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G4796 Sigma-Aldrich

Genipin

≥98% (HPLC), powder

Synonym: Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience, Cytokines, Growth Factors and Hormones,
assay   ≥98% (HPLC)
form   powder
solubility   DMSO: ≥25 mg/mL
  H2O: insoluble
SMILES string   COC(=O)C1=CO[C@@H](O)C2C1CC=C2CO
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
InChI key   AZKVWQKMDGGDSV-BCMRRPTOSA-N

Description

General description

Genipin is a natural cross linking agent, which is extracted from gardenia fruit. It prevents lipid peroxidation and production of nitric oxide. Genipin protects the hippocampal neurons from the toxicity of Alzheimer′s amyloid β protein. It has anti-inflammatory and anti-angiogenesis effects. Genipin is involved in drug delivery system.

Application

Genipin has been used:
• in chemosensitivity assay
• in the preparation of recombinant human (rh)-odontogenic ameloblast-associated protein (ODAM) -impregnated collagen gel and in vitro mineralization assay
• in genipin gel preparation

Packaging

25, 125 mg in glass bottle

Biochem/physiol Actions

Genipin stimulates insulin secretion in UCP2-dependent manner (Uncoupling protein 2). Genipin is a protein, collagen, gelatin, and chitosan cross-linker.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the InsR page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
UN 2811 6.1 / PGIII
WGK Germany 
WGK 3
RTECS 
GY5828000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Nitric Oxide & Cell Stress Research

Exposure to harsh conditions, cellular damage, and other factors can cause stress on cells. Stress attributed directly and indirectly to oxygen is referred to as oxidative stress, which is imposed on...
Keywords: Antimicrobials, Bioactive small molecules, Cancer, Diseases, Neurodegenerative Diseases, Oxidations

InsR

The insulin receptor belongs to a subfamily of receptor tyrosine kinases that also includes the IGF-1 receptor and an orphan receptor called the insulin receptor-related receptor (IRR). It is a tetra...
Keywords: Atomic absorption spectroscopy, Cancer, Diabetes, Gastrointestinal, Gene expression, Genetic, Glycosylations, Growth factors, Infrared spectroscopy, Ligands, Obesity, Phosphorylations

Peer-Reviewed Papers
15

References

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