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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

Niveau de qualité

100

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

Michael E Frohbergh et al.
Biomaterials, 33(36), 9167-9178 (2012-10-02)
Reconstruction of large bone defects remains problematic in orthopedic and craniofacial clinical practice. Autografts are limited in supply and are associated with donor site morbidity while other materials show poor integration with the host's own bone. This lack of integration
Effect of Sulfuric Acid Concentration on Radiological Properties of Genipin Gel Dosimeter
Al-Jarrah A, et al.
International Journal of Chemistry (Canadian Center of Science and Education), 2, 2320-4087 (2014)
Using dairy ingredients to produce edible films and biodegradable packaging materials
Tomasula PM
Dairy-Derived Ingredients: Food and Nutraceutical Uses, 589-624 (2009)
UCP2 expression may represent a predictive marker of neoadjuvant chemotherapy effectiveness for locally advanced uterine cervical cancer
Imai K, et al.
Oncology Letters, 14(1), 951-957 (2017)
Ting Ting Lau et al.
Biomedical materials (Bristol, England), 7(6), 065003-065003 (2012-11-03)
Primary hepatocyte is probably the preferred cell for cell therapy in liver regeneration. However, its non-ideal proliferation capacity and rapid loss of phenotype during 2D culture compromises the quality and quantity of the transplanted hepatocytes, resulting in variable success rates
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