Myristicin → Methyleugenol

HRID 1710319

Reaction equation

HRID 1710319 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:12][CH:13]=[CH2:14])[CH:6]=[C:7]2O[CH2:10][O:9][C:8]=12.COC1C=C(CC=C)C(OC)=C2OCOC=12.CC(C)=CCC/C(/C)=C/COC1C2C=COC=2C=C2C=1C=CC(O2)=O.COC1C=CC(C2OC3C(OC)=C(OC)C(OC)=C(OC)C=3C(=O)C=2)=CC=1.CC1CCC([C@@](O)(CCC=C(C)C)C)CC=1>>[CH3:10][O:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:12][CH:13]=[CH2:14])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

6

Reactant 5

HCID 4276MyristicinHCID 10659ApioleHCID 68077TangeretinHCID 5471349BergamottinHCID 6097621(2S)-6-methyl-2-(4-methylcyclohex-3-en-1-yl)hept-5-en-2-ol

Product 1

HCID 7127Methyleugenol

Procedure

Chemicals were purchased from Sigma-Aldrich Chemical Company (St. Louis, Mo.) unless noted. Plant oils were manufactured by Aura Cacia (Weaverville, Calif.). Juvocimene was synthesized as described (Mestres, R. and E. Munoz, 1996, Synthetic Comm., 26:1309-1319). Myristicin, apiole, bergamotin, tangeretin, bisabolol, and cucurbitacin were obtained from Indofine Chemical Company (Somerville, N.J.). Methyleugenol was provided by the Batelle Chemical Company (Columbus, Ohio). Man-made insecticides were purchased from Chem Service (West Chester, Pa.). The precocene-like suicide substrate 3,4-dimethoxyisopentenylphenol was prepared as described Bowers, W. S., et al., 1976, Science, 217:647-648) except that a 3,4-dimethoxylated reactant was used.

Workup

  1. customJuvocimene was synthesized

Sources & evidence

ORD record
ord-984e2a73d7d14cc7b3a454edf29d3d16
Source dataset
uspto-grants-2010_09
Patent number
US07790377B2

Linked notes

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