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Genipin is an aglycone derived from an iridoid glycoside called geniposide present in fruit of Gardenia jasmindides Ellis.

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 regents. It is also used for pharmaceutical purposes, such as choleretic action for liver diseases control.

Genipin is available for small and large scale production.

Genipin Structure
Genipin Structure

IUPAC name Methyl (1R,2R,6S)-2-hydroxy-9-(hydroxymethyl)- 3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
Identifiers
CAS number [6902-77-8]
PubChem 442424
SMILES COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O
Properties
Molecular formula C11H14O5
Molar mass 226.226 g/mol
Hydrogen Bonds Donors
 2
Hydrogen Bonds Acceptors 5
Rotatable Bonds
 3
Polar Surface Area
 76
XLogP -0.8
Exact Mass
 226.084
MonoIsotopic Mass
 226.084
Charge
 0
Complexity
 357

 
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