# Genipin

> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Genipin
> Markdown URL: https://mediated.wiki/source/Genipin.md
> Source: https://en.wikipedia.org/wiki/Genipin
> Source revision: 1322460629
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)

{{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](/source/chemical_compound) found in ''[Genipa americana](/source/Genipa_americana)'' fruit extract.  It is an [aglycone](/source/aglycone) derived from an [iridoid](/source/iridoid) [glycoside](/source/glycoside) called [geniposide](/source/geniposide) which is also present in fruit of ''[Gardenia jasminoides](/source/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-link](/source/cross-link)er 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](/source/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](/source/FDA)|language=en}}</ref> and as the intermediate for [alkaloid](/source/alkaloid) [syntheses](/source/organic_synthesis).<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](/source/In_vitro)'' experiments have shown that genipin blocks the action of the transporter [uncoupling protein 2](/source/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](/source/E_number)) 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](/source/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

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Adapted from the Wikipedia article [Genipin](https://en.wikipedia.org/wiki/Genipin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Genipin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.