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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14O5
Molecular Weight 226.2259
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GENIPIN

SMILES

COC(=O)C1=CO[C@@H](O)[C@H]2[C@@H]1CC=C2CO

InChI

InChIKey=AZKVWQKMDGGDSV-BCMRRPTOSA-N
InChI=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

HIDE SMILES / InChI
Molecular Formula C11H14O5
Molecular Weight 226.2259
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/7299624 | https://www.ncbi.nlm.nih.gov/pubmed/24041312 | https://www.ncbi.nlm.nih.gov/pubmed/9827681

Genipin is an aglycone derived from an iridoid glycoside called Geniposide (structure on the bottom) present in fruit of Gardenia jasmindides Ellis. Genipin have been demonstrated to have diverse pharmacological activities including anti-inflammatory, antioxidative, neuroprotective, and neurotrophic effects. Genipin is an excellent natural cross-linker for protein, collagen, gelatin, and chitosan cross-linking and can be considered as a substitute for glutaraldehyde. Due to cross-linking properties genipin can be used in controlling drug delivery. In addition genipin exerts choleretic action.

CNS Activity

CNS Active
4002
Curator's Comment: Genipin is CNS active in animal studies. No human data available

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Mitochondrial uncoupling protein 2
1
Target ID: P70406
Gene ID: 22228.0
Gene Symbol: Ucp2
Target Organism: Mus musculus (Mouse)
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Effect of genipin on the biliary excretion of cholephilic compounds in rats.
2008-06
Genipin exhibits neurotrophic effects through a common signaling pathway in nitric oxide synthase-expressing cells.
2008-03-10
Evaluation of the release rate of bioactive recombinant human epidermal growth factor from crosslinking collagen sponges.
2008-03
Genipin-crosslinked chitosan/gelatin blends for biomedical applications.
2008-02
Effects of collagen crosslinking on tissue fragility.
2008-01
Rheological study of genipin cross-linked chitosan hydrogels.
2007-12
A fibrinogen-based precision microporous scaffold for tissue engineering.
2007-12
Immobilization of drugs for glaucoma treatment.
2007-12
Synthesis of monoterpene alkaloid derivatives from the iridoid glucoside geniposide.
2007-11
Molecularly imprinted chitosan-genipin hydrogels with recognition capacity toward o-xylene.
2007-11
Mixed lineage kinase 3 connects reactive oxygen species to c-Jun NH2-terminal kinase-induced mitochondrial apoptosis in genipin-treated PC3 human prostate cancer cells.
2007-10-19
Noninvasive nuclear factor-kappaB bioluminescence imaging for the assessment of host-biomaterial interaction in transgenic mice.
2007-10
Glucose sensing by POMC neurons regulates glucose homeostasis and is impaired in obesity.
2007-09-13
The effect of novel nitrogen-rich plasma polymer coatings on the phenotypic profile of notochordal cells.
2007-09-06
Gelatin microspheres encapsulated with a nonpeptide angiogenic agent, ginsenoside Rg1, for intramyocardial injection in a rat model with infarcted myocardium.
2007-07-16
Preparation and evaluation of ketorolac tromethamine gel containing genipin for periodontal diseases.
2007-07
Effect of genipin, a naturally occurring crosslinker on the properties of kappa-carrageenan.
2007-06-01
Effect of gelatin on the drug release behaviors for the organic hybrid gels based on N-isopropylacrylamide and gelatin.
2007-06
Inchinkoto, a herbal medicine, and its ingredients dually exert Mrp2/MRP2-mediated choleresis and Nrf2-mediated antioxidative action in rat livers.
2007-05
Density quantification of collagen grafted on biodegradable polyester: its application to esophageal smooth muscle cell.
2007-04-01
Effect of process variables on particle size and viability of Bifidobacterium lactis Bb-12 in genipin-gelatin microspheres.
2007-03
Fingerprint reagents with dual action: color and fluorescence.
2007-03
Microstructural and tensile properties of elastin-based polypeptides crosslinked with genipin and pyrroloquinoline quinone.
2007-02-15
Constituents of Gardenia volkensii: their brine shrimp lethality and DPPH radical scavenging properties.
2007-02
In vitro and in vivo tissue repair with laser-activated chitosan adhesive.
2007-01
Application of crosslinkers to dentin collagen enhances the ultimate tensile strength.
2007-01
The effect of nucleus pulposus crosslinking and glycosaminoglycan degradation on disc mechanical function.
2007-01
Influence of cross-linking degree of a biodegradable genipin-cross-linked gelatin guide on peripheral nerve regeneration.
2007
Immobilization of lipase to chitosan beads using a natural cross-linker.
2007
Bonding of articular cartilage using a combination of biochemical degradation and surface cross-linking.
2007
Preparation and characterization of novel polymeric microcapsules for live cell encapsulation and therapy.
2007
Kinetic and mechanistic considerations in the gelation of genipin-crosslinked gelatin.
2006-11-15
Swelling and mechanical properties of biopolymer hydrogels containing chitosan and bovine serum albumin.
2006-11
Characterizing poly(epsilon-caprolactone)-b-chitooligosaccharide-b-poly(ethylene glycol) (PCP) copolymer micelles for doxorubicin (DOX) delivery: effects of crosslinked of amine groups.
2006-10-20
Genipin suppression of fibrogenic behaviors of the alpha-TN4 lens epithelial cell line.
2006-10
Effect of genipin-crosslinked chitin-chitosan scaffolds with hydroxyapatite modifications on the cultivation of bovine knee chondrocytes.
2006-09-05
Controlled in vivo degradation of genipin crosslinked polyethylene glycol hydrogels within osteochondral defects.
2006-09
A new method for microcapsule characterization: use of fluorogenic genipin to characterize polymeric microcapsule membranes.
2006-09
Exogenous cross-linking increases the stability of spinal motion segments.
2006-07-01
Genipin cross-linked alginate-chitosan microcapsules: membrane characterization and optimization of cross-linking reaction.
2006-07
Genipin inhibits UCP2-mediated proton leak and acutely reverses obesity- and high glucose-induced beta cell dysfunction in isolated pancreatic islets.
2006-06
Some physical and microstructural properties of genipin-crosslinked gelatin-maltodextrin hydrogels.
2006-02-28
Anti-inflammatory evaluation of gardenia extract, geniposide and genipin.
2006-02-20
Differences in neuritogenic response to nitric oxide in PC12 and PC12h cells.
2006-01-30
Genipin suppresses subconjunctival fibroblast migration, proliferation and myofibroblast transdifferentiation.
2006
Genipin prevents fulminant hepatic failure resulting in reduction of lethality through the suppression of TNF-alpha production.
2005-12
A novel drug-eluting stent spray-coated with multi-layers of collagen and sirolimus.
2005-11-02
Genipin, a novel fingerprint reagent with colorimetric and fluorogenic activity, part II: optimization, scope and limitations.
2005-11
Tissue regeneration observed in a porous acellular bovine pericardium used to repair a myocardial defect in the right ventricle of a rat model.
2005-09
pH-sensitive behavior of two-component hydrogels composed of N,O-carboxymethyl chitosan and alginate.
2005
Patents

Patents

05078750
2
05272172
2
05374653
2
05459160
2
06262083
1
JP1019092A
1
JP1022820A
1
JP1023861A
1
JP1031796A
1
JP2000053544A
1
JP2000095654A
6
JP2001503299A
1
JP2006500975A
14
JP2007526793A
16
JP2009502364A
1
JP2009525327A
1
JP2010075692A
1
JP2010155830A
1
JP2010521985A
1
JP2010522164A
1
JP2011102297A
1
JP2011115564A
1
JP4746046B2
1
JPH02107162A
1
JPH02107163A
1
JPH02263833A
1
JPH0358791A
1
JPH0366682A
1
JPH05339134A
1
JPH0558859A
1
JPH0656638A
1
JPH0687740A
2
JPH07310023A
1
JPH0995445A
1
JPS5253934A
1
JPS55164625A
1
JPS6147167A
1
JPS63123382A
1
JPS63157981A
1
JPS633064A
1
JPS6419092A
1
JPS6422820A
1
JPS6423861A
1
JPS6431796A
1

Sample Use Guides

In Vivo Use Guide
Oral genipin, at dose 50 mg/kg, exerts anti-inflammatory activity in carrageenan-induced rat paw edema
Route of Administration: Oral
In Vitro Use Guide
Genipin reduced the viability of K562 cells with an IC(50) value of approximately 250 μmol/L. Genipin 200-400 μmol/L induced formation of typical apoptotic bodies and DNA fragmentation.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:48:16 GMT 2025
Edited
by admin
on Mon Mar 31 21:48:16 GMT 2025
Record UNII
A3V2NE52YG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(+)-GENIPIN
Preferred Name English
GENIPIN
Common Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A.ALPHA.,5,7A.ALPHA.-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER
Common Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R,4AS,7AS)-
Systematic Name English
CYCLOPENTA(C)PYRAN-4-CARBOXYLIC ACID, 1,4A,5,7A-TETRAHYDRO-1-HYDROXY-7-(HYDROXYMETHYL)-, METHYL ESTER, (1R-(1.ALPHA.,4A.ALPHA.,7A.ALPHA.))-
Systematic Name English
Code System Code Type Description
WIKIPEDIA
Genipin
Created by admin on Mon Mar 31 21:48:16 GMT 2025 , Edited by admin on Mon Mar 31 21:48:16 GMT 2025
PRIMARY
FDA UNII
A3V2NE52YG
Created by admin on Mon Mar 31 21:48:16 GMT 2025 , Edited by admin on Mon Mar 31 21:48:16 GMT 2025
PRIMARY
PUBCHEM
442424
Created by admin on Mon Mar 31 21:48:16 GMT 2025 , Edited by admin on Mon Mar 31 21:48:16 GMT 2025
PRIMARY
CAS
6902-77-8
Created by admin on Mon Mar 31 21:48:16 GMT 2025 , Edited by admin on Mon Mar 31 21:48:16 GMT 2025
PRIMARY
EPA CompTox
DTXSID30894999
Created by admin on Mon Mar 31 21:48:16 GMT 2025 , Edited by admin on Mon Mar 31 21:48:16 GMT 2025
PRIMARY
NIH
NCATS
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