| Genipin | |
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Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate |
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| Identifiers | |
| CAS number | 6902-77-8 |
| PubChem | 442424 |
| ChemSpider | 390864 |
| KEGG | C09780 |
| ChEMBL | CHEMBL459016 |
| Jmol-3D images | Image 1 |
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| 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, 100 kPa) |
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| Infobox references | |
Genipin is the active compound found in the gardenia fruit extract, which is used in traditional Chinese medicine to relieve the symptoms of type 2 diabetes. Research conducted at the Beth Israel Deaconess Medical Center and Harvard Medical School indicated that the chemical is indeed effective.
Genipin 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. 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 regents. It is also used for pharmaceutical purposes, such as choleretic action for liver diseases control.
Furthermore, genipin can be used as a cross-linking agent for immobilized enzymes, as a regulating agent for drug delivery, as the raw material for gardenia blue pigment preparation, and as the intermediate for alkaloid syntheses.