S.K.H S.K.H Li PingLi Ping Secondary SchoolSecondary School

Group no.: Group no.: C20C20--------------------------------------------------------------------• Man Ka Yan, GraceMan Ka Yan, Grace• Leung Yu Kiu, PearlLeung Yu Kiu, Pearl• Yuen Yuk Man, AlexYuen Yuk Man, Alex• Yeung Siu Hung, EricYeung Siu Hung, Eric• Kwok Tsz Kin, RyanKwok Tsz Kin, Ryan

Problem

Reference books

Some anti-microbial species

Cinnamon Garlic

Ginkgo Oleander

Agar test

Objective:Objective:

• To find out which To find out which herbsherbs is the is the bestbest to to inhibitinhibit the growth of the growth of mould.mould.

Setups: Samples

No. of day that the mould grows on agar jelly

83

37

24

17

17

0 10 20 30 40 50 60 70 80 90Days

Cinnamon

Garlic

Ginkgo

Oleander

Control

神龍本草經Shen Long Ben Cao Jing

摘要：菌桂．味辛溫．主百病．養精神和顏色．久服輕身不老．面生光華

千金翼薰衣濕香方•桂皮 155 克•薰陸香 250 克 •詹糖香 155 克 •藿香各 90克 •甲香 60克

主治：薰衣 ;同時又具解毒止痛消癮疹的作用，可增加皮膚的抗病能力。

民間驗方

Effective components Effective components

The effective The effective components of components of cinnamon are cinnamon are cinnamic aldehyde & cinnamic aldehyde & cinnamic acidcinnamic acid

Project Name

CCinnamon

SSubstances

Investigation

剋剋霉霉桂桂

Extraction Method

•BoilingBoiling

Extraction Method•Steam DistillationSteam Distillation

Extraction MethodSolvent:

•95% ethanol

•Rice wine

Why use ethanol and Rice wine?

Ethanol and Rice wine:Ethanol and Rice wine:• DIY approachDIY approach

• High dissolving power for High dissolving power for

cinnamic aldehyde and acidcinnamic aldehyde and acid

Results

MethodMethod BoilingBoilingSteam Steam

distillationdistillationSolvent Solvent

Extraction Extraction (Rice wine)(Rice wine)

Solvent Solvent Extraction Extraction

(95% Ethanol)(95% Ethanol)

ColourColourLight

BrownMilky

Light Brown

Brown

OdourOdour Cinnamon smell

Deduction

• The The effective componentseffective components in in cinnamon have been cinnamon have been extractedextracted

Chemical Structure VS Chemical Tests

•

Cinnamic Cinnamic acidacid

Cinnamic Cinnamic aldehydealdehyde

Results

---+-+Pure Cinnamic

Acid

++++++Pure Cinnamic Aldehyde

Tollen reagent2,4-Dinitro-

phenylhydrazineFehlingBromineK2Cr2O7KMnO4

--++-+By Boiling

++++++By Steam Distillation

++++++Rice Wine

++++++In 95% Ethanol

Results

---+-+Pure Cinnamic

Acid

++++++Pure Cinnamic Aldehyde

Tollen reagent2,4-Dinitro-

phenylhydrazineFehlingBromineK2Cr2O7KMnO4

--++-+By Boiling

++++++By Steam Distillation

++++++In 29% Rice Wine

++++++In 95% Ethanol

Infrared spectrometry (IR)

Ultra-violet spectrometry (UV)

High Pressure Liquid Chromatography (HPLC)

Objective

• Qualitative:Qualitative: Present or not? Present or not?

• Quantitative:Quantitative: How many? How many?

Chromatogram of Standard4ppm standard (cinnamic aldehyde and cinnamic acid)4ppm standard (cinnamic aldehyde and cinnamic acid)

Cinnamic acid Cinnamic aldehyde

Retention Time(minutes) 12.668 14.55

Integrated Area(mAUS*a) 278.8512 411.25055

Samples

FiveFive samples samples were prepared in were prepared in different waydifferent way

By Boiling

1 2 3

+Water & Boiling

Rotary Ground Cortex

SampleConc. ofCinnamic

acid, (X10-6M)

Conc. ofCinnamicaldehyde, (X10-6M)

1 Rotary+ Boiling 132.2 117.3

2 Ground+ Boiling 102.7 225.4

3 Cortex + Boiling 67.3 51.2

4 Cortex + Extraction (Rice wine) 37.5 3442

5 Cortex + Extraction (95% Ethanol) 42.5 9720

Conc. ofCinnamic

substances, (X10-6M)

249.5

328.1

118.5

3479.5

9762.5

Conclusion IVariations were

due to their differences in:

•Brand

•Origin

•Treatment

132.2 + 117.3 = 249.5

By Solvent Extraction

4

5

Cortex

+Rice wine

+

95% Ethanol

0

10000

1 2 3 4 5

■ Boiling

■ Solvent Extraction

Conclusion IIEffective components are highly dissolved in alcohol

249.5 328.1118.5

3479.5

9762.5

(Sample)

Conclusion III250 x 10-6M

is enough to kill mould !

250

Con

c. O

f C

inna

mic

sub

stan

ces,

(X

10-6M

)

Conclusion IVRice wine is good enough!

Cinnamon Substances Investigation (CSI)

1. In cinnamon, aldehyde content >> 1. In cinnamon, aldehyde content >> acid contentacid content

2. Aldehyde oxidized to acid2. Aldehyde oxidized to acid

3. Both have strong anti-mould power3. Both have strong anti-mould power

4. Rice wine is a cheap and effective 4. Rice wine is a cheap and effective solvent solvent

Investigation - Problem A

• Mould grows on silicon sealantMould grows on silicon sealant

How to make

Cinnamon cortex Honey

wax

Rice wine

Solution

•Apply anti-mould coatingApply anti-mould coating

Investigation - Problem B

• Athlete's foot / Disgusting smellAthlete's foot / Disgusting smell

A homeopathic remedy

Heinerman’s Encyclopedia of Fruits, VegetabHeinerman’s Encyclopedia of Fruits, Vegetables and Herbs, 1998les and Herbs, 1998

“Arresting the fungus among us” http://www.ucsf.edu/today

For athlete’s foot…soaking one’s feet in a lukewarm brew of cinnamon and water to inhibit fungi growth…

How to make• Painting concentrated cinnamic Painting concentrated cinnamic

extract on cotton shoe insoleextract on cotton shoe insole

Is it safe?

LD50 ( pure cinnamic acid) for Rats = 2.2g/kg

157kg cinnamon is required to kill a 45kg man

Be careful

PregnantPregnant

AllergicAllergic

AsthmaAsthma

Summary

• Just a tip of an icebergJust a tip of an iceberg

• Great potential for future Great potential for future

developmentdevelopment

End of Presentation

Some references• Christian, Gary D.; Analytical Chemistry, 5th edition, 1994, J

ohn Wiley & Sons, pg. 112-114, 245-248.• 柯銘清 編 , 中草葯有效成份 --- 理化與葯理特性 , 湖南科學技

術出版社 , pg. 21-22.• 宋小平 , 韓長日 編 , 香料與食品添加劑制造技術 , 科學技術

文獻出版社 , pg. 80-84.• Morrison and Boyd, Organic Chemistry, 3th edition, 1977, Pr

actice-Hall, pg. 186, 634-635, 639-640.• Graham, T.W., Organic Chemistry, 2th edition, 1980, John

Wiley & Sons, p.259, 266, 712, 740.• Skoog, D.A., Holler,F.J., Principles of Instrumental Analysis,

5th edition, 1998, Harcourt Brace & Company Chapter 14, pg.330-331