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G4796

Sigma-Aldrich

Genipin

≥98% (HPLC), powder, insulin stimulator

Sinónimos:

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

Fórmula empírica (notación de Hill):
C11H14O5
Número de CAS:
6902-77-8
Peso molecular:
226.23
MDL number:
MFCD00888600
UNSPSC Code:
12352200
PubChem Substance ID:
329799931
NACRES:
NA.77
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Nombre del producto

Genipin, ≥98% (HPLC), powder

Quality Level

100

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.[1] 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.[2] Genipin is involved in drug delivery system.[3]

Application

Genipin has been used:
  • in chemosensitivity assay[4]
  • in the preparation of recombinant human (rh)-odontogenic ameloblast-associated protein (ODAM) -impregnated collagen gel and in vitro mineralization assay[5]
  • in genipin gel preparation[6][7]

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
GHS06

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificados de análisis (COA)

Lot/Batch Number
0000407639
0000407639
0000397836
0000342616
0000388545

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Visite la Librería de documentos

Implications of protein-and peptide-based nanoparticles as potential vehicles for anticancer drugs
Elzoghby AO, et al.
Advances in Protein Chemistry and Structural Biology, 98, 169-221 (2015)
Effect of inorganic salts and glucose additives on dose-response, melting point and mass density of genipin gel dosimeters
Al-Jarrah AM, et al.
Physica Medica : PM : An International Journal Devoted to the Applications of Physics to Medicine and Biology : Official Journal of the Italian Association of Biomedical Physics (AIFB), 32(1), 36-41 (2016)
The enamel protein ODAM promotes mineralization in a collagen matrix
Ikeda Y, et al.
Connective tissue research, 59(sup1), 62-66 (2018)
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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