Lauric Acid → (5S)-Dihydro-5-octyl-2(3H)-furanone

HRID 249637Notes

Reaction equation

[C:1]([OH:14])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[OH-].[Na+]>>[CH3:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][C@@H:4]1[O:14][C:1](=[O:13])[CH2:2][CH2:3]1

Participants

Reactant 3

HCID 3893Lauric Acid

HCID 14798Sodium Hydroxide

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 12237820(5S)-Dihydro-5-octyl-2(3H)-furanone

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.

Workup

temperatureThe speed is increased to 900 rpm and aeration
waitThe conversion is pursued for 55 hours

Sources & evidence

ORD record: ord-75c09f9ec1264545ae6fcbc597b2599f
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863023B2

Reaction notes

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