Microchemical Journal 79 (2005) 83 90

www.elsevier.com/locate/microc

Characterisation of organic residues in pottery vessels of the Roman

age from Antinoe (Egypt)
M.P. Colombini a,*, G. Giachi b, F. Modugno a, E. Ribechini a
a

Dipartimento di Chimica e Chimica Industriale, Universita` di Pisa, via Risorgimento 35, 56126 Pisa, Italy
Soprintendenza ai Beni Archeologici per la Toscana, Laboratorio di Analisi-Centro di Restauro, Largo del Boschetto 3, 50143 Florence, Italy
Accepted 4 May 2004
Available online 4 July 2004

Abstract
In the framework of a study on the Egyptian ceramic vessels belonging to the archaeological collection of the Istituto Papirologico Vitelli
(Florence), the characterisation of organic residues from three findings of the 5th 7th centuries A.D. has been performed. The materials were
identified by two analytical procedures based on Fourier transformed infrared spectroscopy (FTIR) and on gas chromatography coupled with
mass spectrometry (GC MS), respectively. The first procedure is suitable for detecting the functional groups of organic substances and thus
for distinguishing them; the second permits the simultaneous analysis of several natural substances such as vegetable resins and oils, bitumen,
tar and pitch, and waxes.
The presence of monocarboxylic acids, a,N-dicarboxylic acids, long-chain dihydroxylated acids, and terpenic species, highlights that
although the organic residues showed a high heterogeneity in composition, they mainly consisted of materials of vegetable origin. In
particular, the presence of oxidation products of characteristic unsaturated fatty acids suggests the occurrence of oil produced from plant
seeds of the Cruciferae family, some of which are reported to have been used in ancient Egypt to produce oil. Moreover, the presence of
characteristic diterpenic biomarkers in two of the three pieces of pottery enables us to assess the use of both pine resin and pine pitch.
D 2004 Elsevier B.V. All rights reserved.
Keywords: Organic residue; Archaeological vessel; Infrared spectroscopy; Gas chromatography mass spectrometry; Lipid; Cruciferae seed oil; Pinaceae
resin; Pitch

1. Introduction
Ceramic artefacts were largely employed for preparing
and storing materials and were used for cooking and
containing food. Moreover, adhesives and coatings were
often employed for finishing or repairing pottery. Consequently, traces of organic materials can occur as preserved
surface residues or as adsorbed residues in porous ceramic
vessels. The analysis of the organic residues in pottery can
yield important information concerning past cultural and
technological activities, giving us an insight into the type of
products that people cooked, stored or prepared [1 5].
Plant resins, natural waxes, and lipids of animal and
vegetal origin are often encountered in this archaeological
field. The difficulty in determining them is due not only to

* Corresponding author.
E-mail address: perla@dcci.unipi.it (M.P. Colombini).
0026-265X/$ - see front matter D 2004 Elsevier B.V. All rights reserved.
doi:10.1016/j.microc.2004.05.004

the complexity of the chemical composition of these natural

substances and their mixtures but also to the changes in the
chemical composition due to human activities such as
cooking, heating, or mixing materials, in order to modify
their properties in view of a specific use. Moreover, degradation from ageing under the influence of different burial
circumstances induces further changes in the composition of
the original materials. In addition, further transformations
may occur after the discovery caused by improper storage or
by the museum environment itself. Because of the complexity of organic residues, analytical procedures used to
characterise them are usually based on chromatographic
techniques coupled with mass spectrometry (MS) [6 12].
These hyphenated techniques allow the identification of
molecules which reveal the presence of specific compounds
acting as biomolecular markers which are diagnostic stable
molecules present in the ancient material or are formed over
the centuries due to ageing [13,14]. Identifying the molecular composition is essential in order to establish the natural

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M.P. Colombini et al. / Microchemical Journal 79 (2005) 8390

substances present in the sample and to understand the

alteration processes that have modified the original composition of the samples. However, a preliminary analysis of the
organic residues by Fourier transformed infrared spectroscopy (FTIR) or mass spectrometric techniques (DI MS,
ESI MS) provides a fingerprint and general information on
the nature of organic material and is useful for providing
initial hypotheses about the substances present [15 18].
This work describes an investigation of the chemical
composition of residues of organic materials from three
ceramic vessels (the Roman age, 5th 7th centuries A.D.),
belonging to the collection of Istituto Papirologico Vitelli
(Florence), performed by means of Fourier transformed
infrared spectroscopy (FTIR) and by gas chromatography mass spectrometry (GC MS). The three ceramic
vessels investigated came from the excavation of the
Necropolis of Antinoe which is located at about 6 miles
south of Beni Hasan, on the east bank of the Nile in
Egypt, and were found near the church celebrating the
martyrdom of St. Colluthus in the North Necropolis.
Historically, the importance of Antinoe reached its peak
during the Roman age when it became the capital of the
Thebaid; however, archaeological evidence has revealed
that the area was populated prior to the time of the
Roman Emperor Adrianus.

2.2. Samples
The samples were collected from:
the bottom of a ceramic ointment jar in which the organic
material was present as a massive dark brown residue
(111);
two small ceramic bowls in which the organic residues
were present as an adhering blackish residual deposit
(566 and 307).
The samples were ground, homogenised and separated
into two parts for analysis by FTIR and GC MS.
2.3. Analytical procedures and instrumentations
2.3.1. FTIR
Samples (V10 mg) were extracted twice; first, using 2 ml
of acetone, in order to dissolve any resinous fraction that
may have been present. After washing, the residue was
extracted with the same volume of chloroform in order to
dissolve less-polar and/or more polymerised substances
(e.g., wax, bitumen). After drying them, the two fractions
were analysed as KBr micropellets with a FTIR spectrometer 16PC Perkin Elmer. Transmittance percentage (%) was
collected in the range of 4000 400 cm 1 with 4-cm 1
resolution.

2. Materials and methods

2.1. Reagents
All solvents were Carlo Erba (Milan, Italy) pesticide
analysis grade and were used without further purification.
Hexadecane and N,O,bis(trimethyl)silyltrifluoroacetamide
(BSTFA) containing 1% trimethylchlorosilane were purchased from Sigma Aldrich (Milan, Italy).
The following standards were used to set GC conditions
and for peak assignation: tridecanoic (internal standard,
IS), dodecanoic (lauric, la), tetradecanoic (myristic, my),
hexadecanoic (palmitic, pa), octadecanoic (stearic, st), (Z)9-octadecenoic (oleic, ole), (Z,Z)-9,12-octadecadienoic
(linoleic), (Z,Z,Z)-9,12,15-octadecatrienoic (linolenic),
octadecanedioic (suberic, su), nonanedioic (azelaic, az),
and decanedioic (sebacic, se) acids supplied by Sigma
(St. Louis, MO, USA), all with purity >99%. Abietic acid
from Aldrich (Steinheim, Germany), purity 70%, was also
analysed.
Other analysed reference materials were as follows:
colophony purchased from Fluka, a series of commercial
oils of certified origin (linseed oil, poppyseed oils, olive oil,
palm oil, coconut oil, safflower oil, castor oil, and carthame
oil) and a series of natural resins of known origin including
two kinds of pine resins (from Pinus halepensis and Pinus
pinea) and a pitch derived from wood of Pinus sylvestris,
provided by the Archaeological Superintendence of Tuscany
(Florence, Italy).

2.3.2. GC MS
The gas chromatography mass spectrometry (GC MS)
procedure adopted, which is described in the literature [4,8],
is able to simultaneously characterize natural resins, waxes,
bitumen, pitch, and lipid materials. Peak assignation was
based on comparisons with analysed reference compounds
and materials, with library spectra (NIST 1.7) and with
spectra reported in literature [19 21] and on the interpretation of mass spectra. A brief summary of the GC procedure
follows.
Samples (111, 1.8 mg; 566, 2.3 mg; 307, 2 mg) were
extracted twice with CH2Cl2 (1 ml) by sonication (30 min).
After centrifugation, aliquots of the supernatant organic
extracts were evaporated under a stream of nitrogen and
were submitted to saponification with 10% hydroalcoholic
KOH. Neutral organic components were extracted with nhexane, and after acidification, the acidic organic components were extracted from the residual solution with diethyl
ether. Aliquots of both the extracts were derivatised with
N,O,bis(trimethyl)silyltrifluoroacetammide (BSTFA) containing 1% trimethylchlorosilane using isooctane as the
solvent, and 2 Al were analysed by GC MS using hexadecane and tridecanoic acid as internal standards.
The instrumentation was made up of a Trace GC gas
chromatograph (ThermoFinnigan, USA) equipped with a
PTV injection port and a mass spectrometric detector with
an ion trap analyser ThermoFinnigan Polaris Q (electronic
impact 70 eV, ion source temperature 230 jC, analysed

M.P. Colombini et al. / Microchemical Journal 79 (2005) 8390

mass interval 50 650 a.m.u., interface temperature 280 jC).

Chromatographic separation was performed on a chemically
bonded fused silica capillary column HP-5MS (Hewlett
Packard): stationary phase 5%phenyl 95%methylpolysiloxane, 0.25 mm i.d., 0.25 Am film thickness, 30 m length,
connected to a 2-m-long deactivated fused silica capillary
precolumn, and internal diameter 0.32 mm. The gas chromatographic conditions were as follows: initial temperature
80 jC, 2 min isothermal, 10 up to 200 jC/min, 4 min
isothermal, 6 up to 280 jC/min, 40 min isothermal. Carrier
gas: He (purity 99.9995%), constant flow 1.2 ml/min.

3. Results
The most significant results are reported for each sample
in the following sections.
3.1. Ointment jar, sample 111
The FTIR spectrum of acetone extract (Fig. 1) showed
the typical transmittance profile of a diterpenoid resin such
as that of the Pinus species [22,23]. The presence in these
resins of several carboxylic acids with three-ring structures
leads to strong C H stretching vibration due to CH2 and
CH3 groups at 2935 and 2871 cm 1. O H stretching bands
occur at 3428 and 2646 cm 1, the latter is broad and very
weak due to the vibration of the dimerized carboxyl group in
the solid phase. The strong C=O stretching of carboxylic
acid is at 1712 cm 1. Other bands are those at 1607 and
1487 due to aromatic ring stretches; at 1460 and 1385 cm 1
to CH2 and CH3 bending; at 1240 cm 1 to O H bending in

85

acid resins. The chloroform extract showed the same signals

due to the residue of the substance first extracted.
In the GC MS plot of the acidic fraction of sample 111,
shown in Fig. 2, a series of linear saturated fatty acids is
observed ranging from 8 to 24 carbon atoms, with hexadecanoic acid (palmitic) and octadecanoic acid (stearic) as the
most prominent. Unsaturated fatty acids are not present in
significant amounts, and are, indeed, not common in archaeological remains due to their increased tendency to
decomposition relative to saturated ones [24].
In addition to monocarboxylic acids, a series of a,Ndicarboxylic acids is also present, ranging from 6 up to 14
carbon atoms; nonanedioic acid (azelaic) is the dominant
member of this group.
Moreover, several tricyclic diterpenoid acids with abietane
skeleton are encountered in the range 20 35 min. The main
one is 7-oxo-dehydroabietic acid (7ODA), accompanied by
7-oxo-abietic acid (7OA), 15-hydroxy-7-oxo-dehydroabietic
acid (15Hy7ODA), and 15-hydroxy-dehydroabietic acid
(15HyDA). These compounds are characteristic oxidation
products of a resin from the Pinaceae family [19]. Nonoxygenated species as dehydroabietic (DA) and didehydroabietic acids (DDA) are much less abundant.
In the neutral fraction of the sample, the presence of two
diagnostic peaks relative to retene and to the methyl ester of
dehydroabietic acid was observed. Retene is considered as a
marker for pine pitch because when the resin is heated to
high temperatures or distilled in a low oxygen environment
to obtain a pitch, aromatisation, demethylation, and defunctionalisation reactions occur in the abietadiene and pimaradiene acids. This leads to the formation of a series of
products as norabietatrienes and tetrahydroretene, and the

Fig. 1. FTIR spectrum of the acetone extract of the sample 111.

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M.P. Colombini et al. / Microchemical Journal 79 (2005) 8390

Fig. 2. Total ion chromatogram of the acidic fraction of the sample 111 (the acidic species are present as TMS esters). I.s., internal standards; *, phtalate; DDA,
didehydroabietic acid; DA, dehydroabietic acid; 7ODA, 7-oxo-dehydroabietic acid; 7OA, 7-oxo-abietic acid; 15Hy7ODA, 15-hydroxy-7-oxo-dehydroabietic
acid; 15HyDA, 15-hydroxy-dehydroabietic acid.

final stable product of all these transformations is retene

[20,25]. The methyl-dehydroabietate is formed when the
resin is heated in the presence of wood because the
methanol released when wood is heated to high temperatures reacts easily with diterpenic acids to produce above
all methyl-dehydroabietate, which is absent when the pitch
is produced by pyrolysis of the resin alone [8,26].
The simultaneous presence of abietanic acids, retene and
methyl-dehydroabietate highlights that the material contains
a pitch obtained from a destructive distillation of wood of
plants of the Pinaceae family.

dihydroxyoctadecanoic, 11,12-dihydroxyeicosanoic, and

13,14-dihydroxydocosanoic acids. Among them, 9,10dihydroxyoctadecanoic acid has been previously encountered in archaeological ceramic vessels [6], while, as far as
we know, the recovery of the hydroxylated C20 and C22
acids has not been previously reported in archaeological
remains.
Although there was a high degree of similarity with the
material contained in the ointment jar previously discussed
(sample 111), in this finding retene was absent. In fact, the
ceramic bowl contained a resin from Pinaceae trees rather
than a pitch.

3.2. Ceramic bowl, sample 566

3.3. Ceramic bowl, sample 307
The FTIR spectra of acetone and chloroform extracts are
similar to those collected for sample 111: they show the
typical transmittance bands of diterpenoid resins, such as
those of the Pinus species.
After GC MS analysis, the acidic fraction, whose
chromatogram is shown in Fig. 3, presented the same
series of saturated fatty acids as those seen in sample
111. A pattern of a,N-diacids analogous to the one
previously observed was also present, together with the
same pattern of abietanic diterpenoids, the main one being
7-oxo-dehydroabietic acid.
Moreover, three other long-chain dihydroxylated acids
with 18, 20, and 22 carbon atoms were identified: 9,10-

The FTIR spectra of extracts of the sample (Fig. 4)

indicate the absence of any unsaturated substance. The
bands are due essentially to carboxylic acid groups: C=O
stretching of carboxylic acid appears at 1709 cm 1, while
the signals in the range 1281 1195 cm 1 address to
different C O stretching and bending. Stretching bands of
diversified O H, of carboxylic and alcoholic groups, occur
at 3525, 3112, and 2652 cm 1 (the latter are broad and very
weak due to the vibration of dimerized carboxyl group in the
solid phase); O H bending is evident at 1410 and 935
cm 1. CH2 bending is present at 1464 cm 1. The chloroform extract also highlighted the presence of long linear

M.P. Colombini et al. / Microchemical Journal 79 (2005) 8390

87

Fig. 3. Total ion chromatogram of the acidic fraction of the sample 566 (the acidic and alcoholic species are present as TMS derivatives) I.s., internal standard;
*, phtalate.

molecular chains with a distinct transmittance of CH2

groups at 1471, 1410, 721, and 719 cm 1.
GC MS analysis showed (Fig. 5) a very similar profile
of lipid compounds to that of the other two samples,
exhibiting a very high amount of diacids. On the other
hand, both in the acidic and in the neutral fraction, this

sample did not contain any terpenic compounds, thus, the

presence of a vegetable resin can be ruled out. The same
dihydroxy acids (9,10-dihydroxyoctadecanoic, 11,12-dihydroxyeicosanoic, and 13,14-dihydroxydocosanoic acids)
observed in the organic material from bowl 566 were found.
The fact that they were present only in the two bowls and

Fig. 4. FTIR spectrum of the acetone extract of the sample 307.

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M.P. Colombini et al. / Microchemical Journal 79 (2005) 8390

Fig. 5. Total ion chromatogram of the acidic fraction of the sample 307 (the acidic and alcoholic species are present as TMS derivatives). I.s., internal standards;
*, phtalate; DDA, didehydroabietic acid; DA, dehydroabietic acid; 7ODA, 7-oxo-dehydroabietic acid; 7OA, 7-oxo-abietic acid; 15Hy7ODA, 15-hydroxy-7oxo-dehydroabietic acid.

not in the ointment jar suggests that they probably derive

from commodities.

4. Discussion
A comparison of the composition of the contents of the
three vessels highlights that, although they have a different
shape and use, the organic residues examined showed a very
similar fatty acids profile, with a dominance of saturated,
even carbon number fatty acids and in particular of palmitic
and stearic acids. The profile of a-Ndicarboxylic acids was
also similar in the three samples: the more abundant acids
were from C8 to C13 peaking at C9. In the literature, the
detection of diacids in archaeological residues is rare due to
their relatively higher solubility in water, which facilitates
their leaching in the course of the burial period [27]. In the
case of the Antinoe findings, the very arid context and the
absence of percolating water seem to have hindered such
behaviour, permitting the recovery of relatively high
amounts of dicarboxylic acids. The presence of diacids with
11, 12, and 13 carbon atoms is of particular interest because
dicarboxylic acids with more than 10 carbon atoms are quite
uncommon in nature and mainly encountered in plant waxes
with longer chains than here, typically more than 20 carbon
atoms. Peat and bog might also contain such acids. How-

ever, due to the arid environment of the archaeological site,

which is certainly not characterised by a peat bog, we can
rule out this source. In fact, it is more likely that these
diacids derived from the lipid components present in the
three vessels. Their presence can be explained by the
oxidative cleavage of a carbon carbon double bond of
unsaturated fatty acids originally present in the material.
The natural oxidative processes may be accelerated if
pottery is exposed to oxidising environments or to high
temperatures; and the nature of the oxidation products may
change depending on the processed material, how the vessel
was used, and the burial conditions.
The predominance of the C9 diacid (azelaic acid) implies
the presence of unsaturation above all in position 9 in the
original fatty acids, while the significant presence of diacid
homologues with longer chains suggests unsaturations in
positions 11 and 13. These assumptions are supported by the
presence of dihydroxylated acids, which can be formed via
the hydroxylation of unsaturated acids in correspondence to
the double bond: 9,10-dihydroxyoctadecanoic acid can be
attributed to the oxidation of 9-octanedecanoic acid (oleic
acid) [6], while 11,12-dihydroxyeicosanoic acid and 13,14dihydroxydocosanoic acid can be considered as products of
oxidation of 11-eicosenoic acid (gondoic acid) and 13docosenoic acids (erucic acid), respectively. These acids
are present in substantial amounts in the seeds and in the

M.P. Colombini et al. / Microchemical Journal 79 (2005) 8390

89

seed oil of Brassicaceae plant (Cruciferae family) [28 30],

and in particular, radish (Raphanus sativus), mustard (genus
Sinapis) and turnip (genus Brassica) have been hypothesized as being used in Roman Egypt as sources of oil [24].
Consequently, we hypothesise that the observed dihydroxylated acids derive from a seed oil characterised by a high
content of gondoic and erucic acids, such as rapeseed oil
and other oils from the genus mentioned. Further investigations are needed to confirm that the degradation and
ageing of oils rich in erucic and gondoic acids lead to the
formation of the oxidation products observed in these
samples.
Samples 111 and 566 showed the presence of oxidized
diterpenic acids with abietane skeleton indicating the presence of a pine resin. In the case of the ointment jar (sample
111), the simultaneous occurrence of retene and methyldehydroabietate, highlighted the presence of a pitch produced by the pyrolysis of the resinous wood of Pinaceae
trees.

unguents is also described: the ingredients being some

resins and oils, together with spices and perfumed essences
(NH XIII, 2).
In conclusion, the identification of pine resin, pine pitch,
and the hypothesis made on the presence of Cruciferae seed
oil in the organic remains gives some new information on
the materials used in Egypt in the Roman age. Moreover,
this study confirms the employment of some materials
mentioned by Plinius in Naturalis Historia.

5. Conclusions

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Chemical analysis was performed in order to characterise

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the samples (307 and 566) contained also long-chain dihydroxylated acids. These compounds can be ascribed to plant
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Moreover, pine resin and pitch were found in two of the
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