Genipin

Genipin
Names
	Preferred IUPAC name Methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
Identifiers
CAS Number	6902-77-8 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL459016 ;
ChemSpider	390864 ;
ECHA InfoCard	100.164.015
KEGG	C09780 ;
PubChem CID	442424;
UNII	A3V2NE52YG ;
CompTox Dashboard (EPA)	DTXSID30894999 ;
	InChI 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 Key: AZKVWQKMDGGDSV-BCMRRPTOSA-N ; 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;
	SMILES O=C(OC)\C1=C\O[C@@H](O)[C@@H]2\C(=C/C[C@H]12)CO;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.

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.

In vitro experiments have shown that genipin blocks the action of the transporter uncoupling protein 2.