Beta-Phellandrene → (-)-Zingiberene

HRID 2201341Notes

Reaction equation

HRID 2201341 reaction equation
CC(C1C=CC(=C)CC1)C.[CH3:11][C:12]1[CH:17]=[CH:16][C@@H:15]([C@H:18]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:25])[CH3:24])[CH3:19])[CH2:14][CH:13]=1.[CH3:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33]([CH2:35][CH2:36][CH:37]=[C:38]([CH3:40])[CH3:39])[CH3:34])=[CH:29][CH:28]=1>>[CH3:11][C:12]1[CH:13]=[CH:14][C@@H:15]([C@H:18]([CH2:20][CH2:21][CH:22]=[C:23]([CH3:24])[CH3:25])[CH3:19])[CH2:16][CH:17]=1.[CH3:26][C:27]1[CH:28]=[CH:29][C@@H:30]([C@@H:33]([CH2:35][CH2:36][CH:37]=[C:38]([CH3:39])[CH3:40])[CH3:34])[CH2:31][CH:32]=1

Participants

5

Reactant 3

HCID 11142Beta-PhellandreneHCID 92139CurcumeneHCID 92776(-)-Zingiberene

Product 2

HCID 92776(-)-ZingibereneHCID 217295957-Epizingiberene

Procedure

β-phellandrene, zingiberene and curcumene were not commercially available and had to be synthesised. Zingiberene and R-curcumene were isolated from ginger oil and 7-epi zingiberene and S-curcumene from S. habrochaites (PI27826) leaf material after Millar (1998, J. Nat. Prod 61, 1025).

Workup

  1. customto be synthesised

Sources & evidence

ORD record
ord-262fa8d78ee7497e935eb0266132f6bf
Source dataset
uspto-grants-2016_06
Patent number
US09364002B2

Reaction notes

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