{{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 (1''R'',4a''S'',7a''S'')-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 = C<sub>11</sub>H<sub>14</sub>O<sub>5</sub> | 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''.<ref>{{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 }}</ref>

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&nbsp;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,<ref>{{cite web|url=https://www.fda.gov/news-events/press-announcements/fda-approves-gardenia-genipin-blue-color-additive-while-encouraging-faster-phase-out-fdc-red-no-3|title=FDA Approves Gardenia (Genipin) Blue Color Additive While Encouraging Faster Phase-Out of FD&C Red No. 3|date=14 July 2025 |publisher=FDA|language=en}}</ref> and as the intermediate for alkaloid syntheses.<ref>{{citation |url=http://www.wou.edu/las/physci/ch350/Projects_2006/Vaandering/Genipin.htm |title=Genipin |author=Brenda Vaandering |access-date=22 December 2019}}</ref>

''In vitro'' experiments have shown that genipin blocks the action of the transporter uncoupling protein 2.<ref>{{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 }}</ref>

==Gardenia blue== The pigment Gardenia blue (E165) is made by reacting genipin with soy protein hydrolysate.<ref>{{cite web|url=https://www.cbsnews.com/news/fda-approves-blue-food-dye-gardenia-fruit/|title=FDA approves new blue food dye derived from gardenia fruit|website=CBS News |date=July 15, 2025|accessdate=July 22, 2025}}</ref>

== References == {{Reflist}}

Category:Iridoids Category:Diols Category:Carboxylate esters Category:Cyclopentenes Category:Food colorings Category:Food additives