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GINGER

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mohammed safoty

on 12 June 2014

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Transcript of GINGER

Isolation and Identification of Volatile and Non-Volatile Compounds from Ginger by GC/MS , ( H-NMR, C-NMR) Analysis
Zingiber Officinale (Ginger)
Result of non-volatile compound for first sample by NMR
Result of volatile compound (essential oil) by GC/MS.
Introduction
Aim of the Project
Identification of volatile and non-volatile compounds , and analysis of result
Supervised by: Dr. Nuha Sweidan Done by : (Haneen Alnawayseh & Jamel Yamin) Assistant by: Eman Alzabin
Zingiber officinale is the scientific name of ginger. A proverb from ancient India maintains that everything good can be found in ginger. Ginger is so concentrated with active substance; you don't have to use very much to receive its beneficial effects.
Ginger is one of the world's top ten favored spices. Yet surprisingly, its tremendous medicinal value is virtually unknown.
Extraction and characterization of volatile and non-volatile compounds from ginger by chromatography principle & steam distillation, (Classical LC, TLC & instrumentation GC/MS , NMR) technique.
Conclusion
Reference
Extraction technique
of volatile compound (Essential oil)

An essential oil is a concentrated , hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetherolea, or simply as the "oil of" the plant . An oil is "essential" in the sense that it carries a distinctive scent, or essence, of the plant.

Essential oils are generally extracted by distillation, often by using steam. They are used in perfumes, cosmetics, soaps and other products, for flavoring food and drink, and for adding scents to incense and household cleaning products .
Technique : steam distillation

Steam distillation is a method of isolating compounds which decompose at high temperatures by distilling them in such a way that steam is introduced into the raw material. Normally, distillation is employed in order to separate a substance from another substance with a higher boiling point. The mixture is heated to the boiling point of the substance to be extracted and the vapor cooled and condensed.. For these compounds, steam distillation can be used, providing the compound is not miscible with water.

1-Place 50g of the ginger and 200 ml of water in a 500 ml round –bottomed flask.
2- connect the flask to a distillation apparatus and boil the mixture .
3-collect the distillate until no more droplets of oil come over.
4- cool the distillate to room temperature , transfer to 250 ml separatory funnel , and extract with diethyl ether 15ml, separate the layer and collect the organic layer in a small flask.
5-dry the organic phase with anhydrous sodium sulfate, until the solution is clear.
6- decant the oil extract and evaporate on the steam bath.
7- weigh the oil and calculated the percentage yield .
8- The sample is ready for identification by GC/MS.
Procedure
Extraction technique
Of non-volatile compound
Pungent phenol
Technique : chromatography
Procedure

1-Soaking: we are soaking powder, ginger (500g) in ethanol solvent (2L) for two weeks.
2- To get first crude you should be evaporate Drenched ginger at room temperature for 1 week
3- Weigh the crud (50g) .
Essential oil
Step( 1)
Step(2)
1-preparation of Colum chromatography (Stationery phase) by washing, and then backing of sephadex LH-20 with (mobile phase)
Solvent (95% ethanol: 5% water (for 2 days').
2- Put the sample (5g from crud & a few drop of solvent) in a Colum.
3- I have become number of layers, taking each layer alone and put into small beaker.
4-We get about 6 fractions, and then We have evaporated.
5- The 6 fractions are ready for (TLC) chromatography.
step (3)
1-TLC technique by the silica gel (or the alumina) as the stationary phase & the mobile phase is a suitable liquid solvent or mixture of solvents (hexane , ethyl acetate , Di ethyl ether ) we used it, this preparation by different ratio.
2- by TLC (by a streak method on the pallet ) we found that fractions (5,6) it's one pure component & and extracted.

3- From fractions (3, 4) two components, his point (green, blue color spots) in the pallet.
4- Extraction from TLC by pure ethanol & then evaporate.
5- A three 3 sample is ready for identification by IR &C- NMR.
Analysis equipment
volatile compound
non-volatile compound
Types of Chromatography.
Chromatography techniques
Principle in chromatography
Definition
1
2
3
4
5
6
7
Result of non-volatile compound for third sample by NMR
1- Adsorption Chromatography
2- Partition Chromatography
3- Ion Exchange Chromatography
4- Molecular Exclusion Chromatography
5- Affinity Chromatography
Method for separating the constituents of a solution (gas or liquid) by exploiting the different bonding properties of different molecules. Used in qualitative and quantitative analysis of biological and chemical substances, this technique employs two immiscible substances. One substance (a gas or liquid, called the mobile phase) transports the solution being analyzed through the other substance (a liquid or solid, called the stationary phase). The stationary phase absorbs or impedes different components of the solution to different degrees and, thus, causes their separation as different layers. Invented in 1906 by the Russian botanist Mikhail Tsvet .
laboratory technique for separation of mixture
chroma-"color"- and graphein -" to write"
Colour bands - separation of individual compounds
measured or analyzed.
propose of chromatography
* analytical
Determine chemical composition of a sample
* preparative
used purify sufficient quantities of a substance
Mobile phase = solvent moving through the column.
A Stationary phase = substance that stays fixed inside the column.
Eluent = fluid entering the column.
Eluate = fluid exiting the column.
Gas Chromatography = gas carrier Liquid Chromatography = liquid mobile phase
This method is adopted in techniques like:
1. Using Paper.
2. Thin layer chromatography.
3.High performance thin layer chromatography (HPTLC).
The techniques which employ this method are:
1. Column chromatography LC.
2. Gas chromatography GC.
3. HPLC.
4. Size exclusion.
5. Ion exchange.
Pungency: is the condition of having a strong, sharp smell or taste that is often so strong that it is unpleasant. Pungency is the technical term used by scientists to refer to the characteristic of food commonly referred to as spiciness or hotness and sometimes heat.
Definition:
A Substance that is not capable of changing from a solid or liquid form to a vapor.
Glycerin is a nonvolitile liquid.
NMR - Nuclear magnetic resonance
The absorption of electromagnetic energy (typically radio waves) by the nuclei of atoms placed in a strong magnetic field. The nuclei of different atoms absorb unique frequencies of radiation depending on their environment, thus by observing which frequencies are absorbed by a sample placed in a strong magnetic field (and later emitted again, when the magnetic field is removed), it is possible to learn much about the sample's makeup and structure. Nuclear magnetic resonance has no known side effects on the human body, and is therefore used to analyze soft body tissues in magnetic resonance imaging (MRI).
GC/MS
H-K-N
NMR spectroscopy Map of carbon–hydrogen framework
H and C nuclei are not unique in their ability to exhibit the NMR phenomenon.
All nuclei with an odd number of protons (1H, 2H, 14N, 19F, 31P, for
example) and all nuclei with an odd number of neutrons (13C, for example)
show magnetic properties. Only nuclei with even numbers of both protons and
neutrons (12C, 16O, 32S) do not give rise to magnetic phenomena
Spectroscopy is the study of the interaction of electromagnetic radiation with matter. Nuclear magnetic resonance spectroscopy is the use of the NMR phenomenon to study physical, chemical, and biological properties of matter.
NMR spectroscopy finds applications in several areas of science. NMR spectroscopy is used by chemists to study chemical structure .
Solid state NMR spectroscopy is used to determine the molecular structure of solids. Other scientists have developed NMR methods of measuring diffusion coefficients.
Most of the matter you can examine with NMR is composed of molecules. Molecules are composed of atoms. Here are a few water molecules. Each water molecule has one oxygen and two hydrogen atoms. If we zoom into one of the hydrogens past the electron cloud we see a nucleus composed of a single proton.
Definition:
Ability to exhibit the NMR phenomenon:
Examine with NMR:
Definition:
is an analytical method that combines the features of gas-liquid chromatography and mass spectrometry to identify different substances within a test sample.
Applications
drug detection, fire investigation, environmental analysis, explosives investigation, and identification of unknown samples.Also be used in airport security to detect substances in luggage or on human beings. Additionally, it can identify trace elements in materials.
The difference in the chemical properties between different molecules in a mixture and their relative affinity for the stationary phase of the column will promote separation of the molecules as the sample travels the length of the column. The molecules are retained by the column and then elute (come off) from the column at different times (called the retention time), and this allows the mass spectrometer downstream to capture, ionize, accelerate, deflect, and detect the ionized molecules separately. The mass spectrometer does this by breaking each molecule into ionized fragments and detecting these fragments using their mass-to-charge ratio.
MS are ionized by various methods with typically only one method being used at any given time. Once the sample is fragmented it will then be detected, usually by an electron multiplier diode, which essentially turns the ionized mass fragment into an electrical signal that is then detected.
- Khairu alzam bin ibrahim (2006),extraction of essential oils from ginger using steam distillation method . Science Direct.
- Dr.Chi-Tang Ho, Isolation and charactrrization of natural products from ginger .Science Direct
- Y.O.Usman 1 , S.E.Abechi 2 ,O.O.Benedict1 , O.Victor1, U.U.Udiba1, N.O.Ukwuije1, and S.E.Anyahara1 : Effect of solvents on (6)-gingerol content of ginger rhizome and alligator pepper seed ,Scholars Research Library
Annals of Biological Research.
- Nour,Abdurahman H;M,Ranitha;Nour, Azhari H , (2013), Extraction and characterization of essential oil from ginger and lemongrass by microwave- Assisted Hydrodistillation . International Journal of Chemical.
- Adel P R Shirin , Jamuna Prakash ,(2011). Chemical composition and antioxidant properties of ginger root (Zingiber officinale). Journal of Medicinal Plants Research.
- Nikita Agarwal ,(2011). Thin Layer Chromatography of GINGIR and PEPPER .Delhi Public School Bangalore South .
- Rai S , Mukherjee K, Mal M, WahileA, Saha BP , Mukherjee PK ,(2006).Determination of 6-gingerol in ginger , using high-performance thin -layer chromatography.Science Direct.
-John McMurry ,8e.Organic Chemistry,(2012)
Retention Time
Concentration%
1- alpha-copaene
2- beta-elemene
3- gamma-elemene
4- trans-alpha-bergamotene
5- trans-caryophyllene
6- amorpha-4,11-diene
7- (7-epi-alpha-selinene)
8- gamma-curcumene
9- alpha-Curcumene
10- alpha-selina
11- alpha-zingiberene
12- gamma-muurolene
13- alpha-farnesene
14- beta-bisabolene
15 -bicyclogermacrene
16- beta-cadinene
17- beta-sesquiphellandren
18- sibirene
19- selina-3,7(11)-diene
20- nerolidol
21- valerianol
22- alpha-eudesmol
24.289
24.878
26.526
27.442
27.695
27.812
28.338
28.489
28.672
29.017
29.239
29.424
29.563
29.727
29.983
30.167
30.368
30.914
31.092
31.880
34.381
35.573
compounds
Retention Time
Concentration%
1- alpha-Curcumene


2- beta-sesquiphellandren


3- beta-bisabolene


4- gamma-curcumene


5- alpha-farnesene


6- alpha-zingiberene


7- gamma-muurolene
structure
28.672


30.368


29.727


28.489


29.563


29.239


29.424
compounds
8-gingerol
6-gingerol
Apigenin
Result of non-volatile compound for second sample by NMR
Apigenin (4’,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

Sources in nature:
Apigenin is found in many fruits and vegetables, but parsley, celery and chamomile tea are the most common sources.
Also known as: Chamomile, Spigenin, Apigenol, 4',5,7-Trihydroxyflavone, Apigenine
Molecular Formula: C H O
Molecular Weight: 270.2369 g/mol
Molecular Formula: C H O
Average mass: 294.385895
Gingerol, or sometimes [6]-gingerol, is the active constituent of fresh ginger.
It is normally found as a pungent yellow oil, but also can form a low-melting crystalline solid.
Cooking ginger transforms gingerol into zingerone, which is less pungent and has a spicy-sweet aroma. When ginger is dried, gingerol undergoes a dehydration reaction forming shogaols, which are about twice as pungent as gingerol. This explains why dried ginger is more pungent than fresh ginger.
H-NMR
C-NMR
H-NMR
C-NMR
H-NMR
C-NMR
Chemical Formula:C H O
Molecular Weight:322.44
8-Gingerol is one of several active compounds isolated from the ginger root. 8-Gingerol is believed to inhibit the anti-serotonin 3 receptor function leading to anti-emetic properties.
1
13
1
13
13
19
30
4
17
26
4
15
10
5
1- Volatile compound
Ginger contains (22) essential oil, were isolated by GC/MS , major compounds:

1- alpha-Curcumene
2- beta-sesquiphellandren
3- beta-bisabolene
4- gamma-curcumene
5- alpha-farnesene
6- alpha-zingiberene
7- gamma-muurolene

2- Non-volatile compound
Three (3) compounds were isolated and identified by (NMR)( H, C ):

1- Apigenin
2- 6-Gingerol
3- 8-Gingerol
1
13
0.281%
0.306%
0.449%
0.751%
1.879%
0.439%
0.884%
7.660%
24.00%
1.916%
3.911%
4.750%
7.589%
15.86%
1.070%
1.890%
22.26%
0.396%
0.571%
1.102%
0.585%
0.874%
24.00%


22.26%


15.86%


7.66%


7.58%


3.91%


4.75%
13
1
1
13
Full transcript