ChemicalBook CAS DataBase List (Z)-whiskeylactone,5-butyldihydro-4-methyl-2(3H)-Furanone,(-)-cis-whiskeylactone

(Z)-whiskeylactone,5-butyldihydro-4-methyl-2(3H)-Furanone,(-)-cis-whiskeylactone synthesis

7synthesis methods

Product Name:(Z)-whiskeylactone,5-butyldihydro-4-methyl-2(3H)-Furanone,(-)-cis-whiskeylactone
CAS Number:80041-00-5
Molecular formula:C9H16O2
Molecular Weight:156.22

59086-42-9
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(Z)-whiskeylactone,5-butyldihydro-4-methyl-2(3H)-Furanone,(-)-cis-whiskeylactone

80041-00-5
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2(3H)-Furanone, 5-butyldihydro-4-methyl-, (4R,5R)-

105015-53-0
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(E)-Whiskeylactone,5-butyldihydro-4-methyl-2(3H)-Furanone,(+)-trans-Whiskeylactone

80041-01-6
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Yield:85 % ee ，80041-01-6 36%

Reaction Conditions:

with D-glucose in water;acetone; for 24 h;Microbiological reaction;

Steps:

2.5.1. Screening procedure

General procedure: The fungal and bacterial strains were transferred from theslants to 250-ml Erlenmeyer flask containing 75 ml of medium(3% glucose, 1% aminobac in water). After cultivation at 25 C for four days on a rotary shaker, 0.02 g of substrate 5, dissolved in1.0 ml of acetone was added to the grown cultures. In controlexperiments, the substrates were incubated in the medium withoutfungi. For the time-course analysis after 1, 2 and 4 days,10 ml of the transformation mixture were taken out and extractedthree times with dichloromethane. The extracts were dried overMgSO4 and concentrated in vacuo. Residues were dissolved in1 ml of acetone and analyzed by TLC and GC. Screening procedurewas carried out for 44 strains on 3,7-dimethyl-4-oxooctanoic acid,a representative compound of series of oxoacids we have studied.The screening of microorganisms led to the selection of six strains(B. bassiana AM278, Chaetomium sp.1 KCH6670, D. igniariaKCH6651, L. sulphurens AM525, P. resinae KCH50, S. cerevisiaeAM464) that had ability to biotransformation of 3,7-dimethyl-4-oxooctanoic acid. The selected strains have been applied in microbiallactonization of 3-methyl-4-oxooctanoic acid (5).

References:

Boratyński, Filip;Smuga, Ma?gorzata;Wawrzeńczyk, Czes?aw [Food Chemistry,2013,vol. 141,# 1,p. 419 - 427]