Chapter 2

Methods for the Characterization,

Authentication, and Adulteration
of Essential Oils
Tzi Bun Ng1, Evandro Fei Fang2, Alaa El-Din Ahmed Bekhit3, Jack Ho Wong1
1The

Chinese University of Hong Kong, School of Biomedical Sciences, Faculty of Medicine, Hong Kong, China; 2National Institute on Aging, National
Institutes of Health, Laboratory of Molecular Gerontology, Baltimore, MD, USA; 3University of Otago, Department of Food Science, Dunedin, New Zealand

List of Abbreviations
GCMS Gas chromatographymass spectrometry
SSR Simple sequence repeat
RAPD Random amplified polymorphic DNA
SFE GCMS Supercritical fluid extraction GCMS
MDGC Multidimensional gas chromatography
GCCIRMS Gas chromatographycombustionisotope ratio mass spectrometry

INTRODUCTION
Essential oils extracted from plants are used in cosmetics, in many foods, and for their fragrance, flavoring, and preservative
properties. The bulk is employed for the fragrance or flavor industries, with only a small percentage for therapeutic purposes.
It is imperative that therapeutic oils are unadulterated. Completely pure natural essential oils should be obtained straight
from the grower without intervention by a vendor. Ideally, essential oils should be clearly labeled with the botanical name,
cultivation method, country of origin, the plant tissue employed for distillation, and main constituents. However, very few
people using essential oils know that the oils they are using may be adulterated. Unscrupulous manufacturers of essential
oils may resort to adulterating the oils with the intent to make the price competitive and maximize the profit. Extraordinarily
cheap essential oils and labels such as for external use only, not for internal use, and dilute prior to topical application
should alert one to the possibility of adulteration.
The adulterants are: (1) vegetable carrier oils, alcohol, and synthetic oils used as diluents; (2) cheaper oils of the
same species but of different geographical origins; (3) cheaper essential oils extracted from another part of the plant;
(4) cheaper essential oils from related species; and (5) isolated natural, or (semi) synthetic compounds. Frankincense
may be adulterated with gum resin, alcohol, and other solvents. Many commercial samples of lavender oil are composed of lavandin, camphor, linalyl acetate, propylene glycol, and petrochemicals. Synthetic oils have appeared in
products claimed to be natural oils. Noxious chemicals with health risks, including phthalates and benzyl alcohol,
have been detected in essential oils.
In view of the aforementioned adulteration of plant essential oils, it is of paramount importance to examine the various
methods available for authentication and adulterant detection which are mentioned below.

METHODS OF AUTHENTICATION
Gas ChromatographyMass Spectrometry (GCMS) for Hyssopus cuspidatus Essential Oil
An investigation of the chemical composition of the essential oil of Hyssopus cuspidatus Boriss from Xinjiang,
China employing GCMS led to the identification of 50 compounds. The principal constituents comprised oxygenated
Essential Oils in Food Preservation, Flavor and Safety. http://dx.doi.org/10.1016/B978-0-12-416641-7.00002-X
Copyright 2016 Elsevier Inc. All rights reserved.

11

12 PART | I General Aspects

sesquiterpenes (1.25%), octane (1.85%), monoterpenes (26.14%), and oxygenated terpenes (66.33%). The authenticity
of H. cuspidatus may be confirmed by the physicochemical parameters of the compounds (Zhou etal., 2010).

Determination of Enantiomeric Composition for Essential Oils of Indian Origin

Use of 10% heptakis(2,3-di-O-methyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin as a chiral stationary phase to
ascertain the enantiomeric ratios of linalool in a diversity of authentic essential oils originating from India has been
reported by Chanotiya and Yadav (2009). A complete enantiomeric excess for (3S)-(+)-linalool was typical of leaf
oils from Lippia alba and Cinnamomum tamala while below 90% excess was found in Zanthoxylum armatum leaf,
Zingiberroseum root/rhizome, and Citrus sinensis leaf oils. By contrast, an enantiomeric excess of (3R)-()-linalool
was observed in essential oils of basil (100% for Ocimum basilicum) and bergamot mint (7275% for Mentha citrata).
Thus enantiomeric compositions could be used to assess the authenticity of essential oil (Chanotiya and Yadav, 2009).
In addition, Kreis and Mosandl (1992) reported the stereoanalysis of chiral compounds present in lavandula essential
oil. An example is shown in Table 1.

Supercritical Fluid Extraction GCMS (SFE GCMS) Involving Use of Multidimensional GC

to Resolve Enantiomers for Essential Oils of Lavandula
An approach based on SFE was adopted to investigate, both qualitatively and quantitatively, the compositions of the
predominant volatile aroma constituents in essential oils of different varieties of Lavandula. Under optimal conditions of SFE, relative standard deviations (RSDs) from three replicates below 2% and recoveries up to 59% could be
achieved. For separation of the target enantiomeric compounds, multidimensional gas chromatography was deployed.
The data disclosed an enantiomeric purity exceeding 90% for every compound in the different varieties examined,
lending credence to the natural constant enantiomeric composition of the compounds of interest. The data can be of
value in authenticity investigations and in choosing natural sources of enantiomerically homogeneous compounds
(Flores etal., 2005).

TABLE 1 Enantiomeric Distributions of Chiral Monoterpenoids From Authentic Samples of Lavandula Oils
trans-Linalol
oxide (2R, 5R)

cis-Linalol oxide
(2R, 5S)

Linalyl acetate (R)

Lavandulol (R)

Terpinen-4-ol (S)

Linalol (R)

No.

11

13

16

17

86.4

88.5

>99

93.2

97.4

>99

98.5

97.8

94.5

88.6

86.0

>99

98.0

96.6

84.6

86.7

>99

89.8

98.0

95.1

90.2

91.5

>99

>99

94.2

97.5

96.1

91.5

>99

>99

98.2

97.3

95.8

92.9

>99

98.3

98.0

96.9

>95

>95

>99

98.7

98.3

98.2

85.4

90.0

>99

>99

98.1

96.1

10

87.5

95.8

>99

>99

98.4

97.1

11

>99

>99

98.1

95.2

12

76.7

82.9

98.8

>99

98.1

97.2

13

86.2

89.3

>99

96.2

89.1

95.1

Reproduced from Kreis and Mosandl (1992) with a kind permission from John Wiley and Sons Publishing. Permit No 3341621103500.

Essential Oil AuthenticityChapter | 2 13

Enantioselective Capillary Gas Chromatography and Online Methods of Isotope Ratio Mass
Spectrometry
Mosandl (2004) wrote an excellent review on enantioselective capillary gas chromatography and online methods of isotope
ratio mass spectrometry in the authentication of food flavor and essential oil compounds, covering papers published in the
10years preceding his review.

Enantioselective Capillary Gas Chromatography and Isotope Ratio Mass Spectrometry, Coupled
Online with Capillary Gas Chromatography on an HP5 Column for Various Essential Oils
Enantioselective capillary gas chromatography conducted using a Supelco beta-DEX 225 column heptakis(2,3-di-Oacetyl-6-O-tert-butyldimethylsilyl)-beta-cyclodextrin SPB 20poly-20% diphenyl, 80% dimethylsiloxane) and isotope ratio
mass spectrometry, coupled online with capillary gas chromatography on an HP5 column have been exploited for analysis
and authenticity investigations of essential oils. The essential oils examined included those of the following plants: lemon
(Citrus limon), lemongrass (Cymbopogon citratus and Cymbopogon flexuosus), citronella (Cymbopogon nardus L.Ceylon
type and Cymbopogon winterianusJava type), Litsea cubeba, Lippia citriodora, lemon myrtle (Backhousia citriodora),
lemon gum (Eucalyptus citriodora), and precious lemon balm oil (Melissa officinalis L.). Isotope data (13C(Pee Dee
Belemnite (PDB)) and 2H(Vienna standard mean ocean water (V-SMOW)) for citral (neral + geranial) and citronellal
from isotope ratio mass spectrometry online coupled with capillary gas chromatography (GC-Py-IRMS) and chiral data
for citronellal in these essential oils can yield information on the origin of essential oils and disclose adulterants. Principal
components analysis of specific compounds was carried out for discriminating essential oils from L. cubeba, C. citratus,
and C. flexuosus (Nhu-Trang etal., 2006a).

Online Gas Chromatography Pyrolysis Isotope Ratio Mass Spectrometry (HRGCPIRMS) for
the Flavor Compounds Decanal, Linalool, Linalyl Acetate, E-2-Hexenal, and E-2-Hexenol in
Essential Oils
Hr etal. (2001) applied the HRGCPIRMS technique to find the 2H(SMOW) values of the aforementioned flavor
compounds in foods and essential oils. Procedures such as simultaneous distillation extraction, solvent extraction, and
liquid/liquid extraction used for preparing samples had negligible effects on the 2H values. Only the 2H data recorded for
linalool did not permit distinction between synthetic and natural products. For decanal, linalyl acetate, E-2-hexenal, and
E-2-hexenol, the data appeared to be useful for differentiation purposes (Table 2).

TABLE 2 Application of HRGCPIRMS Technique to Distinguish Between Synthetic

and Natural Flavor Compounds in Essential Oils
2H(SMOW) Values: 2H Abundance
Synthetic decanal samples

From 90 to 156 per 1000

Natural decanal samples

From 138 to 262 per 1000

Synthetic linalyl acetate samples

From 199 to 239 per 1000

Natural linalyl acetate samples

From 213 to 333 per 1000

Synthetic E-2-hexenal samples

From 14 to 109 per 1000

Natural E-2-hexenal samples

From 263 to 415 per 1000

Synthetic E-2-hexenol samples

From 41 to 131 per 1000

Natural E-2-hexenol samples

From 238 to 348 per 1000

Synthetic linalool samples

From 207 to 301 per 1000

Natural linalool samples

From 234 to 333 per 1000

Only the 2H data recorded for linalool did not permit distinction between synthetic and natural products.
Data compiled from Hr etal. (2001).

14 PART | I General Aspects

TABLE 3 2H(V-SMOW) Values Of Various Components in Essential Oils

2H(V-SMOW)
Carvacrol

61 per 1000

Thymol

From 49 to 7 per 1000

p-Cymene

From 300 to 270 per 1000

-Terpinene

From 285 to 248 per 1000

Thymol

From 259 to 234 per 1000

Carvacrol in authentic oregano oils

From 223 to 193 per 1000

p-Cymene in authentic oregano oils

From 284 to 259 per 1000

Aromatic Compounds in Authentic Satureja montana subsp. Montana Essential Oil

Carvacrol

226 per 1000 (SD=1.7 per 1000)

p-Cymene

283 per 1000 (SD=3.0 per 1000)

-Terpinene

273 per 1000

SD, standard deviation.

Data compiled from Nhu-Trang etal. (2006b).

Isotope Ratio Mass Spectrometry Online Coupled with Capillary Gas Chromatography
(GC-Py-IRMS)
GC-Py-IRMS on column INNOWAX has been exploited in studies on the authenticity of phenolic essential oils (Table 3,
Nhu-Trang etal., 2006b).

Gas ChromatographyCombustionIsotope Ratio Mass Spectrometry (GCCIRMS), in

Combination with GCMS and GC Flame Ionization Detector (FID) for Rosa damascene
Essential Oil
Nineteen commercial samples of R. damascena essential oil collected from various localities, together with an authentic sample of essential oil extracted from fresh flowers, were analyzed by GCMS and GCFID. Elemental analyzer
(EA)IRMS and GCCIRMS were employed for analysis of the 13C composition of bulk samples and of some specific
components. It was discovered that essential oils from Turkey and Bulgaria contained mainly citronellol, geraniol, and
nonadecane, while Iranese essential oils were abundant in the aliphatic hydrocarbons nonadecane. The 13C values of bulk
samples fell within the range 28.1 to 26.9, characteristic of C3 plants. The 13C values of specific components were
found within the range for natural aromatic substances from C3 plants, with the exception of geranyl acetate, which demonstrated elevated values (up to 18) caused by adulteration with an oil from a C4 plant (Cymbopogon martinii, palmarosa)
which has a lower cost and existing in the bulk of essential oils (Pellati etal., 2013).

HeadspaceSolid Phase Microextraction Coupled to GCCIRMS for Citrus Oils

Schipilliti etal. (2010) evaluated the authenticity of some mandarin essential oils using GCCIRMS. Schipilliti etal.
(2013) examined the authenticity of Italian liqueurs, bergamot, lemon, and mandarin, by using headspacesolid phase
microextraction coupled to GCCIRMS. Their carbon isotope ratios were compared with those of genuine cold-pressed
peel oils. Direct enantioselective gas chromatography was used to determine the enantiomeric distribution of selected chiral
volatiles and GCMS was employed for qualitative analyses (Schipilliti etal., 2013).

Multi Dimensional Gas Chromatography (MDGC) and GC-C-IRMS for Bitter Orange Flower
Oil (or Neroli) and Lime Oils
Five samples of Egyptian neroli oils, manufactured in 2008 and 2009 in the same factory, and claimed to be authentic,
were used in the study of Bonaccorsi etal. (2011). GCFID and GCMSlinear retention index were employed to analyze

Essential Oil AuthenticityChapter | 2 15

the composition, and enantioselective GC utilized to investigate the enantiomeric distribution of 12 volatile compounds.
GC-C-IRMS was employed to ascertain the 13C(VPDB) values of some alcohols, esters, and monoterpene and sesquiterpene hydrocarbons. The variation of the composition depended on the time of manufacture. Linalool dropped while linalyl
acetate rose from March to April. The RSD for the 13C(VPDB) remained small (max. 3.89%), assuring sample authenticity
(Bonaccorsi etal., 2011).
Bonaccorsi etal. (2012) conducted an investigation on the authenticity of lime oils (Citrus aurantifolia Swingle and
Citrus latifolia Tanaka), by employing MDGC to study the enantiomeric distribution of camphene, limonene, linalool,
-phellandrene, -phellandrene, -pinene,terpinen-4-ol, -terpineol, sabinene, and -thujene. GCCIRMS was used to
ascertain the isotopic ratios of -caryophyllene, geranial, germacrene B, limonene, neral, -pinene, -pinene, -terpineol,
and trans--bergamotene. The concurrent deployment of the two techniques facilitates detection of adulteration in citrus
essential oils. In fact, in some cases detection of adulteration is possible only with one of the two techniques. The merit of
their simultaneous usage is the need to analyze only a small number of constituents hence minimizing the amount of data to
be handled. Moreover, the traditional method of analysis which relies on the assessment of the entire volatile fraction may
not be sensitive enough to disclose the oil quality when there is only a slight level of adulteration (Bonaccorsi etal., 2012).

GCFID and GCMS for Zanthoxylum armatum Leaf Essential Oil

The predominant types of compounds detected in the leaf oils comprised acyclic and menthane monoterpenoids, simple
alcohols, aldehydes, and ketones. The unique composition was characterized by a richness of nonterpenic acyclic ketones,
exemplified by 2-undecanone and 2-tridecanone, and the meager content of undec-10-en-1-al and p-phellandren-8-ol.
Other components encompassed oxygenated monoterpenes like 1,8-cineole, linalool, terpinen-4-ol, and alpha-terpineol.
Sesquiterpene hydrocarbons, in particular trans-caryophyllene, a-humulene, and germacrene D, were present. On the contrary, the oil distilled from the leaves on the second day of distillation was characterized by an abundance of 2-tridecanone
and trans-caryophyllene compared with fresh foliage. Moreover, a rich content of 2-undecanone and 2-tridecanone is characteristic of Z. armatum. Thus, the two acyclic ketones may be utilized in authenticity testing (Bisht and Chanotiya, 2011).

Ultra-High Performance Liquid ChromatographyTime-of-FlightMass Spectrometry (UHPLC

TOFMS) Profiling and 1H Nuclear Magnetic Resonance (NMR) Fingerprinting for Lemon Oil
A metabolomic strategy which depends on UHPLCTOFMS profiling and 1H NMR fingerprinting to reveal variances in
metabolites has been designed for lemon oil samples that find application in the flavor and fragrance industry. Flavonoids,
furocoumarins, fatty acids, and terpenoids present in the mixtures were markers with a differentiating role. Quantitative
NMR unveiled low levels of citropten and an abundance of bergamottin in samples from Italy compared with Argentinian
samples (Marti etal., 2014).

Near Infrared (NIR) Spectroscopy for Sandalwood Oil

NIR spectroscopy in conjunction with multivariate calibration models such as principal component regression and partial
least square regression is qualitative and quantitative analytical tool for detecting adulterants in sandalwood oil with the
advantages of speed, sensitivity, and nondestructiveness. Following appropriate preprocessing of the raw near infrared data,
the models were constructed by cross-validation. To find the optimal number of factors, the smallest root mean square error
of cross-validation and calibration was utilized. The coefficient of determination and the root mean square error of prediction in the prediction sets were employed as the parameters for evaluation (Kuriakose etal., 2010).
Kuriakose and Joe (2013) conducted a study that employed NIR spectroscopy to investigate the authenticity of samples
and quantitate adulteration of sandalwood oils. Quantitative analysis of data was executed using full spectrum or sequential
spectrum. The optimum number of partial least square components was procured according to the smallest root mean square
error of calibration (RMSEC=0.00009% v/v). The smallest root mean square error of prediction (RMSEP=0.00016% v/v)
in the test set and the largest coefficient of determination (R2=0.99989) were employed for assessment for the best model.
Locally weighted regression was introduced to collect nonlinear information and for comparison with the linear partial least
square regression model (Kuriakose and Joe, 2013).

NIR Spectroscopy for Various Essential Oils

Cross-validation models can be used to predict with accuracy virtually all of the constituents of essential oils. In various
cinnamon (Cinnamomum zeylanicum) and clove (Syzygium aromaticum) essential oils, which demonstrated analogous

16 PART | I General Aspects

compositions, 23 components (accounting for the bulk of the oil) were correctly predicted. Likewise, 20 components in
Cinnamomum camphora, 32 components in Ravensara aromatica, and 26 components in Lippia multiflora that made up
the bulk of the oils, were also correctly predicted. For almost all of the components, the modeled and reference values
obtained by GCFID exhibited a high correlation and a variance below 5%. The model was used to disclose erroneous
commercial labeling of C. camphora oil as R. aromatica oil (Juliani etal., 2006).

Simple Sequence Repeat (SSR)

The certification labels protected designation of origin (PDO) and protected geographical indication (PGI) are required
by the European Commission for assuring the authenticity of food products. Regulations for labeling, production, and
commercialization of olive oil were laid down in European Economic Community Regulation No. 510/2006. Genotype is
important in the establishment of PDO and PGI labels. The analysis of 21 olive oil samples was conducted with the help
of nine nuclear and two shortened simple sequence repeats. An array of simple sequence repeat markers can be used to
accurately attribute an olive oil to a certain cultivar (Vietina etal., 2011).

Random Amplified Polymorphic DNA (RAPD) Method

A study of 84 commercial Mediterranean oregano samples collected between 2001 and 2007 disclosed the prevalence of
adulteration. Materials from plants with an oregano-like flavor (Satureja montana and Origanum majorana), and plant
materials devoid of essential oils from Cistus incanus, Rubus sp. and Rhus coriaria, were added as adulterants. The RAPD
methodology devised by Marieschi etal. (2009) using 13 differentiating primers facilitated the sensitive detection of
materials from C.incanus, Rubus sp., and R. oriaria added as adulterants and expedited analysis of big batches of samples
(Marieschi etal., 2009).

Attentuated Total Reflectance (ATR)-Mid-infrared Portable Handheld Spectrometer

for Peruvian Sacha Inchi Seed Oils
Thermally regulated ZnSe ATR mid-infrared benchtop and diamond ATR midinfrared portable handheld spectrometers
were used by Maurer etal. (2012) to investigate Peruvian seed oils abundant in omega-3 fatty acids. A soft independent
model of class analogy and partial least squares regression were utilized for the analysis of the spectral data. Polyunsaturated fatty acid concentrations resembling levels seen in flax oils were revealed. Partial least square regression showed
good correlation between reference tests and spectra from infrared devices with correlation coefficients exceeding 0.9,
facilitating speedy analysis of composition of fatty acids. Results indicated existence of adulteration (Maurer etal., 2012).

SUMMARY POINTS
The bulk of plant essential oils are utilized by the fragrance or flavor industries, with only a small percentage for therapeutic purposes.
l In order to lower the price of the essential oils and hence attract more customers, adulterants are added by the producers to
the oils.
l Adulterants include diluents and cheaper oils from other plant tissues, related plant species, or plants of the same species
but from other countries. Some of the adulterants detected such as phthalates and benzyl alcohol are hazardous to health.
l Various types of methodology are available for authentication and adulterant detection. They include GCMS, determination of enantiomeric composition, SFE GCMS involving use of multidimensional GC to resolve enantiomers, enantioselective capillary GC, and online methods of IRMS.
l Other methods comprise enantioselective capillary gas chromatography and IRMS coupled online with capillary gas chromatography, NIR spectroscopy, SSR, RAPD, and various other methods.
l

DISCLAIMER
This article was written in a personal capacity (E.F.F.) and does not represent the opinions of the United States Food
and Drug Administration, the United States Department of Health and Human Services, or the United States Federal
Government.

Essential Oil AuthenticityChapter | 2 17

ACKNOWLEDGMENT
This research was supported in part by the Intramural Research Program of the NIH, National Institute on Aging, USA.

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