Tobacco Documents Online

[. 1 L CHARGE NUMBER:. PROJECT TITLE: PROJECT LEADER: WRITTEN BY: PERIOD COVERED: DATE OF REPORT: 2515 Flavor-Release Chemistry Y. Houminer W. G. Chan July l- July 31, 1981 August 10, 1981 Last month we reported the result of a series of ketone release system based on 3-0-acylglucose for pi-methylacetophenone. We have extended our coverage to the aliphatic ketone series, using 2-butanone as the target molecule.1 We have also expanded our investigation to the terpenoid area, using nerolidyl acetate as an anchor for ketone release. To this end, the synthesis of ~ was undertaken; however, the thermal decomposition of ~I gave an unexpected product, whi`ch has been tentatively assigned as,~,i~.l Qur research efforts in the release of phenols from glycerol carbonates has been directed towards a particular phenol, 2-methQxy-4-methylphenol (valspice). Treatment of 1,2-0-itopropylideneglycerol with phosgene provided the corresponding dhloroformate , which was reacted with valspice to give the carbonate . Mild acid' hy~lysis of tV yielded glycerol 1-(2-methoxy- 4-metbylphenylcarbonate 2 Both,~V~ and TArv are found to be unstable at room temperature and decojose P valsptce an phenol respectively. On the other hand, on pyrolysis at 250 C for 10 min under air atmosphere,A gave only 13% of phenol, whereas I,~,l~ gave no valspice at a11.2

-2~- a R=C,H90 ~ R=C6H5 -JOR OH OH'I a R=C,HgO I R=C6H5 Last month we h.ad'also begun our investigation of phenyl-glycosides of di;ssacharides as possible phenol release systems. 1:-0-Phenyl-2,3,6,2', 3`,41,fi1-hepta-0-acetyl-cellobiose was deacylated to give the 1-0- phenylcellobtose. Thermolysis produced a good yield' of phenol.l This investigation is now being extended to valspi,ce. 2-Ethylpyraz%ne was treated with lithium diisopropylamide in ether to generate the corresponding pyrazine anion. This was then treated with benzaldehyde to produce 2-(2-hydroxy-l-noethyli-2-phenylethyl)pyrazine.2 r5:;N " , ~ ~ H~ Ph References 1. G. Chan. 7462 2. K. Podraza 7591