The Geranium Family in Perfumery

THE GERANIUM FAMILY IN PERFUMERY

By E. S. MAURER, F.L.S., M.R.I.*

A detailed examination o1' the members o1' the Geranium •mily, the classification o! their odours and the derived essential oils with uses and applications in perhunery.

THE GERANIUMis one of those flowers of which the naming of the garden versionsis somewhat confused,for what most people commonly call a geraniumis not the geraniumof the botanist. The familiar, showy,scarlet- floweredplants so widely usedfor bedding-outpurposes are really pelargoniums,another branch of the same family. The Geraniaceseis an extensivefamily of herbaceousplants and shrubs originally introduced to this country from South Africa about 1675 and now acclimatisedto the temperateregions of the northernhemisphere. It comprisessome twenty generaand upwardsof 750 species. Apart from the flowersit is the foliagewhich is of particularinterest, for that of some speciesexhibits a pleasantlystrong, aromatic resinous scent or a balsamic- citron nuance. In a few instances,however, somewhat nauseating odours are to be found. Furthermore,many of the generahave remarkable astrin- gentproperties, and the tuberousroots of somespecies are eitheredible or usedmedicinally--the term "alum root" for the driedrhizome of Geranium maculatumproviding a casein point. Thetrue cultivated geraniums are hardy perennials or rockplants having brightcrimson, scarlet, red, pink, lilac, mauve, blue or whiteflowers. Some of them are seldomseen unless in a specialcollection, and these,together with the manyhybrids among the pelargoniums,are the particularinterest of the BritishGeranium Society. Thereis quite an extensiveliterature on the subject,the source-bookof whichwould appear to be the five-volume anonymouscontribution upon the "Gerania"(London, 1820-1828). Of theprototype, there are some 15 species of geraniumsgrowing wild in GreatBritain, some of whichare rarely encountered these days, but of the familiarand easily recognisable plants, Geranium Robertianum, the little crimsonherb-Robert, G. pratense,the bluemeadow crane's-bill, and the palehlac G. molle,the dove's-footcrane's-bill, are found in mostfields and waste places.

ETYMOLOGY AND HISTORY In compilingthese studies, • the names of the wild flowers form a prelude to theexamination of thegenera within the N.O. under consideration. It is

* Lautier Fils, London. THE GERANIUM FAMILY IN PERFUMERY

instructive to observe how frequently not only in the Latin and Greek substantivesbut in the homelycountry names as foundin mostEm opean languages,the matrix is preservedand perpetuatedin a brief description centred upon a fancied resemblanceof somepart of a plant to an animal. Thus we find such examplesas adder's-tongue,colt's-foot, dogwood, fox- glove,hound's-tongue, snake-root, wolf's-bane and many others,while quite a number of avian references are also to be discovered. In this direction we have alreadyseen mention of larkspursand the ibis associationwith hibiscus, to which may now be added a botanicallyinteresting trinity, becauseit is from the Greek, geranos= a crane, that this family derives its generic name, a further contributionbeing made by the sub-orders,the Erodiums, erodios= a heron, and the Pelargoniurns,palargos = a stork. In miniature, the ripe seedsof theseplants bear a superficialresemblance to a crane'shead with its longbill. This fanciedappearance was noted by Dioscorides(an army surgeonto Roman troopscirca A.I). $$), who commented uponthis class of whatwe now term "explosive"fruits, i.e., sogreat a tension isbuilt up in the ripeningcapsules on a hot sunnyday that theyare suddenly rupturedand catapult the seedsto a considerabledistance from the.parent planl•wa proclivity which is observedto a remarkabledegree in another genusof this family, namely, the Impatiens or Balsams.

TI-IE WILD GERANIUMS Attention is first directedto the prototype GeraniumRobertianurn, the familiar crimson-or purple-floweredherb Robert of the country roadsides and woodlands. There are severalalternative suggestionsto accountfor the chgiceof name,probably the mostlikely being its derivationfrom Robert, Duke of Normandy, for whom was written the celebratedmedieval medicaltreatise--Regimen Sanitatis Salernitanurn. AsI ambeginning to findusual, the countrynames afford an interesting insightinto the potentialsof the family, for, in this case,the plant is aptly termed"red shanks"because of its very long,thin red stalksand, in autumn, a particularlybright crimsonfoliage; hencesome of its other sobriquets, e.g., dragoh'sblood and blood-wort. In this direction,it is recordedby the old herbaliststhat Nature seems to have set a blood-red seal upon several.of her herbs to indicate their virtue of being able to stop bleedings,this and the tutsan {Hypericurn androsaernurn)have long beenregarded as the two best remediesafforded by the fieldsfor the rapid controlof internaland external h•emorrhages. This russettinge and trend is still morenotable in G. sanguineurnand, as previouslymentioned, it is not undulysurprising to find a namesuch as alumroot bestowed upon the purple-floweredG. rnaculaturn,when it is known that therhizomes contain upwards of 30 percent of tannicacid, thus prorid- 4 JOURNALOF THE SOCIETYOF COSMETICCHEMISTS ing a further instanceof natural astringentswhich may prove of cosmetic interest as an alternative to Witchhazel extracts for facial and other lotions.

DIVERSITY OF ODOURS It is somewhatsurprising to find the extent of the odourgamut among the geraniumsand pelargoniums.E.J. Parry in the Chemistryof Essential Oils lists some40 speciesbased upon the odoursas classifiedby E. M. Holmesin the P. & E. 0. R. (1913,p. 372),while D. McDonald,in Fragrant Flowersand Leaves (1895), among some 30 entries,mentions some varieties not foundin the later list. From theseI haveselected a representativecollec- tion, as is seenin the appendedtable.

A BRIEF LIST OF THE SCENTED-LEAVED GERANIUMS AND PELARGONIUMS Citrus scented: Abrotanifolium Southernwood Asperium .. Verbena Ci'triodora .. Strong lemon Variegatum .. Soft, sweet lemon Crispurn major Lemon-verbena Crispurn minor Citronella Prince of Orange Sweet lemon Lady Scarborough Sweet lemon Triste (Night-scented Lemon-balm

Rose scented: Capitaturn .. .. Rose and diphenyl oxide, Graveolens .. Rose and rue Odoratissimum'' .. Rose and tansy Attar of Roses ß. Strong rose ! Herbal type: Clorinda .. Eucalyptus (cineol) Endsleigh Peppermint, Citronella Moore'sVictor«' Ditto Tormentosum .. Ditto Lady Mary .. Ditto Little Gem .. Ditto

Balsatalc type: Cedronellum ...... Balm of Gilead Quercifolium ...... Balsamic-balm Glutinosum ...... Labdanum type Radulavitifolid• ...... Ditto Radula balsameum ...... Ditto

Miscellaneous: Fulgidum .... Butyric Exstipulatum .... Pennyroyal Glaucifolium . Clove-hyacinth Atrum(night-s•;nted)' Ditto Unique aurore .... Pungent aromatic White Unique .... Ditto Pretty Polly .... Almond scented THE GERANIUM FAMILY IN PERFUMERY 5

This presentsthe pleasantnuances of rose,or rosein conjunctionwith lemon,citronella, eucalyptus, peppermint, pennyroyal, nutmeg, almond, clove,hyacinth a•d balsam; conversely,with the butyric elementvery prominent, we may record some decidedly unpleasant combinations,as we may note from such further epithets bestowedupon herb-Robert as "foxy-geranium"and "stinking Bob," for the foliagewhen bruisedemits a stale, sickly, caproic and skatole•-taintedeffluvium, similar to the odour ascribed to badgers, weasels and foxes--a characteristic which is also observedwith the foliage of someof the "musky" Erodiums,such pelar- goniumsas P. fulgid•m, P. abrotanifoliumand also with the deadnettle (Lamiumalbum), the wood-strawberry(Fragaria v•sca) and the weasel-snout (Galeobdolon luteurn) .

THE SCENTED "GERANIUMS" It is alsoremarkable that the botanytexts concernedwith Europeand N. America only afford informationupon about a dozen speciesof the indigenouswild geraniums,and with the exceptionof the feral smell of herb-Robert,none of the remainingvarieties exhibit the slightestapproach to the geraniumodour so familiar to us in our everydaywork. It would thereforeseem that the scentedvarieties of our gardenshave originatedfrom acclimatisationand cultivation of stock transferred from the native habitat of South Africa, and sometimesexhibiting a prodigious growth (for I observefrom GardenFlowers in Colour, by G. A. Stevens, publishedin 1939 by the MacmillanCompany of New York, that: "The well-knownbedding geranium of Northerngardens is a shrubin California, climbingup the sidesof housesand overfences. Its round,velvety, scented foliageis particularlyhandsome and immune to insectpests, while its jolly, comfortable-lookingflowers are exceedinglybrilliant and long lasting . . . there are many different geraniums,and the plants which we commonly grow under this name are really pelargoniums. The true geraniumsare mostly wildings, suitable for natural plantings or rock-gardens. None of them is very showy,although most speciesare acceptablypretty."). From the country of their origin I have a note regarding one of the mountaingeraniums, locally known as the Wilde Malfa (P. cucullat•m). This is reportedto growinto fair-sizebushes about the size of a smallhay- rick. To cometo the more prosaicplants, however,I note that the earlier gardenmanuals list somesixty varietiesof the "true" geraniums,among whichthe mostimportant would seemto be the scarlet-floweredG. odoratissimum,described as the geranium-oilplant. There is alsothe large-rooted, purple-floweredG. macrorhi•um,the blossomsas well as the leavesof which aredescribed as having a "strongaromatic scent." Thisplant, within recent years, is perhapsmore familiar to perfumersby its Bulgarianname of 6 JOURNALOF THE SOCIETYOF COSMETICCHEMISTS

Zdravets,the foliageupon distillation yielding a greenishconcrete having a. heavy,persistent clary sage-ambertype of fragrance. Mentionmust also be affordedto anotherand somewhat unique fragrance to be found in the foliageof the scarlet-floweredG. moschatum,the muski- nessof whichis very similarto the odourof balsamPeru oil. 'Thisbrief survey, I believe, summarises allthat can be usefully recorded regardingthe genusGeranium, in so far that the geranium-rosefragrance doesnot appear in the native wild plants, but only, and then often in a somewhatlimited degree,to stocksfrom warmerclimates which have become naturalised to northern latitudes. It is instructive, however, to observe in the cataloguesissued by the nurserygardeners that amongthe herbaceous plantsscarcely any mention is affordedto the geraniums,other than perhaps a laconicentry suchas: "G. subcaulescens,the true plant from the Grecian mountains. The flower stemsradiate from tufts of silvery leavesand bear brilliant crimson flowers with a black centre." Mention of the latter colourprompts a passingnote, for it is remarked that G. phoeum,the duskycrane's-bill, is uniquefor the dingy and almost blackhue of the blossoms,a proclivity which is alsoseen in the deepindigo tint of the flowersof G. sylvestrum,and the bluish black sombrenessof the aptly named Pelargoniumnigrescens, and is particularly evident in the blackish-purpleflowers of P. Zonal var. Meteor,which yields easily a dark violet chromo-glucosideknown as pelargonin. Doubtless there is some botanically useful function served by such macabre-shadedblossoms, which from an a•sthetic viewpoint one could perhapsassociate with the asphodel,and perhapsit is fortunatethat such huesare in a minority whencompared with the almostuniversal preponder- ance of the neutral or creamy white and lightly tinted blossomsover all other colours.

THE PELARGONIUMS There are severalclasses of Pelargoniums,namely: (1) the ordinary scarlet-flowered;(2) the zonal, or horse-shoe,also known as the bronze, silver, and gold-leaf tricolours; of these there are hundredsof varieties, both singleand doubleflowered--some 230 speciesand hybridsare recorded as being distributedthroughout South Africa and about a hundredin New Zealand. Then there are (3) the ivy-leaved varieties which are mostly climbers; while group(4) is the oneof greatestinterest to perfumersas this containsthe lemon and rose-scentedkinds remarkable for the fragranceof their leaves,and lastly, (5) the fancy, or large-flowered,also known as the "oak-leaved." THE GERANIUM FAMILY IN PERFUMERY 7

THE GERANIUM OILS It will be noted, whenthe Labiate family is considered,that the essential oil is usuallyfound throughoutthe greenparts, but in somegenera {for example,the Mints and Basils)it is concentratedin the inflorescencejust beforethe flowersopen. A similarmobilisation of the essentialoil takesplace in the Pelargoniums,but with this difference,inasmuch as the essentialoil acquiresa more flowerycharacter as the 'budsopen, by the transformation of the prevailing citral-type odour into a geraniol or rose-like fragrance. Hencethe plant is gatheredfor distillationa little beforethe openingof the flowersand, although the petals yield no odorousproduct, in order to waste no time in detachingthe flowersthey are put into the stills with the leaves. Referenceto the literature from 1802 to date provides a considerable amount of information and someconflicting opinions, but to epitomise,it may be statedthat the originalSouth African parent plants have provided North-westAfrica, SouthernEurope and East Africa, and especiallyBourbon (Reunion),with plantationstock speciallyselected from hybrids among P. capitarum,P. odoratissimum,P. roseurn,P. graveolensand so on. Specimensof the above-named,as grown in England, differ in many respects,but collectively,the foliagewhen freshyields upon distillationthe familiar brownish green geranium oil of commerce, which possessesa characteristicdeep, sweet rose-like odour. Furthermore,it becomesvery evident upon examinationof the analytical data given in the literature regarding the geranium oils, that this reflects the many differencesin odourvalue accordingto the plant species,soil and climatic conditionsprevailing in the locality of the plantations, variations which are immediately obviousupon odour comparisonsbetween authentic samplesfrom different sources. It is therefore expedientto selectfor considerationhere a well-defined type as a standard,for example,Oil GeraniumBourbon. This, incidentally, introducesinto theseessays • the first mentionof probablythe mostimportant and at the same time the 'mostwidely used of our natural perfume materials, namely, the sweet, rose-smellingoils of geranium, the isolated alcohol,geraniol and its esters. Accordingto Piesse,writing in 1855,several varieties of geraniumsbear- ing scent-yieldingleaves were introduced into Europefrom South Africa as far back as lB00, but it was not until 1847that P. capitaturn,the purple- flowered,round-headed geranium began to be systematicallycultivated in the southof Francefor the purposeof extractingits scent-yieldingprinciple, known then in commerceas otto of rose-leafgeranium. It would appear that geraniolwas first isolatedfrom Palmarosaoil by Jacobsenin 1871 by adopting the unique property of calcium chloride to 8 JOURNAL OF THE SOCIETY OF COSMETICCHEMISTS form crystalline magmas with certain alcohols,while Tiemann, in 1898, oxidisedgeraniol to citral and subsequentlyreduced this aldehydeand regeneratedthe alcohol.

0DOUR-PATTERNS It is hereinstructive to recallPie. sse's remark regardi•ng this rose-leaf geranium,for he saysß "... the leavesof this plant yield by distillationa very agreeablerose-smelling otto, so much resemblingthe real Otto of Rose,that it is usedvery extensivelyfor the adulterationof that valuable scent .... ' ' I have usedelsewhere the term "fragrance-pattern"and illustratedit by a diador triad of well-definedfloral types selected from the groupsof fragrancesarranged in tabularfor m a•cordingto myinterpretation oftheir orderof relativeimportance i•n perfumery compounding. This hasbeen basedupon a systematicanalysis of severalhundreds of themore characteristic type-formulaeas presentedin the variousperfumery recipe books from 1855 onwards,and almostautomatically verified by the cumulative indicesin my laboratorynotebooks. From this statistical data definite evidenceemerges of what has often, butsomewhat casually, been mentioned in thelitei'ature, namely, that there is scarcelya perfumebase in which the elementsof rose,j asminor neroli do not appear in some form or other. In my Tabulation of BlossomFragrances, initial considerationis afforded to twogroups each containing f/re basicodours, proportional admixture of whichresults in theevolution, first of thesimple exotics and then the more complexfloral odours, but whateverthe angleof approachmay be, it will invariably be found that attention gravitatestowards the rosecontent. I thereforefeel that in so far as the essentialsof perfumerycompounding areconcerned, theprime odours should be regarded ashaving odour-patterns, reservingthe termfragrance-patterns to define with some precision the osmical end-pointsof prime odour combination. This approachopens a very interestingvista, because,for example,in the caseof the rose, not only doesthe noun name and place the flower, butanalysis of theessential oil derived from it revealsthe type and quantity presentof the dominantand recessiveosmophores, from which, usually with a largemeasure of success,reconstitution of the otto of rosearoma is possible.

THE GERANIUM FRAGRANCE Considerationof the geraniumoils affords another opportunity of dealing with an importantitem in the commerceof perfumeryraw materialsand at the sametime to appreciatethe valueof the data nowavailable in the literature of the essentialoils concerningtheir chemicaland physicalproperties, THE GERANIUM FAMILY IN PERFUMERY 9

whichis of considerablehelp to the perfumer,for not only has he at his disposalfrom the varioussupply houses the segregatedcomponents of an essentialoil in a high degreeof purity but he can profit in severalother directions. Amongthese, for examl•le , is theencouraging th'ought that he is not entirelydependent upon ihe gera, uium oils for his gemniol, as there are far moreeconomical sources in the citronellaand Palmarosa •)ils, which by processingyield isolatesand estersclosely approximating thos• foundin geraniumoil; but others,although alien, possess the familynuance and facilitatethe productionof compoundedoils of outstandingstrength •[nd tenacity--anaccomplishment, incidentally, which is aidedby theincorpora- tion of suchpurely synthetic aromatic's not foundin natureas benz0-and rose-phenonesanddiphenyl-oxide and-methane, which possess •harac- teristic rose-likeand geranium-leafodours. I think that geraniumoil may be regardedas one of Nature's'master- pieces,and one which, early in the experienceof the student-perfumer,will amplyrepay the effortof a prolongedstudy. 'BouRBONAND OTHER GERANIUM 0ILS Referenceto the literaturewill indicatesomewhat prosaically (in round figures)that the total alcoholsin Bourbongeranium, regarded as geraniol, willvary between 65 and70 per •enl; the,ester content, calculated as geranylriglate, about 25 to 30 per cent,while the apparentcitronellol is approximately40 to 50 per cent. Thisis laconicand not particularly'interesting, but a closerapproach revealswhat may •)erhaps beaptly termed an osmical panorama, forin the foreground,andsupporting thegeraniol and citronellol, wefind the presence of smallquantities of terpineol,linalol, bornyl, amyl andhexyl alcohols. In thebackground arethe particularly reactive acids--acetic, burytic, caproic,tiglic and valeric whichin liaisonwith the alcoholsare capable of theoreticallyengendering Upwards,of thirty esters. Of course,such a com- prehensiveinter-esterification does not take place in theplant; nevertheless, it is aswell to bearin mindthat someof themore probable formulations, for example,the acetates and valerates ofamyl alcohol, b9rneol and terpineol, areso powerful that theirnatural (or intentional) incidence must be in such smalltraces just evident enough to beregarded as modifying agents. Toadd to the complexity ofconstitution, yet obviously playing an important part in the composureof the fragrance,are the traceelements--citral, menthone,pulegone, pinene, phellandrene and their isomers. GeraniumBourbon is alsoremarkable for therelatively small amount of terpenesit contains,and, in my opinion,the potential of thefull depthand beautifulfragrance ofthis oil is seen in two d.irections, firstly in theterpene- 10 JOURNALOF THE SOCIETYOF COSMETICCHEMISTS lessoil, and secondlythe result from careful fractionatingwhich yields the rhodinol of commerce. Without attempting any comment upon the unsettled questionof the chemistryof the rhodinols,it may be noted in the pelargoniumand in other flower oils that geraniol is associatedwith the laevorotatory form of citronellol. The proportionalbalance in the R6union oil may be regarded as 50: 50; whereasthe oils of African origin averageabout 80: 20; those of French distillationshowing approximately 70: 30; and the Spanishoils 60: 40, noting in passingthat it is usuallythe French oil which is distilled over rosepetals to yield the beautiful Geraniumsur Rose. It wouldtherefore appear that this equipoisein the Bourbonoil provides an idealfoundation for simulationsof Bulgarianotto of rose,while increasing the content of/-citronellol emphasisesthe lighter and sweeternuances of rose centifolia, Damascene, the moss and the tea roses.

THE "GRASS" OILS It is alsoinstructive briefly to review severalof the economicalsources from which the geraniumoils of commerceare obtained and to note the variationsin the odour-patternsof these oils which are distilled,not from leaves,but from floweringgrasses. In orderof importancethese are Pal- marosaand the Java, Ceylonand Formosacitronella oils. Distillation in India of CymbopogonMartini var. (Motia-.•ass) yields Palmarosaor "Turkish" geraniumoil (containingfrom 75 to 90 per cent of free geraniol)which has a fine, soft, mellowrose-geranium odour singularly free from unwantedalien off-notes, which is not undulysurprising when it is notedthat the addendum isbrief, consisting chiefly of smallquantities of the acetic and caproicgeranyl esters,methyl heptenoneand dipentene. Another example from a similar speciesknown locally as Sofia-grass yields ginger-grassoil, but in this instancethe geraniolin a much smaller yield is associatedwith an entirely differentframework formulated around the presenceof carvone,dihydrocuminol, phellandrene apd dipentene,from whichemerges a strongand somewhatunpleasant herbal back-note which is difficultto eliminatefrom the geranioleven by repeatedfractionation. Java citronella,distilled from C. nardus,is interestingfor severalreasons, firstly becauseit introducesus to a very important sourceof a fine quality geraniol,and secondly, whereas this alcohol is foundin liaisonwith/-citronellol in Bourbon geranium,in the Java oil its companionis the aidehyded- citrondial to the extent of about 35 per cent of each. This aidehyde,when reduced,provides the d-citronellolof commerce,but it must be observedon comparisonthat thereis a considerableodour difference between the relatively coarserose-type scent of the dextro-versionand the refined,suave and sweeter rosy fragranceof the laevo-modification. THE GERANIUM FAMILY IN PERFUMERY 11

The odour-framework,which with the terpenesconstitutes the remaining 30 per cent in the make-upof the Java oil, accordingto the literature, is seen to comprisesome thirty items,but just how someof thesecontribute towards the compositearoma it is difficult to assess,and although the presenceof citronellyl and geranyl acetates is noted, yet some inter-esterificationis probablefrom the occurrenceof butyl and amyl alcoholswhich donate certain fruity notes. These are complementedby green nuances,following the incidenceof hexanol, hexenoland methyl heptenone,while tracesare found of cadinol,methyl eugenoland citral. All of these,be it noted, are very powerfulosmophores, and must there- foreblend to effecta profoundmodifying action upon the basicodours of the two main constituents. CitronellaCeylon. A brief glanceat the build-up of Ceyloncitronella (ex Andropogonnardus) reveals another storehouse of ancillaryaromatics. This oil is important commerciall5 as an economicalsource of a second- grade geraniol and d-citronellal,the approximatebalance of these constituents being as 30:10, but the incidental componentsonly amount, however,to about a dozenitems. Thesecomprise, in addition to the acetic esters,methyl eugenoland methyl heptenone,common to both oils, but the incidenceof small amountsof such dominant osmophoresas borneol, cam- pheneand thujyl alcoholis sufficientto repressthe moredelicate fragrance, due to tracesof a nerol-linalolcomplex and farnesol; hencein comparison with the odourof the Java oil, that from Ceylonis crudeand heavy,being somewhatunbalanced by the backgroundof herbaceouselements. The Formosanoil inclinesclosely towards the Java type, and is interesting for the formulationof economical,yet powerfnlbases for industrialperfumes, as well as being an important commercialsource of the aromatic isolates and their derivatives: geraniol,citronellal, citronellol, the corresponding esters,hydroxycitronellal and synthetic menthol.

INTERESTING FRAGRANCE-PATTERNS One of the most interestingnatural associationsof geraniol,and incidentally a pattern whichwith variationsis typical of quite a numberof fragrant Australasianflora, is to be found in the foliageof BoroniaMuelleri (N.O. Rutaceae),in whichthe rosygeraniol note is complementedby an aromatic- balsamicnuance of the fennel-myrrhtype, backedby pineneand refreshed with geranylacetate. From this ensemblea very pleasingand intriguing bouquet emerges. In the antipodesthere are qui•e a number of these fragrant Boronias with distinctiveand well-definedodours, B. citriodora,for example, yields an oil containingupwards of 80 per cent of/-citronellol, another sourceof whichis Eucalyptuscitriodora; while Verbena(Aloysis or Lippia) citriodora, 12 JOURNALOF THE SOCIETYOF COSMETICCHEMISTS

with its high citral content, is a further example of the lemon-citronella scentfound associated with gerarfioland/or its esters. Among•the myrtles (N.O. Myrtaceae)are found the eugenol-containing cloveand pimentatrees, the oils of whichhave a high contentof this phenol alcohol. It is, however, from the small white flowers and the foliage of Myrtus communis,the well-knownevergreen shrub in its natural habitat, that, in my opinion,the componentbalance of eugenoland geraniolis so adjusted by Nature as to engenderan initial spicy-rosescent, which is supportedand sustainedby the presenceof myrtenol, nerol, cineol and cinnamicaldehyde--a groupingwhich may thus be selectedas a prototype bouquetwhich may be convenientlydescribed as the Myrtle BloomFragrance. With somemodifications, this nuanceis foundextensively in othergenera of this N.O., for instance,among the widely spreadAustralian melaleucas, the well-known "bottle-brushes" of which Callistemonsalignus, the white or willowbottle-brush, is a typical example. The samespicy-rose motif is alsocharacteristic of severalmembers of the N.O. Calycanthaceae,for example,Calycanthus Floridus, the Carolina allspice-treeand Chimonanthusfragrans, the Japanesevariety, while similar sweetodours which perfumethe air for a considerabledistance around are the proclivityof Elaeagnushortensis and other varieties of this "wild olive" family,which, like the myrtles,are prolificin their tiny whiteflowers from which sucha continuousvolume of powerfulfragrance is disseminated.

THE U•igUITOUS GERANIOL The above examplesare representativeof the presenceof geraniolin sufficientproportion in the severalfragrance-patterns to exercisea modifying effect upon the other osmophorespresent and thus engendera natural bouquet,and it is thereforeinstructive to learn, upon referringto the convenientlyarranged lists now available in the several"Aromatic Codices" that, progressingthrough the alphabetfrom acacia to zdravets,the incidence of geraniolin flowerabsolutes and essential oils extends to somefifty itemsq a magnitudewhich is sharedonly with linalol. Moreover,it is remarkedin the literature, albeit somewhatlaconically, that gerani01is extensivelyused as a basefor many types of floral compounds,but it may not perhapsbe realiseduntil an auditis madefrom a comprehensiverange of contemporary

type-formulae(such as is to be foundin Jellinek'sPractice . of ModernPer- fumery)that the incidenceof geranioland/or geranium is seenin morethan half of the examples. Becauseof the normal associationof scentwith the beauty, colourand shapeof flowers,regarding which the premierposition is usuallyaccorded to the rose,we have ampleevidence of the usagemade by the earlierEastern civilisationsof rose-waterand rose-perfumedoils and unguents,while the THE GERANIUM FAMILY IN PERFUMERY 13 popularityof this beautifulprimal fragranceis still beingmaintained, judgingby the frequencyof its choicefor perfumingcreams, brilliantines, lipsticks,face and talcum powders and othertoilet andcosmetic specialities whichdepend for their fragranceupon economical, powerful and persistent compoundsbased upon geraniol. It maytherefore be regardedas a fortuitousproclivity of geraniolthat it possessesan osmophorewhich is alreadyso close to the nuanceof the rose ottosthat, givena little supportfrom/-citronellol and phenylethyl alcohol, the basicoutline of the rose otto fragrance-patternis comparativelyeasily approached.The final touches towards achieving an ideal simulation which is ,estheticallysatisfying must, of course,depend entirely upon the perfumer'sinspiration and his skillin selectingand decidingupon the proportional balancefrom a very brief but carefullychosen list of natural and syntheticaromatics--according to the type of rosebouquet he wishesto emulate. T•E GENUS ERODtUM There are about a dozen wild Erodiums indigenousto Europe, bearing mostlylilac or purpleflowers. Probably the most common is E. cicutarium, knownin this countryas the hemlockstork's-bill, but in North Americait is variouslytermed common heron's-bill, pin-clover, pin-grass or Californian wild musk. E. moschatumis the musky stork's-bill,Muscovy or ground needle. Both theseplants possess foliage somewhat clammy to the touch (cf.Cistaceae) and on further handling emit a strongscent which is described in the gardenbooks as "musky." Here I think we have evidence of a similar balsamic-labdanum nuance whichhas already been noted with someof the Pelargoniums,rather than any suggestionof the vegetable"musky" odour characterised by the musk mallows. The gardenmanuals list someforty varietiesof annualand biennial Erodiumshaving mostly blue or purpleflowers with at leastsome suggestion in the foliageof an aromaticredolence, but this appearsto be moremarked in someof the naturalisedtropical species, for example,E. malapoidesand E. Reichardi,which have a very sweetresinous-balsamic odour.

SOME LESSER-KNOWNPLANTS ALLIED TO GERANIUM Somemembers of the Geraniumfamily on their own terrain have gradu- allyadapted themselves to thepeculiarly dry conditionsof the Karroo--the highpastoral tableland of SouthAfrica. Oneunique specimen known as kaarsbossieor the candle-bush(Sarcocaulon (Burmanil) Patersonii) is a small spinyshrub bearing white flowers and remarkablefor the fact that the succnlentbranches, even when quite fresh and green, contain so much oil thatthey will burn like a torch. Thisgenus is allied to the Monsonia, of which 14 JOURNALOF THE SOCIETYOF COSMETICCHEMISTS there are somehalf a dozen cultivated varieties, with white, red or purple flowers,the foliage exhibiting a pleasantbalsamic-citrus redolence, while Floerkeaprosperpinacoides---known asthe falsemermaid---is a solitaryspecies of a North American genus, having minute white flowers and slightly unpleasant-odouredfoliage. Balsaminais a discardedsynonym of Impatiens, giving name to the sub-orderof the Balsams. Theseare of East Indian origin,now naturalised in Europeand North America,and are tenderherbs, the succulentstems of which are laden with a bland aromaticwatery juice. The genericname Impatiens refers to the characteristicalready noted amongthe crane's-bills,namely, the elasticityof the valvesof the seedpods, which dischargetheir contentsto a considerabledistance when ripe or touched. I. noli-m•-tangere(touch me not) is the only Englishspecies which is indigenousto Europe, but they are very numerousin India, some 125 specieshaving been recorded. The wild balsamis almost a rarity in the English countryside,but is an elegantplant sometwo feet high bearinglarge flowersof a delicateyellow hue beautifully spottedwith orange,while the somewhatlarger plants in North Americaare known as "j ewel-weeds,"and from the proclivity men- tionedare listed in the wild flowerbooks of that countryas "snap-weeds." The gardenmanuals list somethirty varietiesof hardy and half-hardy annualsand generallyfeature the double camellia-floweredbalsams of the nurseries,but theseplants--with their fine spikesof waxy-texturedblossoms which may be pink, rose,scarlet, violet, yellow or white---do not, so far as I can ascertain,possess foliage with any pronouncedaromatic proclivity. It is therefore to someof the tropical varieties, such as I. cornuta,the red- floweredhorned balsam of Ceylon and I. sultani, the scarlet-blossomed Zanzibar balsam-shrub,to which attention may be directed. It is first, however,opportune to take a brief glanceat the genericname, as this revealsseveral hints which aid our understandingof the aromatic- citrousnuance found within the Geraniaceae.Although the Anglicanword is obviousin the Latin (balsamum)and the Greek(balsamon), yet the root is to be found in the Hebrew (bosere),which would appear to have from its meaningas the "chief of oils" a rather specialsignificance. Conversely, whenthe odourbalance of thiscomplex is reversed and the emphasisis upon the citrousside, the redolenceis then a particularlyapt descriptionof "balm," a word whichis derivedfrom the Aramaic--bolsminmmeaninga sweet,leafy scent. This folial fragranceis perhapsbest typified by the herbaceousperennial commonto the Mediterranean,namely, Melissa oy•½inalis (N.O. Labiata•), the lemon-balm,or sweethoney-plant, deriving its name from .thefondness of bees(Greek: mdissa•- a bee)for its flowers. This plant, as well asthe Moldavianbalm and the varietyknown as "balm of Gilead"are particularly THE GERANIUM FAMILY IN PERFUMERY commonto countrygardens in SouthernEngland, and a slightbruising of the foliageimmediately releases a sweetlemon-verbena fragrance. The particularreference to "balm" as anythingwhich healsor soothes pain arisesfrom the query madein Jeremiah,viii, 22: "Is there no balm in Gilead; is there no physicianthere ?..." and althoughit wouldappear that balm and balsamare in ordinaryparlance interchangeable terms, yet from the perfumeryangie we must allocatet o them very specialmeanings, more particularly as I find in the botanicaltexts a considerabledivergence of opinion. For example,balm of Gilead (or Mecca)may properlybe describedas the thick syrupyliquid extractedfrom the sticky,resinous and balsamic-odoured buds of Populusbalsamifera, N.O. Salicaceae,while balsamof Mecca {or Roghen)would seemto be more correctlylisted under Balsamodendron Gileadense,N.O. Amyridaceae,the Abyssinianmyrrh trees,amongst which are found B. mukul, the Bdellium of the Scriptures. Due allowanceshould, however, be affordedto our understandingof the odourand physicalappearance of the familiar balsamsof Copaiba,elemi, Peruand tolu, andso on, belonging to the N.O. Leguminosaeand originating in SouthAmerica, as comparedwith the materiarn•dica of Biblical times,for other authorities consider as the source of the Gileadense balm, trees indigenousto the Syrian-Grecianarchipelago, such membersof the N.O. Anacardiaceae as Pistacia lenticus, the lentisk or common mastic tree, and P. terebinthus,the Algerian or Barberry turpentine tree, from which were obtained,by natural or artificially inducedexudations, fragrant products of a liquid,balsamic or resinous consistency which underwent certain changes uponageing and/or exposure to air. This listing may be concludedwith mentionof Balanites(or Ximenia) Aegyptiaca,N.O. Olacaceae,the Persianzachun-oil tree, and particularly Cedronellatryphylla, N.O. Labiatae,named from the Greek: kedron---- the cedar,in referenceto the fragrant resinousscent of its foliage. This latter plant,also listed as Dracocephalumcanariense, dragon's-head balm, is said to have extensiveusage among Indian womenof to-day, as providingan excellent and fragrant shampoo.

BALSAMITA--A TRUE BALSAMIC FRAGRANCE ? Althoughwe mayobserve within the Geraniaceae instances of the varying proportionalmergers of the balmylemon-verbena nuance with the benzoin- labdanumtype of balsamicfragrance and variousbalsamic-vanilla shadings amongthe spicetrees and myrtleblooms, yet for a longtinhe I haveheld the opinionthat somewherethere shouldbe founda sourceto yield an un- trammelled"quintessence of balsam,"and this I believeto exist in a herb seldomseen these days and difficultto locatein the literature. 16 JOURNALOF THE SOCIETYOF COSMETICCHEMISTS

I referto Chryst,nthemum balsamira, also known as Balsamiravulgaris, N.O. Compositae,and bearingthe almostforgotten names of maudeline, alecostor costmary(Costus Maria), Costisbeing a genericGreek term for certainspicy roots, and in the dayswhen ale washome-brewed, costmary wasusually added to impart an agreeablesharp tang to the beverage,hence the name alecost. Costmaryis a shade-lovingplant growingsome two feet high,bearing insignificantgreenish white flowers. The scentof the living plant hasbeen describedas giving an initial impressionsimilar to that of a weak mint sauce, but the foliage,upon bruising,reveals a uniquefragrance which I can best liken by a liaisonof iso-butylcinnamate and methylionone slightly shaded with carvone. We may perhapsrecollect that the adventof clary sageinto perfumery was asrecent as 1909,and it is very probablein my opinionthat shouldthis equally modest herb--or some of its near relations, such as B. cornuta, the red-floweredAsiatic "horned balsam"---ever achieve commercial importance,it wouldprove to be a valuablealternative to clary sage,for among the other virtues which I believe it to possess,a hint from an old Herbal indicatesthat not only doesit confera deliciousscent to potpourri, but intensifiesthe fragranceof all the ingredientstherein.

BALSAMIC EPITOME I have taken this opportunity in dealingwith the balsamson their own terrain to digresssomewhat upon the balm and balsatalcmotif, because, althoughprior considerationhas alreadypartly positionedthis redolencein the essayupon Labdanum and Cistaceae?as well as the balm and balsam liaisonas noted in the Hypericaceae(St. John's-worts),I wouldregard these sourcesas a preludeto a longerchapter, for amongnatural fragrance there is considerableevidence of the balm or lemon-verbena nuance, either dominant or merging with the balsamic, while the transition of the latter into the "aromatic" by the gradualacquisition of suchosmophores as vanilla, cinna- monand clove provides the patternfor an extensiverange of tropicalblossom odoursin many of whichthe citrouselement again emerges.

MINOR MEMBERS OF THE GERANIUM FAMILY Among the lesser-knownmembers of this unique family are the Lim- nanthes(Latin: limnus = a marsh). Theseare dwarf hardy annualsknown asthe Californianmarsh flowers, of whichL. Douglasiiis a typicalexample. As foundin thewild state,particularly in South-EastEngland, its pretty little yellow and white flowershave earnedfor it the local name of "eggsand bacon." This plant, as well as L. roseaand L. alba, is a favourite with the beesand possessesa sweet melissa-like fragrance--a further exampleof the incidence of the citrous nuance found within this N.O. THE GERANIUM FAMILY IN PERFUMERY 17

THE OXALIDACEAE It is perhapsa little strangeto find that Oxalis acetosella,the familiar sorrel of our woodlandsand hedgerows,belongs to the Geranium family, the namesin most languagesbeing indicative of the sour acid juice in the delicate shamrock-like leaves. Originally also from South Africa and bearing white or pale tinted flowersoften streaked with mauve, it is a large genuscontaining some 30 wild and over 150 cultivated species. It is, however, only occasionally amongthis array that there is any suggestionof scent. O. odorataand 0. montana exhibit a faint, nondescript "neutral" perfume, but this is more evident in the South African 0. magellanica,which inclines to a lily-honey fragrance, while the South American 0. enneaphyllahas characteristic waxen-whitepetals which emit a decidedalmond-like scent. The nasturtium of the flower gardensis another example of misnaming, for the term rightly belongsto the watercressfamily, N. O. Cruciferae. We find that from the Latin: nasus = nose and tortus: tormented, is indicated the proclivity of an acrid nose-stingingpungent smell---thismustard-like odourpeculiar to the cressesbeing sharedby the Tropaeolum, the Indian cress,yellow larkspur or gardennasturtium. The botanicalname through the Greek and Latin refersto a trophy from the fanciedresemblance of the shield-shapedleaves and the helmet-likeflowers. Apparently this was originally a Peruvian climber renownedfor the glowingsunny brilliance and beauty of its scarlet-orange,trumpet-like blossoms,of which T. majus,the large,and T. aduncum,the canarycreeper, are probablythe best known,while the seedspickled in vinegarhave for long beenknown as "false capers." The contentof tracesof benzyl iso- thiocyanate,which is moreevident in the roots,accounts for the "mustard and cress" association. With regardto fragrance,a clusterof blossomson a hot sunnyday may give the impressionof a very faint, nondescriptscent, but under similar circumstances,if left in a coveredjar for a few hours,it is likely that the slightlymedicated odour of phenylethylcyanide will be observed.Although a fairly largegenus, the onlyspecieq I cantrace with any definiteevidence of a perfumeis T. tuberosum,the Peruviantuberous-rooted nasturtium, the red and yellowblossoms of which have a similarlily-honey fragrance as notedwith Oxalismagellanica, which incidentally is just perceptiblein the aquaticHydrocera (or Tytonia)natans and H. trifiora. Theseare the East Indian water balsams,bearing large white flowersvariegated with red and yellow. FRUITS IN THE GERANIUM FAMILY It may perhapsbe a little surprisingto find edible fruits within the Geraniumfamily, nevertheless, indigenous to India maybe foundtwo small, 18 JOURNALOF THE SOCIETYOF COSMETICCHEMISTS butvery interesting trees, as instanced byA verrhoa c•rambola, thekumrunga , which grows to a height of about 16 feet and is remarkable first for the beauty of its crowdedclusters of small pale rose-colouredribes-like flowers which producefruit the size of a lemon. These,when well-ripened,have a strong and agreeablequince-like scent and somethingof a nutty peach flavour. Belongingto the samegenus is A. Bilimbi, the bimblingor cucum- ber tree, which flowersin a similar way to the above,but the fruit is of the form and size of a gherkin,with a smooth,thin, pale green,translucent rind, like that of the white grape. When ripe it is assoft asbutter, with a flavour like an unripegooseberry and afterwardsacquiring the aromaof strawberries.

SUMMARY It is evidentfrom the statisticaldata that Geraniumand/or geraniol are extensivelyused as the basisfor the formulationof all kinds of artificial floral oils and fancy bouquets while the rose odour is particular to the Pelargoniums,which occupythe dominantposition in the Family, and with one exceptionthe remainingitems recordedmay be regardedas of minor importance. This study has directedattention to one of the modestmembers of the family aroundwhich some genera from otherN.O.s have been arranged,a sectorwhich may perhapsconveniently be namedas the Balsamina,and from this groupat sometime there may becomeavailable a companionto clary sage. Regardingthis latter herb, with its musky-ambercharacter, W. A. Poucher,in Volume I, makes a very interesting remark, for he says: "It is this aromawhich is so distinctivein fine quality essentialoils, such as certain varietiesof geraniumand neroli, and which is absentin synthetic aromatic chemicals,as instancedby geraniol and nerol (in comparison)." Although we have observedthe balsamic-labdanumredolence to be an integralpart in manyof the pelargoniumoils, yet by removingthis somewhat heavynuance and replacing it with anEssence of Balsamina, some remarkably interestingresults might, in my view, becomeapparent.

REFERENCES • Maurer, E. S., Th• œss•ntialsof P•rfum• Compounding,Part 2 of which, "The Natural Orders," is currently being serialisedin Soap, P•rf•ery • ½os•tics. • Ibid., a series in which this paper will eventually take its place as the nineteenth essay. • Ibid., July, 1956.