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GARLIC OIL

Synonyms: Oil of garlic; Allium Sativum Bulb Oil;    DAS (57%), allylmethyl (37%), and dimethyl (6%) mono- to hexasulfides.Oils, garlic; Allium sativum oil; LS-2444; 

Garlic oil is the volatile oil derived from garlic. It is usually prepared using steam distillation, and can also be produced via distillation using ether. It is used in cooking and as a seasoning, a nutritional supplement, and also as an insecticide.
 

Synonyms:
Oil of garlic; Allium Sativum Bulb Oil;    DAS (57%), allylmethyl (37%), and dimethyl (6%) mono- to hexasulfides.Oils, garlic; Allium sativum oil; LS-2444; Essential oil of garlic; FEMA No. 2503; CCRIS 4049; Garlic oil (Allium sativum L.);Allium Sativum;  garlic, oil (allium sativum l.); Essential oil of garlic; Allium Arenarium bulb oil; Allium Controversum bulb oil; Allium Longicuspis bulb oil; Allium Ophioscorodon bulb oil; Allium Pekinense bulb oil; Allium Sativum (garlic) bulb oil; Allium Sativum bulb oil; Allium sativum oil; Allium Scorodoprasum subsp. Viviparum bulb oil; Allium Scorodoprasum var. Viviparum bulb oil; Allium Xontroversum bulb oil; CCRIS 4049; Cultivated garlic bulb oil; EINECS 232-371-1; Essential oil of garlic; FEMA No. 2503; Garlic oil; Garlic oil (Allium sativum L.); Garlic oil china; Garlic volatile oil; Oil of garlic ; Oil, garlic; Porrum Ophioscorodon bulb oil; Porrum Sativum bulb oil; UNII-4WG8U28833; GARLIC OIL; sarımsak yağı; sarmısak yağı; L'huile d'ail; huile d'ail; garlik oil; GARLİC OİL; SARMISAK YAĞI; SARIMSAK YAĞI; GARLİK; GARLIC; garlik; garlic; yağ; Garlik yağı; oil of Garlic; Garlique oil
 

GARLIC OIL


Garlic oil

Garlic oil is the volatile oil derived from garlic. It is usually prepared using steam distillation, and can also be produced via distillation using ether. It is used in cooking and as a seasoning, a nutritional supplement, and also as an insecticide.

Preparation
Garlic oil is typically prepared using steam distillation, where crushed garlic is steamed with the resultant condensation containing the oil.[1] Garlic oil contains volatile sulfur compounds such as diallyl disulfide, a 60% constituent of the oil.[1][4][5][6] Steam-distilled garlic oil typically has a pungent and disagreeable odor and a brownish-yellow color.[5] Its odor has been attributed to the presence of diallyl disulfide.[5] To produce around 1 gram of pure steam-distilled garlic oil, around 500 grams of garlic is required.[1] Undiluted garlic oil has 900 times the strength of fresh garlic, and 200 times the strength of dehydrated garlic.[5]

Ether can also be used to extract garlic oil.[1] A type of garlic oil involves soaking diced or crushed garlic in vegetable oil, but this is not pure garlic oil; rather it is a garlic-infused oil.[1]

Uses
Garlic oil is used as a nutritional supplement, and is sometimes marketed in the form of capsules, which may be diluted with other ingredients.[1][5] Some commercial preparations are produced with various levels of dilution, such as a preparation that contains 10% garlic oil.[5] Herbal folklore holds that garlic oil has antifungal and antibiotic properties,[2] but there is no clinical research confirming such effects. It is also sold in health food stores as a digestive aid.[7]

It can also be used as an insecticide, diluted with water and sprayed on plants.[2][8]

Stabilized garlic flavor blend is a proprietary mixture of dehydrated garlic powder infused with garlic oil, which increases the flavor of the garlic powder.[9]

Garlic-flavored oil

Garlic-flavored oil: vegetable oil infused with garlic used for seasoning
Garlic-flavored oil is produced and used for cooking and seasoning purposes, and is sometimes used as an ingredient in seasoning mixtures.[1][5] This differs from essential garlic oil, and typically involves the use of chopped, macerated or crushed garlic placed in various vegetable oils to flavor the oil.

See also
Garlic sauce
List of essential oils
List of garlic dishes
Theodor Wertheim – performed studies about garlic oil.


Garlic, Allium sativum, is broadly used around the world for its numerous culinary and medicinal uses. Wild garlic, Allium vineale, has been used as a substitute for garlic, both in food as well as in herbal medicine. The present study investigated the chemical compositions of A. sativum and A. vineale essential oils. The essential oils from the bulbs of A. sativum, cultivated in Spain, were obtained by three different methods: laboratory hydrodistillation, industrial hydrodistillation, and industrial steam distillation. The essential oils of wild-growing A. vineale from north Alabama were obtained by hydrodistillation. The resulting essential oils were analyzed by gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC-MS). Both A. sativum and A. vineale oils were dominated by allyl polysulfides. There were minor quantitative differences between the A. sativum oils owing to the distillation methods employed, as well as differences from previously reported garlic oils from other geographical locations. Allium vineale oil showed a qualitative similarity to Allium ursinum essential oil. The compositions of garlic and wild garlic are consistent with their use as flavoring agents in foods as well as their uses as herbal medicines. However, quantitative differences are likely to affect the flavor and bioactivity profiles of these Allium species.

Keywords: Allium sativum, Allium vineale, essential oil composition, allyl polysulfides, cluster analysis
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1. Introduction
Garlic (Allium sativum L., Amaryllidaceae) likely originated in Central Asia [1]. The plant has been used as a flavoring agent and a traditional medicine since antiquity, and is now cultivated worldwide [1,2]. Allium vineale L. (wild garlic, crow garlic) is native to Great Britain, most of Europe, North Africa, and the Middle East. The plant has been introduced to North America, Australia, and New Zealand [3].

Allium sativum has been used as a diaphoretic, diuretic, expectorant, and stimulant [4]. Extracts of A. sativum have shown broad-spectrum antibacterial [5] and antifungal [6] activity and the plant has been used to treat tuberculosis, coughs, and colds [7]. Garlic preparations have demonstrated hypotensive activity in moderately hypertensive subjects, and garlic-based phytotherapeutic products are used in France for minor vascular disorders [8]. There is an inverse correlation between regular consumption of garlic and stomach cancer frequency [8], but there seems to be no correlation between garlic consumption and other cancers. Garlic has been used in food preparation not only for its flavor, but also as a digestive aid [4]. Allium vineale has been used as a substitute for A. sativum in cooking; the bulb is used as a flavoring agent and the leaves as an addition to salad [9,10]. Cherokee Native Americans used both A. vineale and A. sativum as carminatives, diuretics, and expectorants [11,12].

Although there have been numerous investigations on the phytochemistry of garlic (A. sativum) [1,13,14], the chemistry of wild garlic (A. vineale) has not been investigated, and because of the history of the uses of Allium species as both condiments and phytopharmaceuticals, we have investigated the essential oil compositions of A. sativum from Spain, obtained by different isolation methods, and A. vineale growing wild in north Alabama, USA.

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2. Materials and Methods
2.1. Plant Material
2.1.1. Allium sativum
Bulbs of Allium sativum were collected from a field in Las Pedroñeras, Spain (39°26′59″ N, 2°40′23″ W, 745 m elevation), in December 2015. Garlic bulbs were finely chopped, and were subjected to three different distillation methods: laboratory hydrodistillation using a Clevenger apparatus for 3 h, industrial hydrodistillation for 4 h, and industrial steam distillation for 5 h. Pale yellow essential oils were obtained in 0.2%, 0.22% and 0.18% yields, respectively. The obtained essential oils and hydrosol were separated by decantation; remaining water was removed from the essential oils with sodium chloride. The collected essential oil samples were stored under refrigeration (−4 °C) until analysis.

2.1.2. Allium vineale
Four different samples of Allium vineale were collected from a field in Huntsville, Alabama (34°38′46″ N, 86°33′27″ W, 191 m elevation) on 10 April 2017, 8 a.m. Each sample was cleaned of debris, the entire plant (leaves and bulbs) chopped, and hydrodistilled using a Likens-Nickerson apparatus for 4 h with continuous extraction with dichloromethane (CH2Cl2). Evaporation of the dichloromethane yielded pale yellow essential oils with an extremely pungent odor (Table 1).

Table 1
Essential oil yields of Allium vineale.

Sample    #1 a    #2    #3    #4
Mass of plant material (g)    94.04    123.29    98.20    72.35
Mass of essential oil (mg)    87.2    258.5    210.5    25.3
Essential oil yield    0.0927%    0.2097%    0.2144%    0.0350%
a #1, #2, #3, and #4 are different essential oil samples.

2.2. Gas Chromatography-Mass Spectrometry (GC-MS)
GC-MS characterization of A. sativum oils was carried out as previously described using a Shimadzu GCMS-QP2010 Ultra (Shimadzu Scientific Instruments, Columbia, MD, USA) [15,16]. This instrument was operated in the electron impact (EI) mode set at electron energy 70 eV with a scan range of 40–400 amu, a scan rate of 3.0 scans per second, and with GC-MS solution software. A ZB-5 fused silica capillary column (Phenomenex, Torrance, CA, USA), 30 m length × 0.25 mm inner diameter, with a (5% phenyl)-polymethylsiloxane stationary phase and a film thickness of 0.25 μm was used as the GC column. Helium was used as the carrier gas and the pressure was set at 551.6 kPa with a flow rate of 1.37 mL/min on the column head. The temperature of the injector was set at 250 °C and the temperature of the ion source was set at 200 °C. The temperature of the GC oven was programmed to be 50 °C initially and was programmed to increase at a rate of 2 °C/min to a final temperature of 260 °C. The samples were prepared with CH2Cl2 in a 5% w/v solution. Then, 0.1 µL of the solutions were injected into the instrument with a split ratio of 30:1.

GC-MS analysis of A. vineale oils was carried out as previously described [17]: Agilent 6890 GC (Agilent Technologies, Santa Clara, CA, USA), Agilent 5973 mass selective detector (Agilent Technologies), EI mode (70 eV), 40–400 mass scan range, 3.99 scans/s scan rate, and operated through an Agilent ChemStation data system (G1701CA, Agilent Technologies); HP-5ms capillary column (30 m length × 0.25 mm inner diameter × 0.25 μm film thickness), helium carrier gas, head pressure (92.4 kPa), flow rate (1.5 mL/min); oven temperature program (60 °C initial temperature, which was held for 5 min, temperature increased at a rate of 3 °C/min up to 280 °C), inlet temperature (250 °C), interface temperature (280 °C). Allium vineale solutions (1 μL of 1% in CH2Cl2) were injected using a splitless mode.

The retention indices were determined by reference to a homologous series of n-alkanes. The components of each essential oil sample were identified based on their retention indices and mass spectral fragmentation patterns compared to reference literature [18,19,20,21,22] and our in-house library.

2.3. Semi-Quantitative Gas Chromatography
Semi-quantitative GC was performed with an Agilent 6890 GC with Agilent FID (flame ionization detector) (Agilent Technologies), HP-5ms column (30 m length × 0.25 mm inner diameter × 0.25 μm film thickness), He carrier gas, head pressure (144.1 kPa), flow rate (2.0 mL/min); oven temperature program (as above). The percent compositions of the essential oils were determined from raw peak area percentages without standardization.

2.4. Hierarchical Cluster Analysis
The chemical compositions of A. sativum from this current study along with garlic oil compositions from previously published works (hydrodistillations and steam distillations only) [6,23,24,25,26,27,28,29,30] were used as operational taxonomic units (OTUs). The percentages of the major sulfur-containing compounds (diallyl sulfide, allyl methyl disulfide, dimethyl trisulfide, diallyl disulfide, allyl (Z)-1-propenyl disulfide, allyl (E)-1-propenyl disulfide, allyl methyl trisulfide, 2-vinyl-4H-1,3-dithiine, diallyl trisulfide, and diallyl tetrasulfide) were used to evaluate the chemical similarities and differences between the garlic oil samples by agglomerative hierarchical cluster (AHC) analysis using the XLSTAT software, version 2015.4.01 (Addinsoft™, New York, NY, USA). Pearson correlation was used to evaluate similarity and clusters were defined by the unweighted pair-group method with arithmetic averaging (UPGMA).
The oil compositions from this study show quantitative similarities and differences from previously published reports on garlic oil [6,23,24,25,26,27,28,29,30]. Egyptian garlic essential oil extracted by hydrodistillation had diallyl disulfide (25.2%), allyl methyl trisulfide (23.8%) and diallyl trisulfide (21.1%) as the major constituents [29]. The major components of Serbian garlic essential oil obtained by hydrodistillation were diallyl trisulfide (33.6%), diallyl disulfide (28.1%), and allyl methyl trisulfide (17.8%) [26]. Diallyl disulfide (49.1%) and diallyl trisulfide (30.4%) were the main components of Tunisian garlic essential oil obtained by hydrodistillation [31]. The profile identified in this study was also different from French garlic oil presented by Mnayer et al. [27] in which the major components were diallyl disulfide (37.9%), diallyl trisulfide (28.1%), allyl methyl trisulfide (7.3%), diallyl sulfide (6.6%), diallyl tetrasulfide (4.1%) and allyl methyl disulfide (3.7%). Douiri et al. [23] showed that A. sativum essential oil obtained by Clevenger hydrodistillation was dominated by diallyl trisulfide (46.5%) followed by diallyl disulfide (16.0%), allyl methyl trisulfide (10.9%) and diallyl disulfide (7.2%). Similarly, Rao and co-workers have analyzed six geographical varieties of essential oils obtained by steam distillation of fresh garlic grown in India. These investigators found diallyl disulfide (27.1–46.8%) and diallyl trisulfide (19.9–34.1%) to be the dominant components, followed by allyl methyl trisulfide (8.3–18.2%), and allyl methyl disulfide (4.4–12.0%) [28]. Commercial Chinese garlic oil has shown abundant diallyl disulfide (45.1–63.2%), diallyl trisulfide (18.5–23.4%), diallyl sulfide (4.5–11.4%), and diallyl tetrasulfide (6.3–10.5%) (unpublished results from our laboratories). Kimbaris and co-workers obtained garlic oil from Greece (Likens-Nickerson hydrodistillation-extraction) and found diallyl disulfide (23.1–28.4%), diallyl trisulfide (18.2–22.1%), allyl methyl trisulfide (16.3–17.5%), and allyl methyl disulfide (8.5–11.2%)

The essential oils of garlic and wild garlic are shown to be dominated by sulfur-containing compounds, particularly allyl polysulfides. Garlic oils from various geographical locations have shown qualitative similarities, but quantitative differences in the concentrations of organosulfur compounds, and are likely to affect both the medicinal and the organoleptic properties of the garlic. Wild garlic is qualitatively similar in composition to garlic, but there are some key differences: diallyl disulfide and diallyl trisulfide concentrations are higher in garlic than in wild garlic, while allyl 1-propenyl disulfide and dimethyl trisulfide concentrations are higher in wild garlic than in garlic.


Allium  sativum is  one of  the  medicinal herbs  placed  in  the family  Alliaceae1.  The  important  chemical  constituents reported from Bulbus Allii Sativi are the  sulfur  compounds. The allicin, ajoenes and sulfides (e.g. diallyl disulfide, diallyl trisulfide), are not naturally  occurring  compounds.  They are formed by naturally occurring alliin. When the garlic bulb is crushed,  alliin  is  released  and  interacts  with  the  enzyme alliinase  to  forms  allicin.2,3  Allicin  itself  is  an  unstable product  and  undergo  additional  reactions  to  form  different derivatives, depending on environmental conditions.4 Due to presence of compounds  such  as, sulfur's  compounds, lipids, complex  of  fructosans,  etheric  oil,  cellulose,  minerals  (Mg, Zn,  Se,  germanium),  vitamins  (C,  A,  from  B  complex), enzymes,  amino  acids,  etc., it  is  particularly  important  in medicine.5  The  presence  of  above chemicals  in  Garlic  helps to inhibit bacteria, fungi, parasites. Cooked garlic  or  various aged  extracts  and  oils  can  in  some  cases  provide  better protection against infection than  raw  garlic.6 Garlic extracts exhibited  activity  against  gram  negative  (E.  coli, Enterobacter,  Pseudomonas,  Kilabsella)  and  gram  positive (S.aureus,  S.  Pneumonia,  Group  A  Streptococcus  and Bacillus  anthrax).


Molecular Weight of Garlic oil:    488.9 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of Garlic oil:    0    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of Garlic oil:    8    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of Garlic oil:    16    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of Garlic oil:    488.049814 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of Garlic oil:    488.049814 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of Garlic oil:    188 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of Garlic oil:    26    Computed by PubChem
Formal Charge of Garlic oil:    0    Computed by PubChem
Complexity of Garlic oil:    243    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of Garlic oil:    0    Computed by PubChem
Defined Atom Stereocenter Count of Garlic oil:    0    Computed by PubChem
Undefined Atom Stereocenter Count of Garlic oil:    1    Computed by PubChem
Defined Bond Stereocenter Count of Garlic oil:    0    Computed by PubChem
Undefined Bond Stereocenter Count of Garlic oil:    0    Computed by PubChem
Covalently-Bonded Unit Count of Garlic oil:    3    Computed by PubChem
Compound  of Garlic oil Is Canonicalized    Yes

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