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Progress in Essential Oils: Spanish Marjoram Oil

Mar 27th, 2017

Brian M. Lawrence

Spanish marjoram is produced from Thymus mastichina L. an endemic Lamiaceae species of the Iberian Peninsula. It is both cultivated and collected from its natural habitat from which oil is produced in Spain and Portugal. It is estimated that ca. 15 metric tonnes of oil are produced annually. The unequivocally characterized constituents of this oil that have been reported in the previous reviews (Lawrence, 1980, 1993, 2001, 2004 and 2012), which are listed in elution order from a non-polar capillary GC column are as follows:

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tricyclene (<0.1−0.3%)

α-thujene (<0.1−2.4%)

α-pinene (0.9−6.8%) (1.0−4.5%)^a

camphene (0.1−6.6%)

sabinene (0.2−4.7%)

β-pinene (1.0−5.9%) (2.0–5.0%)^a

myrcene (0.1−3.1%)

α-terpinene (0.1−1.3%)

p-cymene (0.1−3.4%)

limonene (0.2−6.4%) (1.0−6.0%)^a

1,8-cineole (24.8−76.5%) (30.0−68.0%)^a

(Z)-β-ocimene (<0.1−0.9%)

(E)-β-ocimene (0.1−2.8%)

γ-terpinene (<0.1−2.2%)

cis-sabinene hydrate (0.1−3.0%)

cis-linalool oxide^f (<0.1−0.8%)

terpinolene (<0.1−0.8%)

trans-linalool oxide^f (<0.1−0.8%)

linalool (0.4−24.0%) (3.0−48.0%)^a

trans-sabinene hydrate (<0.1−0.5%)

trans-pinocarveol (<0.1–1.9%)

camphor (0.1−11.0%) (0.1−2.0%)^a

pinocarvone (<0.1−0.3%)

δ-terpineol (<0.1−3.3%) (0.2−2.0%)^a

borneol (0.1−6.5%) (0.1−1.8%)^a

terpinen-4-ol (0.1−3.5%) (0.2−1.2%)^a

α-terpineol (1.0−8.0%)

myrtenal (<0.1−0.2%)

citronellol (<0.1−0.2%)

geraniol (<0.1−1.3%)

linalyl acetate (<0.1−3.9%) (0.2−4.0%)^a

bornyl acetate (<0.1−3.0%)

thymol (<0.1−1.9%)

carvacrol (<0.1−0.5%)

α-terpinyl acetate (<0.1−3.2%)

geranyl acetate (0.1−1.3%)

β-bourbonene (<0.1−0.3%)

β-caryophyllene (0.1−2.9%) (0.5−1.5%)^a

α-humulene (<0.1−0.1%)

allo-aromadendrene (<0.1−0.2%)

germacrene D (<0.1−0.9%)

bicyclogermacrene (<0.1−1.1%)

γ-cadinene (<0.1−0.6%)

δ-cadinene (<0.1−0.3%)

elemol (0.1−3.1%)

spathulenol (<0.1−0.5%)

caryophyllene oxide (0.1−0.6%)

viridiflorol (<0.1−1.1%)

γ-eudesmol (<0.1−0.4%)

T-cadinol (<0.1−0.7%)

β-eudesmol (<0.1−0.9%)

α-eudesmol (<0.1−0.9%)

α-cadinol (<0.1−0.1%)

intermedeol (<0.1−0.9%)

^f= furanoid form

^a = ISO 4728-2003 values

Aerial parts of T. mastichina were collected in the vicinity of Trás-os-Montes (Portugal) during its vegetative stage. Hydrodistillation of the fresh plant material for 4 hr was used to produce an oil in 1.3% yield. Analysis of this oil by Miguel et al. (2004) using GC-FID and GC/MS resulted in the composition being determined as follows:

tricyclene (0.1%)

α-thujene (0.1%)

α-pinene (2.2%)

camphene (0.8%)

sabinene (1.9%)

β-pinene (3.3%)

dehydro-1,8-cineole (0.2%)

myrcene (0.8%)

α-phellandrene (0.1%)

α-terpinene (0.2%)

p-cymene (0.5%)

limonene (10.8%)

1,8-cineole (57.8%)

(Z)-β-ocimene (0.2%)

(E)-β-ocimene (0.8%)

γ-terpinene (0.5%)

cis-sabinene hydrate (0.5%)

terpinolene (0.2%)

linalool (1.8%)

1-octen-3-yl acetate (0.1%)

α-campholenal (0.1%)

camphor (0.2%)

trans-pinocarveol (0.2%)

trans-verbenol (0.1%)

pinocarvone (0.2%)

borneol (2.1%)

terpinen-4-ol (1.1%)

myrtenal (0.1%)

α-terpineol (1.7%)

myrtenol (0.2%)

trans-carveol (0.1%)

bornyl formate (0.1%)

geraniol (0.1%)

bornyl acetate (0.8%)

α-terpinyl acetate (2.4%)

β-caryophyllene (0.3%)

allo-aromadendrene (0.7%)

geranyl propionate (0.1%)

germacrene D (0.3%)

bicyclogermacrene (0.2%)

α-cadinene (0.6%)

caryophyllene oxide (0.2%)

viridiflorol (0.4%)

ledol (0.2%)

geranyl isovalerate (0.2%)

T-cadinol (0.2%)

β-eudesmol (0.3%)

α-eudesmol (0.4%)

Trace amounts (<0.05%) of δ-terpineol and spathulenol were also characterized in this oil.

The main components of nine lab-distillations of the same batch of Spanish M. mastichina plants were determined by Cerpa-Chavez (2007) to range as follows:

α-pinene (4.9−5.3%)

β-pinene (4.3−4.5%)

β-phellandrene^† (3.1−3.6%)

limonene (5.0−5.4%)

1,8-cineole (48.4−52.9%)

(Z)-β-ocimene (2.6−3.0%)

linalool (3.1−3.9%)

α-terpineol (6.5−7.8%)

borneol (3.2−3.8%)

β-caryophyllene (1.5−1.9%)

^†incorrect identification

A commercial oil of Spanish marjoram was screened for its antioxidant and antimicrobial activities by De Martino et al. (2009). Analysis of this oil using GC-FID and GC/MS revealed that it possessed the following composition:

α-thujene (0.1%)

α-pinene (9.0%)

camphene (0.3%)

sabinene (1.1%)

β-pinene (3.8%)

myrcene (0.7%)

α-phellandrene (0.2%)

δ-3-carene (0.3%)

α-terpinene (0.1%)

o-cymene (2.6%)

limonene (6.4%)

p-cymene (0.4%)

1,8-cineole (33.5%)

β-phellandrene (9.1%)

(Z)-β-ocimene (0.1%)

(E)-β-ocimene (0.2%)

γ-terpinene (0.8%)

terpinolene (0.2%)

linalool (9.8%)

trans-pinocarveol (0.1%)

isoborneol (0.1%)

camphor (0.2%)

isopinocamphone (0.2%)

borneol (2.0%)

terpinen-4-ol (0.4%)

dihydrocarveol (0.8%)

p-cymen-8-ol (0.1%)

α-terpineol (0.7%)

myrtenal (0.7%)

methyl chavicol (0.1%)

myrtenol (0.2%)

linalyl acetate (3.3%)

geraniol (0.6%)

bornyl acetate (1.2%)

isobornyl acetate (0.6%)

thymol (0.7%)

carvacrol (4.1%)

α-terpinyl acetate (0.5%)

α-copaene (0.1%)

longifolene^† (0.1%)

β-caryophyllene (0.3%)

β-cedrene^† (0.5%)

α-humulene (0.3%)

γ-gurjunene (0.1%)

bicyclogermacrene (0.1%)

cis-muurola-4(14),5-diene(0.1%)

7-epi-α-selinene (0.1%)

^†incorrect identification

In addition, β-pinene, verbenene, β-thujone, pinocamphone, pinocarvone, myrtenyl acetate, isoledene, β-elemene, aromadendrene and allo-aromadendrene were listed as trace (<0.05%) constituents of this commercial oil.

Oils produced from wild collections of T. mastichina of Spanish and Portuguese origins were reported by Nowak and Ogonowski (2010) to contain similar compositions as shown in T-1.

Mendez-Tovar et al. (2015a) compared the compositions of volatiles produced from Spanish marjoram harvested in full flower using hydrodistillation, micro-distillation and methylene chloride extraction. The results of the comparative analytical results determined by GC-FID and GC/MS are presented in T-2. In addition, trace amounts (<0.1%) of α-phellandrene. (E)-β-ocimene, α-thujone, cis-p-menth-2-en-1-ol α-campholenal, sabina ketone, β-elemene and α-gurjunene were found in the volatiles from the three isolation procedures, while tricyclene was characterized only in the oils.

Mendez-Tovar (2015b) used GC-FID and GC/MS to analyze oils produced from Spanish T. mastichina harvested at full flowering over three different seasons. The oil was found to range in composition as follows:

tricyclene (0−0.11%)

α-thujene (0.04−0.26%)

α-pinene (2.58−3.78%)

camphene (0.05−1.82%)

sabinene (2.36−3.63%)

β-pinene (3.89−5.08%)

myrcene (1.36−2.05%)

α-phellandrene (0−0.13%)

α-terpinene (0.14−0.28%)

p-cymene (0.16−0.51%)

limonene (1.23−6.11%)

1,8-cineole (58.52−68.82%)