A natural diterpene with anti-inflammatory and antiangiogenic properties
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Kahweol

Item No. 14015

Technical Information
Formal Name
3bS,4,5,6,7R,8R,9,10,10aR,10bS-decahydro-7-hydroxy-10b-methyl-5aS,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol
CAS Number
6894-43-5
Molecular Formula
C20H26O3
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 5 mg/mlDMSO: 3 mg/mlEthanol: 5 mg/mlEthanol:PBS (pH7.2)(1:50): 0.02 mg/ml
λmax
289 nm
SMILES
OC[C@]1(O)[C@@]2([H])C[C@]3(C1)CCC4C5=C(OC=C5)C=C[C@@]4(C)C3CC2
InChi Code
InChI=1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15?,17?,18-,19+,20+/m1/s1
InChi Key
JEKMKNDURXDJAD-JUKDXYPLSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Kahweol is a natural diterpene that is isolated from coffee beans.1 It increases glutathione S-transferase activity in the gut mucosa of mice and, with the diterpene cafestol, induces glutathione S-transferase expression in rat livers.1,2 Kahweol has anti-inflammatory effects in RAW macrophages, inhibiting LPS-induced nitric oxide and prostaglandin E2 production (IC50 = 54 and 23 μM, respectively).3 Kahweol also is antiangiogenic, blocking the proliferation of endothelial cells (IC50 = 50 μM) and inhibiting endothelial migration, invasion, and tube formation.4 Kahweol is easily oxidized in the presence of air.1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lam, L.K.T., Sparnins, V.L., and Wattenberg, L.W. Isolation and identification of kahweol palmitate and cafestol palmitate as active constituents of green coffee beans that enhance glutathione S-transferase activity in the mouse. Cancer Res. 42(4), 1193-1198 (1982).

    2. Cavin, C., Holzhäuser, D., Constable, A., et alThe coffee-specific diterpenes cafestol and kahweol protect against aflatoxin B1-induced genotoxicity through a dual mechanism. Carcinogenesis 19(8), 1369-1375 (1998).

    3. Shen, T., Park, Y.C., Kim, S.H., et alNuclear factor-κB/signal transducers and activators of transcription-1-mediated inflammatory responses in lipopolysaccharide-activated macrophages are a major inhibitory target of kahweol, a coffee diterpene. Biol. Pharm. Bull. 33(7), 1159-1164 (2010).

    4. Cárdenas, C., Quesada, A.R., and Medina, M.A. Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene. PLoS One 6(8), (2011).