Cayman Chemical Item Number 10010622

(+)-Genipin (CAS 6902-77-8)

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Uncoupling protein 2 (UCP2) is a mitochondrial carrier protein that is expressed in pancreatic islets and has been shown to negatively regulate glucose-stimulated insulin secretion.1,2 High levels of UCP2 expression can disrupt pancreatic β cell function and downregulate insulin secretion thereby contributing to the development of type 2 diabetes.3 Genipin, a compound isolated from Gardenis jasminoides Ellis fruits, was originally identified as a protein cross-linking agent. Genipin is a cell-permeable inhibitor of UCP2 activity.4 Genipin, at 5 µM, increases glucose-stimulated insulin secretion in isolated pancreatic islets chronically exposed to high levels of glucose.5 Genipin also exhibits anti-inflammatory and anti-angiogenic properties by inducing apoptosis in FaO rat hepatoma cells and human hepatocarcinoma Hep3B cells.6

1. Chan, C.B., De Leo, D., Joseph, J.W., et al. Increased uncoupling protein-2 levels in b-cells are associated with impaired glucose-stimulated insulin secretion mechanism of action. Diabetes 50 1302-1310 (2001).

2. Zhang, C., Baffy, G., Perret, P., et al. Uncoupling protein-2 negatively regulates insulin secretion and is a major link between obesity, b cell dysfunction, and type 2 diabetes. Cell 105 745-755 (2001).

3. Sesti, G., Cardellini, M., Marini, M.A., et al. A common polymorphism in the promoter of UCP2 contributes to the variation in insulin secretion in glucose-tolerant subjects. Diabetes 52 1280-1283 (2003).

4. Parton, L.E., Ye, C.P., Coppari, R., et al. Glucose sensing by POMC neurons regulates glucose homeostasis and is impaired in obesity. Nature 449 228-232 (2007).

5. Zhang, C., Parton, L.E., Ye, C.P., et al. Genipin inhibits UCP2-mediated proton leak and acutely reverses obesity-and high glucose-induced b cell dysfunction in isolated pancreatic islets. Cell Metab 3 417-427 (2006).

6. Kim, B., Kim, H., Lee, S., et al. Genipin-induced apoptosis in hepatoma cells is mediated by reactive oxygen species/c-Jun NH2-terminal kinase-dependent activation of mitochondrial pathway. Biochem Pharmacol 70 1398-1407 (2005).

  • (+)-Genipin
Formal Name 1R,​4aS,​5,​7aS-​tetrahydro-​1-​hydroxy-​7-​(hydroxymethyl)-​cyclopenta[c]pyran-​4-​carboxylic acid,​ methyl ester
CAS Number 6902-77-8
Molecular Formula C11H14O5
Formula Weight 226.2
Formulation A crystalline solid
Purity ≥98%
λmax 240 nm
Stability 2 years
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
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Size Price Quantity Subtotal
5 mg $13.00 $0.00
10 mg $25.00 $0.00
25 mg $59.00 $0.00
50 mg $104.00 $0.00
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Cart Total $0.00

Pricing updated 2015-07-31. Prices are subject to change without notice.

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Cayman Chemical was formed over thirty years ago by demonstrating the value of naturally growing gorgonian corals as a renewable, economically viable source of prostaglandins. Today we operate our business knowing that we owe our start to the renewable resources our environment had provided. As Cayman Chemical continues to grow we consistently evaluate our business processes to ensure we are operating at the highest environmental standards.

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