CAPÍTULO VI. FINANZAS
Cédula 2. Salidas de efectivo
6.5. Indicadores financieros
6.5.4. Razones de rentabilidad
Many of the papers on the quantitative composition of sweet orange oils published before 1979 have been reviewed by Shaw (1979). A summary of these papers was reported by Dugo et al. (2002).
Between 1960 and 1979 more papers than those reviewed by Shaw (1979) report quantitative or qualitative information on the composition of sweet orange oil. Shaw (1977) reported some of these in his earlier review. These papers have been reviewed by Dugo et al. (2002). Most of the papers published from 1979 to 1999 on the composition of sweet orange oils (cold-pressed surely genuine and commercial of not specifi ed origin, industrially processed, and laboratory-extracted oils), have been reviewed by Dugo et al. (2002).
Table 1.13 summarizes the results, relative to these last papers.
TABLE 1.13
Percentage Composition of the Volatile Fraction of Sweet Orange Oils (1979–1999)
Cold-Pressed Oils
Commercial and
Unusual Oils Laboratory-Extracted Oils Hydrocarbons
Monoterpene
Camphene tr–0.01 tr tr
δ-3-Carene 0.04–0.21 0–0.17 0–0.22
p-Cymene tr–0.06 tr–0.2 tr
Limonene 91.15–96.08 85.16–94.51 86.18–96.80
Myrcene 1.71–2.04 1.37–2.3 0.93–2.05
(E)-β-Ocimene tr–0.10 tr–0.21 0.01–0.06
(Ζ)-β-Ocimene tr–0.03 tr tr–0.01
α-Phellandrene tr–0.07 0.05 0.02–0.09
β-Phellandrene 0–0.2 1.5 0–0.20
α-Pinene 0.36–1.4 0.51–0.9 0.28–0.55
β-Pinene tr–0.11 0–1.25 tr–0.06
Sabinene 0.24–0.80 0.13–2.45 0.13–0.93
α-Terpinene 0–0.02 0.09 tr–0.30
γ-Terpinene 0–0.33 tr–4.66 tr–0.18
Terpinolene tr–0.07 tr–0.24 tr–0.08
α-Thujene tr–0.01 0.15–1.72 tr–0.01
Sesquiterpene
cis-α- Bergamotene – 0–tr tr
Bicyclogermacrene tr – 0.01
β-Bisabolene 0.01 0–1.50 0.01–0.02
γ-Cadinene tr–0.11 tr–0.10 tr–0.01
δ-Cadinene tr–0.05 tr–0.07 0.02–0.03
continued
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76 Citrus Oils
TABLE 1.13 (continued)
Percentage Composition of the Volatile Fraction of Sweet Orange Oils (1979–1999)
Cold-Pressed Oils
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Percentage Composition of the Volatile Fraction of Sweet Orange Oils (1979–1999)
Cold-Pressed Oils
Commercial and
Unusual Oils Laboratory-Extracted Oils Monoterpene
Carvone tr–0.09 0.04–0.07 tr
Sesquiterpene
Nootkatone tr–0.03 – 0.01–0.04
Alcohols Aliphatic
Decanol tr – tr
Nonanol 0.04–0.34 0–0.81 tr
Octanol tr–0.16 tr–0.25 tr–0.24
Monoterpene
cis-Carveol tr 0–tr tr–0.01
trans-Carveol 0–0.12 0–0.06 tr
Citronellol tr–0.02 tr–0.18 tr–0.02
Geraniol 0–0.02 0–0.08 tr–0.09
Linalol 0.17–0.8 0.06–1.23 0.31–2.56
Nerol tr–0.05 0–0.10 0–0.02
Perilla alcohol 0.01 0.02 tr
cis-Sabinene hydrate tr–0.01 tr 0.01–0.05
trans-Sabinene hydrate – tr tr
Terpinen-4-ol tr–0.01 0.01 tr–0.31
α-Terpineol 0.02–0.12 0.02–0.34 tr–0.25
Sesquiterpene
Elemol tr 0–tr tr
Farnesol* tr tr –
(E)-Nerolidol tr 0–tr tr–0.01
Esters Aliphatic
Heptyl acetate – – tr–0.01
Decyl acetate 0.01–0.03 0–tr tr–0.03
Nonyl acetate tr – tr–0.01
Octyl acetate tr–0.03 + tr–0.01
Monoterpene
Bornyl acetate 0.01t – 0.01–0.04
Citronellyl acetate tr–0.07 0–0.09 tr–0.01
Geranyl acetate 0–0.03 tr–0.24 tr–0.02
Linalyl acetate tr–0.06 0–0.16 tr
Neryl acetate tr–0.06 0.01–0.09 tr–0.01
α-Terpinyl acetate tr 0–tr tr–0.01
continued
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78 Citrus Oils
TABLE 1.13 (continued)
Percentage Composition of the Volatile Fraction of Sweet Orange Oils (1979–1999)
Cold-Pressed Oils
Notes: tr, traces; *, correct isomer not characterized; t, tentative identifi cation; +, identifi ed but not quantitatively determined;
aα-cubebene + β-elemene.
Appendix to Table 1.13
The results reported in Table 1.13 and in this appendix, for the different types of oils of sweet orange, derive from the
•
following original papers:
Industrial cold-pressed oils: Moshonas and Shaw (1979, 1980); Cappello et al
− . (1981); Koketsu et al. (1983); Vora et al.
(1983); Owusu-Yaw et al. (1986); Ferrer and Matthews (1987); Dugo et al. (1988, 1994, 1999); Inoma et al. (1989);
Boelens and Jimenez (1989a); Boelens (1991); Micali et al. (1990); Lanuzza et al. (1991); Dellacassa et al. (1992); Pino et al. (1992); Thomas and Bassols (1992); Dugo (1994); Mondello et al. (1994a, 1995b); Chamblee et al. (1997).
Commercial and unusual oils: Koketsu et al
− . (1983); Barukadze (1985); Dugo et al. (1988); Haubruge et al. (1989);
Inoma et al. (1989); Baaliouamer et al. (1992).
Laboratory-extracted oils: Uchida et al
− . (1984); Arras et al. (1985); Sugisawa et al. (1987, 1989); Lin and Hua (1988); Verzera et al. (1996c); Caccioni et al. (1998); Trozzi et al. (1999); Sawamura et al. (1999a). Not included in the table are the results by El-Samahy et al. (1982); MacLeod (1988); Usai et al. (1992); Blanco Tirado et al. (1995), who reported unusual composition if compared to other sweet orange oils. El-Samahy et al. determined in an Egyptian sample 3.86% of camphene, 28.89% of limonene, 22.40% of myrcene, 14.83% of α-pinene. MacLeod in a sample from Libia found 52% of limonene, 15.8% of linalol, 4.5% of β-copaene, 3.5% of geranial and 2.5% of carvone. The oils from Sardinia of the cv. Thompson Navel, analyzed by Usai et al. (1992), were characterized high values of α-phellandrene (0.27%), germacrene D (0.02%–0.15%), aliphatic aldehydes (4.13% total), α-terpineol (1.41%), while the Columbian oils analyzed by Blanco Tirado et al. (1995) were characterized by high values of camphene (0.27%–0.52%), β-pinene (0.63%–1.05%), γ-terpinene (0.02%–1.09%), terpinolene (0.58%–2.61%), and by the presence of trace amounts of myrcene; in both the last two groups of oils valencene, α- and β-sinensal, and nootkatone were absent.
Coelution indicated by one or more authors in chromatographic separations of sweet orange oils:
•
Limonene +
− p-cymene; limonene + β-phellandrene; myrcene + octanal; α-phellandrene + octanal; β-pinene + sabinene; terpinolene + octanal; myrcene + β-pinene; β-cubebene + β-elemene; dodecanal + unknown; (E,E)-2,4-decadienal + nonyl acetate; nonanal + linalol; undecanal + unknown; citronellal + octyl acetate; citronellol + nerol;
neral + carvone;
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Percentage Composition of the Volatile Fraction of Sweet Orange Oils (1979–1999)
neral + unknown; cis-limonene oxide + trans-limonene oxide. Ranges reported in Table 1.13, relative to industrial cold-pressed oils, when coelution occurred in the chromatographic separation of some papers for a number of components (p-cymene, α-phellandrene, β-phellandrene, β-pinene, terpinolene, nonanal, octanal, carvone, nerol, octyl acetate, cis-and trans-limonene oxide), are relative to the results reported on papers where coelution did not occur.
Were also not included in the table values unusually high of myrcene (2.95%–3.31%) reported by Koketsu et al. (1983) for Brazilian oils; the range of the values of myrcene (2.49%–3.17%) reported by Inoma et al. (1989) as well as the value of neryl acetate (0.24%) reported by the same authors for a Spanish oil; of myrcene + octanal (4.3%) reported by Pino et al. (1992) for a Cuban oil. The limited number of data, the different geographical and botanical origin of the fruits determine large variability ranges, therefore for the results relative to commercial and unusual oils it was not possible to determine the contribute of single components coeluted, and the data are reported in the table as ranges of variability even for the raw data generated by chromatographic coelutions. Must be highlighted the high content of sabinene (2.45%), α-thujene (1.72%) and octanal (0.82%) found in a sample cold extracted from Navel oranges cultivated in Georgia, ex URSS, (Barukadze, 1985); the high content of γ-terpinene (4.66%), and of (E,E)-α-farnesene (0.69%) in a sample extracted from Wenzhou honey oranges cultivated in China (Dugo et al. 1988); the high content of β-bisabolene (1.07%–1.50%) and of nonanol (0.53%–0.81%) found in oils extracted from Piralima oranges cultivated in Brazil (Koketsu et al., 1983). Variability ranges in Table 1.13 relative to laboratory-extracted oils do not include the values of α-phellandrene + octanal (0.24%–0.49%) reported by Arras et al. (1985) for Sardinia Valencia oils, and those of β-pinene + sabinene (1.93%) reported by Trozzi et al. (1999) for the oils extracted from Maltese oranges cultivated in Calabria, Italy.
In addition to those listed in Table 1.13, in sweet orange oils were found the components listed below:
•
Cold-pressed oils:
− α-cadinenet (0.01%–0.02%), myrtenal (0.03%), nerolidol* (0.01%), p-mentha-1,8-dien-10-yl-acetate (tr–0.01%), peryllene (0.01%), and trace amounts of linear chained hydrocarbons C21–C33 and
correspondent “iso” isomers, C23–C31, ar-curcumene, germacrene B, 7-epi-α-santalene, germacrene D-4-ol, methyl anthranilate, alkyl, acetyl and phenyl pyridines, N-methylaniline, N,N-dimethylaniline, 2-(methylamino) benzyl alcohol.
Commercial and unusual oils: eucarvone
− t (0.10%), neryl propanate (0.12%), linalol oxide* (0.08%), methyl
nopinone* (0.66%), and trace amounts of trans-α-bergamotene, γ-elemene, β-guaiene, α-himachalene, octadecanal, (Z)-9-octadecenal, isopiperitone, δ-cadinol, spathulenol, geranyl formate, linear chained acids C9–C12.
Laboratory-extracted oils: allo-aromadendrene (0.01%). Usai et al
− . (1992) and Blanco Tirado et al. (1995) (their
quantitative data are not reported in Table 1.12) in addition to compounds listed in Table 1.13, identifi ed by other authors, found formaldehyde, pulegone, 3,7-dimethyl-2,6-octadien-1-ol, pentanol, p-mentha-4(8)-en-9-ol,
isopulegol, 1,4-cineole, acetic acid, formic acid; Uchida et al. (1984) and Sugisawa et al. (1987, 1989) also found, in addition to those listed above, in Japanese sweet orange oils, within the fraction of the oxygenated compounds, separated by chromatography on silica gel, the following components: heptanal, (E)-2-hexenal, benzaldehyde, phenyl acetaldehyde, 2-heptanone, dihydrocarvone, camphor, butanol, dodecanol, hexanol, heptanol, (E)-2-hexen-1-ol, (Z)-3-hexen-(E)-2-hexen-1-ol, 2-methyl-butanol, 3-methyl-butanol, 2-methyl-3-buten-2-ol, 3-methyl-2-buten-(E)-2-hexen-1-ol, fenchol*, p-mentha-1,8(10)-dien-9-ol, β-terpineol*, eugenol, methyl eugenol, methyl isoeugenol, 2,6-di tertbutyl-p-cresol, patchouli alcohol, n-butyl butyrate, n-butyl hexanoate, heptyl acetate, (Z)-3-hexenyl hexanoate, ethyl octanoate, (Z)-3-hexenyl butyrate, hexyl acetate, hexyl butyrate, methyl octanoate, octyl butyrate, octyl hexanoate, p-mentha-1,8(10)-dien 9-yl acetate, 1,8-cineole, caryophyllene oxide*, geranyl acetone, β-ionone. The presence of many of these components in sweet orange oils need further confi rmation.
Although the composition of sweet orange can be subject to variation in function of the botanical origin and the harvest
•
period of the fruits (Lifshitz et al., 1970; Shaw and Coleman, 1974; Braddok and Kesterton, 1976; Dugo et al., 1994;
Verzera et al., 1996c), the data reported in the fi rst column of the table vary in a limited range and appear to be representative of the composition of industrially cold-pressed sweet orange oils.
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80 Citrus Oils
1.6.2 1998–2009