AurapteneA cell proliferation and ACAT inhibitor and PPAR agonist

Auraptene (CAS 495-02-3)

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Synonym: 7-Geranyloxycoumarin
Application: A cell proliferation and ACAT inhibitor and PPAR agonist
CAS Number: 495-02-3
Purity: ≥95%
Molecular Weight: 298.38
Molecular Formula: C19H22O3
* Refer to Certificate of Analysis for lot specific data (including water content).
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Auraptene is a prenyloxycoumarin from citrus peels. The compound has been observed to have chemopreventive effects against colitis-related colon and breast cancers through inhibition of cholesterol esterification and modulation of estrogen receptors. In female BALB/c mice, auraptene was observed to increase macrophage and lymphocyte functions. In the established colorectal cancer cells, auraptene displayed apoptotic inhibition of cellular proliferation. Auraptene has also demonstrated antiinflammatory properties. Through disruption of the ERK1/2 pathway, it can mediate the translation of MMP-7. Additionally, auraptene also retains the ability to activate PPAR α and PPARγ to control adipocytekines. It has been suggested to be an acetyl-CoA acetyltranferase (ACAT) inhibitor.


References

1. Tanaka, T., et al. 1999. Carcinogenesis. 20: 1471-1476. PMID: 10426794
2. Mori, H., et al. 2001. Mutat. Res. 480-481: 201-207. PMID: 11506814
3. Curini, M., et al. 2004. Bioorg. Med. Chem. Lett. 14: 2241-2243. PMID: 15081016
4. Kawabata, K., et al. 2006. FEBS Lett. 580: 5288-5294. PMID: 16979634
5. Kuroyanagi, K., et al. 2008. Biochem. Biophys. Res. Commun. 366: 219-225. PMID: 18060855
6. de Medina, P., et al. 2010. Mol. Pharmacol. 78: 827-836. PMID: 20702762

Physical State :
Solid
Derived From :
Isolated from citrus fruit
Solubility :
Soluble in methanol, and 100% ethanol.
Storage :
Store at -20° C
Melting Point :
134.12° C (Predicted)
Boiling Point :
455.54° C at 760 mmHg (Predicted)
Density :
1.08 g/cm3 (Predicted)
Refractive Index :
n20D 1.55 (Predicted)
IC50 :
15-LO: IC50 = 23.9 µM (human); ACAT: IC50 = 4 µM; 3T3-L1: IC50 = 47 µM (mouse); Soyabean 15-lipoxygenase: IC50 = 6.3 µM; PC-3: IC50 = 65 µM (human)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
1550607
MDL Number :
MFCD00075948
SMILES :
CC(=CCC/C(=C/COC1=CC2=C(C=C1)C=CC(=O)O2)/C)C

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Certificate of Analysis

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