GenipinAn inhibitor of uncoupling protein 2 (UCP2)

Genipin (CAS 6902-77-8)

Genipin | CAS 6902-77-8 is rated 5.0 out of 5 by 1.
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Synonym: Methyl (1S,2R,6S)-2-hydroxy-9-(hydroxymethyl)-3-oxabicyclo[4.3.0]nona-4,8-diene-5-carboxylate
Application: An inhibitor of uncoupling protein 2 (UCP2)
CAS Number: 6902-77-8
Purity: >98%
Molecular Weight: 226.23
Molecular Formula: C11H14O5
Supplemental Information: This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Genipin is a compound isolated from Gardenis jasminoides Ellis fruits which acts as a cell permeable inhibitor of UCP2 (uncoupling protein 2). Increases glucose-stimulated insulin secretion, mitochondrial membrane potential and ATP levels in pancreatic island cells. Genipin has been shown to induce apoptosis and is a protein cross-linking agent. Genipin, at 5 μM, increases glucose-stimulated insulin secretion in isolated pancreatic islets chronically exposed to high levels of glucose. Genipin also exhibits anti-inflammatory and anti-angiogenic properties by inducing apoptosis in FaO rat hepatoma cells and human hepatocarcinoma Hep3B cells.


References

1. Zhang, C.Y., et al. 2001. Cell. 105: 745-755. PMID: 11440717
2. Chan, C.B., et al. 2001. Diabetes. 50: 1302-1310. PMID: 11375330
3. Sesti, G., et al. 2003. Diabetes. 52: 1280-1283. PMID: 12716765
4. Kim, B.C., et al. 2005. Biochem. Pharmacol. 70: 1398-1407. PMID: 16143311
5. Zhang, C.Y., et al. 2006. Cell Metab. 3: 417-427. PMID: 16753577
6. Parton, L.E., et al. 2007. Nature. 449: 228-232. PMID: 17728716

Appearance :
Crystalline
Physical State :
Solid
Derived From :
Gardenia jasminoides Ellis.
Solubility :
Soluble in DMSO (50 mg/ml), DMF (≥25 mg/ml), 100% ethanol (5 mg/ml), and methanol. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
121-125° C
Boiling Point :
~416.0° C at 760 mmHg (Predicted)
Density :
~1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.57 (Predicted)
IC50 :
Hepatitis C virus: IC50 = 88.41 µM
pK Values :
pKa: 12.07 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GY5828000
PubChem CID :
442424
MDL Number :
MFCD00888600
SMILES :
COC(=O)C1=CO[C@H]([C@H]2[C@@H]1CC=C2CO)O

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Certificate of Analysis

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Genipin  Product Citations

See how others have used Genipin. Click on the entry to view the PubMed entry .

Citations 1 to 3 of 3 total

PMID: # 28738532  Mahgoub, E. et al. 2017. Biomed. Pharmacother. 93: 1083-1097.

PMID: # 28792088  Han, Y. et al. 2017. Cell Biol. Int. 41: 1296-1306.

PMID: # 29080346  Aksel, H. et al. 2017. Int Endod J.

Citations 1 to 3 of 3 total

Do you have stock of this product (genipine)? Are the quotations up to day? Thanks

Asked by: Ignacio Ruiz
Thank you for your question. Please contact one of our authorized distributors for information about current product availability and shipping lead times.
Answered by: Technical Support
Date published: 2018-12-28

What is the appearance of the compound?

Asked by: two2igm05
Thank you for your question. This chemical is supplied as a white crystalline powder. Please contact Technical Service if you have further questions concerning this product.
Answered by: Tech Service 9
Date published: 2017-01-16
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Rated 5 out of 5 by from Zhang et al Zhang et al. (PubMed ID 16753577) showed that Genipin inhibited UCP2-mediated proton leakage in isolated mitochondria of pancreatic islets. -SCBT Publication Review
Date published: 2015-04-16
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