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PHILIP MORRIS U. S. A.
INTER- OFFICE CORRESPONDENCE
Richmond, Virginia
1752
To:
K. Shafer
Date: June 7, 1990
C90-03139
From:
R. L. Bassfield
R. Banfied
Subject: NMR Characterization of ART Stem Extracts
"H and "C NMR spectra have been taken on four hexane extracts from stems subjected
to the ART process. The four samples labelled Run's 515, 516, 517 and Liquid CO, were
evaporated and redissolved in deutero-chloroform. Proton spectra of 515, 516, and 517, shown
in Figures la-c, were very similar and indicated these samples to be mixtures of solanesol,
probably some other isoprenoids, and aliphatic waxes (long chain hydrocarbon). Not much can
be said about the aliphatic hydrocarbon region due to the overall complexity of this region. The
level of solanesol in each of these samples appeared to be approximately the same. Looking
closely at the region between 3.9 and 4.3 ppm, revealed the subtle differences between these
three samples. If we use solanesol as a model, the methylene with an attached -OH comes in
this region and therefore similar methylene adjacent to oxygen fragments would also appear in
this region. Most noticable in this region was the doublet of doublets, (dd), at 3.95 ppm
(probably from one compound) which appeared strong in Run's 515 and 517, was a fourth as
much in Run 516. Another set of dd at 4.3 ppm that appeared in 515 and 517 is absent (or much
lesser amount) in 516. This would indicate that the presence of filler has some diminishing
effect on the amounts of these compounds. This is also consistent with that "mystery"
compound discussed at a previous meeting.
The region between 4.95 and 5.5 ppm contained several resonances, besides those of
solanesol, indicative of other similar type olephinic compounds. The downfield doublet of
doublets at 6.4 ppm, previously thought to be typical of a terminal vinyl ether methine proton,
has been assigned to neophytadiene. This resonance, as well as three doublets in the 4.95-5.5
ppm region, were identified from a spectrum of neophytadiene, Figure 2.
The sample labelled Liquid CO, gave a much simpler H spectrum, Figure 3a, in that it
appeared to be predominantly solanesol and aliphatic hydrocarbon. The dd at 3.95 ppm is also
visible in this sample. Neophytadiene or the other olephinic compounds that were found in the
three previous spectra were not present in the Liquid CO, spectrum.
Figure 3b is the "C spectrum of the Liquid CO, extract. The three large peaks at 14, 23,
and 32 ppm are from hexane that remains due to incomplete evaporation of all the solvent.
These three peaks are contained in all the carbon spectra. The C spectra of the samples from
Run's 515-517 were very similar as expected from the 'H data. In Figure 4, which is from Run
515, the aliphatic region of the spectrum contains the greatest number of resonaces originating
from the long chain hydrocarbons. The significant peaks in the olephinic region (115-140 ppm)
2022155960
Source: https://www.industrydocuments.ucsf.edu/docs/rhxj0037

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