genipin
{{chembox
| Watchedfields = changed
| verifiedrevid = 415504856
| ImageFile = Genipin.svg
| ImageSize = 160
| ImageAlt = Skeletal formula of genipin
| ImageFile1 = Genipin 3D ball.png
| ImageSize1 = 170
| ImageAlt1 = Ball-and-stick model of the genipin molecule
| PIN = Methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
| OtherNames =
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 390864
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C09780
| 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
| InChIKey = AZKVWQKMDGGDSV-BCMRRPTOBC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 459016
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = AZKVWQKMDGGDSV-BCMRRPTOSA-N
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 6902-77-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = A3V2NE52YG
| PubChem = 442424
| SMILES = O=C(OC)\C1=C\O[C@@H](O)[C@@H]2\C(=C/C[C@H]12)CO
}}
|Section2={{Chembox Properties
| Formula = C11H14O5
| MolarMass = 226.226 g/mol
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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.{{citation |author1=Ramos-de-la-Peña, A.M. |author2=Renard, C.M.G.C. |author3=Montañez, J. |author4=Reyes-Vega, M.L. |author5=Contreras-Esquivel, J.C. |year=2014 |title=A review through recovery, purification and identification of genipin |journal=Phytochemistry Reviews |volume=15 |pages=37–49 |doi=10.1007/s11101-014-9383-z |s2cid=16614004 }}
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.{{citation |url=http://www.wou.edu/las/physci/ch350/Projects_2006/Vaandering/Genipin.htm |title=Genipin |author=Brenda Vaandering |access-date=22 December 2019}}
In vitro experiments have shown that genipin blocks the action of the transporter uncoupling protein 2.{{Cite journal | pmid = 16753577 | year = 2006 | last1 = Zhang | first1 = CY | last2 = Parton | first2 = LE | last3 = Ye | first3 = CP | last4 = Krauss | first4 = S | last5 = Shen | first5 = R | last6 = Lin | first6 = CT | last7 = Porco Jr | first7 = JA | last8 = Lowell | first8 = BB | title = Genipin inhibits UCP2-mediated proton leak and acutely reverses obesity- and high glucose-induced beta cell dysfunction in isolated pancreatic islets | volume = 3 | issue = 6 | pages = 417–27 | doi = 10.1016/j.cmet.2006.04.010 | journal = Cell Metabolism| doi-access = free }}