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 (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

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.

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

^ "The Coffee Diterpene Kahweol Prevents Osteoclastogenesis via Impairment of NFATc1 Expression and Blocking of Erk Phosphorylation". J Pharmacol Sci. 118 (4): 479–86. Mar 2012. doi:10.1254/jphs.11212FP. PMID 22447306. {{cite journal}}: Cite uses deprecated parameter |authors= (help)
^ "Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene". PLoS ONE. 6 (8): e23407. Aug 2011. doi:10.1371/JOURNAL.PONE.0023407. PMC 3153489. PMID 21858104. {{cite journal}}: Cite uses deprecated parameter |authors= (help)CS1 maint: unflagged free DOI (link)

[1] "The Coffee Diterpene Kahweol Prevents Osteoclastogenesis via Impairment of NFATc1 Expression and Blocking of Erk Phosphorylation". J Pharmacol Sci. 118 (4): 479–86. Mar 2012. doi:10.1254/jphs.11212FP. PMID 22447306. {{cite journal}}: Cite uses deprecated parameter |authors= (help)

[2] "Anti-angiogenic and anti-inflammatory properties of kahweol, a coffee diterpene". PLoS ONE. 6 (8): e23407. Aug 2011. doi:10.1371/JOURNAL.PONE.0023407. PMC 3153489. PMID 21858104. {{cite journal}}: Cite uses deprecated parameter |authors= (help)CS1 maint: unflagged free DOI (link)

[1]

[2]

See also

References