball-and-stick model of the genipin molecule | |
| Names | |
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| IUPAC name
Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
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| Identifiers | |
6902-77-8  |
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| ChEMBL | ChEMBL459016 |
| ChemSpider | 390864 |
| Jmol 3D model | Interactive image |
| KEGG | C09780 |
| PubChem | 442424 |
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| Properties | |
| C11H14O5 | |
| Molar mass | 226.226 g/mol |
| Vapor pressure | {{{value}}} |
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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
- ↑ 1.0 1.1 CBC Genipin
- ↑ Introduction of genipin
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
