Tetradecanal Synthesis Essay

Introduction

Microwave heating has an incontestable place in analytical and organic laboratory practices as a very effective and non-polluting method of activation. There are numerous examples of applications of this technology in sample digestion, organic synthesis, analytical chemistry and the food industry [1,2,3,4,5,6,7,8]. Microwave energy, with a frequency of 2.45 GHz, is well known to have a significant effect on the rates of a variety of processes. The number of reported applications, especially in the food industry, is increasing rapidly [4,5,6,8]. The main reason for this increased interest lies in the much shorter operation times achievable. Microwave–assisted extraction of natural compounds is also an alternative to conventional techniques. Essential oils are among the products which have been extracted efficiently from a variety of matrices by this method, and many microwave-assisted essential oil extractions from several plants and subsequent product analyses have been reported [9,10,11,12,13,14,15]. However, no such report was found for Cinnamomum iners, a plant in the Cinnamomum genus. This is a large genus, belonging to the family Lauraceae, many species of which yield an essential oil upon distillation [16]. The composition of the oil, and its value and uses to which it is put depend very much on the species that is distilled, as well as the part of the plant which is utilized. The Cinnamomum genus comprises several hundred species which occur naturally in Asia. C. iners is one such species widespread throughout Southest Asia. Known as ‘Ob Chuei’ in Thai, this plant grows mostly in the northern part of Thailand. Its leaves are traditionally used as an analgesic and antipyretic [17].

A number of papers are available reporting both bioassays and component analysis of Cinnamomum in naturally occurring samples. Antifungal properties of essential oils from eleven species of Cinnamomum were reported, viz C. camphora, C. iners, C. microphyllum, C. mollisimum, C. porectum, C. pubescens, C. rhyncophyllum, C. scortechinii, C. sintoc, C. suvabenium and C. zeylanicum [18]. Amylase inhibitor properties were reported for C. cassia Blume, C. zeylanicum Nees, C. obtusifolium Nees, C. sieboldii Meisn, C. burmanni Blume and C. iners Reinw. ex Blume [19]. The chemical components of the leaf, bark and wood oils of seven Malaysian Cinnamomum species were analyzed using GC-MS and selective proton NMR [20]. Our literature search revealed one study of C. iners Reinw. oil from India reporting 1,8-cineole as a major component (40 %), but this oil was obtained from stem bark [21]. The objective of the work described in this communication was to investigate the components and antioxidant activity of the essential oil from the leaves of C. iners obtained by microwave-assisted hydrodistillation, as compared with the normal hydrodistillation.

Results and Discussion

The extraction time of 30 min with microwave-assisted hydrodistillation using 800 W of microwave power provided the same yield of oil (0.12 %) as that obtained after a 5-hour normal hydrodistillation. The compositions of the oils from both methods were analyzed using GC/MS. Both oils were rich in linalool (ca. 35-50 %). Identification of all components was performed by a comparison of their mass spectra with literature data (NIST and WILEY) and by comparison of their retention indices (RI) with those in the literature [22,23]. The gas chromatograms of the essential oils from both methods are presented in Figure 1 and Figure 2, and Table 1 lists the identified components of the oils. The most prominent components found (conventional/microwaved) were linalool (35.56/50.48 %), caryophyllene oxide (6.61/0.86 %), cadinol (6.65/3.37 %), α-cadinol (5.86/3.44 %), delta-cadinene (4.36/3.54 %), viridiflorol (3.87/3.06 %), unidentified (3.58/2.98 %), and caryophyllene (2.83/1.54 %). It can be seen that most of these components and a few more were obtained in smaller amounts in the microwaved oil, compared with the conventional oil. Furthermore, a few other minor components present in the normal oil were missing altogether in the microwaved oil. On the other hand, there were some minor constituents which appeared only in the microwaved oil.

A possible reason for these minor differences may be the different heat sources used in the two methods. It is known that a microwaved solution is sometimes superheated, with the temperature of the solution being as much as 20 degress higher than normal. This occurs also when tap water is used instead of distilled water [24], as was the case in this present work. Thus, those oil components that are less heat stable, e.g. caryophyllene oxide, might have undergone some decomposition to other compounds not present in the conventional oil.

Figure 1. Gas chromatogram of the hydrodistillate essential oil of C. iners leaves. See Experimental for GC conditions and Table 1 for peak identification.

Figure 1. Gas chromatogram of the hydrodistillate essential oil of C. iners leaves. See Experimental for GC conditions and Table 1 for peak identification.

Figure 2. Gas chromatogram of the microwave-assisted hydrodistillate essential oil of C. iners leaves. See Experimental for GC conditions and Table 1 for peak identification.

Figure 2. Gas chromatogram of the microwave-assisted hydrodistillate essential oil of C. iners leaves. See Experimental for GC conditions and Table 1 for peak identification.

Table 1. Volatile components in leaves of C. iners.

Peak No.Kovát Retention IndexCompounds% Area
HydrodistillationMicrowave-assisted
1-cis-linalool oxide0.22-
2-trans-linaool oxide0.53-
31103linalool36.9055.27
41176borneol L0.521.02
51186terpinen-4-ol0.190.14
61198alpha-terpineol1.500.91
712322,6-octadien-1-ol-0.12
81258geraniol0.370.25
91261propanoic acid-0.17
101291(-)-bornyl acetate0.601.08
111343cyclohexene-0.17
1213623-allyl-6-methoxyphenol-1.29
131382alpha-copaene1.321.19
141396beta-elemene2.321.82
151410dodecanal0.821.51
161420cis-alpha-bergamotene0.460.30
171427caryophyllene2.941.69
181446(+)-aromadendrene0.45-
1914482-propen-1-ol-0.22
201460alpha-humulene
 
octanoic acid
caprilyc acid
 
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Category: flavor and fragrance agents
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Appearance: colorless to pale yellow clear oily liquid to solid (est)
Assay: 98.00 to 100.00 % 
Iodine Value:
Food Chemicals Codex Listed: Yes
Specific Gravity: 0.89300 to 0.92200 @  25.00 °C.
Pounds per Gallon - (est).: 7.431 to  7.672
Melting Point: 16.00 to  17.00 °C. @ 760.00 mm Hg
Boiling Point: 237.00 to  239.00 °C. @ 760.00 mm Hg
Vapor Pressure: 0.022000 mm/Hg @ 25.00 °C. (est)
Vapor Density: 4.9 ( Air = 1 )
Flash Point: > 230.00 °F. TCC ( > 110.00 °C. )
logP (o/w): 3.050
Shelf Life: 24.00 month(s) or longer if stored properly.
Storage: store in cool, dry place in tightly sealed containers, protected from heat and light.
Soluble in:
 alcohol
 water, 789 mg/L @ 30 °C (exp)
Insoluble in:
 water
Odor Type: fatty
Odor Strength: medium
 fatty  waxy  rancid  oily  vegetable  cheesy  
Odor Description:
at 100.00 %. 
fatty waxy rancid oily vegetable cheesy
Luebke, William tgsc, (1988)
 rancid  soapy  cheesy  fatty  brandy  
Taste Description:
rancid soapy cheesy fatty brandy
Substantivity: 400 Hour(s)
  
Acme Synthetic Chemicals
Caprylic Acid
Acme-Hardesty
Caprylic Acid
Odor: characteristic
Use: Intermediate, Activator / Accelerator, Synthetic Lubricants, Solubilizer for Mineral Oils, Anionic and Nonionic Surfactants.
Advanced Biotech
CAPRYLIC ACID NATURAL
Advanced Biotech
CAPRYLIC ACID SYNTHETIC
Alfrebro
CAPRYLIC ACID (Octanoic acid) NATURAL
Odor: Unpleasant, Oily, Fatty, Rancid
Apiscent Labs
OCTANOIC ACID (CAPRYLIC ACID) NATURAL
Odor: Musty, unpleasant
Astral Extracts
Caprylic Acid
Aurochemicals
CAPRYLIC ACID, Natural
Axxence Aromatic
CAPRYLIC ACID (OCTANOIC), Natural
Sustainability
Bedoukian Research
CAPRYLIC ACID (NATURAL)
Use: Can be used in buttery or dairy-type applications.
Flavor: Acidic, cheese, fruity notes
Cheese, milk, and other dairy type flavors, ripe fruit.
Berjé
Caprylic Acid
Happening at Berje
BOC Sciences
For experimental / research use only.
CAPRYLIC ACID (NATURAL)
CG Herbals
Caprylic Acid
Charkit Chemical
OCTANOIC ACID NATURAL FEMA 2799
Charkit Chemical
OCTANOIC ACID O0050 FEMA 2799
Diffusions Aromatiques
ACIDE CAPRYLIQUE
ECSA Chemicals
Caprylic Acid
Company Profile
EMD Millipore
For experimental / research use only.
Caprylic acid (Octanoic acid)
Ernesto Ventós
OCTANOIC ACID
Excellentia International
Caprylic Acid (Octanoic Acid) Natural
FCI SAS
OCTANOIC (Caprylic) ACID NATURAL EU
Flavor: Acid, wax, oily
Fleurchem
caprylic acid natural
Frutarom
NATURAL OCTANOIC ACID (CAPRYLIC)
≥99.00%, natural, Kosher
Odor: Acidic, Fruity, Soapy, Sour
Use: Suggested Uses: Alcoholic Beverages, Blackberry, Cheese, Cherry, Coffee, Dairy Products, Soft Fruits
Frutarom
OCTANOIC ACID
≥99.00%, NI, Kosher
Odor: Acidic, Fruity, Soapy, Sour
Use: Suggested Uses: Alcoholic Beverages, Blackberry, Cheese, Cherry, Coffee, Dairy Products, Soft Fruits
Grau Aromatics
CAPRYLIC ACID
HallStar
HALLSTAR® C-899 CAPRYLIC ACID
Odor: characteristic
Use: HallStar C-899 Caprylic Acid is 99+% pure 1-Octanoic Acid. It is a clear, low viscosity liquid with a musty, pungent odor. It finds use as a raw material in the manufacture of esters (e.g., Capryliic/Capric Triglyceride) and a variety of other products including synthetic lubricants, amides, plasticizers, flavor compounds, perfumes, antiseptics and fungicides.
Indukern F&F
CAPRYLIC ACID
Odor: FATTY, CHEESE, WAX
CROP CALENDAR
Kao Corporation
LUNAC 8-98
Kao Corporation
LUNAC 8-98(E)
Use: Control of variation with time of color phase.
Kun Shan P&A
Natural Octanoic Acid
Kunshan Sainty
Octanoic Acid, Natural
Lluch Essence
CAPRYLIC ACID NATURAL
M&U International
NAT.OCTANOIC ACID, Kosher
M&U International
OCTANOIC ACID, Kosher
Moellhausen
OCTANOIC ACID
Mosselman
Caprylic Acid C8
Nagar Haveli Perfumes & Aromatics
Octanoic Acid 98.0% (min)
Odor: Fatty waxy rancid oily vegetable cheesy
Naturamole
octanoic acid 98% natural EU
Oleo Solutions
Edenor C8-99 MY
Odor: characteristic
Use: Flavours and Fragrances, Adhesives and Lubricants, Industrial, Inks and Coatings
P&G Chemicals
C-810
(Caprylic & Capric Acid)
Odor: characteristic
Use: End-use applications for C-810 include synthetic lubricants base stock, refrigeration lubricants, medium chain triglycerides, fire resistant hydraulic fluids, tailored fats, alkyl chlorides for agricultural products, phosphate ore floatation, amides for agricultural products, production of plasticizer alcohols, corro-sion inhibitors for antifreeze, flavor compounds, perfumes, antiseptics, and fungicides.
P&G Chemicals
C-810L
(Caprylic & Capric Acid)
Odor: characteristic
Use: End-use applications for C-810L include synthetic lubricants base stock, refrigeration lubricants, medium chain triglycerides, fire resistant hydraulic fluids, tailored fats, alkyl chlorides for agricultural products, phosphate ore floatation, amides for agricultural products, production of plasticizer alcohols, corro-sion inhibitors for antifreeze, flavor compounds, perfumes, antiseptics, and fungicides.
P&G Chemicals
C-895
Odor: characteristic
Use: End-use applications for C-895/ C-898/ C-899 include synthetic lubricants base stock, refrigeration lubricants, medium chain triglycerides, fire resistant hydraulic fluids, tailored fats, alkyl chlorides for agricultural products, phosphate ore floatation, amides for agricultural products, production of plasticizer alco-hols, corrosion inhibitors for antifreeze, flavor compounds, perfumes, antiseptics, and fungicides.
P&G Chemicals
C-898
P&G Chemicals
C-899
Penta International
CAPRYLIC ACID, NATURAL, Kosher
Penta International
CAPRYLIC ACID, SYNTHETIC FCC, Kosher
Prodasynth
CAPRYLIIC ACID, NATURAL >98%
Reincke & Fichtner
Caprylic Acid natural
Reincke & Fichtner

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