Citrus Fruit Processing

Citrus Fruit Processing

Zeki Berk

Professor (Emeritus), Department of Biotechnology and Food Engineering

Technion, Israel Institute of Technology, Haifa, Israel

Table of Contents

Cover

Title page

Copyright

Dedication

Chapter 1: Introduction: history, production, trade, and utilization

Abstract

1.1. History of citriculture

1.2. Production of citrus fruit

1.3. Trade and utilization

Chapter 2: Morphology and chemical composition

Abstract

2.1. Anatomy of the citrus fruit

2.2. Constituents of the epicarp

2.3. Constituents of the mesocarp

2.4. Constituents of the endocarp

Chapter 3: Biological aspects of citriculture

Abstract

3.1. The root system

3.2. Shoots, stems, and leaves

3.3. Flowering and fruiting

3.4. Breeding and genetic improvement

Chapter 4: Agricultural production practice

Abstract

4.1. Soil

4.2. Climate

4.3. Propagation

4.4. The orchard

4.5. Irrigation

4.6. Fertilization, plant nutrition

4.7. Pruning

4.8. Pest and disease management, orchard sanitation

4.9. Harvesting

Chapter 5: Diseases and pests

Abstract

5.1. Diseases

5.2. Pests

Chapter 6: Postharvest changes

Abstract

6.1. Respiration

6.2. Transpiration

6.3. Changes in mechanical properties

6.4. Changes in taste and aroma

6.5. Stem-end rind breakdown

6.6. Chilling injury

6.7. Postharvest pathogens

6.8. Optimal storage conditions

Chapter 7: Packing house operations

Abstract

7.1. Location of the packing house

7.2. Packing flow diagram

7.3. Transport and reception of the raw material

7.4. Degreening

7.5. Buffer storage

7.6. Dumping

7.7. Soaking (drenching)

7.8. Presorting

7.9. Washing

7.10. Drying

7.11. Waxing

7.12. Grading, labeling

7.13. Sizing

7.14. Packaging

Chapter 8: Production of single-strength citrus juices

Abstract

8.1. Introduction and terminology

8.2. Procurement of fruit for the processing industry

8.3. Harvesting, loading, and transporting to the processing plant

8.4. Reception and storage

8.5. Washing, inspection, sizing

8.6. Extraction of juice and essential oil

8.7. Chilling

8.8. Screening

8.9. Deaeration

8.10. Homogenization

8.11. Pulp wash

8.12. Pasteurization

8.13. Single-strength juices from concentrate

8.14. Clarified juices

8.15. Reduced acidity and debittered orange and grapefruit juices

8.16. Blended juices

8.17. Raw or unpasteurized juice

8.18. Fermented juices

Chapter 9: Production of citrus juice concentrates

Abstract

9.1. Introduction

9.2. Principles of evaporation

9.3. Energy economy in evaporation

9.4. Types of evaporators

9.5. Condensers

9.6. Essence (aroma) recovery

9.7. The 72 ⁰Bx concentrate

9.8. Concentration by reverse osmosis and osmotic evaporation

9.9. Freeze concentration

9.10. Packaging and storage of concentrates

Chapter 10: By-products of the citrus processing industry

Abstract

10.1. Introduction

10.2. Peels and rag

10.3. Bases for the manufacture of citrus flavored beverages

10.4. Pulp and juice sacs

10.5. Pectin

10.6. Citrus fiber

10.7. Essential oils and limonene

10.8. Citrus seeds

Chapter 11: Miscellaneous citrus products

Abstract

11.1. Introduction

11.2. Canned grapefruit segments

11.3. Canned mandarin segments

11.4. Candied peel and fruit

11.5. Jams, jellies, and marmalades

11.6. Dehydrated citrus juice

Chapter 12: Shelf life of citrus products: packaging and storage

Abstract

12.1. Introduction

12.2. Shelf life of single strength juices

12.3. Shelf life of citrus concentrates

12.4. Shelf life of citrus by-products

12.5. Shelf life of miscellaneous citrus products

Chapter 13: Nutritional and health-promoting aspects of citrus consumption

Abstract

13.1. Vitamins

13.2. Antioxidants

13.3. Bioactivity of citrus essential oils

13.4. Fiber

13.5. Dental health

13.6. Obesity

13.7. Minerals

Chapter 14: Quality assurance and authentication

Abstract

14.1. Routine quality control and quality assurance

14.2. Food safety and HACCP

14.3. Authentication of citrus origin

Appendix I: Codex standard for orange juice preserved exclusively by physical means 1 codex stan 45-1981 (world-wide standard)

Appendix II: Codex standard for concentrated orange juice preserved exclusively by physical means 1 Codex Stan 64-1981 (World-wide Standard)

Appendix III: Codex standard for certain canned citrus fruits (Codex Stan 254-2007)

Index

Copyright

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Dedication

To the memory of

Prof C.H. Mannheim

who did so much for Food Science

C.H. Mannheim

1927–2013

Chapter 1

Introduction: history, production, trade, and utilization

Abstract

The genus "Citrus" belongs to the subfamily of Aurantioideae, family of Rutaceae, order of Geraniales and comprises numerous varieties of most popular fruits such as sweet, sour and bitter oranges, tangerines, grapefruit, lemons, limes, citrons, etc., and a very large number of hybrids and cybrids (cytoplasmatic hybrids). The cultivation of citrus trees is believed to have been practiced at least 4000 years ago in south-east Asia. Citrus fruits are grown almost in every country 30–35 degrees north and south of the Equator. Total world production of citrus fruits in the 2010–2011 season was in excess of 115 million tons, more than any other fruit crop. The leading variety is oranges (61%), followed by tangerines (22%), lemons and limes (11%), and grapefruit (6%). The most important total citrus producing countries are China (24%), Brazil (24%), and the United States (11%).

Keywords

citrus

citrus belt

history of citriculture

citrus statistics

oranges

grapefruit

tangerines

lemons

kumquats

The term citrus (agrumes in French, agrios or citricos in Spanish) is a generic name designating a large group of universally popular edible fruits. According to the current system of plant taxonomy, the genus "Citrus" belongs to the subfamily of Aurantioideae, family of Rutaceae, order of Geraniales (Davies and Albrigo, 1994). The genus comprises numerous varieties of fruits known by their popular names: sweet oranges (Citrus sinensis), sour and bitter oranges (C. aurantium), mandarins (C. reticulata), grapefruit (C. paradise), pomelo (C. grandis), lemons (C. limon), limes (C. latifolia and C. aurantifolia), citrons (C. medica), etc. and a very large number of hybrids and cybrids (cytoplasmatic hybrids). The kumquats (Fig. 1.1) belonging to a related but different genus (Fortunella) are extensively cultivated in southern China and have some commercial importance, particularly in the Greek island of Corfu and elsewhere as candied fruit. The taxonomy of the Citrus genus has been extensively investigated by Swingle (1943). A colorful illustrated guide to the citrus varieties of the world is available (Saunt, 1990).

Figure 1.1   Total world production of citrus fruits, by variety (2010/2011 season). (FAO, 2013)

1.1. History of citriculture

Although the cultivation of citrus trees is believed to have been practiced at least 4000 years ago in the tropical and subtropical areas of the Asian continent and the Malaysian archipelago (in spoken Arabic and portokal in Turkish, indicating clearly the role of the Portuguese in introducing the orange to Europe and the Middle-East via Spain. Mainly because of their fragrance in the flowering season, orange trees were highly appreciated items in the luxurious gardens of European nobility, where special areas known as orangeries were reserved for their culture. For a detailed study of the history of citriculture, see Tolkowsky (1938) and Reuther et al. (1967).

1.2. Production of citrus fruit

Citrus fruits are grown almost in every country 30–35 degrees north and south of the Equator. For some varieties, less susceptible to frost damage, the zone of cultivation reaches 40 degrees on both hemispheres. World production figures place citrus in the leading position among fruit crops. Total world production of citrus fruits in the 2010–11 season was in excess of 115 million tons, more than any other fruit (FAO, 2013). The leading variety is oranges (61%), followed by tangerines (22%), lemons and limes (11%), and grapefruit (6%) (Fig. 1.2). The most important total citrus producing countries are China (24%), Brazil (24%), the United States (11%) (Fig. 1.3). For oranges, Brazil leads with 29%, followed by the United States (11%), India, and China (8% each) (Fig. 1.4). The principal producer of tangerines is China (55%), followed by Spain (9%), Brazil, and Japan (4% each) (Fig. 1.5). India is the largest producer of lemons (21%), then come Mexico (14%), Argentina 12%, Spain, and Brazil (7% each) (Fig. 1.6). China accounts for 44% of the world grapefruit production, followed by the United States (17%), Mexico, and South Africa (6% each) (Fig. 1.7).

Figure 1.2   Total citrus fruits production, by countries (2010/2011 season). (FAO, 2013)

Figure 1.3   Oranges production, by countries (2010/2011 season). (FAO, 2013)

Figure 1.4   Tangerines production, by countries (2010/2011 season). (FAO, 2013)

Figure 1.5   Lemons production, by countries (2010/2011 season). (FAO, 2013)

Figure 1.6   Grapefruit production, by countries (2010/2011 season). (FAO, 2013)

Figure 1.7   Kumquat fruits.

1.3. Trade and utilization

According to Batchelor and Sinclair (1961) the oranges of commerce may be classified into three species: sweet oranges, mandarin or tangerine oranges, and bitter oranges. Sweet oranges may be divided into three groups: oranges with normal fruit (Valencia, Shamouti, etc.), navel oranges, and blood oranges. Some orange varieties are seedless.

The predominant varieties of lemon are Eureka and Lisbon. Other important varieties include Villafranca, Femminello (Italy), Genova (Argentina), Meyer (hybrid, the United States), Verna (Spain), and Yen Ben (Australia, New Zealand). The most important variety of grapefruit worldwide is the Marsh Seedless, followed by Duncan and the pigmented varieties such as the pink Thompson (Sinclair, 1972) and the red Star Ruby. In addition to these varieties a large number of hybrids are being continuously developed by plant breeding techniques. The production of a commercially important class of hybrids, developed mainly from mandarin varieties and called easypeelers, has grown considerably in the last years at the expense of sweet oranges.

In the past, citrus fruit was commercialized and consumed exclusively as fresh fruit, even in countries not producing citrus. This was made possible because of the extraordinary postharvest stability of citrus fruit facilitating international trade and the fact that in most varieties of citrus, the fruit can be left hanging on the tree for a long time after maturation without spoilage. However, as the acreage of plantations and the size of the crops increased steadily, industrialization of citrus fruits became a necessity. Small-scale industries for the production of jams, jellies, and marmalades and somewhat larger centers for the extraction of essential oils have been in activity for many years but large-scale industrialization started with the establishment of the juice factories in California and Florida, in the beginning of the 20th century. The first product was hot-filled canned juice. In the following 40 years or so, important advances in citrus technology were made. Automatic continuous juice extractors were developed and the plate heat exchanger was adopted for the continuous pasteurization of juices. The development of greatly improved evaporators specially designed for citrus juices and the rapid expansion of industrial refrigeration led to the production of frozen concentrated juices that became the most popular citrus product for many years. The development of aseptic processing and aseptic storage had a very strong impact on the food industry, including citrus processing. The ever-increasing consumption of processed citrus products and particularly of frozen concentrated orange juice prompted the development of large citrus processing plants, as an important sector of the food industry. At the same time, citrus-based soft drinks such as lemonades and orangeades became the leading kind of bottled fruit flavored beverages. For many years, the manufacture of canned citrus segments gained considerable importance in China (Satsuma oranges) and Israel (grapefruit). At present, approximately 25% of the total world production of citrus fruit is industrially processed (Tables  1.1–1.3).

Table 1.1

Changes in the Proportion of World Citrus Production Used for Processing

Source: Food and Agriculture Organization of the United Nations (FAO). (2013). The Citrus Bulletin, 2012. Rome.

Table 1.2

Citrus Utilization for Processing by Countries—2010–2011 Season

Source: Food and Agriculture Organization of the United Nations (FAO). (2013). The Citrus Bulletin, 2012. Rome.

Table 1.3

Utilization of Citrus for Processing, by Variety, 2010–2011 Season

Source: Food and Agriculture Organization of the United Nations (FAO). (2013). The Citrus Bulletin, 2012. Rome.

The outstanding popularity of citrus fruit and citrus products is, naturally, due to their convenience of use (eg, ease of peeling), to their refreshing taste and pleasant aroma, and, to some extent, to their fairly good content of Vitamin C. Lately, however, many health promoting properties, ranging from aesthetical benefits to antioxidant activity and improvement of blood circulation, have been attributed to citrus fruit and particularly to some of its minor constituents. This aspect will be treated in more detail in a later chapter.

One of the characteristics of citrus fruits is the relatively large mass proportion of peels and rag. Technologies have been developed to convert these by-products from a huge problem of disposal to a source of additional income. The economic robustness of the citrus processing industry will continue to depend, to a large extent, on its capability to develop sustainable technologies for the optimal utilization of the wastes and by-products (Braddock, 1989; Ledesma-Escobar and Luque de Castro, 2014).

References

Bartholomew ET, Sinclair WB. The Lemon Fruit. Berkeley, CA: University of California Press; 1951.

Batchelor LD, Sinclair WB. World production and important commercial varieties. In: W.B., ed. The Orange, Sinclair. Berkeley, CA: University of California Press; 1961.

Braddock RJ. Handbook of Citrus By-Products and Processing Technology. New York: Wiley; 1989.

Braverman JBS. Citrus Products: Chemical Composition and Chemical Technology. New York: Interscience Publishers; 1949.

Davies FS, Albrigo. Citrus. Oxon, UK: Cab International; 1994.

Dugo G, Di Giacomo A, eds. Citrus: The Genus Citrus. London, UK: Taylor and Francis; 2002.

FAO (Food and Agriculture Organization of the United Nations), 2013. The Citrus Bulletin, 2012. Rome, Italy.

Ledesma-Escobar C, Luque de Castro MD. Towards a comprehensive exploitation of citrus. Trends Food Sci. Technol. 2014;39:63–75.

Reuther, W., Webber, H.J., Batchelor, L.D., 1967. The Citrus Industry, Vol: 1. History, World Distribution, Botany and Varieties. University of California Press, Oakland.

Rouseff RL, Perez-Cacho PR, Jabalpurwala F. Historical review of citrus flavor research during the past 100 years. J. Agric. Food Chem. 2009;57:8115–8124.

Saunt J. Citrus Varieties of the World. Norwich: Sinclair International Limited; 1990.

Sinclair WB. The grapefruit. Its composition. Berkeley, CA: University of California Press; 1972.

Swingle WT, The botany of citrus and its wild relatives. Webber HJ, Batchelor LD, eds. The Citrus Industry, Vol. 1. Berkeley, CA: University of California Press; 1943.

Tolkowsky S. Hesperides: a History of the Culture and Use of Citrus Fruit. London, UK: J. Bales, Sons & Curnow Ltd; 1938.

Chapter 2

Morphology and chemical composition

Abstract

All citrus varieties present a similar fruit morphology. Citrus fruit is covered with a very thin (less than 3 μm) cuticle, consisting of polymerized material and natural waxes. Below the cuticle, the external layer of the peel, or the epicarp, is known as the flavedo. It contains the essential oil and pigments. The essential oils consist of terpenoids, their oxygenated derivatives, and a small amount of nonvolatiles. The peel pigments are chlorophyll and carotenoids. Given certain climatic conditions, the green pigment chlorophyll is destroyed in the course of ripening. If this change, known as color break, does not occur naturally, the fruit is subjected to forced degreening with ethylene. The middle layer, under the flavedo, is the mesocarp, also known as the albedo, a sponge-like white tissue, particularly rich in pectic substances and flavonoids. Flavonoids have antioxidant properties. Some flavonoids and related substances are bitter. Beneath the albedo is the endocarp which is the edible part of the fruit. It is radially divided into segments or carpels, delimited by membranes. The segment are filled with a large number of vesicles or juice cells, each contained in a thin membrane or juice sac. The juice contains carbohydrates, organic acids, nitrogenous substances, lipids, glycosides, vitamins, soluble pigments, and insoluble particles in suspension which constitute the cloud and pulp. Stability of the cloud is an important quality factor. Clarification occurs as a result of the action of the enzyme pectin methylesterase. Ascorbic acid or vitamin C is considered to be the primary health-promoting component of citrus juice. Oxidation of ascorbic acid leads to nonenzymatic browning.

Keywords

cuticle

flavedo

albedo

mesocarp

carpel

juice sacs

essential oil

terpenoids

carotenoids

chlorophyll

flavonoids

Brix

maturity index

cloud stability

pectin methylesterase

ascorbic acid

non-enzymatic browning

aroma

2.1. Anatomy of the citrus fruit

Like all agricultural produce, citrus fruit presents extensive variability in chemical composition and physical characteristics, depending on variety, rootstock, soil, fertilization, irrigation, age, maturity, position in the tree, etc. However, almost all varieties of citrus fruits present a similar general structure or anatomy, schematically shown in Fig. 2.1. A detailed description of the macroscopic and microscopic structure of citrus fruit can be found in Albrigo and Carter (1977).

Figure 2.1   Schematic cross section of a citrus fruit.

Citrus fruit is covered with a very thin (less than 3 μm) cuticle, consisting of polymerized material and natural waxes. The cuticle protects the fruit against insects and microorganisms and regulates the exchange of gases such as oxygen and carbon dioxide. It also limits the loss of water. Below the cuticle, the external layer of the peel, or the epicarp, is known as the flavedo (from the latin flavus meaning yellow). It carries the pigments of the peel concentrated in subcellular bodies or plastids, chloroplasts if green or chromoplasts if yellow, orange, or red. It also contains the peel essential oil, entrapped in quasispherical glands, from 10 μm to about 0.5 mm in diameter. The middle layer, under the flavedo, is the mesocarp, also known as the albedo (from the latin albus, meaning white) or pith. The albedo is a sponge-like white tissue, particularly rich in pectic substances. Its thickness varies widely among the different citrus varieties, from a few millimeters in mandarins to 1–2 cm or more in grapefruit and pummelo. Within the fruit, beneath the peel, is the endocarp. In edible varieties, the endocarp constitutes the major part of the fruit. It is radially divided into segments or carpels, delimited by segment covers or membranes. The segments are filled with a large number of vesicles or juice cells, each contained in a thin membrane or juice sac (Fig. 2.2). The segments are arranged, in a more or less regular pattern, around a core which expands along the central axis of the fruit. The core has the same composition as the albedo and can be considered an extension of the mesocarp. In seeded varieties, seeds are found inside the segments, around the central axis and close to it (Fig. 2.3). Typically, citrus fruit has 8–12 segments. Kumquats have only three and some grapefruit may have as many as 18. Some varieties are seedless or practically seedless. Seeded varieties may have as many as 50 seeds per fruit.

Figure 2.2   Cross section of pink grapefruit, showing seeds.

Figure 2.3   Segment of grapefruit, membrane removed to show juice sacs.

The structure of navel oranges differs somewhat from that of most other varieties, due to the presence of a secondary, smaller fruit at the stylar end of the primary fruit (Fig. 2.4). This fruit inside fruit phenomenon may sometimes result in oranges with tertiary and even quaternary fruits or navels inside an orange (Davies and Albrigo, 1994).

Figure 2.4   Cross section of Navel orange.

With respect to size, citrus fruits usually range from 4 to 12 cm in diameter but some varieties are much smaller (eg, kumquats with about 2 cm, see Fig. 1.7) and some pummelos as large as 18 cm in diameter. Commonly measured diameters are: 3.8–5 cm in limes, 4.4–6.4 cm in lemons, 5–7.5 cm in mandarins, 5.7–9.5 cm in oranges, and 9.5–14.5 in grapefruit (Albrigo and Carter, 1977). The shape varies from nearly spherical in most oranges to oblate in mandarins and grapefruit and prolate spheroid in lemon. The distinctive feature of the lemon fruit is the nipple at the stylar end, present in all commercial varieties (Fig. 2.5). There are also lemons and limes with unusual shapes. The variety known as Buddha’s hand has the shape of a human hand, with fingers closed or open. Very fragrant, it is used as a religious offering to Buddha. The Australian finger lime has the shape of a human finger.

Figure 2.5   Eureca lemon, showing nipple.

2.2. Constituents of the epicarp

2.2.1. The essential oils of the epicarp

The citrus genus is characterized by the presence of odorous volatiles in the flowers, the leaves, the fruit epicarp, and the fruit endocarp. Peel essential oils are the odorous liquid substances that fill the ductless glands in the epicarp, zest, or flavedo. Peel essential oils are different in composition from the fragrant substance distributed in the endocarp, to which the juice of citrus fruits owe their distinctive aroma. Nevertheless, commercially the term citrus essential oils is mostly reserved for peel oils. The fragrant substances of the endocarp or juice are often called alcohol or essence. They are obtained by the operation known as essence recovery, in connection with evaporative concentration of the juice, to be described in a later chapter of the book. Essential oils are not oils in the chemical sense of the word, because they are not triglycerides but rather a mixture of terpenes and terpene-like substances (terpenoids). They are called oils because of their lipophilic/hydrophobic character. Essential oils of citrus have been extracted and commercialized since the middle-ages and concrete reference to the manufacture procedures and the products has been made as early as the 16th century. A number of different production methods are practiced to this date. The most widespread processes will be discussed in the chapters on production technologies.

The oil content of the major citrus cultivars in Florida was determined by Kesterson and Braddock (1975). The approximate values reported, after conversion to metric units (kilogram oil per ton of fruit), are 3.5–6 for oranges, 3 for grapefruit, 7 for tangerines and lemons, and 4 for limes.

According to Sawamura (2010) citrus essential oils account for the major proportion of the natural flavors and fragrances of commerce. They are used in a vast variety of products, from beverages to cosmetics. Regarding their use in foods as flavoring agents, it is comforting to know that essential oils are generally considered as safe by the US Food and Drug Administration (Smith et al., 2005).

1. Chemical composition: Citrus essential oils contain a large number of different chemical species. Due to the development of more precise separation and identification techniques, the number of known constituents is steadily increasing and the detailed composition of oils from different sources is determined (eg, Kirbaşlar et al., 2006; Mondello et al., 2002; Steuer et al., 2001; Shaw, 1979). Ruberto and Rapisarda (2002) detected and fully characterized 78 components in the oil of hybrid cultivars. In general terms, the major part of essential oils (94–96%) consists of volatile constituents. The nonvolatile fraction, representing a few percent of the oil, is made of sterols, carotenoids, fatty acids, waxes, and flavonoids (Mondello et al., 2002). The volatiles are monoterpenes, sesquiterpenes, and their oxygenated derivatives (alcohols, aldehydes, esters of carboxylic acids, ketones). A partial list of known volatile components in various citrus peel oils is given in Table 2.1. Typical concentrations of constituents in the peel oil of orange, mandarin, lemon, and grapefruit are listed in Table 2.2.

a. Terpenes: Terpenes are hydrocarbons widely distributed in plants. They constitute most of the bulk of citrus peel essential oils (frequently over 95%) but contribute little to the characteristic fragrance of citrus fruit, which is due mainly to their oxygenated derivatives. On the contrary, terpenes weaken the fragrance by diluting the aroma substances in the oil. Furthermore, they can be converted into compounds with objectionable odors by oxidation, isomerization, polymerization, etc., upon storage (Turek and Stintzing, 2013; Nguyen et al., 2009). High-quality terpeneless essential oils are produced by different separation techniques (eg, Norman and Craft, 1966; Owusu-Yaw et al., 1986) to be described later.

The molecular structure of terpenes and terpenoids consists basically of the repetition of units of the unsaturated, branched hydrocarbon isoprene (C5H8). Isoprene-based molecular skeleton is very frequent in nature. It is found not only in terpenes but also in carotenoids, etc. This does not mean that the hydrocarbon isoprene actually serves as a precursor in the biosynthesis of these natural products. In fact, the two universal precursors to isoprenoid structures in living systems are dimethylallyl diphosphate and isopentenyl diphosphate.

Limonene is the major component of peel essential oils, usually representing about 90% of the mass of orange oil. It is a monoterpene, with a molecular weight of 136. It has a faint, lemon-like odor. Isolated and purified, it serves as a solvent and a skin cleanser in cosmetics. Lately, it has been used as an environmentally friendly solvent for the Soxhlet extraction of fats in the laboratory (Virot et al., 2008).

An important constituent of pine oil, pinene, is also found in lemon oil and neroli oil.

Phellandrene is an important constituent of eucalyptus oil. The isomer β-phellandrene is also found in lemon oil.

Citrus oils contain a small amount of sesquiterpenoids. Sesquiterpenes have higher molecular weight and are therefore less volatile. Having only a faint smell, most of them do not contribute appreciably to the aroma. The monocyclic sesquiterpene bisabolene and the dicyclic sesquiterpene cadinene are found in lemon oil (Braverman, 1949).

The dicyclic sesqiterpene nootkatone is found in the peel oil and juice of grapefruit. It is considered to be a valuable component of the aroma of grapefruit peel oil but its concentration in the oil-free juice is often below its threshold level for detection. It is also a potent insect and tick repellent. For this application it is more economical to produce it synthetically.

Valencene is another citrus sequiterpene found principally in the peel oil of Valencia oranges. Its oxidation yields nootkatone.

b. Aldehydes: Quantitatively, aldehydes represent only a minor portion of peel essential oils. According to a table in Kefford and Chandler (1970), the proportion of aldehydes in the peel oil of different citrus fruits is 1.8% in Valencia orange, 0.7% in mediterranean mandarin, 3.6% in Sicilian lemon, and 1.2–1.8% in grapefruit. Nevertheless, aldehydes are important constituents, due to their characteristic aroma.

n-Octyl aldehyde, C7H15·CHO, and n-Nonyl aldehyde C8H17·CHO are found in lemon oil. n-Decyl aldehyde C9H19·CHO is the chief aldehyde in orange oil (Braverman, 1949). Citral (3,7-dimethyl-2,6-octadienal) is a nonsaturated aldehyde, widely distributed and well known for its strong, pleasant, lemon-like fragrance. It consists of two stereoisomers: geranial (citral A) and neral (citral B). It is used as a flavoring as well as an antimicrobial agent.

c. Alcohols: The presence of free alcohols in peel oils may be explained, at least partially, as a result of hydrolysis of the corresponding esters. Linalool (C10H18O) has a di-non-saturated chain and occurs as two stereoisomers. An important constituent of the aroma in flowers and spices, linalool, is also found in the peel oil of sweet orange. It is used in cosmetics, soaps, and detergents as a flowery note. Lately, it has been reported that inhalation of linalool may have stress-repressing effects (Nakamura et al., 2009). Geraniol, an unsaturated alcohol, has the same molecular formula as linalool. It is the main odor-bearing component in the perfume of roses, but it also occurs in lemon oil. It is used in perfumery and added