Kahweol

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

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 (JSmol)	Interactive image
ChEBI	CHEBI:138308
ChemSpider	102755
PubChem CID	114778
CompTox Dashboard (EPA)	DTXSID50988667
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	314.425 g·mol^−1
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

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]

See also

• Cafestol

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. 118 (4): 479–86. doi:10.1254/jphs.11212FP. PMID 22447306.CS1 maint: uses authors parameter (link)
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.CS1 maint: uses authors parameter (link)