A prenylated coumarin with diverse biological activities
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Umbelliprenin

Item No. 27894

Technical Information
Formal Name
7-[(3,7,11-trimethyl-2,6,10-dodecatrien-1-yl)oxy]-2H-1-benzopyran-2-one
CAS Number
532-16-1
Synonyms
  • 7-Farnesyloxycoumarin
Molecular Formula
C24H30O3
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 30 mg/mlDMSO: 5 mg/ml
SMILES
C/C(C)=C/CC/C(C)=C/CC/C(C)=C/COC1=CC=C(C=CC(O2)=O)C2=C1
InChi Code
InChI=1S/C24H30O3/c1-18(2)7-5-8-19(3)9-6-10-20(4)15-16-26-22-13-11-21-12-14-24(25)27-23(21)17-22/h7,9,11-15,17H,5-6,8,10,16H2,1-4H3/b19-9+,20-15+
InChi Key
GNMUGVNEWCZUAA-WOWYBKFKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    Product Description

    Umbelliprenin is a prenylated coumarin that has been found in Ferula and has diverse biological activities.1,2 It inhibits 5-lipoxygenase (5-LO) in a cell-free assay (IC50 = 72.5 nM).1 Umbelliprenin is active against L. major promastigotes (IC50 = 13.3 µM). It induces cell cycle arrest at the G1 phase in, as well as inhibits the growth of (IC50 = 12.5 µM), M4Beu metastatic pigmented melanoma cells and reduces tumor volume in a mouse Lewis lung carcinoma model. It reduces tumor growth and the number of metastases in a 4T1 mouse allograft model.2 Umbelliprenin (0.01 mmol/kg) reduces carrageenan-induced paw edema in mice.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Shakeri, A., Iranshahy, M., and Iranshahi, M. Biological properties and molecular targets of umbelliprenin--a mini-review. J. Asian Nat. Prod. Res. 16(8), 884-889 (2014).

    2. Rashidi, M., Khalilnezhad, A., Amani, D., et alUmbelliprenin shows antitumor, antiangiogenesis, antimetastatic, anti-inflammatory, and immunostimulatory activities in 4T1 tumor-bearing Balb/c mice. J. Cell. Physiol. 233(11), 8908-8918 (2018).