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Efficient Odorant Synthesis

Posted on 20. September, 2012.

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2-Nonen-4-olide occurs naturally in the volatile components of various foods and plant extracts, such as stewed beef/vegetable gravy,  sunflower oil,  Chinese white salted noodles watermelon, potato crisps,  lard cured with spices and aromatic herbs,  mushrooms, French fries, and flue-cured tobacco. It has an oily, coconut-like, and rancid odour. A simple, efficient and low cost synthesis of this odorant is reported in the August issue of Journal of Chemical Research.

Efficient synthesis of the odorant, 2-nonen-4-olide

2-Nonen-4-olide occurs naturally in the volatile components of various foods and plant extracts, such as stewed beef/vegetable gravy, sunflower oil, Chinese white salted noodles, watermelon, potato crisps, lard cured with spices and aromatic herbs, mushrooms, French fries, primulaceae and flue-cured tobacco. It was described to have a coconut-like, or sweet odour by gas chromatography-olfactometry (GC-O) analysis. It had been approved as a flavour compound by Flavour and Extract Manufacturers’ Association (FEMA) until 2005 and was included in FEMA GRAS (Generally Recognised as Safe) List 22 with FEMA No. 4188. A three-step synthesis of 2-nonen-4-olide starting from heptanal is reported. (E)-3-Nonenoic acid, prepared by Knoevenagel condensation of malonic acid and heptanal, was oxidised by performic acid, a process accompanied by lactonisation, to give 3-hydroxynonan-4-olide in 85% yield. This lactone when reacted with MsCl in the presence of Et3N gave, by elimination, 2-nonen-4-olide in 88% yield. The overall yield was 75%. The odour of the product was evaluated by GC-olfactory analysis and sniffing blotter confirming an oily, coconut-like, and rancid odour.

Keywords: 2-nonen-4-olide, (E)-3-nonenoic acid, dihydroxylation, cocaonut-like odour

Yi-feng Dai, Hong-yu Tian*, Bao-guo Sun, Yu-mei Sun, Hai-tao Chen and Xiao-yu Liu
 School of Food Chemistry, Beijing Key Laboratory of Flavour Chemistry, Beijing Technology and Business University, Beijing 100048, P.R. China

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