Kahweol

Kahweol

Names
IUPAC name (3bS,5aS,7R,8R,10aR,10bS)-3b,4,5,6,7,8,9,10,10a,10b-Decahydro-7-hydroxy-10b-methyl-5a,8-Methano-5aH-cyclohepta(5,6)naphtho(2,1-b)furan-7-methanol
Identifiers
CAS Number	6894-43-5
3D model (Jmol)	Interactive image
ChemSpider	102755
PubChem	114778
InChI 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 Key: JEKMKNDURXDJAD-HWUKTEKMSA-N InChI=1/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 Key: JEKMKNDURXDJAD-HWUKTEKMBU
SMILES OC[C@@]5(O)C[C@@]43[C@H]([C@@]2(/C=C\c1occc1[C@H]2CC3)C)CC[C@@H]5C4
Properties
Chemical formula	C20H26O3
Molar mass	314.42 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Kahweol is a diterpene molecule found in the beans of Coffea arabica. It is structurally related to cafestol. It gets its name from the Arabic word "A-hah-wa", from which "coffee" derives. In French, it's evolved into the slang word "kawa", to designate coffee.

Recent research suggests that kahweol may have beneficial effects on bone by inhibiting osteoclast differentiation.^[1] Another recent study confirmed that kahweol has anti-inflammatory and anti-angiogenic effects, offering a possible mechanism for the association found in epidemiological studies between consumption of unfiltered coffee and decreased risk of cancer.^[2]

References

1. Fumimoto R, Sakai E, Yamaguchi Y, Sakamoto H, Fukuma Y, Nishishita K, Okamoto K, Tsukuba T (Mar 2012). "The Coffee Diterpene Kahweol Prevents Osteoclastogenesis via Impairment of NFATc1 Expression and Blocking of Erk Phosphorylation.". J Pharmacol Sci. 23 (4): 479–86. doi:10.1254/jphs.11212FP. PMID 22447306.
2. Cárdenas C, Quesada AR, Medina MA (Aug 2011). "Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene.". PLoS ONE. 6 (8): e23407. doi:10.1371/JOURNAL.PONE.0023407. PMC 3153489. PMID 21858104.