Cistus

ladanifer
J. Essent. Oil Res.,
17, XXX-XXX
(March/April 2005)

Characterization of the Portuguese-grown Cistus

ladanifer Essential Oil
Paula B. Gomes, Vera G. Mata* and A.E. Rodrigues
Laboratory of Separation and Reaction Engineering (LSRE), Department of Chemical Engineering, Faculty of
Engineering of University of Porto, Rua Dr Roberto Frias, 4200-465 Porto, Portugal
Abstract
The chemical composition of the cistus oil from Portuguese-grown rockrose (Cistus ladanifer) was determined
using GC and GC/MS. A comparison was also made in terms of the geographical source and use of either dry or
fresh plant material. The cistus oil herein obtained was richer in amber-like compounds and had a low content of
monoterpenes when compared to the usual values found in the literature. Moreover, it presented a relatively high
content of ambrox (amber odor), which usually is only reported in labdanum oil. The major constituents were three
sesquiterpene alcohols: viridiflorol (13.6-17.4%), globulol (3.1-5.0%) and a unknown sesquiterpene alcohol (2.7-6.0%),
as well as the diterpene alcohol 15-nor-labdan-8-ol (1.7-5.2%). Three samples of commercially available cistus oil
were also analyzed and compared.
Key Word Index
Cistus ladanifer, Cistaceae, rockrose, essential oil composition, viridiflorol.

Introduction
Cistus ladanifer, also known as rockrose or labdanum, is a resinous
and extremely fragrant bush that grows wildly in the Mediterranean
region (Portugal, Spain, France, Morocco). The plant is easily recognizable by its white flowers with a crimson spot in the base of the
petals. Labdanum is a valuable raw material in perfumery industry
as a natural fixative and for composing amber and leathery notes.
It is reported to be used in 33% of all modern quality perfumes
and 20% of all quality perfumes for men (1), mainly in Chypre
perfumes (1,2). Moreover, the isolates from C. ladanifer constitute
an important alternative to ambergris, which is a rare ingredient
obtained from a protected animal source (whales), and provides
starting materials for manufacturing synthetic ambers (1).
Spain is the main world producer of labdanum products
(3,4). The cistus oil is obtained by hydrodistillation or steam
distillation of the leaves and stems, being constituted mainly
by monoterpenes (3). Labdanum oil is a different product that
is obtained by distillation of the gum exuded by the plant. The
typical odor is due to the presence of compounds resulting
from oxidative degradation of diterpenes with labdane skeleton
existing in labdanum gum as the main components (3).
The main composition of cistus oil published in the literature
is presented in Table I. These compositions differ significantly
although it is possible to consider two groups: Group A with
-pinene as principal component and Group B with viridiflorol
in higher quantity and low content of -pinene. Group A is
the most common.

Simon-Fuentes et al. (4) identified the main components by

GC/MS in the neutral volatile fraction of a commercial cistus
oil produced in Spain, where the highly volatile monoterpenes
-pinene, camphene and p-cymene constituted almost 50% of
the composition. The norterpene 2,2,6-trimethylcyclohexanone
was also the major compound (5.7%) that has been associated
to the fragrance of the plant (5).
Ramalho et al. (5) studied the aromatic volatile compounds
existing in the leaves of C. ladaniferus from Douro region
(Portugal) that are related to the aroma quality of Porto wine
by GC/MS and GC/Sniffing. In this study, the components 2,2,6trimethylcyclohexanone (rock-rose leaf odor), acetophenone,
2-phenylethanol (floral aroma) and in small amounts 2,6,6trimethylcyclohex-2-enone (woody balsamic-like odor) were
pointed out as the most important odoriferous constituents.
Peyron et al. (6) made a detailed description on the industrial
use of cistus cultivated in Corsica, including data on botanical,
cultivation, extraction technologies and oil characteristics.
Mariotti et al. (7) characterized the chemical composition
of cistus oil isolated from leaves and stems of C. ladaniferus
of Spanish origin but grown in Corsica, using GC/FID and
13
C-NMR. The authors identified 45 components, of which
the main components were pinene (39%), viridiflorol (11.8%),
ledol (3.3%) and bornyl acetate (3.1%). A study of chemical
variability showed that 20 samples of cistus oil displayed significant variations in their composition. They were divided in
six groups, where in Group III to VI the major component was
-pinene (20.4-24.2%, 29.8-33.0%, 36.8-40.3% and 44.1-47.4%,

*Address for correspondence

Received: August 2003

Revised: January 2004
1041-2905/05/0002-00XX$6.00/0 2005 Allured Publishing Corp.

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Accepted: February 2004

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Gomes et al.

Table I. Percentage composition of cistus essential oils found in the literature, comparing the most common compounds
Component

Group A

Group B

-pinene
camphene
limonene
p-cymene
2,2,6-trimethylcyclohexanone
-campholenic aldehyde
bornyl acetate
terpinen-4-ol
allo-aromadendrene
trans-pinocarveol
borneol
myrtenol
ledol
viridiflorol

35.0
10.0
2.3
4.0
5.7
0.8
3.7
1.8
1.2
3.4
1.0
-

5.3-25.6
0.9-6.5
0.2-0.8
1-4.8
4.5-11.9
1.9-3.7
1-2.6
0.5-2.5
1.1-2.4
6.6-13.8
-

56.0
1.9
1.7
1.2
2.5
2.3
2.1
0.8
0.7
0.8
0.6
0.7
2.9

39.0
2.1
1.7
1.7
0.9
3.1
1.1
1.9
1.9
0.8
0.4
3.3
11.8

Reference

(4)

(12)

(8)a

(7)b

24.0
3.1
1.5
1.2
6.0
3.0
3.6
3.5
3.0
1.3
1.8
6.3
(11)

0.4
0.4
0.8
0.8
2.4
0.7
1.0
2.5
1.5
0.0
0.4
12.8

2.3
0.6
1.4
2.1
3.1
7.0
1.4
1.9
6.6
21.3

(8)c

(7)d

Vernin (1992) refered by Lawrence (8); bBulk sample obtained by hydrodistillation in industrial apparatus; cMrabet et al. (1997) refered by Lawrence (8); dAverage composition of
cistus oil from plants of group I

respectively). Group I presented a considerably higher content

of viridiflorol (20-22.6%) and a lower amount of -pinene (2.12.5%), and the remaining Group II was intermediate between
Group III and Group I with -pinene and viridiflorol in high
amount (11.1-16.4 and 9.5-10.7%, respectively).
Mrabet et al., cited by Lawrence (8), characterized the oil
of two varieties of cistus grown in Morocco, which also had
viridiflorol as the main constituent (12.81-20.68%) and a very
low content of -pinene (0.30-0.37%). The variety maculatus
contained an unusual high level of camphor (2.92%) and a low
content of 2,2,6-trimethylcyclohexanone (0.75%).
Weyerstahl et al. (9) described with great detail the composition of a commercial labdanum oil. The composition of the oil
was determined by GC/MS and NMR analysis. The components
found in major quantity were ledene (9.3%), viridiflorol (4.3%) and
cubeban-11-ol (4.1%). The characteristic components of rockrose
such as 2,2,6-trimethylcyclohexanone (1.3%) and 2,2,6-trimethylcyclohex-2-enone (0.3%) were found in smaller amounts. One of
the most interesting aspects of their work was the identification
of the olfactory key components for the amber scent, namely 11nor-driman-8-ol (0.3%, powerful woody-amber), ambrox (1.4%,
strong dry amber), -ambrinol (0.2%, warm animal amber),
drimenone (0.1%, tobacco, amber), 6-acetoxy-nor-drimenone
(0.2%, soft warm, strong amber, woody), oxoambrox (0.1%, soft
animal amber, like ambrox), sclareolide (0.2%, weak fine amber,
woody-resinous tone), labdenols (weak amber-animal) labd-8(17)en-15-ol (0.4%), labd-7-en-15-ol (0.4%) and labd-8-en-15-ol (0.3%).
Sclareol oxide (0.2%) was also identified as a minor component of
labdanum oil, being that component an important intermediate
for the synthesis of ambergris-odorants for perfumery industry
and it is usually obtained from clary sage oils (2).
Ohloff (2) pointed out some components responsible
for labdanum odor, namely ambrox and 6-oxo-isoambrox for
the amber-like scent; phenols for the smoky leathery notes;
methyl -orcinol carboxylate for the powdery moss character;
rose oxides, 2-phenylethyl alcohol, 9-oxodamascone, ledol and
viridiflorol for the floral notes; tagetone and (Z)-ocimenone for
2/Journal of Essential Oil Research

JEOR0503 Mata RN-1892.1st.indd 2

the herbaceous odor; and raspberry ketone and its methoxyderivative, which impart a fruity scent.
Rincn et al. (10) established the best operation conditions of
supercritical CO2 extraction (SFE) of rockrose growing in Spain. The
main components of the supercritical extract obtained at optimum
conditions were camphor (22%), -pinene (19.5%), -terpineol
(4.6%), borneol (4.4%), camphene (4.2%), thymol (4.2%), -terpinene (4.1%) and p-cymene (4,0%). SFE is an interesting alternative to conventional volatile isolation methods of oils and volatile
concentrates from plants since it prevents thermal degradation and
solvent pollution of the extract. Indeed, the authors found that the
odor of the supercritical extract was quite similar to the plant, while
the steam-distilled oil had a slightly sweeter odor.
More recently, Robles et al. (11) compared the composition of
oils of two varieties of C. ladanifer growing in France: C. ladanifer
var. maculatus and C. ladanifer var. albiflorus. The two varieties can
be distinguished by the difference in the chemical composition of
the following eight components: -pinene, -pinene, -terpinene,
verbenone, benzaldehyde, p-cymen-8-ol, ledol and viridiflorol.
Regino et al. (12) studied the composition of cistus grown in
Portugal. They considered the variation of composition and yield
of cistus oil along the year, during storage and using plants from
three different geographical sources. The composition changed
but the main components were always -pinene (5.34-25.56%),
2,2,6-trimethylcyclohexanone (4.46-11.88%) and ledol (6.5913.78%). The higher yields were obtained with plant harvested
in August and September. The authors also compared the oil
with benzene and hexane-dichloroethane extracts obtained from
labdanum concrete, which showed gas chromatographic profiles
very similar to the oil but with lower contents or even absence
of some components, such as -pinene and ledol.
Lawrence (8,13,14) published some reviews on cistus and
labdanum isolates.
In the present work, the main composition of C. ladanifer oil
obtained from plants growing in Portugal is reported, highlighting the
interesting components from the perfumery point of view. A comparison with available commercial samples is also performed.
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Cistus ladanifer

was maintained at 250C. The sample volume injected was 1

mL. The carrier gas was helium He N60, at a constant flow rate
of 1 mL/min. There were made 3 injections per sample and the
sample GC vial was kept cold between injections.
Component identification and quantification: The oil
composition was expressed in percentage values calculated directly
from GC peak areas without the use of correction factors and in
a base without solvent. The linear retention indices (LRI) were
determined relative to the retention times obtained for a standard
mixture containing a series of n-alkanes C8-C20 (Fluka, Spain).
The component identification was made by comparison of mass
spectra using NIST98 spectral library, pure reference compounds
(own laboratory library) and literature data. The identification was
also confirmed by comparison of retention indices with those of
injected pure reference compounds and published values obtained
on the same type of polar column (7,9). The composition of each
sample was determined as the average of three GC injections.

Materials and Methods

Plant material: Cistus ladanifer was collected from two
sites, in July-August 2001, after the flowering season. The major
quantity was brought from the wild, where the plant was growing
in the mountainous region of the center-interior of the country
(site 1). A smaller amount was harvested from a cultivated plant
in the north of Portugal (site 2) that was propagated from a wild
plant found in the dry plain region in the South of Portugal.
Oil isolation: The cistus oil was obtained by hydrodistillation of
fresh and dry plant material (20 g), using leaves and small branches,
in a Clevenger-type glass apparatus. The plant/water proportion was
1:30 and the distillation time was 2 h. The dry cistus oil obtained was
the cumulative oil of several hydrodistillations. The oils were stored
in a glass flask and kept in a freezer prior to their analysis.
GC/MS: Gas chromatography GC/FID and GC/MS were carried out in parallel, using a Varian CP-3800 instrument equipped
with 2 split/splitless injectors, 2 CP-Wax 52 CB bonded fused
silica polar columns (50 m x 0.25 mm, 0.2 m film thickness),
a Varian FID detector and a Varian Saturn 2000 MS ion-trap
mass spectrometer, both controlled by Saturn 2000 WS software.
The oven temperature was programmed isothermal at 50C
for 5 min, then increased from 50-200C at 2C/min and held
isothermal for 20 min. The injectors were set at 240C, with a
split ratio of 1/20 for FID and 1/200 for MS. The FID detector

Results and Discussion

The oil yield calculated from dry plant material was 0.20.3%. The main composition of the oils of cistus growing in
two different sites in Portugal is shown in Table II. Most of
the components identified have been previously reported
as constituents of this oil. The composition is considerably

Table II. Percentage composition and linear retention indexes of components identified in the essential oil of C. ladanifer growing in
two sites in Portugal, hydrodistilled from dry and fresh plant
Site 1

Site 2

Component

LRI*

dry

fresh

dry

fresh

1
2
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29

-pinene
camphene
limonene
p-cymene
2,2,6-trimethylcyclohexanone
p-cymenene
pinocarvone
bornyl acetate
terpinen-4-ol
allo-aromadendrene
trans-pinocarveol
(Z)-ocimenone
viridiflorene
borneol
(E)-ocimenone
unknown1
-cadinene
myrtenol
caryophyllene oxide
unknown2
globulol
viridiflorol
-verbenone
spathulenol
ambrox
C15H26O sesquiterpene alcohol3
sclareoloxide
15-nor-labdan-8-ol**

1015
1055
1190
1259
1302
1424
1562
1562
1585
1624
1636
1673
1677
1682
1692
1710
1739
1773
1950
1954
2000
2043
2059
2069
2087
2108
2152
2295

2.1
0.3
0.2
2.8
1.1
1.6
1.0
0.8
2.1
0.6
1.3
0.7
0.7
1.0
0.7
1.8
1.1
5.0
17.4
0.5
0.8
0.8
6.0
0.3
1.7

4.5
0.1
0.3
2.0
1.7
1.5
1.5
0.7
3.8
0.2
1.0
0.5
1.3
1.6
1.1
3.6
0.5
4.3
15.1
0.9
0.8
0.7
3.3
0.3
1.8

0.1
0.1
0.7
0.3
0.5
4.0
0.1
3.6
0.4
1.7
0.7
3.1
13.6
0.5
0.8
2.7
1.1
5.2

0.2
0.1
0.0
0.3
0.7
1.4
0.8
0.7
2.2
1.0
0.5
1.9
1.1
0.7
2.5
0.9
4.0
14.9
0.1
0.6
0.8
4.0
1.3
3.5

*Linear retention indices determined in a CP-Wax 52 CB column; **Tentatively identified. m/z(rel.int.): 280 (M+) (7), 262 (20), 247 (35), 222 (10), 204 (10), 191 (43), 177 (64),
163 (9), 153 (22), 137 (35), 123 (43), 109 (64), 95 (68), 81 (54), 69 (64), 55 (55), 41 (100).
(1) m/z(rel.int.): 137 (M+) (2), 119 (6), 105 (3), 94 (100), 93 (43), 91 (56), 79 (97), 77 (42), 65 (18), 59 (95), 51 (16), 43 (37), 39 (39); (2) m/z(rel.int.): 264 (M+) (1), 222 (16), 204
(75), 189 (25), 179 (13), 162 (23), 161 (100), 150 (12), 133 (12), 119 (26), 105 (33), 95 (21), 79 (17), 67 (15), 55 (11), 43 (65), 39 (29); (3) m/z(rel.int.): 222 (M+) (3), 204 (34),
189 (22), 179 (13), 161 (100), 147 (10), 133 (16), 119 (33), 109 (50), 95 (46), 81 (30), 67 (32), 55 (22), 41 (55)

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Gomes et al.

Figure 1. Chromatograms of GC/MS analysis of cistus oil obtained from dry and fresh plant, collected at two different sites.

more complex (around 250 components with more than

0.1% and exceeding 400 components when including those
in trace amounts), as can be seen in the chromatograms in
Figures 1 and 2. Therefore there was considered this group
of components in order to allow comparing and distinguishing
the oils. They were also representative of the several kinds
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JEOR0503 Mata RN-1892.1st.indd 4

of components existing in these cistus oils, namely containing: high volatility monoterpenes hydrocarbons (compounds
1 to 5, 7) and oxygenated (compound 6), medium volatility
compounds sesquiterpenes (compounds 11, 14, 18) and oxygenated monoterpenes (compounds 8, 9, 10, 12, 13, 15 and
19), and low volatility oxygenated compounds (compounds
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Cistus ladanifer

Figure 2. Chromatograms of GC/MS analysis of commercial cistus oil: sample A, sample B and sample C.

20 to 29), including those contributing to amber scent (compounds 26 and 29).

Viridiflorol, globulol, an unknown sesquiterpene alcohol
(compound 27) and the diterpene alcohol 15-nor-labdan-8-ol
were the constituents existing in higher quantity in the cistus
oils from both sites. The compound 15-nor-labdan-8-ol was
tentatively identified by comparison with MS data published
by Weyerstahl et al. On the other hand, the content of a-pinene
and other volatile monoterpenes was relatively low, so the oil
here studied was similar to Group B cistus oils. However the
content in 2,2,6-trimethylcyclohexanone, characteristic of
rockrose odor, was 2 to 3 times higher in our oil. Another compound found with olfactory interest was ambrox, with an amber
scent resembling ambergris and very valuable to the perfumery
industry (3). It is noteworthy that ambrox and sclareol oxide
have already been referred as labdanum constituents (9) but
not as main components of the cistus oil, as this work reports.
Moreover, the compound caryophyllene oxide having a woody
slightly ambergris scent (3) was also present in higher amount
than usual. When comparing with the previous works, including the one on Portuguese cistus oil (12), the composition of
our oil is quite different. Therefore, this work reports a novel
composition of cistus oil richer in amber-like compounds.
Considering the oil composition of cistus plants from different sites, there were found some differences. The cistus
oil of site 2 had a high content on the ocimenone isomers, an
absence of trans-pinocarveol and unknown (compound 17) and
a higher quantity of less volatile compounds such as sclareol
oxide and 15-nor-labdan-8-ol. Cistus oil from site 1 was richer
in sesquiterpene alcohols and 2,2,6-trimethylcyclohexanone.
The amount of ambrox was the same for both oils.
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JEOR0503 Mata RN-1892.1st.indd 5

Considering the use of fresh or dry plant, the composition of

cistus from site 2 was more affected, decreasing the amount of
components of middle to high volatility and increasing the amount
of the less volatiles. Drying promoted the doubling of the amount of
ocimenone isomers in cistus oil from site 2 and of unknown (compound 21) and sesquiperpene alcohol (compound 29) in cistus from
site 1. Again the quantity of ambrox was the same for both oils.
From the organoleptic point of view, besides the compounds
already mentioned, there are other contributions to cistus oil
odor, namely: viridiflorol (floral); terpinen-4-ol (spicy floral);
bornyl acetate, borneol and myrtenol (fresh-camphoraceous);
(Z)-ocimenone (green-herbaceous).
Samples A and B of the three commercial oils analyzed
showed a very similar composition, with -pinene constituting
almost 50% of the oil (group A). On the other hand, sample C
had a considerably lower content of this monoterpene (12.8%),
possessing higher contents of the other components, namely
2,2,6-trimethylcyclohexanone, ambrox and 15-nor-labdan-8-ol,
resembling more the Portuguese cistus oils here studied. All
the commercial oils possessed lower contents of ambrox and
other low volatility compounds than our oil.
In conclusion, Portuguese cistus oil herein characterized
is richer in amber-like compounds and has a low content of
hydrocarbon monoterpenes, which is desirable from the organoleptic point of view.
The commercial cistus oils have a high content of monoterpenes
that degrade easily. To obtain a product with better quality for
perfumery further processing is necessary, such as deterpenation
or re-distillation. The fact that our oil already had low levels of
monoterpenes constitutes an advantage for using the Portuguese
plants for the production of good quality cistus oil.
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Gomes et al.

Table III. Percentage composition of commercial cistus essential oils produced in Spain
N

Component

1
2
3
4
5
6

-pinene
50.4
camphene
2.4
-pinene
4.4
limonene
1.4
p-cymene
1.9
2,2,6trimethylcyclohexanone 1.5
p-cymenene
1.3
pinocarvone
.2
bornyl acetate
1.5
terpinen-4-ol
0.9
allo-aromadendrene
0.5
trans-pinocarveol
1.7
(Z)-ocimenone
0.1
viridiflorene
3.7
borneol
0.7

7
8
9
10
11
12
13
14
15

Sample A

Sample B

Sample C

Component

48.9
5.0
0.6
1.0
3.6

12.8
1.9
0.6
0.8
1.9

2.0
0.9
3.1
1.4
0.6
2.8
0.0
1.4
1.1

2.4
1.6
0.8
3.5
2.5
1.2
4.9
0.3
8.0
1.6

16
17
18
19
20
21
22
23
24
25
26
27

(E)-ocimenone
unknown1
-cadinene
myrtenol
caryophyllene oxide
unknown2
globulol
viridiflorol
d-verbenone
spathulenol
ambrox
C15H26O sesquiterpene
alcohol3
sclareoloxide
15-nor-labdan-8-ol**

28
29

Sample A

Sample B

Sample C

0.1
0.3
0.5
0.4
1.1
0.3
0.1
0.2

0.3
0.4
0.5
1.7
0.2
0.1
0.1

0.6
0.9
1.2
0.1
0.2
1.3
3.4
0.7
0.3
0.3

0.3
0.2

0.2
0.1

0.8
0.2
0.3

**tentatively identified. m/z(rel.int.): 280 (M+) (7), 262 (20), 247 (35), 222 (10), 204 (10), 191 (43), 177 (64), 163 (9), 153 (22), 137 (35), 123 (43), 109 (64), 95 (68), 81 (54), 69
(64), 55 (55), 41 (100); (1) m/z(rel.int.): 137 (M+) (2), 119 (6), 105 (3), 94 (100), 93 (43), 91 (56), 79 (97), 77 (42), 65 (18), 59 (95), 51 (16), 43 (37), 39 (39); (2) m/z(rel.int.): 264
(M+) (1), 222 (16), 204 (75), 189 (25), 179 (13), 162 (23), 161 (100), 150 (12), 133 (12), 119 (26), 105 (33), 95 (21), 79 (17), 67 (15), 55 (11), 43 (65), 39 (29); (3) m/z(rel.int.):
222 (M+) (3), 204 (34), 189 (22), 179 (13), 161 (100), 147 (10), 133 (16), 119 (33), 109 (50), 95 (46), 81 (30), 67 (32), 55 (22), 41 (55)

Acknowledgments

We gratefully acknowledge the financial support of FCT

- Fundao para a Cincia e Tecnologia, project grant POCTI/
EQU/39990/2002, PhD grant SFRH/BD/968/2000 and pos-doc grant
SFRH/BPD/1576/2000. The authors are also grateful to the companies
Ventos, Destilerias Muoz Galvez and Biolandes for kindly offering
the samples of cistus oil.

6.

7.

8.
9.

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