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Ferula gummosa Boiss. - Apiaceae - syn. Ferula galbaniflua Boiss. & Buhse; galbanum, **Galbanum**

Native perennial plant of western Asia (Iran).

"Galbanum is an aromatic gum resin, the product of certain umbelliferous Persian plant species, chiefly Ferula gummosa (synonym F. galbaniflua) and Ferula rubricaulis. Galbanum-yielding plants grow plentifully on the slopes of the mountain ranges of northern Iran." [[http://en.wikipedia.org/wiki/Galbanum]]

2-Methoxy-3-isobutyl pyrazine (with its green bell-pepper like odor) was discovered in galbanum oil. \\
[Characterisation of pyrazines in galbanum oil., Bramwell, A.F., Burrell, J.W.K., Riezebos, G., Tetrahedron Letters, 10(37), 3215-3216, 1969]

A series of powerful smelling thio-esters like S-sec-butyl-3-methylbutanethioate, S-sec-butyl-3-methylbut-2-enethioate, S-iso-propyl-3-methylbutanethioate, and S-iso-propyl-3-methylbut-2-enethioate were found in galbanum. \\
[Burrell, J. W. K., et al. "Characterisation of thiol esters in galbanum oil." Tetrahedron Letters 12.30 (1971): 2837-2838]

"The earth is removed around the hypocotyl to gain access to the rhizome. The rhizome is traditionally incised on a length of 3-5 cm with a special iron cutting tool locally forged. Within a few minutes, droplets of a
white resin start to form along the cut, solidifying within a few hours... The resin is collected 4-7 days after the incision, with the help of a forged iron tool formed like a spoon. The already existing cut is reincised, and the newly formed resin is collected one week later. The procedure is repeated a third time, rarely a fourth time. The yield of resin is growing with the number of incisions. In average, every plant gives approximately 20 g per season. One ton of galbanum is thus gained from 50.000 individual plants, and 150.000 incisions... \\
On storage, an essential oil separates from galbanum. This essential oil was separately investigated in samples from 100% pure galbanum. The essential oil is sometimes added to commercial lots of galbanum to 'ameliorate' the quality, even though this measure will lead to a shift in phytochemical parameters. Within the oil, an inversion of the percentage of δ-3-carene and ß-pinene relative to the resin is observed, together with an almost complete lack of undecatrienes (0.07%). Undecatrienes are a major constituent of galbanum. In our screening, we found plant populations where the contents of undecatrienes reached up to 4.2 percent... \\
An intriguing result of our analyses was the distinct difference between the composition of the resin from galbanum from strictly identified plants, and the specifications for galbanum laid down by the AFNOR. The
differences found for the contents of α-pinene, ß-pinene, δ-3-carene and undecatrienes point to a certain percentage of resin of foreign Ferula species in the official specification." \\
[Ferula gummosa: Phytochemical variability in Iran. Michael Thomsen, Mathias Schmidt , Georges Betti, Hervé Casabianca, Reza Omidbai. Poster from the International Congress on Natural Products Research, Phoenix (USA), July 31 - August 4, 2004] {{:posterferulagumosa.pdf|}} \\

{{:3e5zundecatrien.jpg}} (E,Z)-1,3,5-undecatriene = (3E,5Z)-galbanolene (intense green galbanum odor)

"A total of 22 components have been identified in the (essential) oil, representing 97.1% of the total oil. The main group was monoterpene hydrocarbons (88.4%) including sabinene (40.1%), α-pinene (14.3%), and β-pinene (14.1%). Moreover the other main components of this oil were p-cymene (8.5%) and α-thujene (8.1%). The oil contained a lower percentage of limonene (2.2%), terpinene-4-ol (1.5%), myrtenal (1.3%) and γ-terpinene (1.1%)." \\
[Composition and antimicrobial activity of oleogumresin of Ferula gumosa Bioss. essential oil using Alamar Blue(TM), D. Abedi, M. Jalali, G. Asghari and N. Sadeghi, Research in Pharmaceutical Sciences, Vol.3(1), 2008, 41-45] 

"Galbanum oil is composed of monoterpenes in large amounts and pyrazines in small amounts. Although the monoterpenes are the main components of galbanum oil, they hardly contribute to the distinct galbanum aroma. The scanty amounts of pyrazines, in contrast, contribute significantly to the aroma. Considering the complexity and potency of the odor, the essential oil was assumed to contain so far not identified compounds with high odor contribution. By the gas chromatography-mass spectrometry-olfactometry (GC-MS-O) analysis of galbanum oil, fruity-green-balsamic notes were detected at two different retention times. The mass spectra (MS) of the newly discovered notes were elucidated by conducting multidimensional (MD) GC-MS-O. By analyzing the MS data, six chemical structures were proposed: (6E/Z,8E)-undeca-6,8,10-trien-2-one, (6E/Z,8E)-undeca-6,8,10-trien-3-one, and (6E/Z,8E)-undeca-6,8,10-trien-4-one. The compounds were then synthesized in an attempt to match the MS, retention indices (RI), and odor qualities. The MD-GC-MS-O analyses of the candidate compounds led to the identification of the novel key aroma compounds (6Z,8E)-undeca-6,8,10-trien-3-one and (6Z,8E)-undeca-6,8,10-trien-4-one in galbanum oil." \\

| {{:undeca-6_8_10-trien-3-one_6z8e.jpg|}} \\ (6Z,8E)-Undeca-6,8,10-trien-3-one \\ ([[http://www.thegoodscentscompany.com/data/rw1603311.html|yuzunone]]) | {{:undeca-6_8_10-trien-4-one_6z8e.jpg|}} \\ (6Z,8E)-Undeca-6,8,10-trien-4-one | {{:2-isobutyl-3-methoxypyrazine.jpg|}} \\ 2-isobutyl-3-methoxypyrazine |

(6Z,8E)-Undeca-6,8,10-trien-3-one and (6Z,8E)-undeca-6,8,10-trien-4-one have fairly low thresholds in water of 0.010 ppb and 0.072 ppb respectively. These compounds are key aroma compounds (fruity green balsamic) in galbanum oil. \\
[Novel key aroma components of galbanum oil., Miyazawa, N., Nakanishi, A., Tomita, N., Ohkubo, Y., Maeda, T., Fujita, A., Journal of agricultural and food chemistry, Vol.57(4), 2009, 1433-1439] [[https://home.zhaw.ch/~yere/pdf/Teil106%20-%20Expression%20of%20Multidisciplinary.pdf]]

"The chemical composition of oleo-gum-resin from Ferula gummosa collected in the northern part of Iran has been studied. The fraction of oleo-gum-resin soluble in ethanol (ca 67 wt.%) is composed by three major fractions: (i) monoterpenes and monoterpenoids (ca 15 wt.% fraction), (ii) sesquiterpenes and sesquiterpenoids (ca 30 wt.%) and (iii) triterpenes and triterpenoids (ca 55 wt.%)... Almost 25 wt.% of oleo-gum-resin was insoluble in ethanol and, according to wet chemistry analyses, assigned to arabinogalactane structurally associated with protein complex (AGP)." \\
[Jalali, H. T., Ebrahimian, Z. J., Evtuguin, D. V., Pascoal Neto, C., Chemical composition of oleo-gum-resin from// Ferula gummosa//. Industrial Crops and Products, 2011, 33(2), 549-553]

"Among the sesquiterpenoid constituents of the essential oil (from the resin) are the woody-balsamic smelling alcohols (+)-bulnesol, (+)-guai-9-en-11ol, (-)-guaiol, and the tricyclic ether epiligulyl oxide..." The odor character of galbanum oil is, however, not determined by these compounds but by a (5E/5Z)-mixture of 1,3,5-undecatriene, known as galbanolenes. The pure (3E,5Z) isomer has an intense galbanum odor, the other (3E,3E) has a fatty note reminiscent of linseed and cod-liver oil... Also present are 2-isobutyl-3-methoxypyrazine (with an aroma of green bell pepper) and 2-sec-butyl-3-methoxy pyrazine (recalls green peas). Both belong to the group of the strongest smelling organic compounds with odor tresholds in the range of 2ng/l water. Kaiser and Lamparsky discovered musky, woody, cedary and floral smelling macrolides in traces (0.06%), main components are (-)-(13R)-13-tetradecanolide (0.03%; woody, cedary, slightly musky) and (-)-(15R)-15-hexadecanolide (0.02%; musky, floral). \\
[Scent and Chemistry, Günther Ohloff, Wilhelm Pickenhagen, Philip Kraft, Wiley-VCH, 2012, 307-309] 

{{:ferula_gummosa.jpg?600}} \\
Ferula gummosa as Ferula galbaniflua \\
Köhler, F.E., Medizinal Pflanzen, vol.2 t.153 (1890) \\
[[http://plantgenera.org/species.php?id_species=432398]]