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G4796

Sigma-Aldrich

Genipin

≥98% (HPLC), powder

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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:
6902-77-8
Molecular Weight:
226.23
MDL number:
MFCD00888600
UNSPSC Code:
12352200
PubChem Substance ID:
329799931
NACRES:
NA.77

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. 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

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, 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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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
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)
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
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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