Genipin

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.^[1]

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 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL459016 Y
ChemSpider	390864 Y
ECHA InfoCard	100.164.015
KEGG	C09780 Y
PubChem CID	442424
UNII	A3V2NE52YG Y
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 Y Key: AZKVWQKMDGGDSV-BCMRRPTOSA-N Y 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). Y verify (what is YN ?) Infobox references

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^[2], and as the intermediate for alkaloid syntheses.^[3]

In vitro experiments have shown that genipin blocks the action of the transporter uncoupling protein 2.^[4]

Gardenia blue

The pigment Gardenia blue (E165) is made by reacting genipin with soy protein hydrolysate.^[5]