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G4796

Sigma-Aldrich

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
MDL number:
MFCD00888600
UNSPSC Code:
12352200
PubChem Substance ID:
329799931
NACRES:
NA.77

product name

Genipin, ≥98% (HPLC), powder

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

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
The enamel protein ODAM promotes mineralization in a collagen matrix
Ikeda Y, et al.
Connective tissue research, 59(sup1), 62-66 (2018)
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
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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