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G4796

Sigma-Aldrich

Genipin

≥98% (HPLC), powder, insulin stimulator

Synonym(e):

1S,2R,6S)-2-Hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-dien-5-carbonsäure-methylester

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About This Item

Empirische Formel (Hill-System):
C11H14O5
CAS-Nummer:
6902-77-8
Molekulargewicht:
226.23
MDL-Nummer:
MFCD00888600
UNSPSC-Code:
12352200
PubChem Substanz-ID:
329799931
NACRES:
NA.77

product name

Genipin, ≥98% (HPLC), powder

Assay

≥98% (HPLC)

Form

powder

Löslichkeit

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

InChIKey

AZKVWQKMDGGDSV-BCMRRPTOSA-N

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Allgemeine Beschreibung

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.

Anwendung

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

Biochem./physiol. Wirkung

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

Leistungsmerkmale und Vorteile

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

Piktogramme

Skull and crossbones
GHS06

Signalwort

Danger

H-Sätze

H301

Gefahreneinstufungen

Acute Tox. 3 Oral

Lagerklassenschlüssel

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

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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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