Bergamot essential oil – Wikipedia

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Bergamot essential oil
Bergamotti just collected and intended for the production of essence.
The “Calabrian machine” (one of the first pending machines), conceived by Nicola Barillà in 1844, for the processing of bergamot

L’ Bergamot essential oil commonly known as essence of bergamot , is an essential oil obtained for cold pressing of the peels of the fruits of bergamot.

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It is an essential component of the colony water and of the eau de toilette , which are the first products thanks to which the essence has had widespread use all over the world. It is used in perfumery as a fixative.

The collection of bergamot has as its almost exclusive purpose the production of the essence. The essence is contained in the glands or oleifere gaps (Otricoli) present in the peel (Flavedo); These cavities containing the essence originate following the lysis (Lisigenic cavities) of the same cells that produce the essence.

Shade [ change | Modifica Wikitesto ]

Originally the peels of the fruits cut into two and private individuals of the pulp, were repeatedly folded and pressed by hand (operation called shade, which exploits the natural pressure exerted by the essence within the Otricoli) on a natural sponge (sponge); The sponge was impregnated with essence, then it was squeezed and the essence left to praise in a crock container (Concolina). Subsequently, wood presses were used, while today the process was mechanized. To produce a liter of essence, 200 kilos of Bergamotti are required.

Pelatura or scrape [ change | Modifica Wikitesto ]

Modernly the essence is always extracted mechanically with machines called “pelatrics”, these machines “raspano” the exterior of the fruit in water current obtaining an emulsion conveyed to centrifuges that separate the essence from the water for specific weight difference .

The essence presents itself as a clear liquid (sometimes there is a deposit made up of waxes) of green to green yellow. From a chemical-physical point of view it is for the most part (on average 95%) by a volatile fraction and a non-volatile fraction (or residue) (the remaining 5%). Chemically it is a highly complex mixture of numerous classes of organic substances, in particular terpenes, foreign, alcohol and aldehydes, for the volatile fraction, oxygenated heterocyclic compounds, cumarins and furanocumarine, for the non -volatile fraction.

Volatile fraction [ change | Modifica Wikitesto ]

The main components are limonene, acetate of Linalile, Linalol, γ-terpinene and β-pinene, [first] and in smaller geranical quantities and β-bisables.

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Acetate of Linalile and Linalol are the most important qualitative components of the essence.

Bird components essence of bergamot [first]
Composed quota
Limonene 37.2%
Acetate of Linalile 30.1%
Lina loo 8.8%
γ-terpinene 6.8%
β-pinene 2.8%
Others/unknown 14.3%
green : terpenes; blu : foreign; orange : alcohol; red : other components

Non -volatile fraction [ change | Modifica Wikitesto ]

The main components are made up of heaps (Citroptene, 5-Geranilossi-7-Metoxicumarina) and Furanocumarine (Bergaptene, Bergamotina). [2] [3] [4] [5]

Chiral gascromatography of genuine essence of bergamot (high) and distillate of bergamot leaves ( peratoner )

Bergamot essential oil is particularly subject to counterfeiting being a precious essence produced in relatively small quantities. Generally, the counterfeiting consists in “cutting” the essence, or in adding distillers of poor quality and low cost essences, for example of bitter orange and bergamot mint and/or mixtures of natural or synthetic terpenes, or in “reconstructing” The essence starting from synthetic chemicals, coloring it with chlorophyll. Worldwide, every year about three thousand tons of essence of bergamot are marketing, while the genuine essence of bergamot produced annually amounts to no more than one hundred tons. [6]

The use of the fogging analysis with columns with a stationary chiral phase allows you to analyze mixes of enantiomers. The analysis of the enantiomeric distribution of various compounds, such as acetate of Linalile and Linalol, allows the characterization of the essence of bergamot based on the production process and allows you to discover the possible counterfeiting of the essence. [7] [8] [9] [ten]

The combined use of isotopic mass spectrometry and SNIF-NMR (Site-Specific Natural Isotope Frationion-Nuclear Magnetic Resonance) allows you to discover otherwise non-detectable counterfeits, allowing even the identification of the geographical area of ​​origin of the essence. [11]

The GC-C-IRMS technique (Chromatography-BUBUSTION GAS-Isotope Ratio Mass Spectrometer), used more recently, allows you to obtain similar results. [twelfth]

Analytical parameters of reference [ change | Modifica Wikitesto ]

Analytical parameters of reference for the evaluation of the genuineness of the essential oil of Bergamotto (source Ssea) [13]

Chemical-physical characteristics Min Max Unit of measure
Refraction index (20 ° C) 1.4640 1,4690 my name
Optical rotation (20 ° C) +15,0 +34.0 °
Relative density (20 ° C) 0.875 0.883 my name
Foreign (expressed as acetate of Linalile) 30 45 %
Residue 4.50 6.50 %
CD (spectrophotometric analysis in the UV) 0.75 1.20 my name
Enantiomeric relationships of the main chiral compounds Min Max Unit of measure
The lemon ((+)-lemonies / (-)-the lemonies) (97.4 / 2.6) (98.4 / 1.6) %
Linalolola (+) – linalolo / (-) – nightlip) (0.3 / 99,7) (0.7 / 99.3) %
Linalile acetate ((+)-Linalile acetate / (-)-Linalile acetate) (0.3 / 99,7) (0.6 / 99,4) %
Components of the non -volatile residue Min Max Unit of measure
Bergapthene 1800 3800 mg/Kg

In the past, the psoraleni contained in the bergamot oil extract have been used in tanning accelerators and solar filters. Psoraleni penetrate the skin, where they increase the amount of DNA damage. This damage is possible in solar burns and is included with a greater production of melanin. It can also lead to a phytophotodermatosis, a scruing of the skin due to a chemical reaction that makes the skin more sensitive to UV light.

These substances are known to be photocancongogene from 1959, [14] but they were banned from the solar filters after 1995 (in the US) [15] .
These photocancogens have been banned in many states years after causing many cases of malignant melanomas and consequent deaths [16] .
Psoraleni are now used only in the treatment of some pathologies, as in Puva therapy

Through the “defurocumarinization” process it is possible to significantly reduce Bergaptene (the essence generally contains between 0.4 and 0.7% [17] ), Una Furocumarina Phototossica E Fotomutaga [18] Which for exposure to the sun can cause burns even to the deepest skin layers.
Defurocumarization can be carried out hot through a physical process (low pressure distillation), or cold through a chemical process (added under agitation of a basic aqueous solution). A physical method has also been experienced that uses supercritical carbon dioxide to extract Bergaptene. [19]

For the reasons previously exposed, it is preferable to use the defurochumarinized essence.

  1. ^ a b ( IN ) Masayoshi Sawamura, Y. Onishi, J. Ikemoto, N. Thi Minh Tu, N. Thi Lan Phi, Characteristic odour components of bergamot (Citrus bergamia Risso) essential oil , in Flavour and Fragrance Journal , vol. 21, n. 4, 2006, pp. 609–615, DOI: 10.1002 / ffj.1604 .
  2. ^ ( IN ) M. Benincasa, F. Batiarelli, G. P. Cartoni, F. Coccioli, Analysis of lemon and bergamot essential oils by HPLC with microbore columns , in Chromatographia , vol. 30, n. 5-6, 1990, pp. 271–276, DOI: 10.1007/bf02319706 .
  3. ^ ( IN ) Luigi Mondello, I. Stagno d’Alcontres, R. Del Duce, F. Crispo, On the genuineness of citrus essential oils. Part XL. The composition of the coumarins and psoralens of Calabrian bergamot essential oil (Citrus bergamia Risso) , in Flavour and Fragrance Journal , vol. 8, n. 1, 1993, pp. 17–24, doi: 10.1002 / ffj.2730080105 .
  4. ^ ( IN ) A. Cavazza, K. D. Bartle, P. Dugo, L. Mondello, Analysis of oxygen heterocyclic compounds in citrus essential oils by capillary electrochromatography and comparison with HPLC , in Chromatographia , vol. 53, n. 1-2, 2001, pp. 57–62, doi: 10.1007/BF02492428 .
  5. ^ a b ( IN ) Paola Dugo, A. Piperno, R. Romeo, M. Cambria, M. Russo, C. Carnovale, Determination of Oxygen Heterocyclic Components in Citrus Products by HPLC with UV Detection , in Journal of Agricultural and Food Chemistry , vol. 57, n. 15, 2009, pp. 6543–6551, DOI: 10.1021/jf901209r .
  6. ^ Tonio Licordari Reflection now enhance this resource in the wake of the wave … fragrant Gazzetta del Sud Cronaca di Reggio 18/02/2010 [first] [ interrupted connection ]
  7. ^ ( IN ) L. Mondello, A. Verzera, P. Previti, F. Crispo, and Giovanni Dugo Multidimensional Capillary GC−GC for the Analysis of Complex Samples. 5. Enantiomeric Distribution of Monoterpene Hydrocarbons, Monoterpene Alcohols, and Linalyl Acetate of Bergamot (Citrus bergamia Risso et Poiteau) Oils J. Agric. Food Chem., 1998, 46 (10), pp 4275–4282 [2] DOI:  10.1021/jf980228u
  8. ^ ( IN ) M. Eleni, M. Antonios, K. George, S. Alexios-Leandros and M. Prokopios High Quality Bergamot Oil from Greece: Chemical Analysis Using Chiral Gas Chromatography and Larvicidal Activity against the West Nile Virus Vector Molecules 2009, 14, 839-849 [3] DOI:  10.3390/molecules14020839
  9. ^ ( IN ) The Adulteration of Essential Oils – and the Consequences to Aromatherapy & Natural Perfumery Practice By Tony Burfield October 2003 [4]
  10. ^ ( IN ) Cotroneo A., d’Alcontres I. S. & Trozzi A. (1992) On the genuineness of citrus essential oils Part XXXIV Detection of added reconstituted bergamot oil in genuine bergamot oil by high resolution gas chromatography by chiral capillary columns Flav. & Frag. J. 7, 15-17 DOI:  10.1002 / ffj.2730070104
  11. ^ ( IN ) Sophie. Hanneguelle, Jean Noel. Thibault, Norbert. Naulet, Gerard J. Martin, Authentication of essential oils containing linalool and linalyl acetate by isotopic methods , in Journal of Agricultural and Food Chemistry , vol. 40, n. 1, 1992, pp. 81–87, doi: 10.1021/JF00013A016 .
  12. ^ ( IN ) Luisa Schipilliti, G. Dugo, L. Santi, P. Dugo and L. Mondlo, Authentication of Bergamot Essential Oil by Gas Chromatography-Combustion-Isotope Ratio Mass Spectrometer (GC-C-IRMS) , in Journal of Essential Oil Research , vol. 23, n. 2, 2011, pp. 60-71, doi: 10.1080/10412905.2011.9700447 .
  13. ^ ( IT , IN ) Francesco Gionfriddo and Domenico Castaldo, Ridefinition of the Analyzed-compositional parameters of the essential oil of Bergamotto cold extracted / Ridefinition of Analytical Compositional Parameters for “Cold Pressed” Bergamot Essential Oil , in Citrus derivative essences , n. 74, 2004, PP. 151-152.
  14. ^ Urbach, F, Modification of ultraviolet carcinogenesis by photoactive agents , in J Invest Dermatol , vol. 32, 2, Part 2, 1959, pp. 373–378, DOI: 10.1038 / way.1959.63 , PMID  13641813 .
  15. ^ Autier P; Dore j f; Schifflers e; et al., Melanoma and use of sunscreens: An EORTC case control study in Germany, Belgium and France , in Int. J. Cancer , vol. 61, n. 6, 1995, pp. 749–755, doi: 10,1002/IJC.2910610602 , PMID  7790106 .
  16. ^ ( IN ) P. Autier, J.-F. Dore, J.-P. Cesarini and P. Boyle, Should subjects who used psoralen suntan activators be screened for melanoma? ( PDF ), in Annals of oncology , vol. 8, n. 5, 1997, pp. 435–437, DOI: 10.1023/A:1008205513771 , ISSN 0923-7534 ( WC · Acnp ) , PMID  9233521 . URL consulted on May 1, 2015 .
  17. ^ Of Giacomo A. and Calvarano M. The content of Bergaptene in the essence of cold extracted bergamot Essences of the citrus derivatives 48, 51, (1978)
  18. ^ Relative Photomutagenicity of Furocoumarins and Limettin in the Hypoxanthine Phosphoribosyl Transferase Assay in V79 Cells
  19. ^ B. Mincion, A. di Giazzi and F. Crispo, First experimental assessments on the application of extraction techniques with hypercritical fluids to the essence of bergamot , in C.N.R – has put , Volterra, 1991.
  • Angelo Di Giacomo and Biagio Mincione (edited by), The citrus essential oils in Italy Raisa – Cnr Subcord 4 theme 4.3.2 New extraction, separation, splitting and purification products , Reggio Calabria, Laruffa Editore, 1994.
  • ( IN ) ISO 3520:1998 Oil of bergamot [Citrus aurantium L. subsp. bergamia (Wight et Arnott) Engler], Italian type ISO/TC 54 Essential oils
  • ( IN (Saı̈dani Moufida, Brahim Marzouk, Biochemical characterization of blood orange, sweet orange, lemon, bergamot and bitter orange , in Phytochemistry , vol. 62, n. 8, 2003, pp. 1283–1289, DOI: 10.1016/S0031-9422(02)00631-3 .
  • ( IN ) Carlo Mangiola, Enrico Postorino, Francesco Gionfriddo, Maurizio Catalfamo, Renato Manganaro and Giuseppe Calabrò, Evaluation of the Genuineness of Cold-pressed Bergamot Oil , in Perfumer & Flavorist , October 2009, pp. 26-31.
  • Alp kunkar e ennio kunkar, Bergamot and its essences , editions to Z.
  • A. Kunkar, C. Kunkar, V. CUM, Extraction with supercritical carbon dioxide of the essential oil of ” Citrus Bergamia, Risso “. Eskisehir – Turkey 5 – 19 May 1991, 9 ° Symposio sulline piante aromatiche e medicinali.

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