Structure via PubChem · Public domain (PubChem)
genipin
Sign in to saveGenipin 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.
In the Vinony graph
Vinony's link graph records 9 inbound references to genipin, and connects out to chemical compound, digital object identifier and chemical formula.
It is catalogued under topics including Carboxylate esters, Chembox image size set and Cyclopentenes.
Vinony links it to 11 Wikipedia language editions.
Chemical data
- Formula
- C11H14O5
- Molecular weight
- 226.23 g/mol
- IUPAC name
- methyl (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylate
- SMILES
- COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O
- InChIKey
- AZKVWQKMDGGDSV-BCMRRPTOSA-N
- XLogP
- -0.7
- Polar surface area
- 76 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- tendinitis
via ChEMBL · EBI
Research
2,018 papers- Genipin ameliorates diabetic retinopathy via the HIF-1α and AGEs-RAGE pathways.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Genipin-crosslinked hydrogels for food and biomedical applications: A scientometric review.International journal of biological macromolecules · 2024
- Genipin, a natural blue colorant precursor: Source, extraction, properties, and applications.Food chemistry · 2024
- Genipin-cross-linked hydrogels based on biomaterials for drug delivery: a review.Biomaterials science · 2021
- Genipin's potential as an anti-cancer agent: from phytochemical origins to clinical prospects.Medical oncology (Northwood, London, England) · 2024
via PubMed
Wikidata facts
- Subclass of
- iridoid
- Mass
- 226.084124
Show 5 more facts
- found in taxon
- Lamium album
- chemical formula
- C₁₁H₁₄O₅
- isomeric SMILES
- COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O
- canonical SMILES
- COC(=O)C1=COC(C2C1CC=C2CO)O
- Commons category
- Genipin
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- Gardenia blue
- References
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.
Excerpted from Wikipedia’s “genipin” article, available under the CC BY-SA 4.0 licence.