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6. Descripción de puestos
Table 1.16 summarizes the results relative to the papers published from 1979 to 1999 on the com-position of bergamot essential oils already revised by Dugo et al. (2002). In the table are separately reported the data relative to industrially cold-pressed oils and oils that are laboratory extracted by cold extraction or by distillation techniques.
TABLE 1.16
Percentage Composition of the Volatile Fraction of Bergamot Oils (1979–1999)
Cold-Pressed Oils Laboratory-Extracted Oils Cold Extracted Distilled Hydrocarbons
Aliphatic
Dodecane 0–0.01 – 0.03
Monoterpene
Camphene tr–0.11 tr–0.05 0.01–0.21
δ-3-Carene tr–0.01 0.14–0.9 2.04
p-Cymene 0.01–3.61 tr–0.57 0.10–1.56
Limonene 24.07–54.85 23.70–40.80 35.42–45.11
Myrcene 0.36–2.33 0.7–2.0 0.95–1.97
Allo-ocimene tr – –
(E)-β-Ocimene 0.02–1.06 0.14 0–0.74
(Z)-β-Ocimene 0.01–0.43 tr–0.02 –
α-Phellandrene 0.01–0.18 – tr–0.04
β-Phellandrene 0.02–0.04 0.15 –
α-Pinene 0.70–1.84 0.5–1.88 0.52–1.30
β-Pinene 4.11–10.60 3.0–8.9 2.90–5.79
Sabinene 0.72–1.69 0.5–0.55 0.58–1.00
α-Terpinene 0.08–0.28 0.07–0.2 –
γ-Terpinene 1.15–11.38 4.12–12.60 1.35–6.02
Terpinolene tr–0.72 0.18–0.4 0.14–0.44
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Percentage Composition of the Volatile Fraction of Bergamot Oils (1979–1999)
Cold-Pressed Oils Laboratory-Extracted Oils Cold Extracted Distilled
α-Thujene 0.15–0.49 0.2 0–0.18
Tricyclene 0–0.01 – –
Sesquiterpene
α-Bergamotene* – 0.28–0.86 0.02–0.15
cis-α-Bergamotene tr–0.05 tr –
trans-α-Bergamotene 0.09–0.44 0.9 –
Bicyclogermacrene 0.01–0.08 – –
α-Bisabolene* tr – –
β-Bisabolene 0.16–0.73 1.2–1.28 0.02–0.95
(Z)-γ-Bisabolene 0–0.01 – –
δ-Cadinene tr – 0.33
β-Caryophyllene 0.15–0.55 0.25–0.7 0.11–0.53
δ-Elemene 0–0.06 – –
(E,E)-α-Farnesene 0–tr – –
(E)-β-Farnenese tr – 0.15–0.57
(Z)-β-Farnesene 0.03–0.09 0.07–0.1 –
Germacrene B 0–0.04 – –
Germacrene D tr–0.11 0.1 –
α-Humulene tr–0.07 0.1 tr
γ-Muurolene 0.07 0.05 –
β-Santalene tr–0.02 – –
β-Selinene tr–0.04 – –
β-Sesquiphellandrene tr tr –
Aldehydes Aliphatic
Decanal tr–0.16 tr–0.29 0.07–0.12
Dodecanal tr–0.16 tr –
Nonanal tr–0.08 tr–0.09 0.03–0.04
Octanal 0.02–0.08 tr–0.03 0.02–0.11
Tetradecanal 0–0.01 – –
Undecanal 0–0.02 – 0.07–0.23
Monoterpene
Citronellal tr–0.06 tr–0.02 0.02–0.07
Geranial 0.16–1.25 tr–0.3 0.06–0.48
Neral 0.05–0.72 0.16–0.62 0.04–0.36
Perilla aldehyde tr–0.11 – –
Ketones Aliphatic
6-Methyl-5-hepten-2-one
tr–0.01 – 0.01–0.02
Monoterpene
Camphor tr–0.01 – –
continued
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92 Citrus Oils
TABLE 1.16 (continued)
Percentage Composition of the Volatile Fraction of Bergamot Oils (1979–1999)
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Percentage Composition of the Volatile Fraction of Bergamot Oils
Notes: tr, traces; *, correct isomer not characterized; t, tentative identifi cation; a 2,3-dimethyl-3-(4-methyl-3-pentenyl)-2-norbornanol.
Appendix to Table 1.16
The results reported in Table 1.16 and in this appendix, for the different categories of
•
bergamot oils, are taken from the following original papers:
– Cold-pressed industrial oils: Schenk and Lamparsky (1981); Huet (1981); Ricciardi et al. (1982); Koketsu et al. (1983); Mazza (1986); Inoma et al. (1989); Dellacassa et al. (1997); Dugo et al. (1987, 1991, 1999); Dugo (1994); Lamonica et al. (1990);
Verzera et al. (1996b, 1998a); Chouchi et al. (1995). Were also included the qualitative studies carried out by Ehret and Maupetit (1982); Ohloff et al. (1986); Cartoni et al.
(1987); Micali et al. (1990); Lanuzza et al. (1991); Mondello et al. (1994b, 1995a,b).
– Laboratory cold extracted oils: Drescher et al. (1984); Calvarano et al. (1984); Baser et al. (1995); Sawamura et al. (1999a); Kirbaslar et al. (2000).
– Laboratory-distilled oils: Huang et al. (1986, 1987).
Coelutions indicated by one or more authors in chromatographic separations of
•
bergamot oils:
– β-Pinene + sabinene; limonene + β-phellandrene; terpinolene + octanal; citronellal + octyl acetate; geranial + perilla aldehyde; citronellol + nerol; α-humulene + α-terpineol; β-bisabolene + 2,7-dimethyl-2,6-octadien-1-olt; α-terpineol + α-terpinyl acetate.
– Ranges reported in Table 1.16 for some components in cold-pressed oils, coeluted in chromatographic separation reported by few authors (β-pinene, sabinene,
β-phellandrene, citronellal, octyl acetate, perilla aldehyde, citronellol, nerol, α-humulene, β-bisabolene), are determined considering the results where coelutions did not occur.
In addition to those listed in Table 1.16, in bergamot oil were found the components
•
listed below:
– Cold-pressed oils: tridecane (0.05%), δ-2-carene (0.11%), 1,3,8-p-menthatriene (0.17%), aromadendrene (0.36%), (Z)-α-bisabolene (0–tr), (E)-2-decenalt
continued
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94 Citrus Oils
TABLE 1.16 (continued)
Percentage Composition of the Volatile Fraction of Bergamot Oils (1979–1999)
(0%–0.01%), isomenthone (0.01%), menthone (0%–0.06%), dodecanol (0%–0.01%), octen-3-ol* (0.08%), dihydrocitronellol (0.05%), isopulegol (tr–0.01%), menthol (0.16%), neomenthol (0.02%), (E,E)-α-farnesol (0.01%), (Z)-β-santalol (0.01%), isomenthyl acetate (0.10%), cis-sabinene hydrate acetate (0.07%), and trace amounts of linear chained hydrocarbons C21–C33 and correspondent “iso”
isomers, C23–C31,p-cymenene, γ-acoradiene, ar-curcumene, γ-elemene, α-muurolene; α-santalene, epi-β−santalene, α-selinene, lilial, piperitone, 2,6-dimethyl-6-acetoxy-octa-7-en-3-one, 2,6-dimethyl-6-acetoxy-octa-1,7-dien-3-one, 2,6-dimethyl-6-acetoxy-octa-1-en-7-one, (E)-2-hexenol, (Z)-3-hexenol, 1-pentanol, 2-pentanol, borneol, carvacrol, p-cymen-8-ol, cumin alcohol, cis- and trans-2,6-dimethyl-octa-1,5,7-trien-3-ol, 3,7-dimethyl-3-acetoxy-octa-1,5-dien-7-ol, 3,7-dimethyl-3-acetoxy-octa-1,7-dien-6-ol, limonen-4-ol, cis- and trans-p-menth-2,8-dien-1-ol, 3,7-dimethyl-octa-1,5-dien-3,7-diol, 3,7-dimethyl-octa-1,7-dien-3,6-diol, p-mentha-1,8-dien-9-ol, p-menth-1-en-9-ol, cis-and trans-p-menth-2-en-1-ol, trans-pinocarveol, thymol, (–)-(4S,8R)-8-epi-α-bisabolol, (–)-(4R,8S)-4-epi-β-bisabolol, α-cadinol, T-cadinol, caryophyllenol I and II, caryophyllene alcohol, β-eudesmol, farnesol*, spathulenol, cis-hex-3-en-1-yl acetate, undecyl acetate, carvyl acetate, hotrienyl acetate, geranyl propanate, linalyl propanate, p-mentha-1,3-dien-7-yl acetate, p-mentha-1,7-dien-4-yl acetate, p-mentha-1,7(10)-dien-2-yl acetate, p-mentha-1,8-dien-9-yl acetate, p-menth-1-en-9-yl acetate, neomenthyl acetate, neryl propanate, perillyl acetate, trans-pinocarvyl acetate, terpinen-4-yl acetate, 3-(3,4,5-trimethoxyphenyl)-propenyl acetate, cis- and trans-linalol oxide (furanoid and pyranoid form), cis- and trans-2,3-ocimene oxide, p-menth-1-en-4,5-oxide, p-menth-4-en-1,2-p-menth-1-en-4,5-oxide, linalyl acetate oxide (two isomers), caryophyllene oxide*, humulene oxide I, isocaryophyllene oxide, 2,3-geranyl acetate oxide, 2,3 neryl acetate oxide, methyl N-methyl anthranilate, indole, acetic acid, octanoic acid.
Many of these components, identifi ed by a single author need further confi rmation.
– Cold-pressed laboratory oils: m-cymene (0.3%), hexanal (0.02%), 1-hydroxylinalol (0.1%), phenyl ethyl alcohol (0.5%), octadienyl formate (0.1%), and trace amounts of (E)-2-hexenal, 6-methyl-3-heptanol, p-menth-1-en-8-yl acetate.
– Steam distilled laboratory oils: pentadecane (0.21%), dihydrolinalol (0.07%), endo-fenchol (0.01%), isopulegol (0.01%), lavandulol (0.02%), citronellyl formate (0.02%), geranyl formate (0.02%), γ-heptalactone (0.04%), and trace amounts of pulegone, (Z)-nerolidol, butyl acetate, 1,4-cineole.
The values in Table 1.16 show that bergamot oil is subject to wide ranges of variation
•
in its composition. These changes, as proved by many authors, could be due to the period of harvest of the fruits (Calvarano, 1968; Huet and Dupuis, 1969; Dugo et al., 1987, 1991; Dugo, 1994; Verzera et al., 1996b, 1998), to the cultivar of the fruits (Verzera et al., 1996b) and to the area of cultivation of the fruits (Huet and Dupuis, 1969), also if cultivated in very close fi elds (Figure 1.11), as noticed by Dugo et al.
(1987, 1991, 1994) and by Verzera et al. (1998). The most evident changes are, however, noticed during the productive season, in particular for linalol and linalyl acetate. The former, as shown in Figure 1.12 (Dugo, 1994), varied, for a bergamot oil produced in Calabria, during the productive season, from an average content of 13% to about 6%; the latter, during the same period varied from an average content of 25% at the beginning of the season, to that of 31 % at the end. The ratio linalol/linalyl acetate varied from 0.5 to 0.2.
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1.7.2 1998–2009