Grasas y Aceites, Vol 69, No 3 (2018)

Identification of tetrahydrogeranylgeraniol and dihydrogeranylgeraniol in extra virgin olive oil

C. Mariani , Italy

S. Cesa
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Italy

C. Ingallina
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma, Italy

L. Mannina
Dipartimento di Chimica e Tecnologie del Farmaco, Sapienza Università di Roma - Istituto di Metodologie Chimiche, CNR, Laboratorio di Risonanza Magnetica “Annalaura Segre”, Italy


Olive oil contains many different compounds which are responsible for its nutritional and sensorial value. However, some compounds present in olive oil at very low amounts have not yet been identified. Here, the detection of tetrahydrogeranylgeraniol and dihydrogeranylgeraniol, in both the total aliphatic alcohol and waxy fractions of extra virgin olive oil, is reported for the first time using GC and GC-MS methodologies. It was suggested that tetrahydrogeranylgeraniol and dihydrogeranylgeraniol do not originate from the hydrolysis of the chlorophyll but are present as diterpenic esters.


Dihydrogeranylgeraniol; Diterpenic esters; GC; GC-MS; Olive oils; Tetrahydrogeranylgeraniol

Full Text:



Aparicio R, Aparicio-Ruíz R. 2000. Authentication of vegetables oils by Chromatographic Techniques. J. Chromatog. A 881, 93–104.

Artho A, Grob K, Mariani C. 1993. On-line LC-GC for the analysis of the minor components in edible oils and fats - the direct method involving silylation. Fat Sci. Technol. 95, 176–180.

Biedermann M, Haase-Aschoff P, Grob K. 2008. Wax ester fraction of edible oils: Analysis by on-line LC-GC-MS and GCxGC-FID. Eur. J. Lipid Sci. Technol. 110, 1084–1094.

Bonaga G, Capella P. 1997. Manuale degli Oli e dei Grassi, in Cappella P, Fedeli E, Bonaga G, Lercker G (Eds.). Tecniche Nuove, Milano, p. 37.

Boskou D, Blekas G, Tsimidou M. 2006. Olive oil composition, in Boskou D (Ed.) Olive oil: chemistry and technology, 2nd ed. A.O.C.S. press, Champaign, p. 46.

Butinar B, Bucar-Miklavcic M, Mariani C, Raspor P. 2011. New Vitamin E isomers (gamma tocomonoenol and alpha tocomonoenol) in seeds and roasted seed oil from the Slovenian pumpkin variety “Slovenska golica”. Food Chem. 128, 505–512.

Capella P, Fedeli E, Bonaga G, Lercker G. 1997. Gli alcoli triterpenici e diterpenici in Tecniche nuove (Ed.) Manuale degli Oli e dei Grassi. Milano, pp. 2-37-2-38.

Gasparoli A, Mariani C. 2016. Sulla determinazione dei tocoferoli, tocomonoenoli, tocodienoli, tocotrienoli e loro esteri negli oli vegetali. Riv. Ital. Sostanze Grasse 93, 77–94.

Grob K, Mariani C, Lanfranchi M, Artho A, Biedermann M. 1993. Analisys of lipids by on-line coupled liquid chromatography-gas chromatography, in Mukherjee KD, Weber N, Sherma J (Eds.) CRC Handbook of Chromatography. CRC press, Inc., Boca Raton, pp. 71–82.

Grob K, Mariani C. 1994. LC-GC methods for the determination of adulterated edible oils and fats, in Tyman JHP, Gordon MH. (Eds.) Developments in the analysis of lipids, 1st ed. RSC, Cambridge, pp. 73–81.

International Olive Oil Council T20/Doc26/Rev1. 2015. Determination of aliphatic alcohols content by capillary gas chromatography.

Johansson A. 1979. The content and composition of sterol and sterol esters in sunflower and poppy seed oils. Lipids 14, 285–291.

León-Camacho M, Morales MT, Aparicio R. 2013. Chromatographic methodologies: Compounds for Olive oil traceability issue, in Aparicio R, Harwood J (Eds.) Handbook of Olive Oils-Analysis and Properties, 2nd ed., Springer, New York, pp. 163–218.

Mariani C, Fedeli E, Grob K, Artho A. 1991. Indagine sulle variazioni dei componenti minori liberi ed esterificati di oli ottenuti da olive in funzione della maturazione e dello stoccaggio. Riv. Ital. Sostanze Grasse 68, 178–187.

Mariani C, Fedeli E, Grob K. 1991. Valutazione dei componenti minori liberi ed esterificati nelle sostanze grasse. Riv. Ital. Sostanze Grasse 68, 233–242.

Mariani C, Venturini S, Bondioli P, Fedeli E, Grob K. 1992. Valutazione delle variazioni indotte dalla decolorazione sui principali component minori liberi ed esterificati negli oli di olive. Riv. Ital. Sostanze Grasse 69, 393–392.

Mariani C, Bellan G. 1996. Sulla presenza di tocoferoli, deidrotocoferoli, tocodienoli, tocotrienoli negli oli vegetali. Riv. Ital. Sostanze Grasse 73, 533–543.

Mariani C, Bellan G. 1997. Sulla presenza dei derivati dei tocoferoli negli oli vegetali. Riv. Ital. Sostanze Grasse 74, 545–557.

Mariani C, Venturini S. 2002. Sulla struttura delle cere degli oli di oliva. Riv. Ital. Sostanze Grasse 79, 49–57.

Mariani C, Venturini S. 2003. Sulla struttura apolare degli esteri lineari presenti nella frazione apolare dell’olio di Soia. Riv. Ital. Sostanze Grasse 80, 1–6.

Mariani C. 2017a. Sull’analisi degli steroli e degli idrocarburi steroidei nell’olio di Girasole ad alto contenuto di acido oleico. Riv. Ital. Sostanze Grasse 94, 219–229.

Mariani C. 2017b. Sulla determinazione delle cere negli oli extra vergini della varietà Arbequina prodotta in Argentina. Riv. Ital. Sostanze Grasse 94, 139–147.

Mariani C. submitted. Identificazione di nuovi componenti negli oli extra Vergini di Oliva. Nota 1, Riv. Ital. Sostanze Grasse.

Mizouguchi T, Isaji M, Harada J, Watabe K, Tamiaki H. 2009. Structural determination of the ?2, 10-phytadienyl substituent in the 17-propionate of bacteriochlorophyll-b from Halorhodospira halochloris. J. Porphyrins Phthalocyanines 13, 41–50.

Nestola M, Schmidt TC. 2016. Fully automated determination of the sterol composition and total content in edible oils and fats by online liquid chromatography-gas chromatography-flame ionization detection, J. Chromatog. A 9, 136– 143.

Olofsson P, Hultqvist M, Holmdahl, R. 2011. Phytol as a Cholesterol lowering agent. US 2011/0015278 A1.

Reiter B, Lorbeer E. 2001. Analysis of the wax esters fraction of Olive oil and Sunflower oil by Gas Chromatography and Gas Chromatography Mass-spectrometry. J. Am. Oil Chem. Soc. 78, 881–888.

Schoch S, Schafer W. 1978. Tetrahydrogeranylgeraniol, a Precursor of Phytol in the Biosynthesis of Chlorophyll a — Localization of the Double Bonds. Z. Naturforsch. 33C, 408–412.

Soulier J, Farines M. 1992. Insaponifiable, in Karleskind A (Ed.) Manuel des Corps Gras, vol. 1. Ed. Tecnique et documentation Lavoisier, Paris, p. 107.

Copyright (c) 2018 Consejo Superior de Investigaciones Científicas (CSIC)

Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

Contact us

Technical support