1.4 Key Lime Oil (Citrus aurantifolia [Christm.] Swing.) and Persian Lime Oil (Citrus
1.4.2.4 Persian Lime Laboratory Oils
Table 1.7 also shows the results relative to the composition of Persian lime extracted in laboratory by cold extraction and by distillation. Many of these oils are characterized by lower content of lim- onene compared to industrial oils, such as the oil analyzed by Zollo Amvam et al. (1998) and those extracted from the cvs. Tahiti and De Perse by Lota et al. (2002) present high content of p-cymene.
The oils obtained by hydrodistillation also present higher amounts of alcohols than those that are cold extracted. The oil obtained from seedless lime, analyzed by Selvaray et al. (2002), has lower amounts of neral and geranial.
Atti-Santos et al. (2005) also reported the results relative to the oil extracted by supercritical CO2 from the same matrix used for the hydrodistilled oil. They considered the oil obtained by super- critical CO2 of better quality than that obtained by hydrodistillation because of the shorter time of extraction, higher yields, and composition that is closer to what has been reported for commercial oils.
However, it should be mentioned that the unusual value of myrcene (0.01%) also reported by Sawamura (2000) is probably a misprint.
Not included in Table 1.7, nor in the previous review by Dugo et al. (2002), is the paper by Asano (1997) on four oils obtained from fruits cultivated in Thailand (Menawa lime, Large Tahitian lime, Old Tahitian lime, Young Tahitian lime) that presented very important differences among them.
Their composition is reported in detail by Lawrence (2003).
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TABLE 1.7
PercentageComposition of the Volatile Fraction of Persian Lime Oils (1998–2009)
Industrial Oils Laboratory Oils
Cold Extracted Hydrodistilled
1 2 3 4 5 6 7 8 9
Hydrocarbons Monoterpene
Camphene – – 0.05 0.04–0.06 0.05 tr–0.1 0.05 0.1 –
p-Cymene – – b 0.08–0.30 0.05 0.2–5.3 5.54 1.4 1.0
Limonene – 58.64 59.37b 54.20–58.20h 55.47 40.3–46.5 46.41 49.2 47.5
Myrcene – 1.51 1.26 1.26–1.30 0.01i 1.1–1.3 1.25 1.3 1.2
(E)-β-Ocimene – – 0.07 0.06–0.11 – 0.1–0.2 0.10 – –
(Z)-β-Ocimene – – – h 0.05 0–0.1 – – –
α-Phellandrene – – 0.05a 0.04 1.41 tr–0.1 – – –
β-Phellandrene – – – – tr 0.5–0.6g – – –
α-Pinene – 2.13 1.78 1.99–2.05 2.98 1.3–2.4 1.64 1.4 1.9
β-Pinene – 11.17 10.44 10.01–11.82 11.59 11.1–13.7 11.18 9.2 12.4
Sabinene – 1.79 1.45 1.70–1.92 2.10 1.6–2.1 1.28 – 1.6
α-Terpinene – – 0.24 0.20–0.23 0.28 0.2–0.4 – – 0.3
γ-Terpinene – 14.82 14.29 12.84–14.61 14.50 17.3–21.5 12.54 12.1 12.3
Terpinolene – 0.70 0.55 0.49–0.51 0.60 0.7–0.9 0.63 0.7 0.6
α-Thujene – 0.60 0.55 0.48–0.51 – 0.4–0.7 0.44 – 0.5 Sesquiterpene
cis-α-Bergamotene 0.07 – 0.07 0.06–0.08 – – – – 0.3
trans-α-Bergamotene 1.01 1.26 1.01 0.67–0.98 – 1.0–1.6 0.56 – –
(E)-α-Bisabolene 0.05 – – 0–0.03 – – – – –
(Z)-α-Bisabolene 0.12 – 0.12 0.11–0.18 – – – – –
β-Bisabolene 1.47 2.18 1.73e 1.48–1.67 – 1.5–2.4 0.85 – 1.8
(E)-γ-Bisabolene 0.01 – – 0–0.01 – – – – –
(Z)-γ-Bisabolene 0.02 – – 0–0.02 – – – – -
β-Caryophyllene 0.48 0.65 0.46 0.29–0.61k 0.35 0.3–0.5 0.28 – –
γ-Curcumene 0.02 – – 0.01–0.02 – – – – –
β-Elemene 0.02 – – 0.04–0.06 0.11 0–0.2 0.08 – –
δ-Elemene tr – – 0.03–0.07 0.14 – 0.07 – –
(E,E)-α-Farnesene 0.22 – 1.73e 0.21–0.23 0.16 0–0.4 0.15 – –
(E)-β-Farnesene 0.10 – 0.16d 0.09–0.10 0.06 0–0.1 – – –
(Z)-β-Farnesene – – – 0–0.01 – – 0.05 – –
Germacrene B 0.17 – 0.15 0.09–0.12 0.13 – 0.08 – –
Germacrene D 0.08 – – 0–0.05 0.07 tr–0.2 0.06 – –
α-Humulene 0.04 – 0.16d 0.03–0.05 0.04 0–0.2 – – –
β-Santalene 0.06 – 0.04 0.01–0.04 0.02 – – – –
α-Selinene 0.02 – 0.08 0–0.02 – – – – –
Aldehydes Aliphatic
Decanal – – 0.06 0.05–0.06 0.03 tr–0.1 – 0.1 –
continued
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TABLE 1.7 (continued)
PercentageComposition of the Volatile Fraction of Persian Lime Oils (1998–2009)
Industrial Oils Laboratory Oils
Cold Extracted Hydrodistilled
1 2 3 4 5 6 7 8 9
Dodecanal – – – 0.01–0.04 0.02 – – – –
Nonanal – – – 0.01 tr 0–tr – – –
Octanal – – 0.05a 0.01 0.01 0–tr – – –
Undecanal – – – 0.01–0.02 0.01 0–tr – – –
Monoterpene
Citronellal – – – 0.03–0.06 0.04 tr–0.2 – – –
Geranial – 2.09 1.70 1.79–2.20 5.14 2.7–4.0 3.89 0.4 6.4
Neral – 1.26 0.99 1.09–1.35 1.73 1.6–2.3 1.56 0.4 4.7
Perilla aldehyde – – – 0.02–0.03 0.02 – – – –
Sesquiterpene
β-Sinensal – – – – – 0–0.1 0.07 – –
Ketones Aliphatic
6-Methyl-5-hepten-2- one
– – – 0–0.01 – 0–tr 0.09 – –
Monoterpene
Piperitone – – 0.08c – – 0–tr – – –
Alcohols Monoterpene
Citronellol – – – 0.09–0.16j 0.02 – 0.05 – –
Geraniol – – 0.08c 0.03–0.04 0.02 tr 1.55 4.3 0.3
Linalol – 0.17 0.19 0.13–0.14 0.31 0.4–0.5 0.74 1.0 1.3
Nerol – – 0.13 0.09–0.16j 0.06 0–tr 3.10 3.0 0.7
cis-Sabinene hydrate – – 0.04 0.04 0.06 – – – –
trans-Sabinene hydrate
– – – 0–0.05 0.08 0.1 – – –
α-Terpineol – – 0.23 0.21–0.25 0.35 0.4–0.6 1.47 1.9 2.2
Terpinen-4-ol – – 0.14 0.05–0.07 0.04 tr–0.1 0.95 0.8 1.2
Sesquiterpene
α-Bisabolol – – 0.09 0–0.08 0.05 – – – –
Campherenol – – 0.05 0–0.05 – – – – –
Norbornanolf – – 0.06 0–0.05 – – – – –
Esters Monoterpene
Bornyl acetate – – – 0–tr – – 0.05 – –
Citronellyl acetate – – – 0.01 tr 0–0.1 0.05 – –
Geranyl acetate – – 0.19 0.14–0.23 0.36 0.7–2.4 0.38 0.3 0.3
Neryl acetate – 1.05 0.82 1.01–1.11 – 1.2–2.0 – 2.5 –
α-Terpenyl acetate – – – – – 0–tr 1.56 – –
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TABLE 1.7 (continued)
PercentageComposition of the Volatile Fraction of Persian Lime Oils (1998–2009)
Industrial Oils Laboratory Oils
Cold Extracted Hydrodistilled
1 2 3 4 5 6 7 8 9
Ethers and oxides Monoterpene
1,8-Cineole – – b h – 0.5–0.6g – – –
cis-Limonene oxide – – – 0–0.01 – 0–tr 0.09 – –
trans-Limonene oxide
– – – 0–0.01 – 0–0.1 0.05 – –
Sesquiterpene Caryophyllene
oxide*
– – – 0–0.01 – 0–0.1 – – –
Notes: tr, traces; *, correct isomer not characterized; aα-phellandrene + octanal; b limonene + p-cymene + 1,8-cineole;
c piperitone + geraniol; d (E)-β-farnesene + α-humulene; eβ-bisabolene + (E,E)-α-farnesene; f 2,3-dimethyl-3-(4- methyl-3-penthenyl)-norbornanol; gβ-phellandrene + 1,8-cineole; h limonene + (Z)-β-ocimene + 1,8-cineole; i this very low value maybe due to a printing error; j citronellol + nerol; kβ-caryophyllene + α-santalene.
Appendix to Table 1.7
1. Feger et al. (2000). Several samples of Persian lime oils from Brazil. Enrichment of sesquiterpene fraction by vacuum distillation; GC/MS of the enriched fraction on capillary columns coated with OV-1701 (30 m ì 0.25 mm ì 0.25 àm) and DB-1 (33 m ì 0.25 mm ì 0.5 àm). GC/FID of the crude essential oil on the same capillary columns; relative percentage of peak areas. Feger et al. also found germacrene A (0.12%), germacrene C (0.11%), α-santalene (0.02%), β-selinene (0.01%), and trace amounts of epi-β-santalene, 7-epi-α-selinene, β-sesquiphellandrene.
2. Franceschi et al. (2004). Brazil; one sample; GC/FID and GC/MS on capillary column (30 m ì 0.25 mm ì 0.25 àm) coeted with HP-5MS; Wiley MS library; relative percentage of peak areas.
3. Mondello et al. (2004c). One commercial sample; conventional GC/FID on capillary column (30 m ì 0.25 ì 0.25 àm) coated with RTX5-MS; fast GC/FID on capillary column (5 m ì 0.05 mm ì 0.05 àm) coated with SE-52; relative percentage of peak areas. In the table are reported the results obtained with conventional method; the results obtained with fast method were very similar. More information is reported in Chapter 11. Mondello et al. also found α-elemene (0.05%).
4. Dugo et al. (2010b). One cold-pressed oil from the Mexico, two commercial samples; GC/FID and GC/MS on capillary columns (30 m ì 0.25 mm ì 0.25 àm) coated with SLB-5MS; MS libraries: Adams, Flavour and Fragrance Natural and Synthetic Compounds (FFNSC) home-made; LRI on SLB-5MS are reported; relative percentage of peak areas.
Dugo et al. also found tricyclene (0.03%), trans-β-bergamotene (0%–0.05%), γ-elemene (0.01%), β-selinene (0.01%–0.02%), tetradecanal (0%–0.02%), (E)-isocitral (0%–0.01%), borneol (0.01%), cis-sesquisabinene hydrate (tr–0.01%), and trace amounts of δ-3-carene, α-fenchene.
5. Sawamura (2000). Japan, one sample; GC/FID and GC/MS on capillary column (50 m ì 0.25 mm ì 0.25 àm) coated with Thermon 600T; Sawamura also found aromadendrene (0.03%), α-bergamotene* (0.71%), δ-muurolene (0.02%), farnesal* (0.01%), carvone (0.01%), hexadecanol (0.06%), (Z)-nerolidol (0.01%), verbenol (0.01%), neryl acetone (0.02%), limonene dioxide (0.02%), and trace amounts of δ-2-carene, dodecyl acetate.
6. Lota et al. (2002). Corsica, France; range of the composition of the oils cold-pressed from the cvs.: El Kseur, Bearss, De Perse, IAC, Tahiti; GC/FID and GC/MS on capillary column (50 m ì 0.22 ì 0.25 àm) coated with DB-1; GC/FID analysis was also performed on capillary column (50 m ì 0.22 mm ì 0.25 àm) coated with BP-20; LRI on DB-1 and DB-20 are reported; 13C-NMR; relative percentage of peak areas. Lota et al. also found bicyclogermacrene
(0%–0.4%), santal-10-en-2-ol (0%–tr), linalyl acetate (0%–tr).
continued
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