Vanillyl decanoate → Dihydrocapsiate
Reaction equation
[CH3:1]C(C)CCCCCCC(OCCC1C=CC(O)=C(OC)C=1)=O.[C:24]([O:35][CH2:36][C:37]1[CH:45]=[CH:44][C:42]([OH:43])=[C:39]([O:40][CH3:41])[CH:38]=1)(=[O:34])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]C>>[CH3:1][CH:31]([CH3:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]([O:35][CH2:36][C:37]1[CH:45]=[CH:44][C:42]([OH:43])=[C:39]([O:40][CH3:41])[CH:38]=1)=[O:34]Participants
Procedure
Using vanillyl alcohol (1.70 g, 11.0 mmol) instead of homovanillyl alcohol, and n-decanoic acid (1.72 g, 10 mmol) instead of 8-methylnonanoic acid in Example 1, similar reaction was performed. The residue was purified by PTLC to find that the yield of the obtained vanillyl decanoate was 1.33 g (4.31 mmol, 43.1%), and vanillyl decanoate was decomposed (i.e., unstabilized) by the contact with silica gel. In contrast, the isolation yield of homovanillyl 8-methylnonanoate obtained by similar operation was 93.2% as mentioned above, suggesting that homovanillyl 8-methylnonanoate is far stabler than vanillyl decanoate even upon contact with silica gel. In addition, since good isolation yields were obtained in Examples 2 to 23 where isolation and purification were similarly performed by PTLC, it is clear that the compound of the present invention is superior to capsinoids in the stability.
Workup
- customIn addition, since good isolation yields
- customwere obtained in Examples 2 to 23 where isolation and purification
Sources & evidence
- ORD record
- ord-3e86406996004d53900d965c4b8a61b1
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08212068B2
Reaction notes
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