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
ChemSpider	102755
Jmol interactive 3D	Image
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).
verify (what is  ?)
Infobox references

Kahweol is a diterpene molecule found in the beans of Coffea arabica. It is structurally related to cafestol.

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/annotation/38262cc6-07cc-4074-8ce7-2181d4d0fbdc. PMC 3153489. PMID 21858104.