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Merck
CN

G4796

Genipin

≥98% (HPLC), powder, insulin stimulator

Synonym(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

Empirical Formula (Hill Notation):
C11H14O5
CAS Number:
6902-77-8
Molecular Weight:
226.23
UNSPSC Code:
12352200
PubChem Substance ID:
329799931
NACRES:
NA.77
MDL number:
MFCD00888600
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

Genipin, ≥98% (HPLC), powder

SMILES string

COC(=O)C1=CO[C@@H](O)C2C1CC=C2CO

InChI key

AZKVWQKMDGGDSV-BCMRRPTOSA-N

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

assay

≥98% (HPLC)

form

powder

solubility

DMSO: ≥25 mg/mL
H2O: insoluble

Quality Level

100

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Biochem/physiol Actions

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

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

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.

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.

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

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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Certificates of Analysis (COA)

Lot/Batch Number
0000521701
0000521701
0000493152
0000483018
0000483017

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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)
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
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)
Using dairy ingredients to produce edible films and biodegradable packaging materials
Tomasula PM
Dairy-Derived Ingredients: Food and Nutraceutical Uses, 589-624 (2009)
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