Perfumes 1 [PDF]

Zitiervorschau

Perfumes and Flavours

Technology Handbook

By H. Panda MSc.F.I.C.F.I.C.S. Industrial Consultant Technical Consultant. G.I D.C., Fellow of Indian National Science Congress. Member of Chinese Academy of Forestry. Former Chemist (R & D). I.T.R. Co. Ltd. (U.P.)

Asia Pacific Business Press inc. AN ISO 9001 : 2000 COMPANY 106-E. Kamla Nagar. Delhi-110 007 (INDIA) CONTENTS

1.

Classification of Odours and Odorancs

1

2.

Flower Perfumes

15

3.

Sophisticated Perfumes

60

4.

Perfume for Men

86

5.

Perfumes for Many Purposes

99

6.

Essential Oils Used in Perfumes

125

7.

Synthetic Odorants

187

8.

Chemical Used in flavour mid Perluines

190

9.

Aromatic Chemical Used in Flavour and Perfume Compounds

256

10. Natural Odour of Aromatic Chemicals

288

11. Basic Flavouring Materials

309

12. Aromatic Chemicals Used in Flavour Compounding

335

13. Solvents

352

14. Colorant for Ptavour and Perfume

350

15. Stabilizer

367

16. Formulation of Perfumes

371

17. Formulations of Flavours

451

1

CLASSIFICATION OF ODOURS AND ODORANTS When one is dealing with hundreds and win sometimes thousands of raw materials of widely differing characteristics odours, odour intensities, and chemical and physical properties, it is essential to have some means of classifying them, of dividing them into groups and sub groups, in order to facilitate selection, comparison, arrangement, blending and even discussion of their special feature and functions. As McCartney has observed in his scholarly work on olfaction and odours ‘the difficulties of classification are particularly well known to perfumers, of course, and they may often invent systems of their own for private use. Such ‘private’ systems (and there is rarely anything secret or mysterious about them} are usually based on information gained empirically, added to data culled from the existing literature and other professional sources. In devising his own simplified classification of odours in 1708, Fourcroy had the good sense to point out that ’this division, this classification is arbitrary, uncertain and fragile, since our sensory impressions, and above all those, of olfactory origin, are not fixed, permanent or equal in all men at the one time or in one individual at all times’. Even so, a perfumer's classification, based on a perfumer’s expertise and experience, is almost certain to be of greater significance and practical utility to himself and to other perfumers than would he, for example, any of the non-perfumery classification based more or less strictly on botanical, chemical or psychological considerations. Published works on perfumery usually make reference to the odour classifications of Rimmel, Piesse, Zwaardemaker, Heyninx, Henning, von Skramlik, Matteotti and Crocker and Henderson. The last-named co-workers announced in 1927 their ‘semi-quantitative evaluation of odours, making possible the accurate description of any odour by the simple device of a four digit number. Crocker and Henderson‘a digits represent fragrant (or sweet, acid |sour), burnt {empyreumatic| and caprylic: a truly remarkable simplification. They consider that these four elementary odours tuc ‘the principal anti

perhaps the only units which make up all the odours we perceive'. The maximum intensity of each of these elementary odours is arbitrarily allocated the number 8. so that Tonquin musk, whose code number is given as 8476, is top-rated as 8 for fragrance, with a moderate 4 for acidity, 7 for ‘burntneaa’ and 6 for ita auppoaed 'caprylic’ tonality. Similarly Vose’ is coded as 6423-but what is a ‘lose’ odour? ‘A ix>se i* a rose is a lose is a rose' to Gertrude Stein and presumably also to Crocker and Henderson, but to the perfumer the rose odour is a most variable quantity. As perfumers we find it difficult to acknowledge the significance of 6423. The Crocker and Henderson ayatem and the approach that it repreaents have attracted a good deal of attention and support, though not chiefly, one asaumes, among practising perfumer. Of much greater interest to the latter are aome of the classifications, both of complex odours and individual odorants. made by perfumers. These are necessarily subjective but cannot be lightly dismissed, because of this, as unsatisfactory. They not only fill an immediate need but are often extremely reliable. We ourselves have, for example, made a comparative study with six other perfumers, all working separately, of a whole seriea of odoranta aaaeasing characteristics and analogies at three stagea of evaporation The level of agreement was veiy high. When making such tests much depends of course upon professional training and objectivity. A clear distinction must here be made between attempts to classify odours, e.g. as floral, woody, balsamic and so on. and attempts to classify the actual odoranta or constituents of complex odour a, as for example into top note, middle note and base note constituents. Both systems are useful. It is probably more convenient to look first at some current classifications of odorants. Of these the most comprehensive and ambitious is Poucher’s classification, based on a subjective assessment of the relative duration of evaporation of some 330 perfumery chemicals, eascntial oila and other odorous materiala. Obviously thia publiahed liat could be very conaiderably extended, as W.A. Poucher has himself suggested. The main criterion of this type of classification is relative volatility, which may be regarded as the vapour pressure at ordinary temperatures. but in practice. owing to the complex character of essential oils and flower absolutes etc., it is vastly more satisfactory to use a subjective method of comparing odorants. This Poucher accomplished by examining each material, or an appropriately standardised dilution, by meana of smelling slips. When carrying out his testa he 'had to

decide on what should be the end point of each odour. The characteristic note of come natural products may be fleeting while the residual smell lingers on. But since each aromatic substance is employed primarily for its typical odour note, I decided to check and re-check the point at which thia distinguishing feature disappeared. Moreover, I had to place a time limit on these substances of longest duration, such as patchouli, and oakmoss, and 1 gave them the figure or coefficient of 100 ... To those that evaporated in less than one day 1 gave the coefficient 1. and to the others 2 to 100/Thus, eventually, the Poucher classification as published comprised over 300 items, each of which was distinguished by a coefficient ranging from 1 (e.g. amyl acetate) to 100 (e.g. ambergris extract, vanillin and vetivert). Poucher further subdivided hia materials into those with coefficients ranging from 1 to 14, which he called Top Notes; thoae with coefficients ranging from 15 to 60 Middle Notes); and those from 61 to 100. which he termed Basic Notes or Fixers Thus we find, among the top note constituents, such items as: amyl acetate

amyl salicylate

methyl benzoate

petitgrain oil

lime oil. Distilled

bergamot oil

lavender oil

methyl octin carbonate.

Bulgarian roue otto, with a coefficient of 15. narrowly evades inclusion in the top notes, whereas rose de mai absolute has a middle note coefficient of 43. Jasmin absolute is well among the middle notea, also with a coefficient of 43, but decolorized and other jaamina are included among the basic notea with coefficienta of 70 and 90. Other middle notes include: Heliotropin

indole

phenylethyi iaobutyratc

dimethyl hydroquinone

clary sage oil

anisic alcohol

angelica aeed oil

citral

The baaic notea begin with amyl phenyiacetate and natural cinnamic alcohol proceeding through such itema aa methyl naphthyi ketone, civet absolute, hydroxycitronellal and cyclamen aldehyde to a long list of resins, balsams and crystalline materials Icoumarm, vanillin, artificial musks); aldehydes (amyl cinnamic,

methyl nonyl acetic, phenyl acetic), all rated at 100, together with ambergris, castoreum. patchouli, pepper, sandalwood and vetivert. These subdivisions are useful and enhance the value of the list as a source of general reference. They do not. however, supply a ready answer to the questions: 'What is a top note? What ia a fixative?’ Aa Poucher himself has haatened to observe, there are occasion* when longei -lasting odoranta are uaed in such a quantity as to raise them temporarily into a Inkier category. He in fact illustrates this point by giving two simplified but characteristic formulae for a Lilac and a Hyacinth perfume respectively. Among other features, the former contains 1 per cent of a 10 per cent dilution of phenylacetic aldehyde while the latter contain a 10 per cent of the pure, undiluted aldehyde. There ia no doubt that this aldehyde acts aa a top now, despite its persatstent character, when it is utilised in a dominant proportion. When we compare the results arrived at subjectively by different authors, we are apt to find a number of discrepancies indicative of differences in opinion, but in general there is a broad area of agreement. This will be seen from Tables I and 2, taken respectively from the published work of Kilmer and Carlea. Table 1. Odour Persistence of Perfumery Materials (EJliocr| Top tiCU*

MidifiV

Rate ?fc*d*

Unhvl salicvhtr Ann! iiirlalr Benzyl cimiamale ji. Mril !>| u*viojilirji»iiir iJill oil Aniw oil Borftcofc Terpinrol Mnalyl acetate liomvl acetate AniwMelnilc I-OIMI Oil litrgainnt oil I’lu iislcilr.l ulixrfiol

iVtitKrain nil. htr.iKiiav (Vninium oil. Ifcnittoin oil nuiiamoti oil CfenmeUol Neivl Mrlliyl .•uiilir.it liUir Aldehyde CO Methyl lieptln eaitoomte Angel*'u root oil Euteool Cfironella oil. Java Orarikil Amyl solfcyfelc

$tynx oil Un-.iKf nil Btoraiuponr oil Ptniy la trfakkt|.uSc Sonlakood oil &tlil»l»l Vanillin Rcwniwi} nil CuMlnfc akktiwle

Surt oil

Oen*rnl fixm^tr Clary jn#r oil CkinOflUc aldehyde RMchoul oil CUiiuimk* iilroliol

Table 2. Classification according to Volatility (Carle*) Top N«cs>

Uodifto*

fiase AtoC**

Very ivtfafiV? products lacAmp tetuxityr

of tose notes (i e ) iptoducxi o) \TM products 0/ interMteftltfy and rc«iiare ratantey and tenaatyfuph tenacity/

Am>l Mirlalr liott e thought of as tricksof-the-trade, although the main object will always be to approach the true note of each flower. Secondly, we shall give one, two or more complete formulae, by way of illustration. Here it is necessary to point out that such formulae can only be considered as the Bum of the actual materials used in preparing them in the first place; and that subsequent reproduction must involve olfactory adjustments in order to give the desired result. We shall start with the more familiar perfumes based on flower notes. ROSE Rose notes vaiy considerably one from another. In addition to the basic components mentioned below under Red Rose, Damascene Rose and Centifoba Rose, we find some important auxiliary notes in the naturally occurring esters, as well as in a few aldehydes and acetals. Many other odorants also enter, in relatively small amounts but with significant effect, into the composition of specialised rose notes, e.g. those of the tea rose. Red Rose. This is usually considered to be the truest and finest type of rose odour. Its main constituents are rhodinol, phenylethyl alcohol, alpha-ionone and the very

useful nerol. A more flowery effect is obtained by the addition of rose absolute and Bulgarian otto. Bulgarian geranium oil can, when obtainable, impart a much-appreciated green note. Rose damascena Among natural essential oils this is represented by Bulgarian rose. The basis of this odour is given by rhodinol. phenylethyl alcohol, geraniol ex palmarosa oil. and cinnamic alcohol; always in association with certain natural essentia] oils and esters. Rose cenlifoha. The main constituents here are citronellol, geraniol, phenylethyl alcohol and rhodinol, together with smaller amounts of adjuncts which give it a slightly sharp note, such as C, aldehyde, citral, etc. Tea Rose. The basic components are citronellol, phenylethyl alcohol and geraniol. The accessories that impart its special character include guaiyl acetate, menthone and tuberose absolute. Rose Marechal NicL In nature this is a yellow rose with a very special perfume. Basically one uses geraniol ex palmarosa oil, citronellol and synthetic geraniol. in association with isoeugenol, benzoin arid sandalwood oil etc. White Rose. Here the ba*e is rhodinol, phenyl ethyl alcohol, benzyl alcohol and bnalool (to give it the slightly acidulated note by which it is identified). The blend is rounded off with a little bergamot, phenylethyl acetate, etc. In all matters relating to rose perfumes one has to take into consideration the part played by Bulgarian Rose. This note is often required but unfortunately the widespread use of Bulgarian oil of rose in its pure state ia limited by considerations of cost. This necessitates research into compositions i.e. diluents or extenders, and these must be the best possible for the purpose. By using certain raw material** judiciously one can in fact arrive at some very interesting extender* which will blend well with the natural oil. giving an excellent quality of end product at a reasonable price The raw materials in question are relatively few in number. One thinks of: phenylethyl alcohol, oil of geranium such as the Geranium incolore de Grasse, geraniol, rhodinol. I citronellol; and very small quantities of nerol and farnesol. A formula is given below. This is a convenient point to emphasise that no formula can be better than the type and quality of its individual constituents. It is therefore essential for perfumers to make their own trial* and adjust their final formulae accordingly.

Some readers may be surprised to note the recurrence in certain of these formulae of branded specialities, usually made by some of the leading supply houses. We make no apologies for these inclusions, because they are in fact justified. Some are used because they contain new synthetic bodies that are not obtainable on the market in the pure state, while others are the result of the highly skilled blending of standard ingredients that it would be extremely difficult and time-consuming to copy. Rose Extender I Geraniol ex palmares*. 1st quality

1.50

Oil of Orasse Geranium, incofor*

0.50

Phenylethyl alcohol

2.50

linalool ex boia de rose, 1st quality Brazilian

1.20

Rhodinol ex geranium oil

1.20

1 –Citronellol

3.00

Nerol, pure

0.07

Farnesol, pure

0.03 10.00

Parts by weight. All constituents of the finest available quality. With the aid of this ‘extender’, such blends may be made as the following: Rose No. I Rose Bulgarian

75

Rose Extender 1

25 Rose No. 2

Rose Bulgarian

50

Bulgarian absolute oil of rose

4

Ros Extender 1

46 Rose No. 3

Rose Bulgarian

25

Bulgarian rose absolute

3

Rose Extender 1

72

In this way one has at hand three different rose formulae, all of a tonality approaching that of the Bulgarian Roo-e but each at a different price level. Formulation over a reasonably wide price range is thus facilitated. Some formulae of actual rose perfumes follow. The first, called simply P because that happens to be its reference in one's notebooks, is simple and straightforward but has great strength and marked diffusive prop^nies. Rose F Rhodinol,

40

lonone alpha

23

Rose No.2 (as above)

6

Phenylethyl alcohol

12

Bois de rose Brazil

12

Rose de Orasse absolute

6.3

Jasmin absolute

0.5

Menthane

trace 100 Rose H

Rhodinol, 1st quality

10

Phenylethyl alcohol

20

Cinnamic alcohol

6

Geraniol

20

Citronellol

10

Linalool

6

Hydroxycitronellal

5

Linalyl acetate

4

Eugenol

4

Rose de Grasse absolute

4

Geranium (African! oil

10

Phenylethyl acetate

1

100 Rose Rouge Violeuone A Rose No. 1 Roue de Or&ss* absolute Phenylacetic acid Loren* |Pirmenich| Phenylethyl alcohol Rhodinol Rose Blanche Rost* No. 1 Sandalwood oil Patchouli oil Tuberose No. 1 Tuber euse |Synarome| Orris resinoid Jaamonia (Givaudan) Benzyl acetate Geraniol synth. pure Lorena {Firmenich} Phenylethyl alcohol Iraldeine 100% (de Loire) Rhodinol P (Rhone* Poulenc| Aldehyde C9 Aldehyde CIO Aldehyde C. 12 flauhc) Rose• MS Rose M Rhodinol P (Rhone-Poulenc| Geraniol synth., checn. pure Rhodinol (with traces of menthone) Phenylethyl alcohol Geranium Bourbon Hydroxy citronellal

18 4.5 13 0.4 4.5 9.6 50 100 13.50 6.30 6.30 5.50 5 5 3.50 2 12 9 11 9 11.50 0.10 0.15 0.15 100.00 390 110 16 45 150 5 15

Cinnamic alcohol

7.50

Irakteine 100 % |d« Laire|

26.50

Iralia B

3.50

Sandalwood Oil

9

Loiena (n«rol|

100

Boi* do Rhode* (UOP)

1

Diphenyl oxide

5

Aromel (OivAudAnl

1

GuaiAC wood oil

14.50

GerAnyl acetate

2

Phenylethyl AcetAte

2

Rhodinol acetate

9

Citron oily] formate

14.50

Geranyl formate

5

Rhodinyl formate

4.50

Phenylacetic aldehyde 50 %

10

Verbenol

15

Musk ketone

39 1000.00

Where specialities are cited under the names of specific furns, this simply means that no one firm makes and offers exactly the same end product aa the others. In each case one must take into account the fact that chemicals included in a process) as trAce impurities Are not likely to be pre*ent in exactly the same pattern or proportions in a competitive product. Examples of special shades of odour even among standard chemicals are provided, for example, by Givaudan's Laurine, which is a hydroxycitronellal with a note of its own - often in great demand and Lorena of Pirmenich, which though a nerol. is yet distinguishable from other nerols. A footnote to rose compounding: modem perfumery now also makes use, with restraint, of rose oxide. JASMIN Rose and jasmin are still the moat important flower notes used in perfumery. Singly or together, they provide a conventional floral background for a great diversity of perfumes). Oil of jasmin has been the subject of much analytical research and, on thi* basis.

It 15 possible lo devise a wide range of formulae for 'jasmin artificial'. Among the basic components one may note benzyl acetate, amyl and hexyl cinnamic aldehydes; benzyl alcohol, formate, salicylate and other esters; indole and derivatives; phenylethyl alcohol, dimethyl benzyl carbinyl acetate, Itydroxycitronellal, linalool, linalyl acetate; eater#* of propionic and butyric add*; Peru balsam etc. To sweeten formulae for artificial asmins that may be somewhat crude and synthetic, use can be made of jasmin absolute chassis, which is the absolute obtained by petroleum ether or benzene extraction from jasmin flowers that have previously been treated by the enfleurage process but which have nevertheless retained some of their perfume. This must not be confused with the actual absolute of jaamin d'enfleurage. It is a principle in fine perfumery’ that natural materials should be used to sweeten and soften the odours of synthetic blend*. When costing considerations prevent the more liberal u»e of 'naturals', the result of judiciously incorporating even small quantities will usually prove conclusive. Jasmin No. 1 Benzyl acetate, pure

28

ci-Amyl cinnamic aldehyde Prima IDescollonges)

20

Jasmin chassis absolute ex benzene (Schmoller & Bompardji 10 % in benzyl benzoate

10

Benzyl propionate

4

Paracresyl isobutyrate

3.2

Dimethyl benzyl carbinyl acetate

1.6

Benzyl alcohol

9.2

Linalyl acetate

2

Methyl anthranilate

0.4

Isojasmone |Descollonges|

0.05

Bois de rose oil. Brazil

6

Geraniol (synth., chem. pure, Firmenich)

1.6

Iraldeine 100% (de Laire)

2

Allofloral (Allondon- Firmeriichl

6.75

YlAng-ylang oil

2.4

Indole, 10%

2.8 100.00

Jasrnonone No. 4 Benzyl alcohol extra

19

Phenylethyl alcohol

1

Jasmin absolute

2

Benzyl acetate, chem pure (BBA|

10

Castoreum absolute (Deacollonj»es) 10%

3.5

Narcissus absolute ICharabot)

1

A-Amyl cinnamic Aldehyde

20

Jasmin de Provence (Deacollonj»es)

30

Indole 10%

2

Linalyl AcetAte ex boia de rose

6

Linalool

3.65

pAi'Aeresol 10%

0.7

Isojasmone 10%

0.65

Bitter almond oil \Wo

0.5

Jasmononc No. 4a

100.00

Benzyl acetate

30

Benzyl alcohol

30

Benzyl propionate

5

Methyl anthranilate

2.5

Indole 10%

2.5

Linalyl acetate

5

Linalool

7.5

Buxine (Givaudan)

7.5

Ylang-ylang oil

10 100.0

This composition has a rather fresh note that facilitates its use in numerous combinations, both with other jasmin components and in perfumes where a sharp and fresh jasmin note* contributes to the overall odour. Jasmin Base No. 5 Cinnamyl acetate

0.8

p. Cresy] isobutyrate

1.1

Methyl anthranilate

0.3

Benzyl alcohol

18

Benzyl acetate

18

Lirialool

4.6

Benzyl propionate

3.1

Terpmeol, pure

3.1

Amyl cinnAmic Aldehyde

15.3

Methyl euftenol

1.3

Lin Alyl Acetate

7.5

Raldeine D (CJivAudAnl

3.8

HydroxycitronelUl

3.1

p. X< ethyl methylsalieylAt*

1.5

p. Cresyl phenylacetate

0.7

Phcnylpropyl Aldehyde

2

Aldehyde C. 10

0.15

Indole

0.45

Tolu tincture

15 100.00

This base may be improved, as in the following formula (5a|. Jasmin Base No. 5a Jasmin Base No. 5

70

Jasmin dEspagne (Givaudan)

13

Jasmin Frutal (Polak's Frutal Works

13

Jasmin chassis absolute ex benzene (Schmoller & Bompard)

4 100

ORANGE FLOWER AND ZVBROLI Perfumer* will be well aw Aie of the difference* that exist between these two closely related odour®. Both are frequently used, and it could even be said that there are relatively few compositions into which the orange flower note does not enter. Neroli is particularly valuable in eau de Cologne and related notes. Here are some examples. Orange flower A Linalyl acetate

7.1

Petitgrain oil. terpeneless

33.4

Flonol 160 (de Laire)

14.3

Ftoaer Perfjmes Indole 10%

25 4.7

Eugenol

2.2

Geraniol synthetic

5.6

Geranyl acetate

3.7

Broutt absolute JRobertet)

19

Ylang-yl^ng oil

1.2

Phenylethyl alcohol

4.7

LentUqu* (Mast»c| oil

0.8

Methyl anthranilate

2.4

Citral

0.9 100.0

Neroli A Petitgrain oil pays (Grasae)

31.5

Methyl anthranilate

25

Rugenol

18.5

Geraniol Phenylethyl alcohol

6 4.25

Linaiyi acetate

7.3

Indole 10%

4.7

Aldehyde C.8 10%

2.75

100.00 This is a useful type of formula for blending with natural neroli, in oertain applications, as a diluent. A suggested proportion ift 1 part of natural neroli oil to 2 part* of Neroli A. In flower perfumes closely associated with the orangeblossom note, e.g. honeysuckle, *yringa (Philadelphia* ooroftAfiu*), gardenia And narcissus, the fruity note of Apricot is often pi*aent and (should always be borne in mind VIOLET The classic note of violet was adored by ladies at the turn of the century. Two apecies of the flower should be distinguished. The simple Violet (Nice or Toulous*) may be based on a blend of methyl ionone, alpha ionone, orris absolute or resinoid, violet leaf absolute and phenylethyl alcohol. A floral note, projected as it were by a trace of MNA aldehyde, is imparted by jasmin or cassie. The double or Parma violet is based on varying proportions of beta ionone, alpha ionone and methyl ionone, together with orris retnnoid or concrete. a little phenylethyl alcohol, methyl octin carbonate, a trace of vetiver, and a email quantity of hydroxycitronellal and even, sometimes, bergamot. Very small amounts of violet leaf absolute may be included, but the green leafy note of Parma violets is much le*s aoeentuated. Por imparting the necessa/y sweetness to the ba*e of Parma violet, use may be made of a ptum or mirwbelle note. It is difficult to ftive a violet perfume the thrust’ required by modern perfumes. An interesting result has been obtained, however, with a very fresh lily-of-the-valley

composition, used in just sufficient quantity to impart an exuberant freshness but not enough to impair the basic violet note. Wood violets, with their rather earthy background, may be simulated by the inclusion of very small quantities of a pure grade of amyl acetate, which helps to provide the odour of damp earth And humus Other humus notes may be similarly employed. Violet No. I lonone alpha

10

Iralia (Pirmenich)

10

Irison# extra (Oivaudan)

10

Jasmin No. 2

20

Ysminia {Pirmcnich)

5

Jasmonia (Givaudan)

2

Violet leaf absolute

2

Orris absolute or Irophore (Firmenich|

1.1

Ylang ylang oil

1

Ylang ylang absolute

0.6

Cassie absolute

0.55

Rose No. 1

0.1

Neroli oil

0.06

Phenylethyi alcohol

1

Bitter orange oil

0.6

Oakmoss absolute (Robertet|

0.16

Folione (Givaudan)

0.03

Linalool

0.5

Bois de rose Brazil

3

Cinnamylal (Givaudan)

4.5

Heliotropm

2

Muck ainbrette

0.1

Musk ketone Vanillin Civet tincture

0.3 0.2 16.5

Peru balsam tincture

8.3 100.00

Violet AV>. 2 Violet No- 1 Irisone Beta (Givaudan) Iralia (Pirmenich} Cetone V (allyl ionone, OivAudan) Ylang ylang absolute lrophore (Pirmenich) Violet leaf absolute Cas&ie absolute Mimosa absolute Jasmin absolute Mirabelle (Firmenichl 1%

60 6 10 9 4 1.6 2.6 0.8 1.3 1.2 3.5 100.0

The absolute oil of Parma violets, which had a delightful odour, is no longer an item of commerce. The following formula yields a product of fine odour which may be utilised as a ‘reconstituted* absolute oil of Parma violet®. Parma Motets Absolute, Art. Violet leaf absolute (Schmoller & Bompard| lrophore (Pirmenichl Violettone B extra fine 100% (Pirmenich) Parmanthene (Pirmenich) Benzyl benzoate

1.8 4 4 0.2 90 100.0

The basic formula that follows gives a product of fine quality, which can be used in a multitude of different combinations in order to give effects approaching those of a little violet bouquet. The delicate odour of earth and humus that is no often found in a bunch of violet® can be given by Descollonges* Humu»col or by a mixture of amyl salicylate and pure amyl acetate, etc. Violet Base Paracetone (Givaudan)

24

Beta-iso Methyl Tonone

32

Irisone extra incolore (Givaudan)

24

Beta methyl ionone

3

Boronia absolute

1

Ionone alpha

16

Violet leaf absolute

10

Orris absolute |Rohertet)

10 120

The concrete and absolute oils of Boronia, which contain ionone beta in its natural state, are much sought after in violet compositions, where they sofcen any harshness and add a tendency towards the Parma violet note. Many other formulae for violet perfumes could be given but we feel that the foregoing should suffice as a general indication to the practicing perfumer. Lilac, lily-of-the-Valley, Carnation and Tuberose are also, like the fore-going flower perfumes, widely used to ‘floralisc’ sophisticated perfume blend* It is convenient, however, to ananfte them in alphabetical order rather than attempt to do so on the basis of their relative importance. ACACIA This is not in fact a true acacia. althouRh the latter species is well represented in perfumery as Ctt&Sie. The acacia perfume, which finds acceptance chiefly in wamer climates, represents the fragrant and somewhat orangeflower-like odour of the tree. Robinia pseudacacia. The basic odorants entering into its composition are; phenylethyl alcohol, cinnamic alcohol, benzyl acetate, liydroxycitronella], methyl naphthyl ketone, methyl anthranilate, linaloot, terpineol, anisic aldehyde ex anethole, and just a touch of apneot BROOM Broom, genista or genet is a shrub very popular in the south of France and in Spain; particularly in Catalonia, where the hills of Barcelona and the Tibidabo are covered with rexama |the Catalan name for broom| at the approach of summer. Fragrant varieties of broom are also found in the U.K. and elsewhere. From the p«rfurner>* point of view, the base is one of orange blossom: methyl anthranilate. fleur d'oranger, etc.. associated with methyl paracresol, methyl acetophenone, anisaldehyde and Grasse absolute of genet. Other constituents include alpha ionone,. terpineol, linalool, phenyl ethyl alcohol, heliotropin, synthetic musk and olibanum. CARHATIOH

From the perfumer's point of view there are three main types of carnation. The carnation of Nice has a rather rosy, honeyed odour. The garden pink has a spicy odour recalling cloves and pepper. The so-called sea pink (not to be confused with Armoria maritima\ ha* the basic odour of carnation plus a note of phenylacetic aldehyde. In all carnations there is a slightly resinous note suggesting olibanum and labdanum: hence the use of such oleoresins as fixatives. Oeitlet de JVice. Here the basis is a blend of eugenol. lsoeugenol and methyl eugenol. in varying proportions, accompanied by phenylethyl alcohol, benzyl salicylate, and sometimes amyl salicylate, vanilla, vanillin or ethyl vanillin. This base is sweetened with rose notes from rhodinol or rose de Mai absolute, carnation absolute or concrete and, above all, tuberose absolute. Unfortunately, as the latter has become very expensive, it must usually be replaced - as by a blend of synthetic tuberose with the natural material, or by a good ylang-ylang oil or ylang-ylang absolute. As aids to fixation there are benzyl isoeugenol, heliotropin and so-called heliotropin amorphous |a mixture of htliotropin, vanillin, Anisic and benzoic acids). Garden Pink, known as Otnltex mignardisc, has a slightly more clove-like odour. Hence the use of more eugenol and less isoeugenol in the base, together with a trace of clove od. The vanilla base will preferably contain methyl vanillin (veratraldehyde). The characteristic note is given by oalc of pimento, bay or black pepper. Sea Pink. This small pink, which has a simple flower whose colour is actually mauve, is found growing wild on dunes by the sea. Its strong odour may be imitated by adding to a garden pink formula amyl salicylate, phenylacetic aldehyde and, if desired, a trace of hyacinth absolute. Carnation notes have a major role in all kinds of perfumery. Even so, they could probably be exploited yet more fully in the field of masculine perfumes. A straightforward carnation note could be used, in this way. instead of the all too familiar spiced - Cologne complexes. Some formulae follow. Base Clavetine No. I Eugenol

51.35

Canan&M oil

25.7

YlAn^-ylang oil

2.55

Rose No. 2

5.6

Benzyl AcetAte

2.55

Orris absolute

4.25

Ceylon cinnamon oil

0.5

Nutmeg concrete

1.5

Nutmeg oil

1

Benzyl benzoate

3.45

Heliotropin

1.55 100.00 Base Claveline No. 2

Eugenol

61.5

Ylang ylang oil

4.6

Cananga oil

4

Rose No. 2

4.6

Cinnamic alcohol

16.7

Benzyl acetate

2.5

Vetiver oil, Java type

1.25

Nutmeg oil

0.65

Labdanum absolute |Lautier|

0.20

Heliotropin

4 100.00 Orillet de Nice No. 3

Base Claveline No. 2

55.9

Isoeugenol

13.9

Rhodinol

1.2

Pimento oil

1.3

Phenylelhyl alcohol

0.65

Ionone alpha

0.35

Tubero»e absolute synth. ISynarome)

2.5

Carnation absolute (Charabot)

5.9

Vanillin

139

Couroarin

3

Musk ketone

1

Musk ambrette

0.4 100.00 Co manor) Flowers No. 4

Base Clavelin* No. 2

18.3

Oeillet de Nice No. 3

3

Bugtnol

6

Isoeugenol

31

Ro»c No. 3

4.5

Bulgarian rose oil

4.5

Phenylethyi alcohol

9.5

Jaamoide 215 (Synartone)

0.6

Jonquil synth. (Roure-Dupont)

0.6

Terpeneleaa peticgrain oil

3

Methyl ionone

6

Bois de rose oil, Brazil

3.8

Jasmonis (Givaudan)

0.6

Amyl salicylate

0.4

Hydroxy citronellal

0.5

Phenylpropyl aldehyde

0.4

Benzyl benzoate

1

Ylang-ylang oil

1.5

Peru Balsam Clair (Lautier|

0.5

Vanillin

3.6

Musk ketone

0.5

Musk ambrette

0.2 100.0

‘OeiVei des Dunes Ato. 5 Eugenol

15

Base Clnvehne No. 2

15

Isoeugenol

10.9

Methyl ionone

6.7

Amyl salicylate

5

Jonquil synth. (Roure-Dupont|

0.65

Tuberose absolute synth. iSynardme)

0.35

Ylang-ylang oil

6.7

Bois de rose oil. Brazil

3.3

Phenylethyi alcohol

13.3

Rose No. 3

3.3

Neroli A

3.3

Waidia IKirmenich)

4

Phenylacetic aldehyde

3.3

jAsmonis (Givaudan)

0.65

Jasmin chassis absolute

0.65

Vanillin

0.6

Musk ketone

1.6

Anisic aldehyde

0.35

Benzyl benzoate

5

Heliotropin

0.35 100.00

CYCLAMEN Many species of cyclamen ore scented, notably C. pcrscum and C. curopacTim. The odour of the original small mauve flowers from the mountainous districts of southern Europe is quite mild And may typically be given by cyclamen aldehyde. The basic elements of cyclamen perfumes as a class are hydroxycitroriellal. linalool, phenylethyi alcohol, terpineol, cinnamic alcohol, amyl cinnamic aldehyde, styrallyl acetate, rhodinol. phenylacetic aldehyde, ionone, Lilial, Lyral • and. finally, the essential cyclamen aldehyde and some of the classic ‘freshness’ components. This perfume theme could, we feel, be subjected to some interesting variations and thus result in novel and interesting compositions. Think, for example, of its Association with a group containing cyclopentadecanolide, aldehyde MNA. incense and vanilla Thu* type of association might well provide a very attractive ensemble. The cyclamen odour and its possible derivatives have not yet. in our vieur. been fully exploited - especially if the cumin note is one of the elements used in its formation. FOUGBRS (TERN) The fern or f&KQtre may be one of several thousand species, but in any case it will rarely have an odour other than a mild and vague effluvium of humus, greenery and earth. The perfumes known aa fern or fougere are entirely the creations of imaginative perfumers. Most of them have a more or less pronounced note of verdure and moss. The honour of creating the first Fougere went to Paul Parquet circa 1880. Fern perfumes are nowadays divisible into two main groups (a) one baaed on the triad bergamot. Tonka bean tincture or coumarin, and a product of muaky odour; and |b| the other, in which bnalyl, terpinyl. geranyl and above all bomyl and i bo bomyl acetates, gjve a compound of more or leas rustic or woodland character. Figure No. I Tree moss absolute

2

Bergamot oil

10.1

Lavender oil

10.1

Rhodinol

10.1

Rose M.S.

6.1

Patchouli oil

3.1

Geranium absolute incolore |Graaa*|

4.1

Methyl ionone

12.15

Cyclopentadecanolide

1

Pctitgrain oil, Paraguay

2

Coumarin

14.3

Muftk ketone

6.1

Heliotropin

6.1

Phenylethyi salicylate

3.1

Methyl aalicylatc

1

Eugenol

1

Jaamin No. 1

3.1

Clary sage oil

1.35

Amyl salicylate

2

Musk tincture

1

Tobacco (I.P.F.J

0.2 100.00

This is a formula of the category (a| type. See note above. The following belonga to category (b). Figure No. 2 Musk ketone

0.4

Patchouli oil

1

Vetiver oil. Java

1

Lavender oil, Mitcham type

6.3

Lavender absolute

1.6

Bergamot oil

35

Linalyl acetate

2.2

Ter piny 1 acetate

2

Coumarin

31.4

Cyclopentadecanolide

0.2

Tobacco O-P-P.)

0.2

Oakmo&s absolute, Yugoslav

0.8

Moua*e de Chene 1026 (Roure-Dupont|

0.2

Alliantone |Givaudan)

1.3

Allofloral (Pirmenich) 10%

0.2

Rose No. 3

4.3

Palmarose oil

1.1

Geranium oil

4.7

Neroli A

4.7

Myrtle oil

0.2

Cuir 1073 (Firmenich)

0.8

Bomyl acetate

0.2 100.0

When it is desired to impart a fruity note other than the classic peach, apricot, pmne or mirabelle, one such note that can be extremely successful is strawberry, and this has in fact been incorporated in the above formula. GARDENIA In the reproduction of the gardenia odour one uses several of the components of tuberose, but gives more emphasis to the roselike tonalities. Thus in the first place consideration is given to ytang, jasmin, benzyl salicylate, phenylethyi alcohol; An orange blossom note, etc. Secondly, one turns to dimethyl bensyl ctubitiol, acetyl isoeugenol, hydroxycitronellal, rose de mai absolute, benryl acetate, terpineol. etc. And. above all. there is styrallyl acetate, which provides the peculiarly green and fmity note of gardenia, and gamma nonyl lactone. Apart from its general acceptance as a flower, gardenia has on important role in perfumery. It contribute* fragrance to auch perfume » a» Millofg Crepe dc Chine. Abac lute oil of gar drum has been produced and is, when available, a remarkable and attractive product. Among the gardenia compounds introduced by the aynthetic chemical houses, one of the beat and a contributory factor »Q some celebrated perfume* i» Oivaudan's Gardenia 9058. Gardenia So. I StyiaNyl {methyl phenyl carbinyll acetate

5

Neroli D

2.5

teoeugenot

4

Rose dc Mai absolute

1

Ylang-ylang oil

7

Benzyl acetate

4

J asmin .absolute

1

Lilol (Oivaudml

6

lonone alpha

10

Hydroxy citronellal

20

Phenylethyl alcohol

8

Phenylacetic aldehyde 50%

1.5

CiuotwUol

4.5

Cinnamic alcohol ex styrax

7

Coumartn

2.5

Heliotropin

7.5

Crardfnid So 2

100.0

Musk ketone

2.5

Musk ojubretle

1

Jasmin de Provence R (Dcscollonges|

1

Jasmin absolute

1

Rose de Mai absolute

3.5

Jonquil absolute

1

Tuberose absolute

3

Gpopanax L.G. {Givaudan|

16.9

Muguet No. 2

10.2

Styrall.vl acetate

12

Hydroxy citronellal

15

Ylmg-ylang oil

5

Cinnamic alcohol ex styrax

2

Phenylethyi alcohol

2

Gardenia 9058 (Givaudanl

23.9 100.0

At current raw material price# it would obviously be essential to replace most of the natural absolutes with the beat ‘artificials* available within costing limits. In the case of tuberose we suggest the use of one of the compounds given under that name lsewhere in this chapter, or a selected speciality such

as Synarome's Tubereuse S,

for example. Gardenia No. 1 Benzyl acetate

3.00

Bergamot oil

3.00

Jasmin absolute, artificial

6.00

Rose de mai, art.

2.00

Absolu Roae. Lot 1. Robertet

2.00

Muguet 33 |de Laire|

3.50

Amyl salicylate

3.50

Hydroxycitronellal

4.50

Ionone alpha

3.00

Dianthme (Firmenich|

1.50

Ylang-ylang oil

5.00

Methyl ionone

4.50

Styrallyl acetate

3.50

Wardia IFirmenich)

2.00

Aurantiol

1.00

Iris Liquid* (de Lau*|

1.50

Linalool

6.00

Vetiver oil

0.75

Patchouli oil

0.25

Civectone

0.15

Caatorcum Anhydrol (Givaudan)

0.25

Musk ketone

4.10

Musk ambrette

5.50

Coumarin

6.50

Ethyl vanillin

1.50

Liquidambar II Aldehyde C12 (lauric) 10%

2.50

CII (undecylenic) 10%

2.00

C10

2.00

Diethyl phthalate

17.00 100.00

HAWTHORN The base of hawthorn perfumes is anisic aldehyde, in association with anisic alcohol arid methyl acetophenoue. For middle notes one uses hydroxycitronellal, cinnamic alcohol, citronellal, linalool and terpineol. The lower notes are provided by heliotropin and coumarin. The noted English horticulturist, Graham Thomas, listed 'Crataegus, all species' (including of course the common may or hawthorn, C. oxyacantha) among thirty or so flower scents that he considered \inauitable for aenaitive noaea’. The perfumer may here and in similar cases improve on nature by ifcnorin** the methylamine or other off-notes present in the actual flowers and create, as it were, an idealised version of the natural floral odour HELIOTROPE The heady, delightful and charactcriatic perfume of the heliotrope \Hetiotropium Peruvianum and other spp.| is duplicated chiefly with heliotropin and heliotropin amorphous; the latter beinf: a mixture of heliotropin with vanillin, etc. With these are associated benzoic and anisic acids, phenylethyi alcohol, ylang- ylang oil, rhodinol. cinnamic alcohol, anisic aldehyde, benzal- dehyde (traces) and benzoin resinoid. A synthetic of hazel nut odour, used discreetly, will help to give an impresaion of the real flower. The sli&ht note of fcroenery is obtainable with an oakmosa or. better still, a mi&nouette absolute or base Another useful constituent is paramethyl hydrocinnamic aldehyde,

HONEYSUCKLE The honeysuckles, Lonic#ra /ragro?wss\mat I brachy/>odat I CXiprijoUum and other species, familiar also in the perfumery literature by their French name, ctxevrefeuitle, are among the most fragrant of flowers. Their general odour, sweet and diffusive but only slightly honeyed, can be simulated with such basic constituenta aa: muguet, orange bloaaom, roae and jaamin odorants; cinnamic alcohol, phenylethyi alcohol, terpineol, citronellol, linalool, hydroxycitronellal, paracresyl phenyl acetate and anisic aldehyde. Small quantities of methyl cinnarnate. methyl naphthyl ketone, phenylethyl acetate, isoeugenol, and yiang-ylang, enter into consideration. To ensure the correct emphasis on the fruitiness of the natural flower odour, use may be made of an apricot note. A trace of Rirmcnich'a Abricot Base 4512, for example, will 8etve this purpose quite well. Chevrefeuittc No. 1 Petitgrain oil, Paraguay

5

Neroli B

6.55

Brouta absolute (Robertet)

1

lonone alpha

4.85

Anisic aldehyde

2.5

Linalool

3

Terpineol

10

Geraniol

5.1

Hydroxy citronellal

3.8

Lilac No. 3

5.1

Phenylacetic acid

1

Bergamot oil

5

Benzyl acetate

5.1

Jasmonone No. 4

5

ChevrefeuiDe 2035 |Firmenich)

10

Chevrefeutlle LG. (Givaudan)

25

Musk ketone

1.25

Musk ambrette

0.75 100.00

HYACINTH The odour of the hyacinth flower is often rather harsh and strident. Variants based towards the xose or orange blossom are more acceptable. The basic odorants are phenylacetic aldehyde, hydroxycitronellal. cinnamic and phenylethyl alcohols, terpineol and phenylethyl acetate. And, as products contributing towards the piquant note of hyacinth, which is more or leas green: dimethyl benzyl carbinol and it* acetate, bromatyrole (tract*), methyl octin carbonate, cinnamyl acetate; and, for rounding off the composition, when costing limits permit, hyacinth absolute. There was at one time, incidentally, an absolute of wild hyacinths Ibluebells} available, but despite its remarkable odour properties it proved too expensive, owing to the high coot of gathering the flowers even before they were treated. Hyacinth ha#** have found quite a number of Application* in currently popular perfume*, but we feel that theie is sldl further scope for their use. particularly m perfumes with a green note. Hyacinth No. I Lilac No. 3

10

Jacinthone (Givaudan)

20

Cinnamic alcohol

20

Neroli A

5

Jasmononc No. 4 a

10

Jasmin chassis ex benzene

4

Hyacinth absolute

5

Phenylacetic aldehyde 50%

6

Hydratropic aldehyde

3

Dimethyl benzyl carbinol

2

Hvdroxvcitroneellal

10

Rose de Mai absolute

5