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G4796

Sigma-Aldrich

Genipin

≥98% (HPLC), powder

Synonym(s):
Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
Empirical Formula (Hill Notation):
C11H14O5
CAS Number:
Molecular Weight:
226.23
MDL number:
PubChem Substance ID:

Quality Level

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

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

Pictograms

Skull and crossbones

Signal Word

Danger

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

More Documents

Quotes and Ordering

Ilaria Dando et al.
Biochimica et biophysica acta, 1833(3), 672-679 (2012-11-06)
Mitochondrial uncoupling protein 2 (UCP2) can moderate oxidative stress by favoring the influx of protons into the mitochondrial matrix, thus reducing electron leakage from respiratory chain and mitochondrial superoxide production. Here, we demonstrate that UCP2 inhibition by genipin or UCP2
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)
Ahmed O Elzoghby et al.
Pharmaceutical research, 30(2), 512-522 (2012-11-09)
To propose a simple method for the development of genipin-crosslinked casein micelles as a new delivery platform for prolonged release of alfuzosin hydrochloride. Crosslinked casein micelles entrapping alfuzosin were transformed into solid redispersible nanoparticles via spray-drying technique with no need
Costantino Del Gaudio et al.
Biomaterials, 34(31), 7754-7765 (2013-07-19)
Rapid and controlled vascularization of engineered tissues remains one of the key limitations in tissue engineering applications. This study investigates the possible use of natural extracellular matrix-like scaffolds made of gelatin loaded with human vascular endothelial growth factor (VEGF), as

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