Suresh Chandra Rastogi zyxwvutsrqp

Analysis of Fragrances in Cosmetics by Gas

Chromatography-Mass Spectrometry
Mini\try of Environment, National Environmental Research Institute, Department of EnVlronInelJtdl Chermstry, P 0 Box 358 DK-4000 Ro\kildc, Denmdrk

Key Words:
Gas chromatography
Mass spectrometry
Fragrance analysis
Cosmetics

Summary
A gas chromatographic(GC)-massspectrometric(GC-MS)method
has been developed for the rnutine analysis of 11 fragrance sub-
stances in cosmetics: cinnamic alcohol,cinnamicaldehyde,eugenol,
hydroxy citronellal, a-amyl cinnamic aldehyde, geraniol, isoeuge-
iiol, coumarin, dihydrocoumarin, citronellal and citral.Methods for
in various consumer products together with epidemiological
studies to reveal sensitization reactions or other toxic effects due
to the use of respective products. A step in this direction has been
taken in Denmark. Ten fragrance substances (Table 1 ), which are

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well known to cause allergic contact dermatitis [6-151, have been
sample preparation of various types of cosmetic products, prior to selected for an epidemiological study. Citronella1 is included as
GC analysis, have also been developed and proved to be rugged. the 11th fragrance substance in the present study because its
Detection limits of all of target fragrance substanceswere approxi- chemical structure is related to several of the selected fragrances.
mately 1 ppm. Calibration curves of the target fragrance substances
analyzed by GC were found to be linear in the investigated concen- Table 1. Target fragrance substances for the developement of an analytical
tration range, 0.005% - 0.50%. The recoveries of the target fra- method.
grances from various types of cosmetic products were 80%- 116%
and the relative standard deviations of the quantitative analysis of
Fragrance substance CAS Reg. No. Chemical structure
the target fragrance substances were within 5%.

Cinnamic alcohol 101-54-1 3-Phenyl-2-propen-l-ol

1 Introduction Cinnaniic aldchyde 14371-IO-9 3-Phcnyl-2-propenal
Eugenol 95-53-0 2-Methoxy-4-(2-propenyl) phenol
The use of fragrances (perfumes) in cosmetics is associated with
pleasure and some times with therapeutics. A perfumer has sev-
eral thousands of fragrance substances to compose a perfume.
All known fragrance substances are organic compounds or mix-
tures of organic compounds, derived from natural sources or
produced synthetically. Recently described guidelines for per-
fuming various types of consumer products [ 1, 21 indicate that
these products may contain from a single fragrance up to a
Hydroxycitronellal
a-Amylcinnamic
aldehyde
Geraniol
Tsocugenol
Coumarin
107-75-5
122-40-7

1 06-24-1
97-54- 1
91-64-5
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3,7-Dimethyl-7-hydroxy octanal
2-Phenylmethylene heptanal

1-01
3,7-Dimethyl-2,6-octadicn-
2-Methoxy-4-( 1-propenyl) phenol
2H- 1-Benzopyran-Z-one
mixture of 50 (or even more) fragrance substances in various Dihydrocoumadn 1 19-84-6 3,4-Dihydro 2H-1 -hcnzo-2-pyranone
concentrations. The recommended concentrations (0.10% - Citral 5392-40-5 3,7-Dimethyl-2,6-octadienal
30%) of perfumes in various categories of cosmetics are de- Citronellal 106-23-0 3,7-Dimethyl-6-octenal
scribed elsewhere [i, 21.
Perfumes are considered to be one of the major causes of cosmetic
dependent allergic contact dermatitis [3 - 51. Official regulation Although gas chromatography with flame ionization detection
of ingredients that go into fragrances or the compound fragrances (GC-FTD) and GC-mass spectrometry (GC-MS) have occasio-
itself is lacking in most countries. There are n o requirements to nally been used for the identification of fragrance substances, no
test fragrance materials for safety for use in consumer products single method is available for the quantitative analysis of the
and there is no requirement to list the fragrance ingredients on target fragrance substances in cosmetic products. Similarly, none

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coiisumer products. However, perfume industres are self-regu-
lating the use of perfumes in consumer products, including cos-
metics. Even though the industries’ organizations, International
Fragrance Association (IFRA) and the Research Institute of Fra-
grance Materials (RIFM) have been supporting the industries for
more than 25 years, perfume allergy still prevails.
The reason for lack of an official regulation on perfumes may be
that there are too many (r5000) of them, and reliable toxicologi-
cal data on many of the fragrance substances is lacking. For an
optimal regulation of perfume$, systematic investigations are
needed to unravel the trend of use of allergic fragrance substances
of the described methods for sample preparation for the GC
analysis of fragrances in cosmetics [ 161 have been shown to be
suitable for the analysis of all of the target fragrance substances.
The analytical method should be sensitive for identification and
determination of the target fragrance substances, in the concen-
tration range that are used in the formulation of various types of
cosmetics, and it should be suitable for routine analysis of the
target fragrance substances. In the present work, an analytical
method is developed for the sample preparation followed by
GC-FID and GC-MS analyses of the target fragrance substances
in cosmetics.

J High Kesol. Chromatogr. VOL. 18, OCTOBER 1995 653

 zyxwvutsrqp
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Analysis of Fragrunces in Cosmetics by GC-MS
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2 Materials and Methods
2.1 Cosmetic Products
Randomly chosen 18 cosmetic products - 5 shampoos, 7 creams
and lotions, 2 eau de toilette, 1 deodorant spray, 1 lipstick, 1 face
powder and 1 soap bar were used for the development of the
method.
2.2 Apparatus
Hewlett Packard (HP) gas chromatograph HP 5890 with
splithplitless injector and a flame ionization detector (FID) has
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been used for GC analysis. Autosampler HP 7673 was used for
sample introduction and HP 3396 integrator was used for the
collection of GC-data. For GC-MS analysis, a Finnigan INCOS
50 mass spectrometer coupled to a HP 5890 gas chromatograph
was used. The GC-column used was a 50 m x 0.32 mm (i.d.)
WCOT fused silica coated with CP-Sil 5CB, df 1,2 pm, from
Chrompack, The Netherlands (Cat. No. 7770).
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2.3 Chenzicals
Eugenol99%, isoeugenol98%, geraniol98?hC,dihydrocoumarin
99 %, cinnamic alcohol 98%, a-amylcinnamic aldehyde 97% and
citral (mixture of cis- and trans- isomers) 95% were from Aldrich,
Gelmany; cinnamic aldehyde 98% was from Fluka, Switzerland;
crystalline coumarin and citronella1 85-Y0% were from Sigma
Chemical Co., USA, and hydroxycitronellal 95% was from
Biomedicals Ltd., UK Silica gel for column chromatography was
ICN Active Silica 100-200 mesh from ICN, England. All other
chemicals of analytical grade were from E. Merck, Germany. All
the chemical were used as obtained.
2.4 Sample Preparution
2.4.1 Eau de Toilette, Aftershave and Deodorant Sprays
Depending upon the concentrations of various fragrance substan-
ces, these samples were appropriately diluted in methanol. The
concentrations of the target fragrance substances in the diluted
solutions were kept below 0.1%.
Deodorant spray products in aerosol cans were taken out of the
cans as described before [17]. If necessary, the samples were
centrifuged before GC analysis. The amount of propellant and
the weight of the residue, Obtained by centrifugation, were re-
corded. These values were used in the calculation of contents of
fragrances in the product.
2.4.2 Shampoos, Creams, Lotions, Lipstick and Face Powder
Approximately 1 g sample was accurately weighed in a 10 ml
volumetric flask. A small portion of boiling chips were added to
the samplc and the flask was filled up to the mark with methanol.
The mixture was shaken gently and then heated at 60 "C for
10 inin (15 min for lipstick). The solution/ homogeneous suspen-
sion thus obtained was immediately cooled to room temperature
(20 "C). The fragrance substances from the solution/ suspension
were extracted as described below.
654 VOL. 18. OCTOBER 1995
A 20 cin x 1.8 (i.d,) cm glass column was packed with wet silica
gel (in methanol) to 7 cm. The cooled sample solutionlsuspension
in the volumetric flask was quantitatively transferred into the
column and that was allowed to pass through the column. First
5 ml of the eluate was discarded. The fragrances, which eluted
thereafter, were collected in a 25 ml volumetric tlask. The column
was further eluted with additional 20 ml methanol and the eluate
was collected in the same 25 ml volumetric flask. The flask was
filled with methanol up to the mark. The fragrance extract was
immediately transferred into autosampler vials and analyzed
within 24 h.
2.4.3 Soap Bar
The soap sample was scraped to thin flakes. Approximately 1 g
of the flakes were accurately weighed in a 50 ml conical flask.
The sample was suspended in 10 ml distilled water and dissolved
by heating for 5 min at 60 "C. The solution was quickly cooled
to room temperature. 10 ml ethyl acetate was added and the
mixture was vigorously shaken for 2 min. The aqueous and
organic phases were allowed to separate. The organic phase was
centrifuged for 5 min at 3500 rpm. The clear organic phase was
transferred into autosampler vials and analyzed within 24 h.
2.4.4 Suinple Preparation with Internal Standard
GC-screening analyses of fragrance substances present in the
diluted samples/sample extracts were performed (see Section 2.6
Analysis). One of the target fragrance substance, which was not
present in a sample, was used as an internal standard. The con-
centration of internal standard in diluted samples/sample extract
was kept at 0.02%. Appropriate amount of internal standard was
mixed with the diluted sample/sample extract, before making up
to the final volume.
2.5 Analysis
Calibration standards 0.005% - 0.50% were analyzed by GC-
FID (Section 2.6) to prepare calibration curves. A mixture con-
taining all target fragrance substances at concentration 0.05%
was analyzed 10 times by GC-FID (Section 2.6) to determine the
relative standard deviation of the method. To determine recovery
of the fragrance substances from cosmetic products, the test
samples were spiked with the target fragrance substances to
concentration 0.45%. Spiked and non-spiked samples were
treated as described above (Section 2.4) and analyzed by GC-
FID. Qualitative analysis of fragrance substances in the sam-
ples/sample extracts was performed by both GC-FID and
GC-MS (Section 2.6). The fragrance substances in the samples
were identified on the basis of their relative retention times in
GC as well as on the basis of their mass spectra. The determina-
tion of the identified target fragrance substances was performed
by GC-FID. A standard fragrance mixture containing 0.02% of
all of the target fragrance substances was analyzed after every
second sample. GC-response factors of the standard target fra-
grance substances were used for the calculation of their contcnts
in the samples. All the samples were analyzed in duplicate.
J High Resol. Chromatogr.
 zyxwvutsrqp
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Injector:
Injection volume:
Detector:
Carrier gas:

Ionization:

Scan descriptor:
Library:
z
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2.6Conditionsfor GC-FID und GC-MS
I. GC-FID
Oven temperature:

Column head-pressure:
Make-up gas:

ILGC-MS

3 Results and Discussion

140 "C to 280 "C, 5 "/min.
1 min at 280 "C
Split, temperature 300 "C
1 P1
FID, temperature 300 "C
N2, flow 54 ml/min
14 psi (1.8 mumin)
Nz, flow 29 ml/min

GC as described in I except that He was used as carrier gas,

and
Interface:

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temperature 290 "C
70 eV, electron impact at
175 "C
i d z 50 - m/z 250 in 0.73 s
National Bureau of Standards

The fragrance substances which are well known to cause allergic

contact dermatitis in humans [6-151 were selected for the devel-
opment an analytical method in the present study. The product
categories chosen for the method development were those which
are commonly used by the general population. i.e. shampoo,
cream and lotion, soap bar, deodorant spray, lipstick, face pow-
der, aftershave and eau de toilette.
The target fragrance substances in the present study are relatively
0
:I

5 10
Analysis of Fragrances in Coarnetics by GC-MS

15
-
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Figure 1. Chromatogram of a mixture of target fragrance substances (0.02%)

MLN

analysed by GC-FID. Peak no.1 - citronellal, 2 - citral (trans), 3 - gearniol, 4 -

cinnamic aldehyde, 5- hydroxycitroncllal, 6 citral (cis),7 - cinnamic alcohol,
-

8 - eugenol, 9 - dihydrocoumarin, 10 - coumarin, 11 - isoeugenol. 12 -

a-ainylcinnamic aldehyde. The major peak is the solvent peak and other peaks
represent impurities in the reference substances.

ploying MS will be necessary. Fragrance substances were quan-

tified employing GC-FID. The quantification of the fragrance
substances was, therefore, only possible when their contents in
a cosmetic product were < 0.01% (diluted to 5 4 ppm during
sample preparation). These limits were acceptable for routine
analysis of target fragrance substances in cosmetics which con-
tain I0.10% fragrances [l,21.
Table 2. GC rctention tinies (IR), relative
the fragrance substances.

Fragrance substance t~ (min)

mean f s.d.
Q of and coeficients of variation of

Relative t~
relative to
R C,
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polar compounds with boiling points 47 "C - 299 "C. A relatively citronellal
polar column may be preferred for the GC analysis of polar
compounds, However, commercially available polar GC-col-
umns are not suitable for use at high temperatures (>250 "C). A Cinnamic alcohol 11.094+_ 0.048 1.356 0.430
relatively non-polar GC-column CP-Sil-SCB, suitable for use up
to 325 "C, was therefore chosen for fragrance analysis in the Cinnamic aldehydc 10.454f 0.008 1.278 0.077
present work. A number of preliminary GC-experiments, em- Eugenol 12.365 f 0.013 1.511 0.104
ploying 0.10%of fragrance solutions, were performed to estab-
lish optimal conditions for GC-FID analysis of target fragrance Hydroxy citronellal 10.544 f 0.010 1.289 0.095
substances, All of the target fragrance substances could be re- a-Amylcinnamic aldehyde 19.292 ? 0.013 2.358 0.065
solved from each other by the optimized GC-method described
in Section 2.6 (Figure 1). The GC method was then applied to Geraniol 10.037f 0.009 1.227 0.090
establish optimal conditions for the analysis of the target fra- Isoeugenol 14.473i 0.01 1 1.769 0.073

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grance substances by GC-MS.
Coumarin 14.283i 0.015 1.746 0.105
Retention times (h)and relative t R (relative to @ of citronellal)
of the investigated fragrance substances under the optimal GC Dihydrocournarin 13.918f 0.012 1.701 0.088

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conditions are described in Table 2. Coefficients of variation
(C,) of the GC-relative & of all the fragrance substances except
Citral +
9.849 0.010 1.204 0.101

cinnamic alcohol, over a period of 3 weeks, were found to be 5 Citronellal 8.182 i0.008 1 .000 0.095
0.10% (Table 2). The Cv of relative t R of cinnamk alcohol was
0.43%. Identification of the fragrance substances was performed
on the basis of their relative t~ as well as their mass spectra. The Investigation of Stdbihty of standard fragrance solutions (con-
detection limits of the target fragrance substances by the GC-FlD centration 0.02%) revealed more than 10% decrease in their
were 2-5 ppm (signal to noise ratio, S N >3), and the detection concentration after 24-30 hours' storage both at 20 "C and 4 "C.
limits of all the target fragrance substances by GC-MS were less Therefore, it was necessary to perform fragrance analysis within

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than 1 ppm (S/N >25). For lower detection limits of fragrance 24 hours after sample preparation. Freshly prepared calibration
substances in cosmetic products, selective ion monitoring em- standards (0.005% - 0.50%) analyLed by GC-FID revealed that

J Hlgh Rerol. Chromatogi. VOL. 18. OCTOBER 19% 655

 zyxwvutsrqp
Analysis of Fragrances in Cometics by GC-MS

siihstances

Fragrance
9ubstance
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Table 3. Recovcnes of fragranccs from blanks (frdgrance solut~onwithout any sample) and from the cosmetlc products \piked wlth 0 45% of the target fragiancc

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% Recovery
Blank

( n = 8)
9% Recovery
Creams and
lotions
(11 = 7)
7cRccovery
Shampoos

( n = 5)
9b Recoveiy
Eau dr toilette

( n = 2)
% Kewvery
Face powdei

( n = 1)
Ic Recovery
Ltpstick

( n =1 )
96 Recovery
Soap bar

in = 1)
96 Recovery
Deodorant
spray
( n = 1)

Cirinamic alcohol 83 - 102 S8-112 83 - 105 96,98 92 89 53 102

Cinnarnic aldehyde 79 - 107 85 111
~ 84- 112 n.d. 91 91 31 n.d.
Eugenol 83 -97 92- 116 88 - 109 n.d. 92 107 94 n.d.
Hydroxy citronellal 87 - 105 88- 106 93 - 114 n.d. 90 87 84 n.d.
a-Amylcinn
amic aldehydc 82 - 96 91 - 104 92 - 107 n.d. 91 97 92 n.d.
Geraniol 84 - 108 92-112 96- 116 96.96 91 91 90 96
Isoeugenol 83- 112 88 - 106 86- 107 91,93 91 113 94 100
Coumarin 84-112 91 - 113 95 - 115 n.d. 98 86 87 n.d.
Dihydrocaumarin 87-116 89 - 109 94 - 108 92.94 111 97 8 104
Citral 80 - 94 80 - 92 80 - 95 n.d. 93 92 40 n.d.
Citronella1 83-114 81 - 100 82 - 98 91,95 91 88 100 90

the calibration curves for all of the target fragrances were linear
(r2 = 0.9950 - 0.9999). Replicate analysis of a mixture of fra-
grance substances, containing 0.05% of each of the target frag-
rance substance, revealed that the relative standard deviation
(RSD) of the method of quantikation was within 5% for all of
the fragrance substances investigated, except for geraniol and
compounds were found to be 79-1 16% (Table 3) from the blanks
(fragrance mixture without any cosmetics, treated as a sample)
and 80-1 16% from the spiked samples. This method was also
found to be suitable for the extraction of target fragrance sub-
stances from a face powder product and a lipstick sample. The
recoveries of target fragrance substances from the face powder

cinnamic alcohol. The RSD for geraniol and cinnamic alcohol
determination were found to be 7% and 11%respectively. Con-
sidering that the method involves analysis of 11 fragrance sub-
stances all of which are susceptiblc to oxidation by air-oxygen,
the RSD of the method was also considered to be acceptable for
routine analysis of the target fragrance substances in cosmetics.
Analyses of fragrances in liquid samples without a complex
matrix, for example, eau de toilette, and deodorant spray, were
performed by GC without involving any sample preparation step.
Practical experiences havc although revealed that dilution of
these samples in methanol, 1:2, 1 5 or 1:10, may be necessary
forthe analysis of fragrances that were present in relatively higher
concentrations (>O. 10%).The recoveries of the investigated fra-
grance substances from the spiked deodorant sprays and eau de
toilettc products were found to be 90-104% (Table 3). These
samples were spiked only with 5 of the investigated fragrance
substances, because GC-MS screening of these products revealed
the presence of relatively major peaks with tR similar to other
target fragrance substances.
A satisfactory sample preparation method, described in Section
2.4.2, was achieved after a number of trials to extract target
fragrance substances from shampoos and creams spiked with
these substances. The sample preparation method has been made
nigged by changing following parameters: alcohol type (ethanol/
methanol), amount of sample (lg/2g), volume of alcohol used
for suspending the sample (5 m1/10 ml), time of heating of the
sample suspension at 60 "C (5 min/lO min/l5 min), use of acti-
vated and non-activated silica gel for column chromatography,
hcight of the silica gel column (5 cm/ 6 cm/7 cm), and the
spike-level of fragrances (0.045% and 0.450%). Under the opti-
mal conditions (Section 2.4.2) the recoveries of all of the target
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product and from the lipstick were similar to those from sham-
poos and creams.
The sample preparation method for shampoos and creams was,
however, not found to be suitable for a soap bar sample. Attempts
were then made to extract fragrances in an organic solvent from
the aqueous solution of soap bar spiked with 0.45% of all of the
investigated fragrance substances. The expenmental conditions
described in Section 2.4.3 are the best compromise, at present,
for the extraction of target fragrances from a soap bar, because
the recoveries of all of the target fragrance substances from the
samples were 80% - loo%, except for citral, cinnamaldehyde,
and dihydrocoumarin (Table 3). The recoveries of citral and
cinnamic aldehyde from the soap bar were 40 and 37% respec-
tively. Dihydrocoumarin, however, was not possible to recover
from the soap, recovery only 8%. Further investigations for com-
plete extraction of citral, cinnamic aldehyde and dihydrocouma-
rin from soap bar have not been performed.
The determination of target fragrance substances in the cosmetic
products was performed using GC-response factors ofthe respec-
tive substances. As the recoveries of the target fragrance sub-
stances from the spiked samples were 80%-116% (Table 3), the
results of quantitative analysis of fragrances may have an uncer-
tainty of < +20%. A rather great variation (80-1 16%) in recov-
eries of fragrances may partly be due to their uncontrolled
evaporation during sample preparation.
GC-FID and GC-MS chromatograms ofa few of the investigated
samples are shown in Figures 2-4. When the GC-MS screening
showed the presence of a target fragrance substance that was not
identified by GC-FLD, 2 g \ample was used for the GC analysis.
The identification by MS was considered to be correct when the

656 VOL. 18, OCTOBER 1995 J High Resol. Chromatngr.

 100.0

1
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Analytis of Fragrances in Cometics by GC-MS

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I
0
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coumarin, 14.469 - isoeugenol.

15 20 25
tR
Min
Figure 2. Analysis of the target fragrance snbstances in a body lotion (1-0904)
hy GC-FTD. k 8.179 -internal standard (citronellal), 10.031 - geraniol, 10.530
- hydroxycitronellal, 11 . I 10 - cinnamic alcohol, 12.355 - eugenol, 14.260 -
I ,
1
188
12:4i
r
1400
14148 16:55
1608
,
l8DB
19:82

choscn as an internal standard for the quantitative analysis of

fragrances in the sample - for our purpose citronellal was found
to be quite suitable because this substance was not detected in
any of the products investigated.

The method developed for the analysis of target fragrance sub-

stances in cosmetics is routinely used in our laboratory. More
than I00 cosmetic products of various types have been analyzed
so far. All the samples were appropriately treated and analyzed
for the fragrance substances by GC-FID and GC-MS. No pro-
blems have been encountered in adapting the procedures estab-
lished for the analysis of fragrances (Section 2.4 - Section 2.6).
Thus, it may be concluded that the method described in the
I
lase
21:M

GC-MS. Scan no. 1261 - citral. 12x2 - hydroxy citronellal, 1351 - cimamic
alcohol, 1678 - coumarin.

match fit and purity were >950 and >900 respectively . One of
the target fragrance substances which was not found to be present
in a sample, as revealed by GC-FID/GC-MS screening, was
SCIN
TINE

Figure 4. Analysis of the target fragrances in a deodorant spray (2-01 I ) by

present communication is suitable for routine analysis of target

fragrances in cosmetics.

GC-MS investigationof target fragrance substances also revealed

that the method described in the present communication may also
be suitable for the analysis of some other fragrance substances
in cosmetm. Thus, GC-MS screening revealed that several of
the investigated samples also contained some of the following
fragrance substances: various types of terpenes and sesqui-ter-
penes, benzyl alcohol, 2-phenyl ethanol, 3-phenyl propanol,
phenyl methyl acetate, methoxy benzaldchyde and esters of ben-
zoic acid. No attempt has been made to quantify these substances
in the investigated products.

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As the fragrances are also used in various other consumer prod-
ucts besides cosmetics, it was tempting to evaluate the applica-
bility of the above mentioned method for the analysis of target
. fragrances in some commonly used products: dishwasher and a

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granular laundry detergent. It was found that the method for the
b 5 io 1s 20 25 Min frdgrance analysis of shampoos was applicable to a dishwasher
product and the method for the fragrance analysis for soap was
Figure3.Analysisofthe tar~etf~~~rancesubstances inaneaude toilette (3-1714) applicable to a laundry detergent. The recoveries of the target
by GC-FID. t~ 8.815 -internal standard (citronellal), 10.099 - geraniol. 10.548 fragrance from the respective products were similar to those
- hydroxycitronellal, 11.124 - cinnamic alcohol, 12.371 - engenol. described before.

J High Resol. Chromatogr. VOL. 18, OCTOBER 1995 657

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Analysis of Fragrances in Cosmetics by GC-MS

Acknowledgments
Skillful technical asislance was provided by Mrs. Gitte H. Jensen.
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z
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H.J. Eirmaun. W. Larsen, H.1. Maibach, and J.S. Taylor. J. Am. Acad. Dermatol. 6 Ms received: October 1 0 , 1994:
(1982) 909-917. Accepted: May 11, 1995

658 VOL. 18, OCTOBER 1995 J High Resol Chromatogr.