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Below are summarised the results reported by Shaw's review (1979) relative to tangerine oil. The papers originating the values reported below, were by Attaway etal. (1967), by Moshonas and Shaw (1974) and by Braddock and Kesterson (1976). The first two were on the analysis of the whole volatile fraction, while that by Braddock and Kesterson was on the total content of aldehydes, esters, alcohols, and only the quantitative composition of the aldehydes was reported in detail. The paper by Attaway etal. (1967) studied the variation of the oil composition during ripening; Shaw (1979) in his review considered only the composition of oils extracted in January from ripe fruits. The same approach has been chosen here.

limonene

87-88.34%

myrcene

1.2-2.26%

ocimene*

0.08%

a-pinene

0.81%

a-pinene + a-thujene

0.54%

/3-pinene + sabinene

0.39%

a-terpinene

0.08%

7-terpinene

2.23%

7-terpinene + octanal

3.9%

terpinolene

0.31%

/3-elemene

0.07%

7-elemene

0.15%

¿-elemene

0.10%

decanal

0.16-0.26%

dodecanal

0.15%

hexanal

tr

octanal

0.25%

tetradecanal

0.05%

citronellal

0.13%

geranial

0.07-0.31%

neral

0.05%

perilla aldehyde

0.10%

a-sinensal

0.18%

geraniol

0.04%

linalool

0.87-4.2%

terpinen-4-ol + thymol

methyl ether 0.27%

a-terpineol

0.06-0.89%

thymol

0.04-0.23%

elemol

tr

thymol methyl ether

0.9%

Among the results listed above those obtained by Ashoor and Bernhard (1967) were not included. These were relative to the composition of the monoterpene hydrocarbon fraction, and therefore not directly comparable with the data calculated relatively to the whole volatile fraction. The results obtained by these Authors (Ashoor and Bernhard, 1967) from the analysis of three tangerine oils, were the following:

camphene 0.01-0.02%

6- 3-carene 0-tr ¿-cymene 0.35-0.82% limonene 92.7-93.6% myrcene +/3-pinene 1.69-2.06% a-phellandrene 0.03-0.06% /3-phellandrene 0.39-0.42% a-pinene 0.62-0.99% a-terpinene 0.08-0.09%

7-terpinene 2.72-3.75%

During rhe years before rhe review by Shaw (1979) some papers, on rhe qualitative composition of tangerine oil, were reported by the same author in a former review (Shaw,1977)

Hunter and Brogden (1965) identified the following aliphatic, monoterpene and sesquiterpene hydrocarbons: pentadecane, ^-cymene, limonene, myrcene, a-pinene, ,/3-pinene, 7-terpinene, terpinolene, <5-cadinene, caryophyllene*, a-, ¡3-, and <5-elemene, a- and /3-humulene, a-ylangene (as already mentioned a misidentification of a-copaene).

Hunter and Moshonas (1966) identified the following alcohols: dodecanol, nonanol, octanol, citronellol, trans-carveol, geraniol, linalool, cis- and ¿n»M-/>-mentha-2,8-dien-l-ol, /?-mentha-l,8-dien-9-ol, /;-menth-l-en-9-ol, />-menth-8-en-l,2-diol, nerol, a-terpineol, thymol, elemol, »-phenyl phenol.

Moreover, Hussein and Pidel (1976) carried out a study for the quantitative determination of the composition of tangerine oil produced in Florida, California, Mexico and Brasil. The results obtained are reported below:

camphene + unknown p-cy mene + octanal limonene myrcene a-phellandrene

Q-pinene

/3-pinene + unknown a-terpinene 7-terpinene terpinolene

/3-caryophyllene + nonanol decanal dodecanal + neryl acetate nonanal + unknown citronellal geranial + decanol + citronellol neral + a-terpineol perilla aldehyde sinensal*

carvone + nerol trans-c arveol linalool sabinene hydrate* + unknown thymol decyl acetate geranyl acetate + unknown 1,8-cineole

0-0.01% 0.14-0.39% 89.95-94.17% 1.95-2.10% 0.03-0.04% 0.70-1.21% 0.44-1.07% 0.02-0.06% 0.48-3.40% 0.04-0.15% 0.02-0.04% 0.04-0.11% 0.02-0.04% 0.01-0.03% 0.02-0.05% 0.02-0.03%' 0.04-0.07% 0.03% tr-0.08% 0.03% tr—0.01% 0.30-0.98% 0.01% tr-0.04% tr-0.05% 0.03-0.06% 0.63-0.76%

Hussein and Pidel also found, in one or more of the oils analysed, trace amounts of 6-methyl-5-hepten-2-one, dodecanol, heptanol, (Z)-3-hexenol, undecanol, «j-carveol, geraniol, thymol, benzyl alcohol, methyl N-methylanthranilate.

254 Giovanni Dugo et al. 1979-2000

In this period there is a scant literature on the volatile fraction of tangerine essential oil. Two papers, Koketsu etal. (1983) and Lancas etal. (1988) are on the Brazilian tangerine oil, one, Inoma etal. (1989) is on commercial tangerine oils. The results relative to these papers are summarised in Table 13.9-

The data reported in Table 13.9, in particular for the major components, are enough homogeneous. However the results relative to the minor components cannot be considered reliable. The latest paper cited in the table is from 1989, and to our knowledge, no later investigations have been done on tangerine oils in the last decade, while the analytical techniques for separation and identification of complex matrices have been greatly improved. In fact, more detailed information could be obtained today on the composition of this oil, if such techniques were applied.

Table 13-9 Percentage composition of the volatile fraction of tangerine oil

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