Reaction #336819

ord-75c09f9ec1264545ae6fcbc597b2599f

Reaction equation

CCCCCCCCCCCC(=O)O
lauric acid
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Glucose
[Na+].[OH-]
NaOH
→
CCCCCCCC[C@H]1CCC(=O)O1
(S)-gamma-dodecalactone

Reactants

CCCCCCCCCCCC(=O)O
lauric acid
O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO
Glucose
[Na+].[OH-]
NaOH

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    TemperatureThe speed is increased to 900 rpm and aeration
  2. 2
    workup.WAITThe conversion is pursued for 55 hours

Procedure

Once the amount and the quality of mycelium have been attained, the substrate (lauric acid) is dispensed in mygliol. Glucose is continuously dispensed, in parallel, at the flow rate of 0.36 g/l/h for 55 h. The pH is regulated at 7 throughout the duration of the fermentation, with 5 N NaOH. The speed is increased to 900 rpm and aeration is carried out at the flow rate of 1 vvm, i.e. 12 m3/h. The conversion is pursued for 55 hours. A yield of 12 g/l of (S)-gamma-dodecalactone is obtained. By way of comparison, gamma-dodecalactones are prepared according to the teaching of patent U.S. Pat. No. 5,457,036 (Han), using the Mortierella strains described in U.S. Pat. No. 5,457,036.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07863023B2uspto-grants-2011_01