A natural diterpene which increases serum cholesterol
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Cafestol

Item No. 13999

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3bS,4,5,6,7R,8R,9,10,10aR,10bS,11,12-dodecahydro-7-hydroxy-10b-methyl-5aS,8-methano-5aH-cyclohepta[5,6]naphtho[2,1-b]furan-7-methanol
CAS Number
469-83-0
Molecular Formula
C20H28O3
Formula Weight
316.4
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:50): Slightly solubleDMSO: 5 mg/mlEthanol: 5 mg/ml
λmax
224 nm
SMILES
O[C@]1(CO)C[C@]23[C@](CC[C@]1([H])C3)([H])[C@@](CCC4=C5C=CO4)(C)[C@]5([H])CC2
InChi Code
InChI=1S/C20H28O3/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/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1
InChi Key
DNJVYWXIDISQRD-HWUKTEKMSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $43

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    10 mg

    $73

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    50 mg

    $215

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    Product Description

    Cafestol is a natural diterpene which is abundant in unfiltered coffee.1,2 It elevates serum cholesterol and triglycerides in humans, an effect which does not seem to occur in monkeys, hamsters, rats, or gerbils.3,4 Dietary cafestol does increase total cholesterol and triglycerides in ApoE3Leiden mice, an effect which is associated with selective activation of farnesoid X receptors and pregnane X receptors.5 Cafestol (20 μM) also inhibits the proliferation of human umbilical vein endothelial cells and prevents their migration and tube formation on Matrigel™.6

    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. Naidoo, N., Chen, C., Rebello, S.A., et al. Cholesterol-raising diterpenes in types of coffee commonly consumed in Singapore, Indonesia and India and associations with blood lipids: A survey and cross sectional study. Nutr.J. 10(48), (2011).

    3. Urgert, R., Schulz, A.G.M., and Katan, M.B. Effects of cafestol and kahweol from coffee grounds on serum lipids and serum liver enzymes in humans. Am. J. Clin. Nutr. 61, 149-154 (1995).

    4. de Roos, B., Sawyer, J.K., Katan, M.B., et al. Validity of animal models for the cholesterol-raising effects of coffee diterpenes in human subjects. Proc. Nutr. Soc. 58(3), 551-557 (1999).

    5. Ricketts, M.L., Boekschoten, M.V., Kreeft, A.J., et al. The cholesterol-raising factor from coffee beans, cafestol, as an agonist ligand for the farnesoid and pregnane X receptors. Mol. Endocrinol. 21(7), 1603-1616 (2007).

    6. Wang, S., Yoon, Y.C., Sung, M.J., et al. Antiangiogenic properties of cafestol, a coffee diterpene, in human umbilical vein endothelial cells. Biochem. Biophys. Res. Commun. 421(3), 567-571 (2012).