Kaban S. Muhamad and Darya J. raheem

Department of chemistry, college of education, university of salahaddin-hweler, erbil

kurdistane region, Iraq

Abstract

There Are Two Type Of Synthesis Of Henna Are Natural And Synthetic In The Natural Henna Contain

Lawsone But In Synthetic Henna Include PPD.The PPD Have Some Side Effect Very Strong Potential Skin

Sensitizer, Eye Irritation And Tearing, Asthma, Gastritis, Renal Failure, Vertigo In This Research We Tried To

Extracted The Molecule Of Dye From Henna Five Samples From Erbil City By Aqueous And Alcoholic

Solution Then The Samples Was Characterized By UV-VISIBL And FT-Irspectroscopy.

Keywords: henna, lawsonia , PPD, extraction, synthetic henna

1.1 Introduction

Henna Is Very Popular Among The People Of India, The Mideast And Africa Especially In

United Arab Emirates (UAE); It Is Part Of The Culture And Traditions. (Nadkarnis, 1955).

Henna Is Commonly Used As A Natural Medicines And Cosmetics Among Many Different

Cultures Is Well Known Prior To The Beginning Of Modern Medicine And Cosmetology

(Dimkov 1977, 1978, 1979). In North America And Europe Henna Is Primarily Used As A

Hair Dye, And Especially To Which It Is Being Applied (Carleton Et Al., 1976). Until The

Middle Of The Nineteenth Century, All Dyes Available To Man Came From Natural

Sources, Mainly Vegetable Extracts And A Few From Animal Products(Asressu, Et Al

2013).Despite The Wide Spread Use Of Natural Henna, Specially, In Countries Where Henna

Art Is Traditionally Practiced, Reports Of Allergic Contact Dermatitis To Natural Henna Are

Very Rare In The Literature. It Can Therefore Be Assumed That Natural Henna Is A Very

Weak Skin Allergen(Al‐Tufail Et Al 1999).

The Use Of Natural Dyes On The Hair Has Not Made Very Great Progress, And This Is Due

To A Number Of Factors That Should Not Be The Reason For Despair. Natural Dyes Are

Not Very Stable In Solution, Are Prone To Oxidation, Browning, Discoloration, Ph Colour

Shift, Fading And Attack By UV Light. However, None Of These Adverse Effects Are

Applicable To The Dry Powdered Natural Dye But There Is A Concern Of That The Range

Of Colors Was Limited As The Utility Of Dyes. Though The Permanent Synthetic Hair Dyes

Are Available In Different Ranges And Retain Natural Luster, They Have The Chief

Disadvantage Of Producing Hypersensitive Reactions In Some Individuals.

The Use Of Natural Plant Based Permanent Patent Pending Hair Colorant That Is Free Of:

Para-Phenylene Diamine And Its Derivatives, Resorcinol, M-Aminophenol, P-Aminophenol,

Toluene- 2, 5-Diamine, Azo-Dyes, Diazo-Dyes, Disperse Dyes, Ammonia, And Parabens -

All Synthetic Chemicals Which Are Known Allergens And Suspected Carcinogens

(Chauhan, M.G Et Al 2007).

The Present Work Was Planned To Extract The Colouring Component In Five Henna

Samples With Aqueous And Alcoholic Medium Keeping The Environment Friendly

Extraction Procedure Excluding The Extensive Application Of Organic Solvents. The

Solvent Was Chosen To View The Acidic Chemical Nature Of Lawsone. The Samples Were

Identified And Characterized Using FT-IR And UV-Viss. Spectroscopy(Boubaya, A Et Al

2011).

1.2 Types Of Henna Dye

There Are Three Types Of Henna Like Neutral Henna, Red Henna And Black Henna.

1.2.1 Neutral Henna

Neutral Henna, A Green Powder That Smells Like Freshly Cut Grass, Is Neither Henna Nor

Neutral. Neutral Henna Or Cassiaobovata Does Not Stain Hair.

1.2.2 Red Henna

Red Henna, Agreen Powder That Smells Like Hay. The Leaves Of The Henna Plant Possess

A Red-Orange Stain Molecule: Lawsone, Anaphthaquinone Compound. Henna Cause To

Dye Your Hair Reddish; But This Stain Is Translucent And Will Combine With Your Natural

Color. Pure Henna, 100% Lawsonia Inermis, Can Condition And Strengthen Hair. The

Lawsone Molecule, When Bound Into Keratin, Is A Complete Sunblock, Protecting Hair

From UV Damage. Pure Henna Preserves Moisture In Hair By Making It Less Prone To

Weathering And Desiccation. Hennaed Hair Can Appear To Grow Faster Because The Ends

Are No Longer Drying And Breaking Off.

1.2.3 Black Henna

Black Henna, A Green Powder That Smells Like Frozen Peas, Is Neither Black Nor Henna. It

Is Indigo, Indigofera Tinctoria. Black Henna Is The Combination Of Red Henna And The

Dye PPD.Black Henna [Or Blue Henna] Is The Combination Of Red Henna And PPD. There

Is No Natural Black Henna. Some Of These ‘Henna’ Preparations Do Not Even Contain Red

Henna At All (Dimkov P. (1977-1979).

Black Henna Is A Hair Colorant That Is Contain One Of These Of Chemical Substances:

Paraphenylene Diamine And Its Derivatives, Resorcinol, M-Aminophenol, P-Aminophenol,

Toluene- 2, 5-Diamine, Azo-Dyes, Diazo-Dyes, Disperse Dyes, Ammonia, And Parabens -

All Synthetic Chemicals Which Are Known Allergens And Suspected Carcinogens.

PPD Is The Major Element Of Black Henna. Heavy Metals Were Found In Black Henna

Including Cobalt, Mercury, Nickel, Chromium, Lead, Silver Nitrate, Iron Oxide, And

Titanium Dioxide, Pyrogallol And Substances Such As Ethyl Cellulose And Tartaric Acid

May Be Added To Black Henna. In 12 Commercial And Traditional Henna Samples, Lead

Was Found At Concentrations In Some Types Of Black Henna Paste . Nickel And Cobalt

Were Identified In Some Henna Samples Available In Taiwan, But At Very Low

Concentrations (Chaibi, R Et Al 2017).

1. 3 What Is PPD?

PPD Or Para-Phenylenediamine Is An Aromatic Amine Compound; Is Added As A Strong

Oxidizer And Dying Accelerator To Henna Powder Its Chemical Formula Is C6H8N2 And Its

Molecular Weight Is 108.15 G/Mol. It Is White To Light Purple Powder That Darkens On

Exposure To Air (It Oxidizes, Turning First Red, Then Brown Then Finally Black); It Is

Slightly Soluble In Water . It Is Primarily Used As An Ingredient Of Oxidative Hair Coloring

Products At A Maximal Concentration Of 4.0%, However, After Mixing In A 1:1 Ratio With

Hydrogen Peroxide Prior To Use This Concentration Will Be 2% At The Time Of

Application To The Hair. In Addition To Hair Dyes, PPD May Also Be Found In Fur Or

Textile Dyes. Para-Phenylenediamine Is Also Used As A Photographic Developing Agent As

Well As An Antioxidant In Rubber Compounds. Individuals May Be Occupationally

Exposed To PPD During Its Manufacture Or Use, And The Exposure May Occur Through

Inhalation, Skin And/Or Eye Contact, And Ingestion (Chukwu, O.O.Et Al 2011).

1.4 The Need For PPD

Recently Para-Phenylenediamine Has Been Mixed With Natural Henna To Give An Ebony

Color (Black Henna) Instead Of The Orange/Reddish Color Given By Natural Henna. PPD

Is Added To Henna To Fast The Dyeing And Drying Process, To Strengthen And Darken

The Color, To Improve The Design Pattern Of The Tattoo, And To Cause The Tattoo Last

Longer. These Tattoos Stain The Skin Black, And Look Like A Real Tattoo. The Other

Reason For Adding PPD To The Natural Henna Is To Speed Up (Shorten The Time) Of The

Tattooing Process, While Natural Henna Staining Takes 4 To 12 Hours, Addition Of PPD

Can Reduce This Time To An Hour Or Two And Also There Will Be A Longer Lasting

Effect As Well. Thus, A New Pattern Of Exposure To PPD Has Been Recognized Through

Henna Art Which Increases The Risk Of Developing Adverse Health Effects Related To

PPD(.Gupta, A.K Et Al 2005).

1.4 Side Effects Of Black Henna

Side Effects Of Henna Were Divided Into Three Types: Allergic Side-Effects Of Black

Henna Tattoos, Non-Allergic Sideeffects Of Black Henna Tattoos And Systemic Side

Effects.

Many Cases Of Contact Allergy Have Been Reported In UAE After The Use Of Black

Henna. Picture 1&2 Shows One Of These Cases Where The Patient Has Developed Hand

Sensitization Few Days After The Use Of Black Henna. Short-Term Exposure To High

Levels Of PPD (Acute Effects) May Cause Severe Dermatitis, Eye Irritation And Tearing,

Asthma, Gastritis, Renal Failure, Vertigo, Tremors, Convulsions, And Coma In Humans.

Eczematous Contact Dermatitis May Result From Long-Term Exposure (Chronic Effect) In

Humans (Gupta, A.K Et Al 2005). According To Scientific Committee On Consumer

Products (SCCP),

Para-Phenylenediamine Is A Very Strong Potential Skin Sensitizer And It Is Included As

Such In The European Standard Series For Diagnostic Patch Testing For Eczema Patients

(Greenway, P.J., 1941). Para Phenylenediamine (PPD) Is An Allergen; Even If Someone

Does Not Have A Reaction The First Time They Are Exposed To It, They Can Become

“Sensitized” To PPD Over Time And Can Have Adverse Reaction Upon Re-Exposure .

In Addition, PPD Provokes Cross-Allergy, Making People Allergic To Other Substances

Which Contain Para-Substituted Amino Compounds . No Information Is Available On The

Reproductive, Developmental, Or Carcinogenic Effects Of PPD In Humans . However,

SCCP Reported That PPD Together With Hydrogen Peroxide May Be Carcinogenic

According To Experimental Studies With Rats.

Acute Allergic Contact Dermatitis, Eczema, Chemical Burn, Acute Renal Failure, Acute And

Severe Angioneurotic Edema, Abdominal Pain And Vomiting As Adverse Health Effects

Associated With The Use Of Henna Containing PPD (Black Henna) Are Well Documented

In The Literature [10–16]. In Addition, Cases Of Persons Being Sensitized From Use Of

Black Henna (Containing PPD) Followed By Cross Reaction To Oxidative Hair Dyes And

To Clothing Dyes Have Also Been Described In The Literature ( Zavada, M.S., 1993)

Picture 1: Hand Dermatitis, Reaction To Black Henna.

Picture 2: Positive Reaction To Patch Test Done Using 0.1% PPD.

In Addition, It Is Reported In The Literature That Henna Has Been Known To Cause

Haemolytic Crisis In G6PD-Deficient Infants And Others (Chauhan, M.G Et Al 2007). In

The UAE, Raupp And His Colleagues Have Reported The Occurrence Of Haemolytic Crisis

In Four G6PD-Deficient Children Following Topical Application Of Henna; Of These A

Female Neonate Recovered After Exchange Transfusion, And A Male Infant Died Despite

Receiving A Transfusion (.Gupta, A.K Et Al 2005).

1.5 The Substitutions For Black Henna

The Latest Scientific Achievements In Green Chemistry And Utilizes A Revolutionary

Breakthrough In Dye Technology Based On More Than 30 Years Of Research By Leading

Experts In Hair Coloring Industry And The Result Is A New, 100% Natural Plant Based

Permanent Patent Pending Hair Colorant That Is Free Of PPD.

The Food And Drug Administration Has Issued A Monograph That Approves Henna For The

Use As Hair Colorant. Henna Is One Of A Select Group Of Natural Products To Achieve

Official FDA Recognition (Kanniappan, R., 2015). Therefore,

Need Was Felt To Formulate A Dye Containing Only Plant Products Which Is Safe For Use

And Does Not Have The Problems Like Staining Skin During Use And Hypersensitive

Reactions. This Include To Formulate Henna And Polyherbal Hair Colorant Which Is Safe

To Use. Dyeing Gray Hair Black Is Challenging And The Holy Grail Of Henna And Indigo

Because Black Chemical Para-Phenylenediamine Dye Is Extremely Hazardous To Your

Health. It Is Linked To Asthma, Non-Hodgkins Lymphoma, Lupus, And Bladder Cancer, As

Well As Causing Hair Loss And Horrific Allergic Reactions. Also The Plants You Can Use

To Dye Your Hair Black Are GOOD For Soil, And Give Farmers In Marginal Areas A Cash

Crop When All Their Other Crops Fail. Learn To Use Henna And Indigo To Dye Your Hair

Black, Save Your Health, And Save Farmland(Dimkov P. 1977-1979)

When You Dye Gray Hair With Henna, The Lawsone Molecules Will Penetrate The Keratin

In The Hair Shaft And Dye It Orange. If You Dye Your Hair With Indigo Immediately

Afterward, The Indigo Molecules Will Penetrate The Keratin In The Outer Layers Of The

Hair Shaft With Indigol Molecules Which Will Oxidize To Dark Blue. Powdered Indigo

Leaves Prepared For Hair Will React With The Acidic Henna To Blacken The Orange. Your

Hair Will Be Dyed Black As The Result Of This Interaction

The Indigo Molecules Are Slightly Larger Than Lawsone Molecules, So They Stain The

Outer Layers Of The Hair Shaft. Some People Find The Indigo Color Fades Slightly Over

Several Weeks, And The Henna Begins To Show Through. You Can Refresh The Color By

Dying Your Hair With A Mix Of Mostly Indigo, And A Little Henna.

Fig.1: Schematic Diagram Of Gray Hair Dyed With Henna Then Indigo

1.6 APPLICATION OF HENNA

1. Antifungal Activity

Lawsone Was Found To Be An Anti-Fungal Toward Alternaria, Aspergillius, Absidia, And

Penicillium. The Minimum Dose Effective Again Test Organism Is Found To Be 0.1%. It

Exhibits Fungicidal Activity, Wide Fungi Toxic Spectrum And Nonphytotoxicity.

2. Antibacterial Activity

Antibacterial Activities Toward Brucella, Neisseria, Salmonella, And Streptococcus With A

Concentrationof .005-.02% Were Observed. Additionally, Lawsone Extract From The Leaves

Showed Mild Anti-Bacterial Activity Against S. Aureus And E. Coli.

3. Benefits In Alopecia

In Applications Described In Patent Literature, Henna Extract Was Used With Other Hair

Growth Promoting Agents Delivered Transdermally. Lawsone May Promote Hair Growth By

Acting On 5-Alpha- Reductase, An Intracellular Enzyme That Converts The Androgen

Testosterone Into DHT (Dihydrotestosterone). As DHT Is Implicated In The Development Of

Androgenic Alopecia, Lawsone Offers Benefits By Preventing Its Formation(Sherifa, M.S et

al 2015).

4. Hair Conditioning Properties

Natural Henna Is An Excellent Conditioning Agent. Lawsone Is Widely Used In Shampoos,

Hair Rinses,And Conditioners.

5. Hair Dye

Henna Has Been Used To Dye Hair For Centuries. Lawsone By Itself Is Colorless. However

When Exposed To Sunlight Or To Air, It Is Converted To A New Compound That Has The

Characteristic Red Color. When Lawsone Is Blended With Indigofera Tinctoria, The Hair

Dye Can Impart Color In Various Shades Ranging From Brown To Black.The Addition Of

Herbs Such As Rhubarb, Calendula, Chamomile, And Others To Lawsone Produces Various

Shades Of Red. It Can Be Used To Cover Gray Hair Without Any Adverse Effects On Hair

Structure. To Obtain A Long –Lasting Color, The Ph Of The Composition Must Be In The

Acidic Range (Gallo, F.R et al 2017) Facilitated By Using A Weak Acid Such As Adipic,

Citric Or Boric Acid). Other Applications Of Henna Include Its Use In Creating“Temporary

Tattoos” To Decorate The Skin(Nadkarnis K.M. 1955)

1.6 Literature Review

Chukwu And Co-Worker Extracted Aqueous (Cold And Hot) And Ethanol Solutions Of The

Henna Plant (Lawsonia Inamis) Leaves Then Formulated Into Various Staining Solutions Of

Different Concentrations And Modified With Hydrogen Peroxide, Ferric Chloride, Potassium

Alum And Potassium Permanganate(Habbal, O et al 2011).

Kidanemariam And Co-Worker Studied The Chemical Constituents Of The Hydrodistilled

Oil And N- Hexane Extract Of L. Inermis Leaves. The Essential Oil Of L. Inermis Leaves

Was Analyzed Using GC-MS And Revealed The Presence Of Twenty Eight Components.

Nine Components Comprising 80.6% Of The Total Oil Have Been Identified By

MS(Kanniappan, R., 2015).

Kannanmarikani And Co-Worker Found The Red Dye Obtained Through Alkaline Extraction

Has Better Colour Strength I.E. The Maximum Colour Intensity At 3M Naoh.Sonia And Co-

Worker The Potency Of Different Solvent Systems On Extraction Of Phenolic Compounds

From Henna Leaf. Methanolic, Ethanolic And Acetone Extracts Of Different Henna Leaf

Samples Were Evaluated For Amount Of Extract Obtained(.Kiani, S., 2016).

Rao And Co-Worker. Studied Lawsonia By Extracting With Distilled Water, Ethanol,

Methanol And Acetone. By Following All These Studies, Lawsonia Now Considered As

Most Valuable Resource For Unique Natural Products And Also In The Development Of

Pharmacological Products(Sherifa, M.S et al 2015).

Chaibi And Co-Werker Extracted By Methanol The Lawsonia Inermis From Seed That

Show A Very Good Antioxidant Activity. The Strongest Activity Of Henna Seed Against

Human Breast Cancer Cells (HTC-116) Were Obtained For The Chloroform Extract (IC50 =

45 Mg/L)( Zavada, M.S., 1993).

Chapter Two: Materials And Methods

2.1 Materials

2.1.1 Collection Of Henna Samples.

Four Samples Of Henna Are Selected.The Henna 1.Ali Akber 2.Sultan 3.Amir Kbeir 4.Emri

5.Arabian Emarat Henna Amples Are Collected Randomly From Herb Shop In Erbil City.

2.2 Extraction Of Colorants From Henna Samples.

The Extraction Efficiency Of Colorants Component Present In Henna Samples Depends On

The Media Type Like Aqueous, Organic Solvent, Acid, Alkali, Ph Of The Media And

Condition Of Extraction, Such As Temperature, Time, And Material To Liquor Ratio Particle

Size Of The Substrate [9].

In This Study Two Medias For Extraction Aqueous And Ethanol, Ph Of The Media Was 5

Which Is The Best Ph For Extraction.

Two Sets Of 0.1gm Of Henna Samples Was Weighted. The First Set Was Extract With 20ml

Of Water Was Filtered And The Contents Were Centrifuged And The Sediments Were

Discarded. The Solution Containing The Dye Was Evaporated In Oven At 40 Co To Dryness.

The Second Set Was Extract By 20ml Of Ethanol And The Same Procedure Of The First Set

Extraction Was Repeated.

2.3 Spectral Characterization

The 10 Dyes Extracted And Characterized By FT-IR And UV-Vissible Spectroscopy. The IR

Spectra Was Recorded For All The Samples, Using Fourier Transform Infrared Spectroscopy

(FTIR)-Model And UV-Visible Spectrophotometer.

2.4 RESULTS AND DISCUSSION

The Study Shows That The Samples Of Henna Bought From The Henna Herbs Shop In Erbil

City Which Included In This Study Shows That The A1, A2, A3, And A5 Henna Samples

Are Natural Henna But Only A4 Sample Contained Para-Phenylenediamine, And This

Increases The Risk Of Sensitization Among Those Using Black Henna.

UV-Visible Spectra Of Any Henna Samples Show Its Own Peaks At Predominating Wave

Length, Indicating Main Color. UV-Visible Spectroscopic Studies Of Different Henna

Samples Were Carried Out By Using Different Solvents For Extraction. Some Of The Henna

Samples Are; (I) Natural Henna As In A1, A2, A3, And A5 Shows One Strong Absorption

Maxima It 446 Nm In Both Water And Ethanol (Ii) Black Henna A4 Shows Three

Absorption Peak The First Shows Maximum Absorption At 271 Nm And The Second At 330

And The Third At 464 Nm In Both Water And Ethanol.

The Infrared Spectroscopy Is One Of The Efficient Techniques Used In The Characterization

Of Organic Compounds.

IR Spectrophotometers As FTIR Which Was Used In The Present Study To Confirm The

Presence Of Functional Groups As Following Distinguish Stretching Vibration Band Of 2-

Hydroxy-1,4-Naphthoquinone (-C=O-) From 1685-1666cm-1 And (O-H) From 3300-3500

Cm-1as Shown In Fig. 4and Fig.5 For Standard Infrared Spectrum, And In Spectrum Of P-

Phenylenediammie The Characteristic Of (N-H) At 3300 – 3400 Cm-1 In Two Stretching

Adsorption Bands Of Primary Amines In Fig.6 And Fig. 7 For Standard Infrared Spectrum .

2.5 CONCLUSION

The Spectral Interpretation Of Henna Samples Spectra Revealed Valuable Information About

The Identification And Characterization Of Different Types Of Henna Samples. In Table 1,

Selected Typical Bands Are Shown.

The Methods FTIR Is Non-Destructive, Fast And Very Useful Even For Small Sample

Quantities And Can Be Used For Monitoring The Compounds In Environment As Well As In

Consumer Products.

The UV-VIS. Analysis Of Henna Samples Show That The A1, A2, A3, &A5 Samples Are

Contain 2- Hydroxy-1, 4-Naphthoquinone. Principal Colouring Matter Of Henna (The

Lawsone) Was Identified On The Basis Of Comparison With Standard Chart Of 2-Hydroxy-

1, 4-Naphthoquinone. The Aqueous And Ethanolic Henna Extract Show Uv Λmax At 446

Nm. In A1, A2, A3, &A5 Samples Shown In Fig.2. While The Aqueous And Ethanolic

Henna Extract Shows Uv Λmax At 271 Nm. In A4 Sample, Which Is A Good Characteristic

Of Present Of P-Phenylenediammie Shown In Fig.3 .

Table 1. Typical Vibration Bands And Structures Of Hennas Component.

Wavenumber [Cm-1] Function Group Assignment Structures

3300 – 3500

1685-1666

1608.55

1465

1420-1330

O-H Stretching

C=O Stretching Of Aromatic

Ketone

C=C Stretching Of Aromatic

Ring

O-H Bending Of Alcohol

3300 – 3400

2900

1700 - 1500 (M,M)

1266 Strong

860 - 680

Two N-H Str. Of Primary

Amines

Aromatic C-H Stretch

Aromatic C=C Bending

C-N Str. Of Aromatic Amine

C-H Bending Aromatic

Figure 2: UV-Viss. Spectrum Of 2- Hydroxy-1,4-Naphthoquinone In A1,A2,A3&A5

Samples

nm.

350.00 400.00 450.00 500.00 550.00 600.00

Ab

s.

3.000

2.000

1.000

0.000

Figure 3: UV-Viss. Spectrum Of P-Phenylenediammie In A4 Samples

Fig.4 : IR Spectrum Of 2- Hydroxy-1,4-Naphthoquinone

nm.

250.00 300.00 400.00 500.00 600.00

Ab

s.3.795

3.000

2.000

1.000

0.000

-0.351

Fig.5 : IR Spectrum Of Standard 2- Hydroxy-1,4-Naphthoquinone

Fig.6 : IR Spectrum Of P-Phenylenediammie

Fig.7 : IR Spectrum Of Standard P-Phenylenediammie

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