Fragrance Materials Research Articles

Chemical reactions in perfume ageing

Summary The interactions between a typical range of perfume materials, alcohol, water, air, elevated temperatures and daylight have been studied. The changes of composition, acidity, peroxide content and the formation of new molecules were followed. The stabilizing effects of UV absorbers, antioxidants and sequestering agents were examined; - the formation of acid reaction products was accelerated by air, temperature, daylight and the presence of natural products; - peroxide formation was accelerated by heat and light and the presence of air; as the acidity increased, the peroxides decomposed; - the acetalization of other aldehydes was accelerated by temperature and daylight and the presence of natural products up to 40% of certain aldehydes may be converted into acetals after 3 months at 37 degrees C; - many stereoisomerizations occur, e.g., transisoeugenol is converted up to 10% into the cis isomer after 3 months at 37 degrees C and 58% in daylight; - evaluation of antioxidants UV absorbers and sequestering agents showed a significant protection against deterioration only by EDTA dipotassium salt; - ethanol was converted into acetaldehyde and its diethylacetal by peroxides present and formed on ageing up to 0.08%. Natural products accelerated this formation; - the reaction between benzoyl peroxide and ethanol was shown to yield up to 63% of acetaldehyde+diethyl acetal whilst di-t-butyl peroxide gave only 23% under the same conditions. These results go some way to explaining odour changes in perfume ageing.

Biotechnology of Flavours and Fragrances

The flavour of many foods are formed as a result of the action of microorganisms or enzymes. Some studies have been carried out on the formation of flavour and fragrance materials using microorganism, enzymes and tissus cultures. In this review, some of these studies are shown, and furthermore, the future contributions of biotechnology to this field are also described.

市販天然香料の抗菌性試験

Antimicrobial activity of 235 natural flavor and fragrance materials was investigated using 4 bacteria and 2 fungi. Antimicrobial activity against bacteria and yeast was defined as percent inhibition of viable cell count after incubation with sample in phosphate buffer for 10min. Antimicrobial activity against mold was defined as percent inhibition of colony area on agar plate containing sample. Two hundred and three samples were very effective against at least one of the six test microorganisms. Samples consisting of chain terpene alcohols, cyclic carbonyl compounds, cyclic ethers and phenolic compounds as major components were very effective against S. aureus and/or P. aeruginosa. Minimum inhibitory concentration (MIC) was determined by agar dilution method. Samples which showed 100% of antimicrobial activity against B. subtilis, E. coli, P. aeruginosa and A. niger at 1000ppm gave a MIC of 2000ppm or over. Antimicrobial activities of samples were compared with that of p-hydroxybenzoic acid esters. Forty-eight samples were more effective than methyl p-hydroxybenzoate. The degree of antimicrobial activities of eight samples followed the same order as that of n-propyl p-hydroxybenzoate and n-butyl p-hydroxybenzoate.

Book Review: Common Fragrance and Flavor Materials. By K. Bauer and D. Garbe

Book Review: Common Fragrance and Flavor Materials. By K. Bauer and D. Garbe

The application of carnation in perfumery

AbstractCarnation, Dianthus caryophyllus L., which originated in the Mediterranean countries, holds an important place in perfumery. Southern France, Italy, Egypt, and Kenya are now the main sources of carnation flowers for perfumery use. The flowers are extracted with volatile solvents, yielding carnation concrete, which on treatment with alcohol, gives carnation absolute.Until the 1930s, only a few components of steam‐distilled carnation oil were known. Carnation was not the subject of further research until in the 1980s over a hundred components were revealed in the steam‐distilled oil and in Egyptian carnation absolute. The difference in chemical compositions of absolutes and steam‐distilled oils, obtained from flowers cultivated in Kenya, Egypt and in South of France was also shown. Carnation absolute is very expensive, therefore synthetic carnation compounds have been developed, the main components being eugenol and its derivatives combined with salicylates, benzoates and rose components. Few illustrative conventional carnation formulas are shown. More recent carnation compounds include newer aromatics, amongst which cis‐hex‐3‐enyl esters are important. At the beginning of this century, pure concentrated carnation essence were used as perfumes. Later, carnation absolute served as modifier in many perfume compositions.Early carnation fragrances were based mostly on a few natural perfume materials, including carnation absolute. Later, a few essential oils and aromatics were added as they became available. Examples of carnation perfumes are given. In the late 1930s, alcohol‐free perfume concentrates were developed, among them carnation. Spicy notes are appealing to men, and many men's fragrances, ranging from the early to the sophisticated modern formulations contain carnation notes. Carnation perfumes have been used in brilliantines, hair oils, talcum powders and soaps. Apart from soap perfumes, they contained small amounts of carnation absolute. Carnation fragrances are still used to perfume colored soaps. In modern cosmetic perfumes, carnation is mostly used as a modifying component of a fragrance to give a warm spicy floral note. Carnation absolute is used today only in de luxe fragrances, because of its high price.* Synthetic carnation compounds or their components have replaced the absolute in less expensive perfumes. Efforts are being made to introduce a lower priced carnation ingredient, cultivated and produced in Kenya, to encourage its use in perfumery. The carnation odor is important in both women's and men's fragrances, and it will remain an indispensable component of fragrances created in the future.

Patch tests with fragrance materials and preservatives.

179 patients suspected of cosmetic allergy were patch tested with a series of 16 fragrance materials and 9 preservatives. In 67 patients (37.4%), 1 or more of these substances gave positive reactions. In the group of fragrance materials, the largest numbers of positive patch test reactions were seen to isoeugenol, oak moss, geraniol, alpha-amylcinnamic alcohol, and a mixture of alpha-amylcinnamic aldehyde and alpha-hexylcinnamic aldehyde. The fragrance mix in the ICDRG standard series detected nearly 80% of cases of contact allergy to fragrance materials other than its constituents. In the group of preservatives, Kathon CG and quaternium-15 scored the highest number of positive reactions. It is argued that the commonly used patch test concentrations of 2% for oak moss and geraniol may be too low to detect all cases of sensitization.

Perfume dermatitis

The most common reaction to fragrance materials seen by practicing dermatologists is allergic contact dermatitis. Photodermatitis is occasionally seen, as is contact urticaria, irritation, and depigmentation. Fragrances are the leading cause of allergic contact dermatitis due to cosmetics. The fragrance mixture can cause false-positive reactions; therefore, it is more desirable to test with a separate series of fragrance materials.

Comparison of percutaneous absorption of fragrances by humans and monkeys

The percutaneous absorption of two cosmetic fragrance materials, safrole and cinnamyl anthranilate, as well as of cinnamic alcohol and cinnamic acid, h

Reactions in selected patients to 22 fragrance materials.

182 patients on the basis of 6 criteria were suspected of suffering from contact sensitization to cosmetics. 77 (42%) gave a positive reaction to one or more of a series of 22 fragrance and flavor raw materials. The hands were most often involved. Cinnamic alcohol, hydroxycitronellal, eugenol, coumarin, and abitol gave the most common positive reactions; less frequent were cinnamic aldehyde, dihydrocoumarin and dimethylcitraconate. Their relevance could not be traced. However, the first 4 substances were the most frequently identified in 79 suspected cosmetics sent in for analysis by the patients or their physicians. The stability of room-stored petrolatum-fragrance mixtures should be checked.

Substantivity of perfume materials to hair

SynopsisThe substantivity of seven fragrance materials from a surfactant solution to human hair has been followed both olfactively and by gas chromatography. From an 0.5% solution in sodium lauryl 2 ethoxy sulphate solution between 0.13 mg g−1 hair and 0.72 mg g−1 hair were absorbed, giving strong retained odour on the hair; amyl salicylate showed the greatest absorption. After 24 h air drying, up to 0.01 to 0.08 mg g−1 hair remained, giving different odour strengths dependent on the molecule used.Mixtures gave somewhat lower substantivity and increased concentration in the shampoo base gave an increase in the amount absorbed on the hair. The percentage uptake however decreased. The mechanism appears to be a simple partitioning of the organic molecules between the water phase and keratin, the effect being wholly reversible as the molecules evaporate when left in air.The technique gives a method of objectively studying perfume substantivity to hair.Substantivité des parfums aux cheveuxRésuméLa substantivité aux cheveux humains de sept matiéres premières de parfumerie en shampooing, a été étudiée olfactivement et par chromatographie en phase gazeuse. Les matières premières ont été incorporées dans la solution de shampooing (lauryl ether sulfate à raison de 0.5%). Les cheveux absorbent entre 0.13 mg g−1 et 0.72 mg g−1 donnant une forte rétention olfactive sur les cheveux. Le salicylate d'amyle montre l'absorption la plus importante. Après 24 heures à tempàrature ambiante, il persiste 0.01 à 0.08 mg g−1 sur les cheveux.Les mélanges sont moins substantifs que les molécules prises individuellement, mais l'augmentation de la concentration dans la base shampooing permet l'accroissement de la quantité dc mélange absorbé par les cheveux. Le mécanisme de la substantivité ne parait être qu'une répartition des molécules organiques entre la phase aqueuse et la kératine, l'effet est totalement réversible du fait de l'évaporation des molécules lors du séchage des cheveux à température ambiante.La technique donne un méthode objective pour étudier la substantivité des matières premières do parfumerie aux cheveux.

Photochemistry of Fragrance Materials. I. Unsaturated Compounds

AbstractFragrance materials are used widely in consumer products such as cosmetics, toiletries, detergents, soaps and household products. Approximately 150 natural and 4000 synthetic chemicals have been used to create appropriate fragrances for these products today. Because of the large number of chemicals used in fragrances, one might expect that various chemical changes can occur in products during production, storage, and after application or use by the consumer. Among these chemical changes, photochemical reactions of certain compounds are beginning to receive attention as those reactions which produce photosensitizing chemical products in fragrances. This is an especially serious problem for skin care products which undergo the most exposure to sunlight. This can promote photochemical reactions in product fragrances after they are applied to the human skin. Photochemical reactions which trigger new organic syntheses are some of the most important reactions in organic chemistry today. Reactions which ...

Photochemistry of Fragrance Materials. II. Aromatic Compounds and Phototoxicity

AbstractFragrance materials are used widely in consumer products such as cosmetics, toiletries, detergents, soaps and household products. Approximately 150 natural and 4000 synthetic chemicals have been used to create appropriate fragrances for these products today. Because of the large number of chemicals used in fragrances, one might expect that various chemical changes can occur in products during production, storage, and after application or use by the consumer. Among these chemical changes, photochemical reactions of certain compounds are beginning to receive attention as those reactions which produce photosensitizing chemical products in fragrances. This is an especially serious problem for skin care products which undergo the most exposure to sunlight. This can promote photochemical reactions in product fragrances after they are applied to the human skin. Photochemical reactions which trigger new organic syntheses are some of the most important reactions in organic chemistry today. Reactions which ...

The relationship between exposure to fragrance materials and persistent light reaction in the photosensitivity dermatitis with actinic reticuloid syndrome.

Contact allergic sensitivity to allergens such as plants of the Compositae family is a feature of the chronic skin reaction seen in the photosensitivity dermatitis with actinic reticuloid syndrome. In fifty patients with this syndrome an increased incidence of contact allergic sensitivity to some common fragrance materials was demonstrated. Evidence is also presented, both by in vitro and in vivo studies, which indicates that a phototoxic mechanism is involved. The relevance of continued exposure to common allergens and their involvement in photosensitization mechanisms is discussed in an attempt to explain the state of 'persistent light reaction'.

香料及び精油のガスクロマトグラフィーによる分析

The column selection is one of the most important matter for the gas chromatographic analysis of flavor and fragrance materials, and essential oils. The glass capillary columns give a highest resolution, especially a fused silica capillary column performs excellent resolution.Using the retention index system, qualitative gas chromatographic analysis gives a quite satisfactlory result.

Antimicrobial activity of aroma chemicals and essential oils.

AbstractDetermination of the minimum inhibitory concen‐trations (MIC) of 212 common soap fragrance raw materials demonstrated that the paper disc‐petri plate technique does not reflect the relative anti‐microbial activity of these materials. Commonly used soap bacteriostats were shown to be 100 to 1000 times more effective than the most active fragrance materials. Of 521 fragrance materials initially screened by the petri plate method, 44% were inhibitory against one of the three test organisms, and 15% were effective against all three(Staphylococcus aureus, Escherichia coli, Candida albicans). Of a selected number (212) of these positive materials, subsequently screened against a lipophilic diphtheroid organism(Corynebacterium sp.), 64 materials (30%) were positive against all four test organisms. However, only nine materials (4%) had a MIC as low as 50 ppm compared to the common soap bacteriostat TCC, which had a MIC of 0.08 ppm (vs.S. aureus). In hand‐degerming tests, no reduction of bacterial counts was obtained with a soap containing the most active fragrance materials. These results demonstrate that creation of a practical antimicrobial soap fragrance does not appear to be possible.

The Progress of Perfume Materials

The Progress of Perfume Materials

Absence of contact hypersensitivity to some perfume materials derived from Compositae species.

Absence of contact hypersensitivity to some perfume materials derived from Compositae species.

Perfume Dermatitis

• Patch tests to several screening sets of fragrance materials were performed on 20 perfume-sensitive patients. The most common allergens were found to be a jasmin synthetic (18 of 20 patients), cinnamic alcohol (15 of 20 patients), and hydroxycitronellal (9 of 20 patients). More than half of the patients were also contact sensitive to other ingredients of cosmetics and over-the-counter and prescription preparations. (<i>Arch Dermatol</i>113:623-626, 1977)

Contact hypersensitivity to some perfume materials.

Some recent publications concerning perfume contact sensitivity are briefly reviewed. Japanese workers have identified some perfume sensitizers and have devised an allergen replacement system. Costus absolute of perfumery has been found to sensitize guinea-pig and man; sesquiterpene lactones are responsible for cross-sensitivity with some other plant products. Balsam of Peru is a useful screen for perfume sensitivity; terpenoids of balsams require study.

Natural perfume materials: a study of concretes, resinoids, floral oils and pomades.

ADVERTISEMENT RETURN TO ISSUEPREVBook and Media Revie...Book and Media ReviewNEXTNatural perfume materials: a study of concretes, resinoids, floral oils and pomades.Florence E. Wall Cite this: J. Chem. Educ. 1948, 25, 1, 59Publication Date (Print):January 1, 1948Publication History Received3 August 2009Published online1 January 1948Published inissue 1 January 1948https://doi.org/10.1021/ed025p59.1RIGHTS & PERMISSIONSArticle Views395Altmetric-Citations-LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (1 MB) Get e-Alerts Get e-Alerts