Genipin

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title: "Genipin" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["iridoids", "diols", "carboxylate-esters", "cyclopentenes", "food-colorings", "food-additives"] topic_path: "general/iridoids" source: "https://en.wikipedia.org/wiki/Genipin" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| 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 = | ChemSpiderID = 390864 | KEGG_Ref = | 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 = | ChEMBL = 459016 | StdInChI_Ref = | 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 = | StdInChIKey = AZKVWQKMDGGDSV-BCMRRPTOSA-N | CASNo_Ref = | CASNo = 6902-77-8 | UNII_Ref = | UNII = A3V2NE52YG | PubChem = 442424 | SMILES = O=C(OC)\C1=C\OC@@H[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.

Genipin is an excellent natural cross-linker for proteins, collagen, gelatin, and chitosan cross-linking. It has a low acute toxicity, with 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.

Gardenia blue

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

References

References

  1. (2014). "A review through recovery, purification and identification of genipin". Phytochemistry Reviews.
  2. (14 July 2025). "FDA Approves Gardenia (Genipin) Blue Color Additive While Encouraging Faster Phase-Out of FD&C Red No. 3". [[FDA]].
  3. Brenda Vaandering. "Genipin".
  4. (2006). "Genipin inhibits UCP2-mediated proton leak and acutely reverses obesity- and high glucose-induced beta cell dysfunction in isolated pancreatic islets". Cell Metabolism.
  5. (July 15, 2025). "FDA approves new blue food dye derived from gardenia fruit".

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iridoidsdiolscarboxylate-esterscyclopentenesfood-coloringsfood-additives