LEMON GRASS OIL KIMIA MINYAK ATSIRI • Lemon Grass - Cymbopogon citratus Staph, Andropogon citratus DC - Family: Poaceae or Gramineae. Common Names: - Sereh, serai (Java); tanglad (Tag., Bik., Bis.) ; lioko (Bis.); barani (Ilk.); salai (Tag.); sai (Mbo., Mand., Sul.); salaid (Tag.) - paja de meca (Span.); zacate limon (Span.); lemon grass (Engl.); oil grass (Engl.); sweet rush (Engl.); ginger-grass (Engl.); fever grass (Caribbean); hierba Luisa (Amazonia); xiang mao, xiang ma, mao ju ma, yun xiang cao (China) • Botanical Description – a perennial, tufted, aromatic grass with numerous erect culms arising from a short, oblique, ringshaped and sparingly branched rhizome. – stem is smooth and is up to 2(-3) m tall with waxy powdery secretion below the nodes. – Leaves are leathery-textured sheaths • Extraction Procedure The majority of volatile oils are produced by distillation. Outlet Condenser Inlet Fractionating Column Bottomed Flask Hot plate/boiler Hydro-steam Distillation using Clevenger Apparatus • Medicinal Uses – Internal Uses: stomachache, headache, diarrhea, vomiting, fever – External Uses: athlete's foot, cuts, lower back pain, sprains, tendonitis, rheumatism – Antiseptic & astringent, cholesterol control, flatulence, ringworm, digestive and menstrual disorder • Folklore Uses – Caribbean: fever-reducing herb – India: a paste of the leaves is smeared on patches of ringworm. – Philippines: used in Suob ,for toothaches, diuretic – Cuba: to lower blood pressure and anti-inflammatory. – Brazil: sedative and for fever in a tea called "abafado" – Malaya: potion after childbirth • Industrial Uses: perfumery, cosmetics, beverages, flavoring ANALISIS MINYAK SEREH Spektrum Massa Puncak Utama • Main Constituent – Citral or Citronelal • only aliphatic aldehyde that has far been isolated from volatile oils. • thin, light yellow liquid, which is optically inactive and possesses a penetrating odor of lemon. COMPOSITION • Minyak sereh Jawa : Sitronelal 32-45% Geraniol 12-18% CHO Sitronelol 11-15% Geranil asetat 3-8% sitronelal Sitronelil asetat 2-4% Eugenol, vanilin, limonen, dll CH2OH sitronelol CH2OCOCH3 sitronelil asetat CH2OH geraniol CH2OCOCH3 geranil asetat limonen General Tests -tests for lipids A. Solubility in Polar and Nonpolar Solvents Reagents: Distilled water (polar solvent), Olive oil (non-polar solvent) Procedure: • Add 1mL of the sample in each pair of liquids indicated. • Mix the contents of each tube by agitating. • Wait for 2 minutes and examine the tube carefully. Principle: Solubility, Polarity Positive result: Two separate layers in water and dissolved in olive oil Experimental result: Two separate layers in water and dissolved in olive oil B. “Grease Spot” Test Procedure: • Put a drop of the sample on a piece of unglazed paper. • Draw a circle around the spot with a soft pencil. • Allow the spot to dry thoroughly. • Hold the paper in front of a light source and observe the spot. Principle: Opacity Positive result: Translucent Experimental result: Translucent C. Physical Properties Positive result: Color= palest yellow to greenish yellow Appearance= mobile liquid Odor= typical grapefruit/lemon-like odor Experimental result: Color= palest yellow to greenish yellow Appearance= mobile liquid Odor= typical grapefruit/lemon-like odor D. Refractive Index Refractive index at 20°C= 1.472-1.479 Principle: Determination of concentration of volatile oils. Determination of oil whether it falls at the expected range. Positive result: Within the range 1.472-1.479 Experimental result: 1.472 refractometer E. Differentiation test of Volatile oils from Fixed oils (Spot Test) Procedure: • Place a drop of the sample on a filter paper and let it dry. Principle: Volatile oils do not produce permanent spot unlike fixed oils. olive oil (fixed oil) lemon grass oil Positive result: No stain in volatile oil Experimental result: No stain in volatile oil Specific Tests A. Baeyer Test for Multiple Bonds (Potassium Permanganate Solution) - test for active unsaturation Alkene Alkyne Reagent: Potassium Permanganate Principle: Oxidation Procedure: • Add a 1% aqueous solution of potassium permanganate dropwise with shaking. • If more than one drop of reagent is required to give a purple color to the solution, unsaturation or an easily oxidized functional group is present. Positive Result: Disappearance of the KMnO4's purple color and the appearance of a brown suspension of MnO2 Experimental Result: Disappearance of the KMnO4's purple color and the appearance of a brown suspension of MnO2 B. 2,4- Dinitrophenylhydrazone Test - Test for aldehydes & sterically unhinedered ketone Reagents: 95% ethanol and 2,5-DNP reagent Procedure: • Dissolve 2-3 drops of test compound in 2 mL 95% ethanol in a small test tube and mix with 2 mL of the 2,4-DNP reagent. • Look for the formation of an orange-yellow precipitate to indicate the presence of an aldehyde or ketone. Principle: ANE Positive Result: Orange hydrazone ppt. indicates the presence of a ketone (conjugated), yellow hydrazone ppt. indicates an aldehyde (nonconjugated) Experimental Result: Yellow globules C. Fehling’s Test Reagent: Fehling’s reagent Procedure: • Add 3 drops of sample to 1mL of Fehling’s reagent • Water bath for 10-15 minutes Principle: Oxidation of strong alkaline medium Positive Result: Brick red precipitate Experimental Result: Brick red precipitate D. Benedict’s Test Reagent: Benedict’s reagent Procedure: • Add 2 mL Benedict’s solution and 2-3 drops of test compound to the test tubes • Water bath for 10-15 mins • Look for the formation first of a pale green color followed by the formation of the reddish precipitate of cuprous oxide Principle: Oxidation in less basic medium Positive Result: Pale green color followed by the formation of the reddish precipitate Experimental Result: Greenish color followed by the formation of red precipitate E. Bromine Test - Test for unsaturation Alkene Alkyne Principle: Radical substitution reaction Procedure: • Bromine is added drop by drop to the test compound, with shaking, until the bromine color persists Positive Result: Discharging of the bromine color without the evolution of hydrogen bromide gas Experimental Result: Discharging of the bromine color (colorless solution) ADDITIONAL SPECIFIC TEST Nitration Test: -Test for aromaticity Procedure: • Place 2 mL of conc. HNO3 in an Erlenmeyer flask. Immerse the flask in a water bath and gradually add 2 mL conc. H2SO4. • Place 5 drops of the sample in a test tube. Add 8 drops of the nitrating mixture and shake the test tube to ensure complete mixing. Note the formation of a yellow oily layer or droplet. Principle: Oxidation Positive result: yellow oily layer Experimental result: brown oily layer ISOLASI SITRONELAL • Secara fisis dengan destilasi fraksinasi dengan pengurangan tekanan. • Secara kimia dengan mereaksikan dengan natrium bisulfit (NaHSO3) REAKSI SITRONELAL DAN BISULFIT ISOLASI RHODINOL • RHODINOL (CAMPURAN SITRONELOL DAN GERANIOL) • DESTILASI FRAKSINASI PENGURANGAN TEKANAN • UNTUK MENINGKATKAN RENDEMEN, DAPAT DILAKUKAN PROSES HIDROLISIS sitronelil asetat , geranil asetat, dan ester lainnya CONTOH KOMPOSISI PARFUM DERIVATISASI SITRONELAL Sintesis mentol H2, Ni H+ CHO sitronelal OH OH isopulegol mentol SINTESIS HIDROKSI SITRONELAL • King of the perfumes • Bau harum seperti bunga lili