Zearalenone → Zearalenone

HRID 1415379Notes

Reaction equation

HRID 1415379 reaction equation
[CH3:1][C@@H:2]1[O:21][C:19](=[O:20])[C:18]2[C:17]([OH:22])=[CH:16][C:15]([OH:23])=[CH:14][C:13]=2[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3]1>C(Cl)Cl>[CH3:1][C@@H:2]1[O:21][C:19](=[O:20])[C:18]2[C:17]([OH:22])=[CH:16][C:15]([OH:23])=[CH:14][C:13]=2[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][C:6](=[O:7])[CH2:5][CH2:4][CH2:3]1.[CH3:1][C@@H:2]1[O:21][C:19](=[O:20])[C:18]2[C:13](=[CH:14][C:15]([OH:23])=[CH:16][C:17]=2[OH:22])[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8][C@@H:6]([OH:7])[CH2:5][CH2:4][CH2:3]1

Participants

4

Reactant 1

HCID 5281576Zearalenone

Product 2

HCID 5281576ZearalenoneHCID 5284645alpha-Zearalenol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

One hundred milliliters of fermentation medium prepared as described in Example I, was transferred to a 500 ml Erlenmeyer flask. The flask was capped with two milk filters and one sheet of Kraft paper (paper removed before inoculation). The flask was autoclaved at 15 lb. steam pressure for 15 minutes and cooled to about 30° C. The medium was inoculated with a culture of the yeast Rhodotorula rubra and incubated under vigorous agitation for 24 hours at 30° C. An alcoholic solution of zearalenone (1 ml, 50 mg zearalenone) was aseptically added, and the medium was further incubated for 72 hours without agitation. The medium was then shaken with 50 ml of methylene chloride and centrifuged. The lower, methylene chloride layer was withdrawn with a syringe and evaporated to dryness. The residue was redissolved in one ml of methylene chloride and spotted on a thin-layer chromatography plate. The thin-layer plate was developed in chloroform:glacial acetic acid (90:10). The zearalenone and zearalenol bands were scraped off the plate and separately eluted with methanol. Since the two compounds have approximately the same U.V. maxima, and extinction coefficients, the % conversion was calculated as follows: ##EQU1## The experiment resulted in about a 44% conversion of zearalenone to zearalenol.

Workup

  1. customOne hundred milliliters of fermentation medium prepared
  2. customThe flask was capped with two milk filters and one sheet of Kraft paper (paper removed before inoculation)
  3. waitincubated under vigorous agitation for 24 hours at 30° C
  4. waitthe medium was further incubated for 72 hours without agitation
  5. customThe lower, methylene chloride layer was withdrawn with a syringe
  6. customevaporated to dryness
  7. dissolutionThe residue was redissolved in one ml of methylene chloride
  8. washseparately eluted with methanol

Sources & evidence

ORD record
ord-de039165066949cba3d80b96f90c1bba
Source dataset
uspto-grants-1977_01
Patent number
US04004978

Reaction notes

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