The chemistry of natural colour cannot failto fascinate and intrigue. Nature providesa huge portfolio of possibilities and I ampleased to report that since one of my first papers on the topic,1 in 2002, theavailability of natural materials for colourhas increased greatly.

The chemistry of natural dyes will be focused on comprehensively, andalphabetically, in two parts – the first beingthis article and the second an article to be published in the September edition of Personal Care Europe.

Alkanin or AnchusinAlkanna tinctoria, AlkanetIn addition to the common name, it is calledOrchanet and Spanish Bugloss and by theapothecaries it was known as enchusa. It has blue or reddish-purple flowers.Currently, alkanna root has no recognisedmedical uses except for its older use asan astringent. It is used as a cosmeticdye. The esteric pigments displayedexcellent antibiotic and wound-healingproperties in a clinical study on 72 patientswith ulcus cruris (indolent leg ulcers).

Alkanet root contains a red colouringmatter known as anchusin (alkannin oralkanet-red). Alkanet is an ancient dyestuff known throughout Europe.

AnnattoAnnatto or norbixin is extracted from theBixa orellana or lipstick tree, and gives ayellow to deep orange colour. The plant

has entered into commercial cultivation for the production of this dye which is used mainly in the food industry and forcolouring dairy products such as butterand cheese, margarine, edible oils, etc.

Bixa orellana, AnnattoAnnatto is a red to orange natural (goldenyellow) pigment derived from the seed of the tropical bush Bixa orellana.

The major colour present is cis-bixin,the monomethyl ester of thediapocarotenoic acid norbixin, which isfound as a resinous coating surroundingthe seed itself. Also present, as minorconstituents, are trans-bixin and cis-norbixin. The annatto bush is native toCentral and South America where its seedsare used as a spice in traditional cooking.

It has been reported that the dye isalso used in Brazil in pottery and as aninsect-repellent, and in the Philippines in furniture and shoe polishes, nail varnish, brass lacquer, hair oil, etc. It is further stated that Jamaica and SouthIndia have been major producers of thetop quality product. From other countries

the dye has lacked the bright colourrequired. In South America the shrub is cultivated around villages, where it isnative to and widespread throughout theneotropics. It is called kiswe or kyswi bythe Waimiri Atroari. A red dye is obtainedfrom the aril of the seed that is sometimesused for body painting. It is called urucumin the local vernacular.

Another chemical found in the plantthat is responsible for some of the colouris bixin. Bixin is one of the more stablenatural yellow colours. However, it losesmuch of its tinctorial power gradually onstorage, the process being accelerated bylight and heat. Hence for manufacturingpurposes fresh seeds are preferred. Thetinctorial strength of bixin is comparable to that of β-carotene. However, bixin is the more stable.

Anthocyanins [Category]Anthocyanins are natural red, blue or violet plant pigments present in the cell sap of many flowers, fruits andvegetables. Anthocyanins are contained in cherries, plums, blackberries, blackcarrot, blueberries, cranberries, grapes,elderberry, mulberry, purple corn, rosehips, red cabbage, redcurrant, and red radish.

They have the general structure shownin Figure 4. Cyanidin is found specifically in purple corn. They are used as pHindicators and are heat, oxygen andenzyme labile, but the stability is a major

June 2009 PERSONAL CARE 61

Anthony C. Dweck FLS FRSC FRSPH – Technical Editor COLOUR COSMETICS

Nature provides huge rangeof colour possibilities

Figure 1: Alkannin.

Figure 2: Norbixin.

Figure 3: Bixin.

Figure 4: Anthocyanin.

Anthocyanin R1 R2Pelargonidin H HCyanidin OH HDelphinidin OH OHPeonidin OCH3 HPetunidin OCH3 OHMalvidin OCH3 OCH3Radish red.

OH

OH

OH

OH OH

O

O

O

O

OH

O

O OH

CH3

CH3

CH3 CH3

CH3 CH3

R1

R2

OH

OH

HO+O

CH3 CH3

CH3

CH3

limitation for use. Red cabbage “juice” has been used in barbecue sauce and for colouring pink lemonade.

Anthraquinones [Category]Rubia tinctorum, roots of MadderMadder is native to the Mediterranean andthe Near East and was once widely grownas a dye plant and was used in centralEurope since around the 9th Century. Thecommon name Madder comes from theAnglo-Saxon name maedere for the plant.The generic name, Rubia means red andthe plant has been used as a source of a permanent red dye.

The two to three year old rootstock of the plants is used medicinally, and itremains red when dried. The constituentsinclude anthraquinone glycosides whichare two red chemical entities derived from the roots and tubers, and which are known as alizarin and purpurin. The isolation requires the prior hydrolysis of the glucoside precursor in the roots(Alizarin red from Rubia tinctorum occursin nature as the glycoside and is calledruberythrinic or ruberythric acid and is its6-O-β-D-xylopyranosyl-β-D-glucopyranoside).The Indian madder mainly yields purpurin(see Figure 5).

In the care of the skin it is consideredan astringent, tonic, vulnerary andantiseptic. Madder is also used to cleanse open wounds and can remove skin blemishes if bruised leaves areapplied externally. Externally, a decoctionof madder can be used for skin problems,especially tubercular conditions of the skinand mucous tissue. The decoction canalso be used as a bath additive.

Galium mollugo, White BedstrawThe native Indians used Bedstraw roots(Galium mollugo) to obtain a red colourand the root of this plant is an importantsource of the dye alizarin.

Galium odoratum, Sweet Woodruff Sweet Woodruff is similar to WhiteBedstraw and its roots can be used toproduce a red/pink dye. It is the samefamily as Madder.

ApigeninMatricaria recutita, German ChamomileThis flavonoid, which occurs widely inplants gives a dull, golden yellow and isusually obtained from German Chamomileor Matricaria recutita. Apigenin and lutolinwere more active than the other flavonoidstested. The spasomolytic activity ofchamomile has been attributed toapigenin, apingenin-7-0-glucoside and (-) - bisabolol, which have activity similarto papaverine. Apigenin and lutolin weremore active than the other flavonoidstested.

Calendula officinalis, Marigold It is also found in Marigold (Calendulaofficinalis), where it was shown, using themouse ear test, that the flavonoids – andnot the essential oil – were responsible forthe activity and, of these, apigenin wasmore active than indomethacin in the test.

Artemisia inculta, ArtemisiaArtemisia (Artemisia inculta) also containsapigenin and in a recent study wasdemonstrated to have anti-inflammatoryactivity.

Cuminum cyminum, CuminCuminum cyminum or Cumin also containsapigenin and luteolin and their derivativesin addition to plants like Carrot (Daucuscarota), Agrimony (Agrimonia eupatoria),Arnica (Arnica montana), PurpleConeflower (Echinacea purpurea)and Eyebright (Euphrasia officinalis) –all of which have demonstrated anti-

inflammatory activity when used under theright conditions. Yellow apigenin is alsofound in Parsley (Petroselinum crispum)and Celery (Apium graveolens).

ArbutinShepherdia canadensis,Canada BuffaloberryThe Canada Buffaloberry (Shepherdiacanadensis), also known as CanadaBuffaloberry, Soopolallie, Soapberry orFoamberry, is one of a small number ofshrubs of the genus Shepherdia bearingedible red berries. One recognised form,however, bears yellow fruits. The fruitproduces a red dye, and it containsericolin glucoside, and chimaphilin which is a yellow naphthoquinone.

AstacinAstacin is found in the shells of crabs andlobsters Homarus, algae, sponges andfish. Is practically insoluble in water.

AstaxanthinAstaxanthin, a carotenoid, is classified as a xanthophyll (having yellow leaves).

AzuleneSadly, this wonderful blue (blue-black) nolonger seems to be available commercially.Azulene is a prime component of theessential oil of chamomile flowers,Matricaria recutita L. and related plantspecies. Products containing azulenegenerally also contain the othercharacteristic components of chamomile’sessential oil. Azulene extracts are used in

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62 PERSONAL CARE June 2009

Figure 5: Alizarin. Figure 6: Apigenin. Figure 7: Arbutin (Ericolin).

R1 R2 R3 R4 R5 R6 R7 R8

Alizarin OH PH H H H H H HPurpurin OH OH H OH H H H H

Figure 8: Astaxanthin.

Figure 9: Chamazulene. Figure 10: Azulene.

OHOH

HO

OHO

O CH3

CH3

H3C

OH

OO

O

O

O

O R1

R2

R3

R4R5

R6

R7

R8

OH

HO

HO

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64 PERSONAL CARE June 2009

skin creams for reducing skin puffinessand wrinkles and are also known for theiranti-irritant and vulnerary properties.

It has never been clear whether thematerial was extracted from one of the chamomiles or from Myoporumcrassifolium Forst or Vanillosmopsiserythropappa Schultz-Bip in which thismaterial is also found. Maybe the sourcehas become too scarce for there to be a reliable commercial supply.

Betalains and Betacyanins[Category]BetaninDried beet juice contains 0.2%-1.0%betanin and is most stable between pH 4.0-5.0. It is heat, oxygen and lightlabile. Beets give rust/red or pink colours,but fade with time.

This colour occurs in the fruits ofPhytolacca americana (Phytolaccaceae)and in Portulaca grandiflora(Portulacaceae). It is a purple pigment.Other places where it may be found areCarpobrotus acinaciformis, Drosanthemumfloribundum, Mesembryanthemum spp.,Opuntia bergeriana and other Opuntia spp.(Cactaceae).

Brazilein, BrazilinCaesalpinia echinata, BrazilwoodThe heartwood of American Brazilwood,Caesalpinia echinata, contains a water-soluble compound called Brazilin,which on oxidation transforms to a red

dyestuff called Brazilein. As a mordanteddye the colours can range from purple tobright red depending on the chemicalsused.

In an acidic solution Brazilin will appearyellow, but in an alkaline preparation it willappear red. Brazilin is closely related to theblue-black dye haematoxylin, having oneless hydroxyl group.

CanthaxanthinThis is a carotenoid that naturally occurs in fungi but is more usually produced by“nature identical” synthesis. It is also acomponent of Spirulina-Dunaliella algae.The colour can be yellow to an almostorange red.

Canthaxanthin is a natural orangexanthophyll (E161a) isolated from somemushrooms, crustacea, fish and alsoflamingo feathers. It is used to enhancethe colour of fish flesh, particularly troutand salmon. There is some evidence thatprolonged ingestion of canthaxanthin inlarge amounts may cause spotting of theretina.

Capsanthin and CapsorubinCapsanthin and the related capsorubin are most commonly found in paprika orCapsicum annuum. It is rich in carotenoidpigments, including capsanthin,capsorubrin, carotene, luteine, zeaxanthin,and cucurbitaxanthin.

As well as being a dyestuff, it is alsoused in cosmetics in ointments, oils and

emulsions for its stimulating effect and asa sports massage product ingredient.

Capsicum annuum, CapsicumIt is also called Cayenne pepper, AfricanPepper, Chillies, Bird Pepper. It contains0.1% capsaicin, capsacutin, capsico (avolatile alkaloid) together with fixed oils.Capsicum in the form of an alcoholictincture is sometimes incorporated intohair lotions as a stimulant, particularly inpreparations designed for alopecia. Thepigments present in paprika are a mixtureof carotenoids, in which capsanthin andcapsorubin dominate. These are oil-soluble, are stable to heat and pHvariation but may deteriorate in light.

It is employed in preparations toprevent chilblains and is the purest andmost certain stimulant in materia medica.It produces natural warmth and equalisesthe circulation. It is an important herbalremedy. It is used externally as a counter-irritant, rubefacient and antiseptic. It is recommended for use in neuralgia,rheumatic pains, unbroken chilblains and is also used in cases of lumbago.

Capsicum is especially useful forproviding counter-irritation when applied to skin overlying an inflamed or irritatedjoint. Combined with myrrh it makes a good antiseptic wash.

CaramelCaramel colouring is produced by heattreatment of carbohydrates such as glucose

Betanin: 5–O–beta–D–GlycopyranosylbetanidinPhytolaccanin

Figure 11: Betanin. Figure 12: Brazilein.

Figure 13: Brazilin, Natural Red 24.

Figure 15: Capsorubin.

Figure 14: Capsanthin.

Beet red.

CH2OH

C0OH

HO

O

OO

O

O

O

O–

O

O

O

O

H

HO HO

HOHO

HO HO

H

HO

HON+

NH

HO

HO

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OHOH

OH

OH

OH

O

O

OH

OH

OHOH

OH

OH

N+

syrup and sucrose, in the presence ofammonia, ammonium sulphate, sulphurdioxide or sodium hydroxide. The types ofcaramel colour available include plain (spirit)caramel (prepared by controlled heattreatment of carbohydrates with or without an acid or base), caustic sulphite caramel(produced by heat treatment of carbohydrateswith sulphur containing compounds),ammonia caramel (heat treatment in thepresence of ammonia) and sulphite ammoniacaramel. Caramelised sugar or burnt sugar isformed by heating sugars without a catalyst.

Carminic acidCoccus cacti, CochinealThis extract is associated with the proteinmaterial of the cochineal beetle and gives

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June 2009 PERSONAL CARE 65

Figure 16: Carminic acid.

Figure 17: Carotenes.

Figure 18: Carthamin.

Canthaxanthin (No vitamin A activity)

Beta-Apo-Carotenal (0.83 µg = 1 IU)

Beta Carotene (0.6 µg = 1 IU)

Bixin (Annatto)

Carthamus yellow.

OH

OH

OH

OH

O

OH

OH

OH

OH

OHOH

OH

OH

OH

HO

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HO HO

HO

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H

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OOO

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O O

CH3

OCH3

HOH2C

O

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O

O

OO

H

O

OH

OHHO

HO

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66 PERSONAL CARE June 2009

red, yellow and orange colours dependingon the products and pH. Coccus cacti orscale insects are insects that live and feedon the prickly pear cactus (Opuntiamegacantha) of Mexico and CentralAmerica. They increase rapidly in size andlose their original shape until they appearas protuberances of the plant. The driedpulverised bodies of these insects yield thered dyestuff cochineal, which the AztecIndians used as body paint and for dyeingtheir fabrics a brilliant crimson. They alsoused cochineal for medicinal purposes.

It has been used as a pigment and as acolouring agent in cosmetics, paints andbeverages, but it is expensive as it takes70,000 insects to make one pound of dye.

The homoeopathic tincture is preparedfrom the dried bodies of the femaleinsects, which are larger than the maleand have no wings. It is one of the mainwhooping cough remedies.

In both India and Australia particularattempts have been made concerning theproduction of cochineal, for purposes suchas dyeing soldiers’ uniforms red. But chaosresulted. Either the insects fed so heartilythat they wiped out the cacti; or the cactimultiplied so excessively that they becamea real plague.

This can be purified to yield carminicacid or reacted with alumina to producethe aluminium lake of carminic acid whichis referred to as carmine.

Carminic acid is a polyhydroxy-anthraquinone acid or a red glucosidalhydroxyanthrapurin. It is water soluble, andacid stable yielding orange to red shadesdepending on the pH. Its aluminium lake,carmine, is soluble in alkaline media and is very stable in relation to heat, light and oxygen. In alkaline conditionscarmine provides a blue-red shade which becomes progressively less blue as the pH is decreased. Under acidicconditions below pH 3 carmine becomesinsoluble.

Carotenes [Category]Carotenes are fat soluble and oftensynthetically produced natural pigments.The colours range from yellow to red. The pigment is sensitive to oxidationbecause of the conjugated double bondsand the molecule may be isomerised if involved in heat processing. There are a number of related chemicals:w β-Carotene (0.6 µg = 1IU) w β-Apo-8’-Carotenal (0.83 µg = 1IU) w Canthaxanthin (No vitamin A activity) w Bixin (Annatto extract)

(No vitamin A activity) w Lycopene (No vitamin A activity)

This is a group of yellow/orange coloursextracted from such diverse sources asalgae, carrots and palm oil. It is alsoavailable as a “nature identical” product.

Crystalline β-carotene is sensitive to airand light. Vegetable fat and oil solutionsand suspensions are quite stable inproducts.

The carotenoids – apart from thechlorophylls – are the largest group of oilsoluble pigments found in nature. Theyconsist of molecules with long chainsmade up of carbon, hydrogen and mostlyoxygen (β-carotene consists of onlycarbon and hydrogen). One of thecarotenoid’s characteristics is that thecolour varies (according to the type ofcarotenoid) from yellow to red-orange.Carotenoids, like chlorophylls, exist ingreen plants. They are responsible for the yellow colour of flowers and thepigments of many fruits and vegetablessuch as carrots, paprika and tomato. The first discovery of the colour in carrotswas the reason for the generic name ofcarotenoids. It is converted by mammalsinto vitamin A and as a result is calledprovitamin A.

β-carotene is one of the major yellowcolours used in the food industry and thelargest use is by the dairy industry (forbutter, cheese and ice cream). The use of β-carotene has almost entirely replacedE102 Tartrazine yellow, which for variousreasons has received a bad press in recentyears.

β-carotene is one of the popular freeradical scavengers and antioxidants.

Figure 20: Chimaphilin.Figure 19: Chlorophyll. Figure 21: Chrysophanic acid.

Figure 22: Citranaxanthin.

Figure 23: β-Citraurin.

Figure 24: Crocetin.

Copper chlorophyll.

CH3 CH

CH

OH

OH

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CHO

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OH

C C

H

H C C

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N

N Mg N

CH

HC

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CH2

CH2

CH3

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CH3 CH3

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CH3

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CH3C20H39

CarthaminCarthamus tinctoria, SafflorCarthamin is found in the flowers ofCarthamus tinctoria or Safflor (BastardSaffron), Dyer’s Saffron, American Saffron,Fake Saffron, or Flores Carthami. It yieldsa pigment carthamin, which is a yellow-orange colour. On closer examination it is shown to contain two colouring matters,one yellow the other red. Safflower(Carthamus tinctorius L.) was formerlyused as a red dyestuff for textiles and is also currently used as a colorant by the food industry in small amounts.

The florets contain three majorpigments, all of which are present aschalcone glucosides: the scarlet redcarthamin is water insoluble but the“safflor yellow” A and B or safflomin(e) Aand B are both insoluble in water.

The seeds yield an oil which is used in India for burning and for culinary use.The flowers are used for their laxative anddiaphoretic properties, and also used forchildren’s complaints of measles, feversand eruptive skin conditions.

Apart from the seeds for oil and theflowers for dyeing, the Egyptians found theflower pleasing to the eye and included it in garlands placed on mummies.Remains of safflower were found in thetomb of Tutankhamun.

The safflower florets are gathered justbefore they die off, and are used for dyeingwool, silk and leather. The flowers give a yellow dye, and the Chinese used analkaline solution to produce the bright redsand purples for their silks. Also produced is a pink dye that was used by the Indians to dye their official red tape used on legaldocuments. Mixed with talc it wasemployed as rouge by actors.

It was also the principal ingredient inMacassar Oil, the hair oil so very popularwith Victorian gentlemen. Certain oil paints are based on carthamin. Anotherlittle known fact is that it was used toimpart a pink-red colour to the ribbon used to bind legal documents (and is stillused to this day). Hence the expression“tied up in red tape”

ChimaphilinChimaphilin is a yellow naphthoquinonefound in Shepherdia canadensis (seearbutin) [Syn: Hippophae canadensis]. The fruit juice has been drunk in thetreatment of digestive disorders and has also been applied externally in the treatment of acne and boils. Thealternative name for the plant “Soopolallie”is from the Chinook language for soap(soop) and berry (olallie) and the frothfrom the berries (which contain a naturalsaponin) or a jelly of the fruit, have beeneaten as an insect repellent as it was

said that mosquitoes were far less likely to bite a person who had eaten them.

Chlorophyll Extracted from grass and alfalfa, this ispresent in all green plants and has alwaysbeen a part of man’s diet. It gives mossgreen colour. It is naturally oil soluble, andis also found in green vegetables such as spinach or Spinacia oleracea and thecommon stinging nettle or Urtica dioica.

Copper chlorophyllDerived from plants (as above) but gives abrighter more intense green colour due tothe replacement of the naturally occurringmagnesium in the chlorophyll by copper.It is naturally oil soluble.

This is produced as the copperchlorophyll but a saponification processrenders this form water soluble. The colouris a bright green to green/blue.

Chrysophanic acidChrysophanic acid was discovered bySchrader, in 1819, in Parmelia parietina,Linné, a common wall lichen. It waspurified in 1843 by Rochleder and Heldt,who gave it the name chrysophanic acid,from its yellow colour and laterSchlossberger and Dopping decided thecolouring matter obtained from rhubarbwas identical. This colouring matter hadbeen known under the names of rheine,rheumine, rhabarberic acid, rhubarb yellow,etc. Chrysophanic acid is chiefly obtainedfrom a vegetable powder, called Goa orPoh di Bahia, which is the product of someunknown Brazilian plant probably Andiraararoba (Leguminosae) and also known as Araroba. The powder contains 70% to80% of acid.

Chrysophanic acid has been chieflyemployed as a local application for certain

cutaneous conditions, e.g. eczema, variousherpes conditions, psoriasis, acne androsacea, etc.

Rheum rhaponticum, RhubarbRhubarb roots makes yellow, orange or red shades and were sometimes used fordyeing hair. Rhubarb root has chrysophanicacid, a yellow dye, which will bind tokeratin. Chrysophanic acid, as such, doesnot perhaps exist to any large extent inrhubarb, but is formed by the splitting upof chrysophane.

CitranaxanthinThis is a carotenoid pigment. There arenatural sources of citranaxanthin, but it isgenerally prepared synthetically. It is usedas an animal feed additive to impart ayellow colour to chicken fat and egg yolks.

ββ-Citraurinβ-citraurin from Citrus sinensis (SweetOrange, Navel Orange) is a carotenoidpigment found in orange peel.

CrocetinCrocus sativus, CrocusIt is also known CI Natural Yellow 6; CI 75100; Croci Stigma; Crocus; Safran.The dried stigmas and tops of the styles of the Crocus sativus contain crocines,crocetins and picrocrocine. They aredelicate colours and should be protectedfrom light.

Saffron is used as a food and cosmeticdye and flavouring agent. In some circles it is considered to be a food. It was oncewidely used for colouring medicines. There have been early reports of poisoningwith saffron. This may be because ofconfusion with Autumn Crocus (Colchicumautumnale).

For years English saffron was the most

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Figure 25: Crocin.

Gardenia blue.

Gardenia yellow.

CH3 OR

O

O

O

OGentiobiose

Gentiobiose

O

O

ROR=

CH3

CH3 CH3

CH3 CH3

H2C

HOH2C

HO

HOHO

HOHO

HO

O

OO

CH3 CH3

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highly esteemed (grown in Saffron Waldenfrom about 1350), and most expensive, in Europe. Today, however, the best saffroncomes from the barren plain of La Manchain Spain. One kilogramme of plant yieldsabout 460,000 stigmas. The colour is due to a pigment called crocin, so strongthat 1 part crocin in 100,000 parts ofwater is a deep golden colour. The flavour comes from a related compound calledpicrocrocin. Saffron also seems to containa substance that helps blood to clot. It is as a water-soluble dye that saffronprobably found most use. The colour isdeep and rich, and most familiar today in the saffron robes of Buddhist monks.

Folkloric uses of saffron have includedits use as a sedative, expectorant,aphrodisiac and diaphoretic. Anecdotalreports from the tropical regions of Asiadescribe the use of a paste composed of sandalwood and saffron as a soothingbalm for dry skin.

The stigmas of Crocus sativus are rich in riboflavin, a yellow pigment andvitamins.

In addition, saffron contains crocin, the major source of yellow-red pigment. An hypothetical protocrocin of the freshplant is decomposed on drying into onemolecule of crocin (a coloured glycoside)and two molecules of picrocrocin (a colourless bitter glycoside). Crocin is a mixture of glycosides: crocetin, adicarboxylic terpene lipid, and alpha-crocin,a digentiobiose ester of crocetin. In addition, cis- and trans-crocetindimethylesters have been identified.

Similar compounds have been isolatedfrom other members of the family. A compound named gardenidin, obtainedfrom gardenias, has been shown to beidentical with crocetin.

CrocinCrocin extract is the trade term for theyellow, water-soluble food colorantobtained from cape jasmine (Gardeniajasminoides L.) and from red stigmas of

saffron (Crocus sativus L.). However, theextracts are not used interchangeably in all applications since saffron is valued asmuch for its aroma and flavour as for itscolouring properties. It is an expensivespice which may prohibit its commercialuse as a natural colorant.

Gardenia jasminoides, GardeniaA bright yellow colour that has been in use for over a thousand years. Extractedfrom the fruit of Gardenia jasminoides.Gardenia florida [possibly a synonym for G. jasminoides] also contains crocin and isprescribed as an antipyretic, haemostatic,and antiphlogistic, and in cases ofjaundice.

A paste of the herb with flour and wineis used as a poultice on twists, sprains,strains, bruises, and abscesses. It is veryeffective in cases of injury to tendons,ligaments, joints and muscles. Chinesemedicine considers it to have anti-inflammatory, antipyretic, astringent, andhaemostatic functions as well as use in the treatment of mastitis. The maincomponent of its yellow pigment is crocin,which is now generally used as a naturalyellow pigment. It is also used for irritation,sore and swollen eyes and abscesses.Fructus gardeeniae is widely used inChinese medicine. The fruits of Gardeniajasminoides also contain ursolic acid whichpossesses hypothermic, sedative andanticonvulsant characteristics. Theattributes of this plant may, therefore, be in part due to the ursolic acid present.Gardenia Blue is derived from Gardeniajasminoides Ellis.

Crocus sativus, CrocusThe characteristic yellow-orange colour of saffron (Crocus sativus L.) comes fromwater-soluble pigment, the carotenoidcrocin. Saffron carotenoids with ethanol-extractable mostly contain safranal as anantibacterial, and were used in Persiantraditional medicine to treat some skindisorders. The extracted carotenoids from

saffron as an antioxidant prevent manycommon diseases by taming harmfulmolecules known as free radicals.

Crocin is 8,8’-Diapo-ψ,ψ-carotenedioicacid bis (6-O-β-D-glucopyranosyl-β-D-glucopyranosyl) ester; α-crocin; di-gentiobiose ester of crocetin. It is also thecolouring principal of saffron and alsooccurs in crocus.

CryptoxanthinCryptoxanthin is a xanthophyll (E161a) and is found naturally in members of thepotato and tomato family, as well as in egg yolks and butter. It provides a naturalyellow colour but is not available forcommercial colouring use. Cryptoxanthin is also found in corn and strawberries.

CurcuminCurcumin provides a water soluble orange-yellow colour. It is a natural extractobtained by solvent extraction from thedried rhizomes of turmeric (used in Indiancuisine as a flavouring agent). Curcuminmay be used to compensate for fading of natural colouring in pre-packed foods. It was recognised as an anticarcinogenicagent during laboratory tests.

This is the pigment of the spiceturmeric and will give a range of colourfrom yellow to a deep orange.

This has been in use as a foodingredient for over 2,000 years. It alsocontains a closely related chemical calleddesmethoxycurcumin, where one of themethoxy groups is replaced with ahydrogen atom.

Curcuma longa, TurmericThe rhizome of Curcuma longa has beenused as a medicine, spice and colouringagent for thousands of years. Turmeric was listed in an Assyrian herbal referencework dating from about 600 BC and wasalso mentioned by Dioscorides. It hasmany medicinal properties including those of being an antioxidant and an anti-inflammatory.

Figure 28: Flavoxanthin.Figure 29: Fumigatin.

Figure 26: Curcumin. Figure 27: Datiscetin.

OCH3

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HO O

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OH OH

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O

The anti-inflammatory activity ofcurcumin was first reported in 1971. In anextension of this work, it was reported thatoral doses of curcumin possess significantanti-inflammatory action in both acute and chronic animal models. Curcumin wasas potent as cortisone in the acute test(carrageenan oedema), but only about half as potent as phenylbutazone inchronic tests.

The Negritoes of the Philippines utilisethe fresh rhizome to treat recent wounds,bumps, bruises and leech bites. Mixedwith gingelly oil (a localy produced oil), it is applied to the body to prevent furtherskin eruptions. Turmeric paste mixed with a little lime and saltpetre and applied hotis a popular application for sprains andbruises among other Filipino blacks. In smallpox and chickenpox, the Negritoesmake a thin paste of turmeric powder and apply it to the entire body in order to prevent pock marks from occurring by facilitating the scabbing process. It is also used for ringworm.

The blacks of Trinidad in the WestIndies use turmeric rhizome poultices toreduce the swellings of sprains and pulledtendons, while the rhizome juice and oil is used for its antiseptic properties onvarious skin affections – i.e. razor bumps,herpes lesions and venereal sores.

Among the dark races of India, turmerichas been used since time immemorial totreat skin problems. Both the Ayurvedicand the Unani practitioners have used a paste of powdered turmeric or its freshjuice made into a paste or a decoction ofthe whole plant as a local application inthe treatment of leprosy and cobra bites. It is especially useful for indolent ulcers on the surface of the skin and gangrene in the flesh. A paste made from thepowdered rhizomes along with caustic lime forms a soothing remedy for inflamedjoints.

Turmeric is also used as an externalapplication of “rouge” and is utilised by some women in India to suppress theunwelcome growth of facial hairs andupper lip moustaches.

In Northern India the rhizome is used by many natives for treating cuts, burnsand scalds.

The natives of Samoa use thepowdered rhizome to sprinkle on newborninfants to help heal a recently cut umbilicalcord, to prevent nappy rash fromoccurring, and to keep the skin continuallysoft and resilient. The powder is also usedas a paste or poultice to treat skin ulcersand to help heal extensive skin eruptions.

In parts of Africa, turmeric has beensuccessfully tested for healing rashes dueto allergies and psoriasis inflammation and itching accompanying arthritis.

DatiscetinThis flavonoid has a yellow colour and isfound in Bastard Hemp (Datisca cannabina).

DelphinidinDelphinidin is an anthocyanidin that givescolours from red wine to brown.

Deoxyisosantalin,DeoxysantalinThe heartwood (camwood) and roots ofBaphia nitida yield a red dye calledDeoxyisosantalin that was used untilrecently to dye raffia and cotton textiles.

The powdered heartwood is a used as a red body paint and the paste is usedas a cosmetic for the skin. As a body paintit is considered to have magic powers.

The leaves or leaf juice are appliedagainst parasitic skin diseases. The leavesand bark are considered haemostatic andanti-inflammatory, and are used for healingsores and wounds. The powdered heartwoodis made into an ointment with shea butterwhich is applied against stiff and swollenjoints, sprains and rheumatic complaints.

FlavoxanthinFlavoxanthin is a xanthophyll, providing anatural yellow colour. Xanthophylls aremixtures of hydroxy derivatives of alpha-,beta- and gamma-carotenes, their naturalepoxides and fatty acid esters.

FumigatinFumigatin is isolated from Aspergillusfumigatus (a brown fungal toxin withantibiotic properties).

FustinFustin is closely related to morin and thesetwo flavones are found in the wood fromChlorophora tinctoria and Morinda citrifolia(Indian Mulberry) whose pigments aremixtures of yellow to orange flavonessimilar in structure to fustin and morin. It is called maclurin which has long beenused as a yellowish-brown or khaki dye.

GenisteinGenistein is one of several knownisoflavones. Isoflavones, such as genisteinand daidzein, are found in a number ofplants, with soybeans and soy products liketofu. Genistein functions as an antioxidantand many isoflavones have been shown tointeract with oestrogen receptors and causean effect in the body similar to thosecaused by the hormone oestrogen. It is aprotein tyrosinase kinase inhibitor. Both theoestrogenic effect and the inhibition ofkinases positively influence skin collagencontent which is good for anti-ageingproducts. In adipose tissue it produces alipolytic activity and is so useful in thetreatment of cellulite.

Genista tinctoria, Dyer’s GreenweedGenistein is a yellow dye contained as theglucoside genistin in Dyer’s Greenweed,Genista tinctoria. An infusion is usedagainst rheumatism, arthritis, dropsy andchronic skin disorders. In the past theflowers were used for dyeing fabrics.

GentisinGentisin is a yellow flavone found in the roots of Genista tinctoria, Dyer’sGreenweed.

AcknowledgementI would like to thank Union Swiss in South Africa for itsvalued sponsorship of the oil soluble colour research.

Reference1 International Journal of Cosmetic Science 24,

5, 287-302, (2002). Natural ingredients forcolouring and styling.

PPCC

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June 2009 PERSONAL CARE 69

Figure 30: Fustin.

Figure 31: Genistein.

Figure 32: Gentisin.

Details at a glance

On the following four pages arecomprehensive details of natural coloursmentioned in the text. The second part ofthe article, together with another extensivetable, will be published in the Septemberedition of Personal Care Europe.

OCH3

OH

OH

OH

OHOH

OH

HO

HO

HO

HO

O

O

O

OO

O

Code CI number Common name Name Chemical class Colour Plant name Source Solubility Supplier Trade name Special comments

75330 Natural Red 6,8,9,10,11,12 Alizarin Anthraquinone Red Rubia tinctorum Madder, chay

75330 Natural Red 6,8,9,10,11,12 Alizarin, ruberythric acid Anthraquinone Red Rubia tinctorum Madder colour Water soluble Kiriya Chemical Co Ltd Akane Red RM A substance composed mainly of alizarin and ruberythric acid obtained from madder roots

75330 Natural Red 6,8,9,10,11,12 Alizarin, rubiadin Anthraquinone Red Rubia tinctorum Madder root Water soluble Alban Muller (agent IMCD) Amicolor

75520 Natural Red 20 Alkanet Naphthoquinones Red Alkanna tinctoria Alkanna root Water soluble

75530 Natural Red 20 Alkanet Naphthoquinones Red Alkanna tinctoria Alkanna root, orchanet, Water solubleSpanish bugloss

75530 Natural Red 20 Alkanin or anchusin Naphthoquinones Red Anchusa tinctoria

75520 Natural Red 20 Alkannan Naphthoquinones Red Anchusa tinctoria

E160a 40800 Food Orange 5 Alpha-carotene, beta-carotene, Carotenoid Orange Wgamma-carotene D

E160a 40800 Food Orange 5 Apha-carotene, beta-carotene, Orange Extract of natural carotene Water dispersible Oversealgamma-carotene

E173 Aluminium Element Silver O

E150c Ammonia caramel

E160b 75120 Natural Orange 4 Annatto, bixin, norbixin Xanthophyll pigment Yellow orange Bixa orellana Seeds, lipstick tree, urucum Oil soluble

E160b 75120 Natural Orange 4 Annatto, bixin, norbixin Carotenoids Yellow orange Bixa orellana Annatto extract Oil soluble Kiriya Chemical Co Ltd Annabejin A-08 A substance composed mainly of norbixin and bixin obtained from the seed coats of annatto

E163 Anthocyanins Extract of anthocyanins Water soluble Overseal Overseal Blue OF 3100

E163 Anthocyanins Anthocyanins Red, blue Various Many sources Water soluble Paroxite Natural Blue Colour 3947 –or violet A

E163 Anthocyanins Anthocyanins Deep magenta Vitis vinifera Grape skin Water soluble Overseal Anthocyanin Extract OF 0039

E163 Anthocyanins Anthocyanins Red Perilla frutescens Perilla colour W

E163 Anthocyanins Anthocyanins Purple Brassica oleracea Red cabbage colour Water soluble Overseal Overseal Magento OF 1000 Extract of anthocyanins with addition of invert sugar and potassium sorbate

E163 Anthocyanins Anthocyanins Mauve Brassica oleracea Red cabbage colour W

E163 Anthocyanins Aanthocyanins Red Raphanus sativus Red radish colour W

E163 Anthocyanins Anthocyanins Purple Ipomoea batatas Purple sweet potato colour Water soluble Kiriya Chemical Co Ltd Kiriyasu Red PSP A substance composed mainly of cyanidine acylglucosides and peonidin acylglucosides

E163 Anthocyanins Anthocyanins Deep magenta Vitis vinifera Grape skin colour W

75590 Natural Yellow 1,2 Apigenin Flavonoid dyes Yellow Matricaria recutita Greek chamomile, weld W

Arbutin Naphthoquinones Red Shepherdia canadensis Canada buffaloberry W

Astacin Red Homarus Crab, lobster shells Almost insoluble in water

E161j Astaxanthin Xanthophyll pigment Red Haematococcus pluvialis Microalgae A

Azulene Naphthalene Dark blue Vanillosmopsis Candeia tree Serythropappa

E162 Beetroot red, betanin Betalains, Purple-red Beta vulgaris Beetroot Wbetacyanins W

E162 Betanin, beetroot red Betalains, Red Beta vulgaris Beet red Water soluble Kiriya Chemical Co Ltd Beet Pink SA A substance composed mainly of betanin and isobetanin obtained from beetrootsbetacyanins

Berberine Isoquinoline alkaloid Yellow Berberis vulgaris Barberry

E160e 40820 Food Orange 6 Beta-apo-8’-carotenal (C 30) Orange

Brazilin Yellow Caesalpinia sappan Heartwood Water soluble Sabinsa Corporation (agent Unifect) Sappan Extract Colour changes from yellow to red depending on pH

75280 Natural Red 24 Brazilein Red Caesalpinia sappan Heartwood Water soluble Sabinsa Corporation (agent Unifect) Sappan Extract Colour changes from yellow to red depending on pH

E120 75470 Natural Red 4 Carminic acid or cochineal Anthraquinone Red Coccus cacti Opuntia cactus beetle Water soluble Univar Colour Cochineal Powder 44000

75560 Natural Red 22 Camwood, deoxyisosantalin Red Baphia nitida Heartwood (camwood) Water solubleand roots

E161g 40850 Food Orange 8 Canthaxanthin Xanthophyll pigment Orange Chlorella zofingiensis Edible mushrooms, green algae

E160c Capsanthin Carotenoid Red-orange Capsicum annuum Paprika W

E159 Natural Brown 10 Caramel Melanoidin pigment Golden red/brown Burnt sugar Water soluble Overseal Caramelised Sugar Syrup Controlled heating of sugar solution to produce burnt sugar or caramelU

E153 Pigment Black 7 Carbon black, vegetable carbon Black O

E153 Pigment Black 7 Carbon black, vegetable carbon Others Black Vegetable carbon black K

E120 75470 Natural Red 4 Carmine Anthraquinone Red Coccus cacti Opuntia cactus beetle Water soluble Overseal Carmine Extract OF 0063

Natural Red 26 Carthamin, carthamine Flavonoid Red Carthamus tinctorius Safflor, Dyer’s Saffron Water soluble (slightly)

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70 PERSONAL CARE June 2009

Solubility Supplier Trade name Special comments

Water soluble Kiriya Chemical Co Ltd Akane Red RM A substance composed mainly of alizarin and ruberythric acid obtained from madder roots

Water soluble Alban Muller (agent IMCD) Amicolor® Madder Red

Water soluble

Water soluble

Water soluble

Water soluble

Water soluble Paroxite Natural Carotene WD 10 AP Rendered water soluble using maltodextrin, mod, starch. Sugar and MCT oilDD Williamson Natural Carotene OSS 200 standardised in carrot oil

Water dispersible Overseal Em-Seal Natural Carotene OF 3221

Oil/water dispersible

Oil soluble

Oil soluble Kiriya Chemical Co Ltd Annabejin A-08 A substance composed mainly of norbixin and bixin obtained from the seed coats of annatto

Water soluble Overseal Overseal Blue OF 3100

Water soluble Paroxite Natural Blue Colour 3947 –Almost oil soluble Univar Colour NET Anthocyane OS Triglyceride from middle chain fatty acids, elderberry juice concentrate, maltodextrin, citric acidOil soluble Overseal MiChroma Blue OF 3200 Extract of anthocyanins sprayed on starch suspended in vegetable oil

Water soluble Overseal Anthocyanin Extract OF 0039

Water soluble Kiriya Chemical Co Ltd Kiriyasu Shisonin L A substance composed mainly of terpenoids obtained from Perilla seeds or leaves

Water soluble Overseal Overseal Magento OF 1000 Extract of anthocyanins with addition of invert sugar and potassium sorbate

Water soluble Kiriya Chemical Co Ltd Kiriyasu Red RC-N A substance composed mainly of anthocyanins obtained from Brassica oleracea L. var. capitata DC

Water soluble Kiriya Chemical Co Ltd Kiriyasu Red RR-F A substance composed mainly of anthocyanins obtained from Raphanus sativus L.

Water soluble Kiriya Chemical Co Ltd Kiriyasu Red PSP A substance composed mainly of cyanidine acylglucosides and peonidin acylglucosides obtained from the tuberous roots of sweet potatoes.

Water soluble Kiriya Chemical Co Ltd Grape Colour BC-120 A substance composed mainly of anthocyanins obtained from the pericarps of American grapes or other grapes.

Water soluble

Water soluble

Almost insoluble in water

Almost oil soluble

Sparingly water soluble

Water soluble Paroxite BeetRed WSP1Water soluble Paroxite Beetroot Red P03Water soluble Univar Colour Beetroot Powder 42047

Water soluble Kiriya Chemical Co Ltd Beet Pink SA A substance composed mainly of betanin and isobetanin obtained from beetroots

Water soluble Sabinsa Corporation (agent Unifect) Sappan Extract Colour changes from yellow to red depending on pH

Water soluble Sabinsa Corporation (agent Unifect) Sappan Extract Colour changes from yellow to red depending on pH

Water soluble Univar Colour Cochineal Powder 44000

Water soluble

Water dispersible

Water soluble Overseal Caramelised Sugar Syrup Controlled heating of sugar solution to produce burnt sugar or caramelUnivar Caramel LiquidUnivar Caramel Powder

Oil dispersible Overseal MiChroma Carbon Black OF 1569 Vegetable carbon black in sunflower oil

Kiriya Chemical Co Ltd Kiriyasu Black T A substance composed mainly of carbon obtained by carbonising plants

Water soluble Overseal Carmine Extract OF 0063

Water soluble (slightly)

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June 2009 PERSONAL CARE 71

Code CI number Common name Name Chemical class Colour Plant name Source Solubility Supplier Trade name Special comments

E150b Caustic sulfite caramel

75580 Natural Yellow 12 Chamomile, apigenin Flavonoid Yellow Matricaria recutita Greek chamomile, weld Water soluble

Pigment Black 8 Charcoal Black

Chimaphilin Naphthoquinones Yellow Chimaphila umbellata Wintergreen, pipsissewa, Water solublePrince’s Pine

E140 75810 Natural Green 3 Chlorophylls and chlorophyllins: (i) chlorophylls (ii) chlorophyllins

E140 75810 Natural Green 3 Chlorophylls and chlorophyllins: Others Chlorophylline K(i) chlorophylls (ii) chlorophyllins

E140 75810 Natural Green 3 Chlorophylls and chlorophyllins: Chlorophyll Green Medicago sativa Leaves of alfalfa Water soluble Alban Muller (agent IMCD) Amicolor(i) chlorophylls (ii) chlorophyllins

E103 Chrysoine resorcinol

75400 Natural Yellow 23 Chrysophanic acid, chrysophanol Anthraquinone Yellow Rheum palmatum Turkey rhubarb Water soluble

75400 Natural Yellow 23 Chrysophanic acid, chrysophanol Anthraquinone Yellow Rumex crispus Yellow dock Water soluble

E161i Citranaxanthin Carotenoid Yellow Produced synthetically Insoluble in water,

β-citraurin Carotenoid Orange Citrus sinensis Sweet orange peel, Water solubleCitrus tangerina tangerine peel

75570 Natural Yellow 10 Clover, pratol Flavonoid Yellow Trifolium pratense Red clover

E120 75470 Natural Red 4 Cochineal, carminic acid, carmines Anthraquinone Red Coccus cacti

E120 75470 Natural Red 4 Cochineal, carminic acid, carmines Anthraquinone Red Coccus cacti Cochineal extract Water soluble Kiriya Chemical Co Ltd Carmin Red K A substance composed mainly of carminic acid obtained from cochineal insects

E141 75815 Copper complexes of chlorophylls Chlorophyll Bright green Wand chlorophyllins W(i) copper complexes of chlorophylls W(ii) copper complexes of chlorophyllins

E141 75815 Copper complexes of chlorophylls Chlorophyll Bright green – Oil soluble Overseal Copper Chlorophyll Extract OF 0709 Sunflower oiland chlorophyllins Bright green – Oil soluble DD Williamson Copper Chlorophyll OS 140 Standardised in vegetable oil(i) copper complexes of chlorophylls Bright green – Oil soluble Sensient LCW (agent Adina) Natpure Col Green LC 718L Standardised in vegetable oil, ascorbyl palmitate, alpha-tocopherol(ii) copper complexes of chlorophyllins Olive green Spinach O

Olive green Stinging nettles Oil soluble Univar Colour Stinging Nettle Extract OS 10 Triglyceryl fatty acid esters (middle chained), complete extract stinging nettle, alpha-tocopherol

Crocetin Carotenoid Yellow Gardenia grandiflora Chinese crocin Water solubledicarboxylic acid

75100 Natural Yellow 6 Crocin Carotenoid Yellow Gardenia jasminoides Cape jasmine Water soluble Hayashibara Ujo GYSP Sold as a laked powder on silk

75100 Natural Yellow 6 Crocin Carotenoid Yellow Gardenia spp W

75100 Natural Yellow 6 Crocin Carotenoid Yellow Gardenia florida

E161c Cryptoxanthin Xanthophyll pigment Yellow Physalis spp Cape gooseberry Oil soluble

E100 75300 Natural Yellow 3 Curcumin, turmeric Curcuminoids Orange yellow Curcuma longa Rhizomes Water soluble Givaudan (agent Adina) Turmeric Yellow Curcumin(polyphenols) W

75630 Natural Yellow 12 Datiscetin Flavonoid Yellow Datisca cannabina Bastard hemp

75510 Natural Red 22,23 Deoxysantalin Naphthoquinones Red Pterocarpus santalinus Sanderswood, barwood

75440 Natural Green 2 Emodin or frangula-emodin Anthraquinone Rhamnus frangula Persian berriesYellow 14

E160f 40825 Food Orange 7 Ethyl ester of beta-apo-8’- Carotenoid Orange Often produced from apocarotenal carotenic acid (C 30) (E160e)

75620 Natural Brown I Fisetin Flavonoid Brown Rhus cotinus Venetian sumac

Natural Yellow 10 Flavine Pteridines Yellow

E161a Flavoxanthin Xanthophyll pigment Golden yellow Rananuclus spp Buttercup species

Fucoxanthin Carotenoid Olive green, Fucus virsoides Fresh brown algae Water solublebrown Zygnema pectinatum

Undaria pinnatifida

75600 Fulsugetin Flavonoid Garcinia spicata Dyers

Fumigatin Benzoquinone Maroon Aspergillus fumigatus Fungus derivative Sparingly water soluble

Fustin Flavonoid Yellow Rhus verniciflua Venice sumac WRhus cotinus Venetian sumacRhus succedanea

Genipin Iridoid glycoside Blue Genipa americana Fruit of Genipa Water soluble Alban Muller (agent IMCD) Amicolor

75610 Genistein or prunetol Flavonoid Yellow Genista tinctoria Broom, Dyer’s Greenweed W

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72 PERSONAL CARE June 2009

Solubility Supplier Trade name Special comments

Water soluble

Water soluble

Kiriya Chemical Co Ltd Kiriyasu Green CWS A substance composed mainly of chlorophyl obtained from Spinacia oleracea L.

Water soluble Alban Muller (agent IMCD) Amicolor® Alfalfa Green

Water soluble

Water soluble

Insoluble in water,slightly oil soluble

Water soluble

Water soluble Univar Colour Carmine Powder 44002

Water soluble Kiriya Chemical Co Ltd Carmin Red K A substance composed mainly of carminic acid obtained from cochineal insects

Water soluble Paroxite Copper Chlorophyllin WS 95AP Polysorbate 80, potassium hydroxide, sodium copper chlorophyllinWater soluble Givaudan (agent Adina) Super Green Copper chlorophyllinWater soluble Univar Colour Chlorophyllin AS Liquid –

Oil soluble Overseal Copper Chlorophyll Extract OF 0709 Sunflower oilOil soluble DD Williamson Copper Chlorophyll OS 140 Standardised in vegetable oilOil soluble Sensient LCW (agent Adina) Natpure Col Green LC 718L Standardised in vegetable oil, ascorbyl palmitate, alpha-tocopherolOil soluble Univar Colour Spinach Extract OS 20 Triglyceryl fatty acid esters, complete extract spinach, alpha-tocopherolOil soluble Univar Colour Stinging Nettle Extract OS 10 Triglyceryl fatty acid esters (middle chained), complete extract stinging nettle, alpha-tocopherolOil soluble Univar Colour Chlorophyll OS Liquid 42058 –

Water soluble

Water soluble Hayashibara Ujo GYSP Sold as a laked powder on silk(Gardenia Yellow Dyed Silk)

Water soluble Kiriya Chemical Co Ltd Kirishin-L Conc A substance composed mainly of crocin and crocetin obtained from gardenia fruits

Water soluble Univar Colour Gardenia Florida Extract

Oil soluble

Water soluble Givaudan (agent Adina) Turmeric Yellow CurcuminWater soluble Univar Colour Curcumin Powder 42066 90% dyestuff

Water soluble

Sparingly water soluble

Water soluble

Water soluble Alban Muller (agent IMCD) Amicolor® Genipa Blue

Water soluble

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