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G4796

Sigma-Aldrich

Genipin

≥98% (HPLC), powder, insulin stimulator

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C11H14O5
Numéro CAS:
6902-77-8
Poids moléculaire :
226.23
Numéro MDL:
MFCD00888600
Code UNSPSC :
12352200
ID de substance PubChem :
329799931
Nomenclature NACRES :
NA.77

product name

Genipin, ≥98% (HPLC), powder

Pureté

≥98% (HPLC)

Forme

powder

Solubilité

DMSO: ≥25 mg/mL
H2O: insoluble

Chaîne SMILES 

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

Clé InChI

AZKVWQKMDGGDSV-BCMRRPTOSA-N

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Description générale

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

Actions biochimiques/physiologiques

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

Caractéristiques et avantages

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

Pictogrammes

Skull and crossbones
GHS06

Mention d'avertissement

Danger

Mentions de danger

H301

Classification des risques

Acute Tox. 3 Oral

Code de la classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

Using dairy ingredients to produce edible films and biodegradable packaging materials
Tomasula PM
Dairy-Derived Ingredients: Food and Nutraceutical Uses, 589-624 (2009)
Genipin-crosslinked chitosan hydrogels as biomedical and pharmaceutical aids
Muzzarelli RAA
Carbohydrate Polymers, 77(1), 1-9 (2009)
Daniel J Macaya et al.
Biomaterials, 34(14), 3591-3602 (2013-02-19)
Astrocytes can play dual roles in the response to spinal cord injury (SCI) acting as both an inhibitory barrier and a trophic support for growth axons. Therefore, migration of these cells into the defect as opposed to forming a scar
Yuanting Xu et al.
Carbohydrate polymers, 92(1), 448-454 (2012-12-12)
Biological tissues must be chemically fixed before they can be implanted in humans, due to the immediate degradation and presence of antigenicity of naturally derived tissues. To provide a crosslinking reagent which is cytocompatible and may prepare biocompatible fixed tissues
Aji P Mathew et al.
Macromolecular bioscience, 13(3), 289-298 (2012-12-12)
Bio-based fibrous nanocomposites of cellulose nanofibres and non-crosslinked/crosslinked collagen were prepared by in situ pH-induced fibrillation of collagen phase and sterilized using gamma rays at 25 KGy. Collagen phase is crosslinked using genipin, a bio-based crosslinker that introduces flexible crosslinks.
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