16-O-Methylcafestol

16-O-Methylcafestol, a derivative of cafestol, is an isolate of green coffee beans.^[1]

Quick facts Names, Identifiers ...

16-O-Methylcafestol

Names
IUPAC name 16α-Methoxy-3,18-(epoxymetheno)-19-nor-5β,8α,9β,10α,13β,16β-kaur-3-en-17-ol
Systematic IUPAC name [(3bS,5aS,7R,8R,10aR,10bS)-7-Methoxy-10b-methyl-3b,4,5,6,7,8,9,10,10a,10b,11,12-dodecahydro-5a,8-methanocyclohepta[5,6]naphtho[2,1-b]furan-7-yl]methanol
Identifiers
CAS Number	108214-28-4 Y
3D model (JSmol)	Interactive image
ChemSpider	22901058
PubChem CID	68103163
UNII	TJ95S36BVX Y
CompTox Dashboard (EPA)	DTXSID30737953
InChI InChI=1S/C21H30O3/c1-19-8-6-17-15(7-10-24-17)16(19)5-9-20-11-14(3-4-18(19)20)21(12-20,13-22)23-2/h7,10,14,16,18,22H,3-6,8-9,11-13H2,1-2H3/t14-,16-,18+,19-,20+,21+/m1/s1 Key: BDVVNPOGDNWUOI-GVOJMRIRSA-N
SMILES C[C@@]12CCC3=C([C@H]1CC[C@]45[C@H]2CC[C@H](C4)[C@](C5)(CO)OC)C=CO3
Properties
Chemical formula	C21H30O3
Molar mass	330.468 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa). Infobox references

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This derivative only occurs in the robusta variant of coffee (as opposed to the more expensive arabica, where only cafestol is present). Thus 16-O-Methylcafestol is used as an analytical marker for determining the robusta content of coffee blends.^[2]