Bergamot Bergaptene

Oil of bergamot contains about 5 per cent, of an odourless solid body known as bergaptene. This body has the formula Cj HgO, and melts at... 

Genotoxicity of bergapten and bergamot oil in Saccharomyces cerevisiae. Journal of Photochemistry and Photobiology. B, Biology, 7, 209-229. 

Bergamot Citrus aurantium ssp. bergamia (Rutaceae) fresh fruit peel (expression) 0.5 limonene (42) linalyl acetate (27) y-terpinene (8) linalool (7) flavouring, aromatherapy, perfumery also contains the furocoumarin bergapten (up to 5%) and may cause severe photosensitization (see page 146)... 

Furocoumarins, e.g. bergaptene (5-methyloxypsoralen) (Fig. 3.11) Found in essential oil of bergamot (about 0.3%) and in small amounts in orange, mandarin and lemon. 

Some aromatherapists prefer to use bergamot essential oil with the compound bergapten< Soved. Bergaptene is an example of a furocoumarin, not a terpene, and it is phototoxic. 

Bergamot is an essential oil with a potentially harmful constituent. Some aromatherapists choose to use ones with the bergaptene removed. However, many professional aromatherapists will use the expressed oil, observing the IFRA guidelines limiting a maximum concentration up to 0.04%. 

However, this is an example of an essential oil in which the minor components are of great significance it contains a furocoumarin called bergaptene (0.2-0.5%), which is a phototoxic compound and needs to be used with caution. Many oils have it removed and are called FCF (furocoumarin-free) oils, even though this is technically a rectification of the whole oil. This is discussed under safety in Chapter 8. The odour of this oil is also influenced by the presence of trace components guaienol, spathulenol, nerolidol, farnesol and (i-sinensal. Box 7.8 shows safety data for bergamot oil and Box 7.9 shows a material data safety sheet. 

Comments A treated oil, sometimes rectified by distillation, is obtainable as bergapten-free oil. This oil is also known as furanocoumarin-free bergamot or bergamot FCF. Its odour is inferior to that of the untreated, cold pressed oil, but it is not phototoxic or photocarcinogenic. 

Furanocoumarins Also called furocoumarins, methoxypsoralens or bergaptenes. Found in cold-pressed citrus oils, e.g. bergamot. An oxygen-containing cyclic structure associated with phototoxicity on exposure to ultraviolet light. 

Citrus oil dominates this class of essential oil. It is obtained by the cold press method with the exception of lime oil, which is also prepared by steam distillation of essential oil separated during the production of juice.106,107 Aside from bergamot, these oils are primarily monoterpene hydrocarbon mixtures of which (if)-limonene (3) is usually the dominant compound. Since odor contribution of this monoterpene compound is low, it is often removed by distillation or repeated solvent extraction. The resulting oil rich in odor-active compounds is called terpeneless oil and is used extensively. In the case of bergamot and lemon oils, psoralen derivates like bergaptene (64) causing photosensitivity are problematic, and those for fragrance use are rectified to remove it (Table 8). 

Oils of bergamot, lemon, citron and lime, fully or partially reduced in bergapten - Determination of bergapten content by high-pressure liquid chromatography (HPLC)... 

Oil Bergamot Volatile oil expressed Irom rind of fresh fruit of Cirrus aurantium L.. var. bergamia Wight A Am., Rutaceae. Constit 36-45% /-linalyl acetate, about 6% f-linalool d-limonene, dipentene, bergaptene. 

Figure 5. Removal of Bergapten from bergamot oil (Reproduced with permission from reference 1. Copyright 2002 Elsevier.)...

Commercial processing can remove bergapten from bergamot orange products, and bergapten-free products are commercially available. 

Averbeck, D., S. Averbeck, L. Dubertret, A.R. Young, and P. Morliere. 1990. Genotoxicity of bergapten and bergamot oil in Saccharomyces cerevisiae.. Photochem. Photobiol. B 7(2-4) 209-229. Cocks, H., and D. Wilson. 1998. Dangers of the intake of psoralens and subsequent UV exposure producing significant bums. Bums 24(1) 82. 

Xanthotoxin occurs in the fruits of Fagara xanthoxyloides Lam [548], Ruta chalapensis [549] and in the berries of Luvanga scandeus [550]. Imperatorin was first isolated from the rhizomes of Imperatoria osthnitium L. [551] bergapten from bergamot oil [525]. 

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