Rusearch Department
TRIP REPORT
November 15, 1971
SYMPOSIUM ON COMPOSITION OF TOBACCO AND TOBACCO
SMOK9 - 162nd NATIONAL
MEETING OF THE A14ERICAN CHF04ICAL SOCTETY/003
This meeting was held in Washingtop, D.C. on
September 16 and 17, 1971.
04
Much of the information presented was for survey
purposes, and has already
been published. This note will cover what appears
to be new.
H. Wakeham - Recent.Trendo fift Tobacco and
Tobacco Smoke Research
This was an excellent paper, presenting both new
data.and an authorative
survey. All of the-reyults presented were on smoke
and the smoking process.
Transfer results, based on the amount of tobacco
consumed, are: Menthol,
39%; Nicotine, 24%; Glycerol, 22%; Neophytadieae,
20%; NornLcotine, 8%;
DotrLacontane, 30%; and Solanesol, 3%. These
results are for compounds
indigenous in tobacco.
As an example of radiochemLcal tracer work to
determine conversions, it was
found'that tryptophan added to tobacco gives 0.47%
conversion to mainstream
smoke norharmane and 0.15% harmane conversion.
Some data was-presented on how smokers smoke
cigarettes. LoW/High parameter
values are: puff.volume irt duration in sec.,
0.9/3.2; rate
in ml/sec., 5.6/81.0; and inter~ii'in-sec.,
22.0/72.0.
Kdestream/MaiastreAm ratios of compounds were
presented :.. acetic acid, 0,,A_2~
acetamide,- 0,68; hydrogen cyanide, .0;03;
acetonitrile,,_ 2 .3.; benzo(a.)pyrefte,
2.1; benzene, 1.9.; toluene,_-3.5; Phe&1-1 2.1;
"nicotine,, 2.5; myosmine, '7.0;
pyrrale,'7,1,- p ridine, 3-vLaylpyridLne,
A
y . 16.0; ammonia_08.b.
, carbon
dioxide, 3.8~10.0; cArbon wmoxide, 1.3-3.0.
COJVO ratios are: Mainstream. 2-Z--6j01 and Sidett
-11.o
R#taults for added C-14 tracero were pl;eaented ,
based on - ammsat of tobacco,
Wainstr Sidest ream
C.44 Compound Gas Particulate Gas Pa rticulate
menthol 1.4,:., 38.0 .29.0 32.0'..
Dotriacontafte .1.9 .28. V 13.0 5S.0,
Anthracene 0.3. V.0 4, Q_~.~.'
62,
-tt)p~ 7: _294-5. ,
40 :,3.0
.
Glucose
7 A -2.7
`73. 0
-5.1
Sucrose
9 r.4 4'8'
o 82.5 9 6.1--
Oxalic -Acid 19.7 5.0 73.9 0.8
Citric kcid
12 5 3.4
*
-76J 4.'.4
Wale Anhy$ride. 21
6 .3.1.- 55. 0 3.'7
302057636
13 ATCo document for Province of British Columbia
19 April 1999


-2-
Finally, the butLs from cigarettes in the
experiments above were assayed
to determine filtration by the tobacco column. No
enrichment of C-14
nicotine or dotriaconLane was found in the butte,
and Wakeham concluded
that the tobacco column is a very poor filter for
particulate phase smoke.
However, it is possible.Lhat deposition
fortuitously matches aerosol
extraction of material from the tobacco colamn.
J. A. Weybrew - Projected Changes in the
Composition of Bright (Flue-cured)
Tobacco
The labor situation in the Flue-Cured belts is
going to force some changes
in cultural practices. The most likely results
will be:
Total Alkaloids in Blended Cigarette Now, 3.11%;
Then, 3.16%
Reducing Sugars in.Blended Cigarette Now,.8.9%;
Then, 11.3%
In the discussion session, John Campbell.(Imperial
Tobacco) claimed that
once-over harvesting may prove superior to priming
because of gains in
uni ormity.
T. C,. Too - Effects of Tobacco -ChatatterLstico
on CiRdrette SMOke- CdMoOditiork
The experiments described in the abstract are far
from complete. Biological
test results from the smoke fractions are not yet
in and more results on
smoke analytical are pending. Correlations for
Group A.(flue-cured stalk
positions) are generally better than for Group B
(blended cigarettes). A
huge amount,of data-was-presented.
Some..instances. in which the two expert--
menta A-..-t agree iii direction of correlation
coefficients are:
Corrolations between dry TPM Correlation
Coefficients--
Test A Test B
Total Mytostefo-1 -A99 .742
SUSmAsterol -.714. -718
Petroleum Extracts -.033* ..739
Vex .299* .625
'*Not significAnt, at 1% level
-0. S. Sc~lbt~ha~ier Produdi-ts'fiom v7rolysiis a
Tobacco' ixtracts
Thts.paper appeared to be,largo-ly.presentati*n of
ola.data., Noni~otine
am~lysels.were presented for-~he Vrtract-
fractlons,'so ve.cAnnot c.otmen't.
on. the Implicat Up ifi -tbe abstraet . that.
-pyrldioes ate - fotined. ftom nieotine -
'I nts
.and .8me
B.- ftuiath - Recedt Advances-in.fto4ledge-a
Chemical COMWIffition, of _77
--ThbacQo Smoke
Smoke-was ftactionated-by chromatography.-tito, it
number.,of-subfractiow of
incrtacing polarity. Neurath preeented a gas chr-
to 6A 4-~d,-then A' table s
-igicati tks -for -eaob fr4rctl a
of ident 9 _0n. lmyl.qkthe supW.s dl
302057637
BATCo document for Province of British Columbia 19
April 1999


-3-
components are those which.we identified several
years ago in low
temperature pyrolysis products from tobacco. This
paper will soon be
published. These semi-volatiles comprise 7.6% of
TPM.
14. J. Chamb,_-rlain - Fractionation of Tobacco
Smoke Condensate for Chemical
Composition Studies
A number of new smoke component identifications
were rade, including the
following secondary amines: diphanylamine, 13
ng/cig; 9, 9- dime thylacridan,
40 ng/cig~ N-phenyl-4-isopropylphenylamine, 20
ng/cig; and N-phenyl-2-
naphthylamine, 100 ng/cig.
The biologically active, polar subfraction
referred to in the abstract is
obtained by silicic acid chromatography
(non-a6tivated). The methanol
IP eluate fraction is partitioned between
petroleum ether and 90/10 methanol/
water. Materials in the methanol-water layer are
the *&L-fraction which
.has activity as a tumor promoter. The biological
data were presented in
Bock's paper which followed.
F. G. Bock Methods for. Bivagoairs.of !Zobocco
9moke
This was a general, paper which strongly stressed
the high costs of
biological testing; inhalation testing was deemed
prohibitive in cost,
although ptobably more valid.
Some test results were pXesented.which suggest the
9-W fraction to be
Vedkly promoting. However, in.combination with
other promoting fractions
(PAR -or weak acids) it either gavp- a fractiona-I
response .9r.. actuaLly appeared
to act as an inhibitior.- it certaiftly did not
provide a synergistic increase
in promoting activity.
D. Hoffftnn-- Chemical compos'it~oin- a'Vd
Tumo'rigenicity of Tobacco. smoke
This paper wits a *ixtqre of relatively nev
infohr4tiozvand.old result's.
Further. fracfionation of Ehe xkit'romethane
fracti _. (31, Qi6%-,of-tAt)
_9 n
Florisil chromatography --nexane. eluate i9f"Bra
(0.32%Y
2. 90%'Methanol/Hex4ne &*afte Loer is Bld (0.i3%)
.3, 2~Ws 2 - CS layer is BIf (0.18%)
Z. CH Cal -1 &M tiyr is Kh (0~09%)
5. Alumina Xomatograpjiy '80 - subfacti0he
tw t,umor-iniviating fractions vere'found:
Eluites,05-66pontsu
18,-alkylcarbazq~ep, _ tEpA-4.41~diehlorostdben
Zjjrt-A-h-`j%d#. 4kfid-
gibv t&0 -7-1- ?R-aj!4--UIe active FA0.
Tptst-reiults were-preseated vhich.sho~
4,4!4,dichlorostilbene.. to.
bwa
0 mo
pr. tor, butnot an i it lamor.,
n
'Skin irritation' was c1atm~dd to correl4tte witb
.-tumqr, promortigaw ~-jmd.wav use4
to assay- fraitions 10tained daring
su~fractionatlon -of the -weak
fra~EG'n Of kr1q) 11
302057638
BATCo document for Province of BritiSh Columbia 19
April 1999


1. SilieR get chroii"Lography 30.2 g in active
fractions.
2. Alumina chromatography (benzone/acetone) - 3.0
g in most
active fractions.
3. Silica gal chromatography (chloroform/acotone)
- most active
fraction is the aminophcnols fraction which shows
25 components
on GLC analysis. Composition studies were reported
at the TC=1
and will be coverf-d in that repurt:.
Two complex slides were presented on smoke
compound metabolites which
might be involved in bladder cancer.
Hoffmann claimed thar unaged gas phase of smoke
does not appear to be
"g. carcinogenic.
W.-
;QA'
fle C. 11. KeiLh - Modification of Tobacco Smoke
A' Nothing new was presented.
J. E. Kiefer - Filtration of Cigarette Smoke
Nothing new was presented.
J. F. BeRner - Composition of. SOpke from
chemically - Mod-ifted CiRarettes
The abstract for this paper does a poor job of
describing what was presented.
This group at tL of Ky. has put a huge effort into
the combustion additives
program, and appears to have done the job-weli.
Previously reported work was presenteA on
differential thermogravimetric
analysis as a tool for predicting effects-of
additives om deliveries (BaP,.
phenols) Results were presented for a large number
of inorganic additives.
Barium aceitate showed -the largest.BaF reduction
(- 55%).
Activation energies for additive-treated fobaccos
were obtained, by;,'
idothetimal TCA at 'temperatures from 215'-to
416'C:
k - 100 (wt.' change per mid. 14t.
In (k)
A-fairly good correlation waiB found between E
and.BaP deliveritts; decreasing
E correspondh -to incroastag - BaP. The BaP.me
--involves -& radioa~6tive
thod.
a
spike, ~ut.has..nat_badtx pebliAed. Dr. Benner
-claims that a good technician
can run aight determinationv ina,daa~, and that he
can run twelve'*
Organie tobacco additives have also been',
investigatied.' Changes'.U cl."tte
deltveries are-~pFesented. below,,-based on a gram
of tobacco c9neumqd.
Additive
_9% -21%-
.28% -29
ene
Iftosixol.. .-36
Ggtlllc.Acid -30
Azoboaz -19 !-23-
Anthraquinone -9 _+%3
Fractode -4
7
302057639
BATCo document for Province of British Columbia 19
April 1999


-5-
These results are.for 5% add-on of additive. The
inositol cigarette was
judged to have considerably better taste than the
control; its reduction
in BaP delivery has been confimed by d duplicALe
experiment. They are
now working further with inositol.
R. R. Johnson
RRJ/bfw
KEYWORD INDEX: ACS Meeting, Tobacco Symposium,
Radiochemical Transfer,
Smoke Fractionation, Bioassaya, Combustion
Additives,
S(doke Composition
302057640
BATCo document for Province of British Columbia 19
April 1999