LEMON GRASS OIL

KIM

IA M

INYA

K A

TSIR

I

• 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, ring-

shaped 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.

Bottomed Flask

Condenser

Outlet

Inlet

Hot plate/boiler

Fractionating Column

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%

Sitronelol 11-15%

Geranil asetat 3-8%

Sitronelil asetat 2-4%

Eugenol, vanilin, limonen, dll

CHO

sitronelal sitronelol

CH2OH

geraniol

CH2OH

sitronelil asetat

CH2OCOCH3 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.

Positive result: No stain in

volatile oil

Experimental result: No stain in

volatile oil

olive oil (fixed oil)

lemon grass 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 (non-

conjugated)

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 fraksinasidengan pengurangan tekanan.

• Secara kimia dengan mereaksikan dengannatrium bisulfit (NaHSO3)

REAKSI SITRONELAL DAN BISULFIT

ISOLASI RHODINOL

• RHODINOL (CAMPURAN SITRONELOL DAN GERANIOL)

• DESTILASI FRAKSINASI PENGURANGAN TEKANAN

• UNTUK MENINGKATKAN RENDEMEN, DAPAT DILAKUKAN PROSES HIDROLISIS sitronelilasetat , geranil asetat, dan ester lainnya

CONTOH KOMPOSISI

PARFUM

DERIVATISASI SITRONELAL

sitronelal

CHO

H+

OH

isopulegol

OH

mentol

H2, Ni

Sintesis mentol

SINTESIS HIDROKSI SITRONELAL• King of the perfumes

• Bau harum seperti bunga lili