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Dong-Sun Lee Chemical Analysis & Technology Lab. Department of Chemistry Seoul Women’s University 2012 Spring version Copyright. All rights reserved.

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Presentation on theme: "Dong-Sun Lee Chemical Analysis & Technology Lab. Department of Chemistry Seoul Women’s University 2012 Spring version Copyright. All rights reserved."— Presentation transcript:


2 Dong-Sun Lee Chemical Analysis & Technology Lab. Department of Chemistry Seoul Women’s University 2012 Spring version Copyright. All rights reserved. Expedition

3 ? Delta Pyramid Triangularity A = ½bh Theorem of Pythagorus a 2 = b 2 + c 2 Triple alliance Triangular Trade Three Kingdom Three branch of government Eternal triangle Tetrahedron Point : Cursor : Dot Hierarchy Three Worlds Trade Mark Hyundai Sign : Symbol : Logo …… Mountain

4 Cyclopropane CH 2 CH 2 CH 2 Research Interest Flower aroma Seeds Environment

5 aroma noun [C] a strong pleasant smell, usually from food or drink: the aroma of freshly baked bread a wine with a light fruity aroma expedition noun [C] 1. an organized journey for a particular purpose: We're going on a shopping expedition on Saturday. Scott died while he was on an expedition to the Antarctic in 1912. 2. the people, vehicles, animals, etc. taking part in an expedition: The British expedition to Mount Everest is leaving next month.

6 Aroma (L. aromata, Gr. , F. parfum ) refers to the spice and the distinctive fragrance exhaled from a spice, plant, etc.; generally an agreeable odor, a sweet smell; a distinctive odor that is pleasant. Fragrance (L. fragrantia) refers to quality or state of being fragrant; sweetness of smell; a sweet smell; a pleasing odor; perfume (L. per fumum = through smoke) cf. scent / smell / odour Flavor (L. flare = to blow) refers to the element in the taste of a substance which depends on the cooperation of the sense of smell; a more or less subtle peculiarity of taste distinguishing a substance from others. Terminology

7 The noun "perfume" has 2 senses in WordNet. 1. perfume, essence -- (a toiletry that emits and diffuses a fragrant odor) 2. aroma, fragrance, perfume, scent -- (a distinctive odor that is pleasant) Perfume means simply “from smoke” (Latin, per fumum), the first perfumes having been obtained by the combustion of aromatic woods and gums, Their original use was in sacrifices, to counteract the offensive odours of the burning flesh. THE DICTIONARY OF PHRASE AND FABLE BY E. COBHAM BREWER FROM THE NEW AND ENLARGED EDITION OF 1894

8 Perfume is a mixture of fragrant essential oils, a fixative, and alcohol used to give various objects (usually parts of the human body) a long-lasting and pleasant smell. The essential oils are obtained by distillation of flowers, plants, and grasses, such as orange blossom, jasmine, and roses. Aromatic chemicals are also used. Fixatives, which bind the various fragrances together, include balsams, ambergris, and secretions from the scent glands of civets and musk deer (undiluted these have unpleasant smells but in alcoholic solution they act as preserving agents). The amount of alcohol added depends on whether perfumes, Eaux de toilette, or Eaux de Cologne are required. Eau de - means "water of" in French. The mixture is normally aged for one year. On application, body heat causes the alcohol to evaporate quickly, leaving the fragrant substances on the skin to evaporate gradually over several hours. The art of making perfume began in ancient Egypt, was developed by the Romans and the Arabs, and came to Europe in the Renaissance period. By the 14th century flowers were being grown for perfume in France, which remains the centre of the European perfume design and trade. In some cases, an excessive use of perfumes may cause allergic reactions of the skin (specifically, acetophenone is a well-known allergen present in many perfumes). See also: incense, aromatherapy, pheromone, Base_note, Top note

9 Perfume And FragrancesPerfume And Fragrances : Definitions Perfume or Parfum: Contains a highly concentrated amount of fragrance oil. This is the richest, strongest and longest lasting full-bodied fragrance. Perfume is the most expensive form of fragrance and contains 20 to 50% perfume compound. Eau de Parfum: A less concentrated form of perfume. Contains approximately 10 - 20% perfume compound. Eau de Toilette: A typically more diluted form of Eau de Parfum. Contains approximately 8 - 10% perfume compound. Cologne, Women's: A light form of fragrance with about 3% perfume compound. Cologne, Men's: More concentrated than women's colognes contains 5 - 8% perfume compound. Similar to the strength of Eau de Toilette. By comparison, Mens After Shave usually contains only 3 - 5% perfume compound. Perfume Compound: The term used in the industry for the concentrated perfume or flavour mixture before it is diluted or used in fragrance products.

10 Nard (perfume) Nard is a perfume, also known as spikenard, made from a Himalayan flower. It was perhaps most famously used in John`s description of Jesus`s anointing by Mary. Nard an aromatic ointment used in antiquity (Bot.) An East Indian plant (Nardostachys Jatamansi) of the Valerian family, used from remote ages in Oriental perfumery.

11 Webster's 1913 Dictionary mal`o´dor An offensive odor. WordNet Dictionary malodor - a distinctive odor that is offensively unpleasant Synonyms: fetor, foetor, malodour, reek, stench, stink, mephitis Related Words fetor, foetor, malodour, mephitis, niff, odor, odour, olfactory perception, olfactory sensation, pong, reek, smell, stench, stink

12 Perfume And FragrancesPerfume And Fragrances : Perfume Notes French perfumer Piesse changed the perception of perfumery in the 19th century. Piesse discovered that fragrances went through many different phases once the perfume had come into contact with the skin. Piesse went on to describe these phases as compared to great a symphony that features many different movements and went on to develop the concept of the musical harmony classification of perfume. Classifying the phases or the fragrances of perfume on the basis of notes in a musical scale determined that a balanced fragrances contained elements of the top, middle and base notes and each phase or groups of 'notes' has a differing degree of volatility. "The notes of a fragrance are the different phases through which a perfume develops when you spray it on your skin," explains fragrance expert Michael Edwards.

13 Classification of Scents Scents are classified as notes based on their olfactory character. TOP NOTES: peak note: initial fragrance The initial hint of each fragrance - the fresh, light quality that you senses first pick up on. The top notes evaporate fairly quickly and can fade after 5 to 20 minutes of being in contact with the skin. The top notes can be described as light volatile notes that burst on your skin and serves as the first impression of the fragrance. MIDDLE NOTES : heart note : coeur notes : central character (bouquet) As the tope notes fade the middle or 'heart' notes form. The middle or 'heart' notes form the actual fragrance character of the perfume and can last for up to 4 or 5 hours. The middle note is most often composed of flower extracts and lasts for around four hours. They aren't as volatile as the top notes, so they emerge a bit later and last longer. BASE NOTES: bottom note: fond note : Dry Down, Less volatile, stays on your skin Base notes emerge slowly but usually are richly scented and are usually the lasting notes of the fragrance. Nowadays the base note takes its warmth and tenacity (from one to twenty-four hours and up to three months on an isolated dipstick) from very long-lasting fixatives or base raw materials such as oak moss and patchouli. The base notes have two functions in a perfume. First, they're the least volatile elements, so they emerge more slowly, and their aroma will remain the longest. So it's very important to make sure you like your base note! Second, they can have a "fixative" effect on the entire blend, keeping the top and middle notes from evaporating as quickly.

14 Top Notes : citrus oils (bergamot, lemon, mandarin, orange, tangerine, etc), conifer oils (cypress, fir, pine, spruce, etc), mint oils, basil, cardamom, chamomile, ginger, juniperberry, petitgrain, rosemary, cajuput, caraway, clary sage, coriander, eucalyptus, lemongrass, niaouli, petitgrain, sage, tea tree Middle Notes : floral oils/absolutes, black pepper, caraway, cinnamon, clary sage, clove bud, coriander, elemi, galbanum, geranium, lavender, sweet marjoram, nutmeg, palmarosa, thyme, violet leaf absolute, ylang ylang, jasmine, rose, lily Base Notes : wood oils (cedarwood, gaiac, linaloe wood, sandalwood, etc.), resin oils (frankincense, myrrh, etc), labdanum, oakmoss absolute, patchouli, vanilla, peach, plum, bay rum, vetiver, oak moss, honey, amber, musk, civet, and castoreum.

15 Moods The type of note is often associated with a particular mental or emotional effect - or to induce a particular mood swing. Top Notes Stimulating and Uplifting Middle Notes General Body Tonics, Neutral Mood Base Notes Relaxing and Sed

16 French perfume making’s technical body has classified the fragrances in eight scents’ families. The citruses (masculine and feminine): Citrus oils (Hesperidia) are the key elements in this family such as bergamot, orange, lemon, grapefruit and other orange-tree element as neroli, petit grain (anis, nutmeg) etc. These fragrances are characterized by their freshness and lightness. Floral (feminine): The floral fragrances are composed of a large variety of flowers and floral bouquets such as rose, jasmine, violets, ylang-ylang, orange tuberose and carnation with an additional woody and musky note. These can be described as fresh and bubbly. Oriental (masculine and feminine): Powdery floral fragrances combined with warm oriental scents. They associate heady substances like musk, vanilla, amber with precious woods (sandalwood, cedar).

17 Woody (masculine notes): A family based on woody scents such as sandalwood, patchouli, cedar, vetiver. These warm and dry masculine accords combine aromatics (lavender) and citruses fragrances. The Chypre (feminine): Based on mossy, woody floral and fruity notes (bergamot, lavender and nutmeg). Chypre perfumes have a rich and lingering scent. chypre means "very sincere" in French. The ferns (masculine): Aromatics and woody notes with lavender, coumarin, geranium, oak moss, etc. The leathers (masculine): These fragrances evoke smells such as tobacco, smoke and leather. The aromatics (masculine): Perfumes based on bay, thyme, rosemary, verbena, mint, etc and complemented with citrus and spicy notes. These manly compositions make them an all-time favorite in men’s perfumery.

18 What is a fragrance family? Fragrance families are classifications of fragrances. How they are classified depends on the notes that make up the scent. For example, if a fragrance is composed of several key floral notes, such as rose, jasmine, or white peony to name a few, it's considered a floral fragrance. The most common families for women are: Floral: Stirs a single specific flower or a blend of floral notes To try: Ralph Lauren Blue, Lanvin Eclat D'Arpege, Dolce & Gabbana Sicily Fresh: A mix of citrus, green, and marine notes To try: Clean; Guerlain Aqua Allegoria Lemon Fresca; Comptoir Sud Pacifique O'Pomelo Woody: Combines warm notes that evoke the scent of wood To try: Bulgari Omnia, Chanel Chance, Michael Kors Oriental: Warm, rich, full bodied fragrances To try: Giorgio Armani Sensi, Giorgio Armani Night for Her, Gucci Eau de Parfum

19 The profession and art of being a “ Nose ” A little known but essential profession, the "Nose", or perfumer, invents perfumes. His craft has little to do with science. He works surrounded by raw materials using a set of precision scales, and by experimental dosages, trial and error he gradually succeeds in creating a good perfume. He is both artist and technician and his nose is of more use than any modern instrument. A "Nose" can remember and recognize up to 3000 different smells. Seated at his perfume organ (a miniature laboratory), the perfumer mixes his formulae and smells them on small dipsticks of paper soaked in perfume. He works at compositions for months, sometimes years, until he finds a definitive accord. His aim is to create a harmony of fragrances as one creates a color harmony or a melody in music. There are approximately one thousand perfumers in the world but less than fifty of them are "Noses", that is, perfumers whose creativity and originality are such that they are able to launch real trends. Every factory uses the services of one, two or three perfumers. Grasse is the main school and every "Nose" in existence is either a native of Grasse or has worked in Grasse perfume making.

20 What is aroma ? - Volatile (or semi-volatile) Compound some water solubility, high vapor pressure, low polarity, dissolve in fat(lipophilicity), surface activity, molecular weight  294. - Untouchable - Sensible (smell or taste) - Invisible

21 On Smell What is this strange power of suggestion that scents and especially perfumes possess, which allows them to reawaken associations in our minds' memories in a fleeting but most intense moment ? Deep inside our brains, smell, feelings, and memory are intimately bound. The primary function of smell is to provide vital information about the olfactory world which surrounds us. In order to be detected by the nose, odoriferous molecules have to be soluble and volatile : a dry nose is insensitive to smells. Odoriferous molecules are breathed in and dissolve on the mucus-lined walls of the nose. Sensory cells located in the nasal cavities pick up from there and transmit the information to the brain's olfactory bulbs by way of the sensory nerves. The whole process takes place in one/thousandth of a second.

22 Basic flow of olfactory information in the brain 100602 Brain command to sniff Sensory perception in nose Olfactory bulb Olfactory cortex Thalamus Limbic System Frontal cortex Motor cortex Recognition

23 Olfactory bulb Olfactory tubercle The Olfactory System: Anatomy and Physiology

24 냄새로 인지되는 분자들을 냄새물질 (odorants) 이라고 부른다. 냄새물질 분 자들이 코 속의 비강 천정부에 존재하 는 후각 신경세포를 자극하고 이 반응 이 뇌를 충동하게 된다. 후각신경세포 를 수용체 세포 (receptor cells) 라 부르 고 그 표면에 수용체 부위가 있다. 냄새 물질 분자가 후각수용체에서 검출되면 세포내부에 전기신호를 발생시키는 방 아쇠를 당기게 된다. 수용체 부위는 신 경세포막의 안쪽과 바깥쪽에 삐죽이 나 와 있는 단백질 분자들이라고 과학자들 은 믿고 있다. 단백질이 끼워져 있는 기 본 골격의 한쪽 끝은 세포 벽 내부와 외 부로 서로 지그재그로 어긋나게 일곱번 정도 늘어선 모습이다.

25 단백질 분자는 세포벽을 통해 나선 이 차구조를 갖는다. 나선 구조가 모이어 실린더 모양을 이루고 있다. 이 실린 더 내부에 냄새물질 결합부위가 존재 하는 것으로 과학자들은 믿고 있다. 냄새 물질 분자가 후각 수용체 단백질 과 만나면 단백질 구조에 변화가 일어 난다. 그 다음 단계는 보조 G 단백질 이 아데닐레이트 싸이클라제라는 효 소를 활성화 시키게 된다. 이 효소는 세포내에 존재하는 아데노신 트리 포 스페이트로 (ATP) 부터 싸이클릭 아데 노신 모노포스페이트 (cAMP) 라는 메 신저 분자 생성을 촉진시킨다. CAMP 는 나트륨 이온경로를 열어 나트륨 이 온이 세포막을 통과하게 된다. 만약 냄새물질이 없어지면 수용체 세포내 에서 더 이상 신호발생이 일어나지 않 는다.

26 영장류는 시각이 뛰어나고 조류는 청각이 뛰어나며 곤충류는 후각이 뛰 어나지만 어류는 후각과 미각이 발달되지 못하였다. 자외선을 감지할 능력이 없는 사람 눈에는 핑크색으로 보이는 꽃이 자외선을 감지하는 곤충에게는 다른 색깔로 보일 수 있다. 따라서 오감을 통해 인지된 정보 에는 개체차와 편견이 많다. 인간은 주변 사람들의 몸에서 나오는 특정한 화학신호를 감지할 수 있 는 능력을 갖고 있다. 다른 포유류 동물들도 같은 종족이 내어 놓는 사회 적 또는 성적 정보를 인지할 수 있는 후각 수용체를 코 속에 갖고 있다. 예를 들면 암컷 생쥐에서 나오는 화학물질의 냄새를 맡았을 경우 수컷 생쥐는 금방 짝짓기 준비를 갖추게 된다. 만약 한 수컷이 다른 수컷이 내 어 놓는 어떤 냄새를 인지하였을 경우에는 매우 공격적인 반응을 보이 게 된다. 따라서 냄새는 동물들의 생리반응에 변화를 일으키는 메시지 이기도 하다. 사람의 경우 이러한 냄새의 효과는 다른 동물처럼 분명하 지는 못하지만 다른 여러 가지 복합적 요소들과 함께 이러한 신호를 받 아들이어 행동에 영향을 주게 된다.


28 뉴욕 콜럼비아대학교의 리차드 액셀 (Richard Axel) 과 시애 틀 후레드 허친슨 암연구센터 (Fred Hutchinson Cancer Research Center) 의 린다 버크 (Linda Buck) 는 생쥐 ( 마우스 ) 의 후각에 대한 1000 여개의 유전자와 냄새수용체를 규명한 업 적으로 2004 년 노벨 생리 - 의학상을 수상하였다. 그들의 연구 결과에 따르면 사람들의 두뇌는 약 1 만여 종류의 서로 다른 냄새에 대한 기억 형태들을 구분할 수 있다고 한다. 즉, 특정 한 냄새는 어린 시절의 특이한 기억 또는 살아오며 경험한 긍 정적 또는 부정적 느낌의 순간을 떠올리게 하는 방아쇠라 할 수 있다. 포유동물의 경우 신생아가 어머니의 젖꼭지를 찾아 젖을 빠는데 필수적인 것이 후각기능이다.

29 The Physiology of Perception By Walter J. Freeman "PHASE PORTRAITS" made from electroencephalograms (EEGs) generated by a computer model of the brain reflect the overall activity of the olfactory system at rest (top) and during perception of a familiar scent (bottom). Resemblance of the portraits to irregularly shaped, but still structured, coils of wire reveals that brain activity in both conditions is chaotic: complex but having some underlying order. The more circular shape of the bottom image, together with its greater segregation of color, indicates that olfactory EEGs are more ordered-more nearly periodic-during perception than during rest. 100602

30 While there are clear trends (see figure on right) - rosemary depresses alpha-activity while ylang ylang enhances it, a longer recovery period following exposure to the odorant is needed and additional "no odour" controls are also required. In aromatherapy rosemary is used as a stimulant and ylang ylang is a soothing, relaxing aroma. Time (sec) Blank Jasmine Lavender Effects of essential oils on CNV (contingent negative variation)

31 Measurement of smell perception threshold GC-sniffer Olfactometer Relative perceived intensity to 1-butanol (87ppm)

32 Smell perception threshold Example Chloroform : 30 ~ 300 mg/m 3 Vanillin : 5 × 10 –3 ~ 1 × 10 –6 mg/m 3 Stevens’ law

33 log C log I B A CxCx TATA TBTB Diagram showing the effect of the concentration on the relative perceived intensities of two materials, A and B, which have different thresholds (T A, T B ) and log I / log C gradients.

34 Smell type vs concentration p-menth-1-ene-8-thiol ppb level : pleasant pineapple or grapefruit scent high level : disagreeable sulfur odor Indole highly diluted level ( 0.001% alcoholic solution): pleasant jasmine scent high level : disagreeable fecal odor

35 Sources of aromas Animal Botanical Microorganism Fermentation Synthesis

36 - Aroma compounds are found throughout the plant kingdom. A large number of chemical compounds are characterized by particular fruit and flower fragrances.

37 Glossary absolute - an alcohol extract of a concentrate to remove waxes and most odorless materials, producing an alcohol - soluble liquid or semi-liquid oil. It is the most concentrated form of perfumery material. accord - The basic character or theme of a fragrance. An perfume accord comes about when three or four notes blend together and lose their individual identities to create a new odor. alcohol - Specially denatured ethyl alcohol is added to a fragrance to serve as the carrier. amber - Obtained from fir trees. Gives a fragrance a very rich, warm fragrance tone. It is commonly used in fragrances that fall into the "oriental" category. attar (otto) - From the ancient persian word "to smell sweet". An extracted substance derived from the distillation of flowers. That of the Bulgarian rose is one of the most precious materials used in perfumery. balsam - a water insoluble, semi-solid or viscous, resinous exudate of trees and bushes similar to gum resins. blend - Harmonious mixture of perfumery ingredients. body - The main fragrance theme. The heart of the perfume.

38 chypre - A fragrance family - a complex of moss mixed with woods, flowers or fruit odors. Chypre fragrances often contain "oakmoss absolute". Chypre means "very sincere" in French citrus - Odors from orange, mandarin, lemon, lime etc... Used as top notes and popular men's colognes. compound (composition) - A completed formulation. dry down - The final phase of a fragrance, this is what you will smell hours after application. concrete - Extraction of fresh natural plant materials, usually with non-polar organic solvents (e.g. hexane) which yield, after removal of the solvent by vacuum distillation, a semi-solid wax. They represent the closest odor duplication of the flower, bark, leaves etc... essential oil - an oil collected in the water distillate during the production and concentration of fruit juices. Upon separation from the water, the remaining oil contains the highly volatile top notes of natural juices. Essential oils are normally liquid, but in some cases may be solid, depending on temperature. They are the essence of plants. evaporation - The process of changing from a liquid to a vapor.

39 FCC - Food Chemicals Codex, the industry-standard listing of food-grade ingredients; indicates materials safe for use in food and cosmetics. fixative - a material which slows down the rate of evaporation of the more volatile components in a perfume composition. fixed oils - non-volatile oils derived from plant materials, commonly referred to as vegetable oils. floral - The most common fragrance family. Either characteristic of a specific flower or a blend of several flower notes. green - A fragrance family whose odor is reminiscent of grass and leaves. harmonious - VERY IMPORTANT! Odor, accord and unity in fragrance. This is where you will have to work on your skills. harsh - A crude, unbalanced odor. No harmony! This is what you will discover on your first tries. heady - Exhilirating, sparkling, stimulating. heart - The core of a perfume composition which gives it its character. heavy - An odor which can be forceful, intense.

40 middle notes - The "heart" notes make up a main blend of a fragrance that classifies the fragrance family or accord. note - Indicates an olfactory impression of a single smell, or to indicate the three parts of a perfume - top note, middle note, base note. organ (perfume) - A unit of semi-circular stepped shelving containing hundreds of bottles of raw materials. oriental - A fragrance family devoting heavy, full bodied perfumes. Often contain "amber". perfume (parfum) - most highly concentrated form of fragrance. perfume dip sticks - strips of odorless white blotting paper which the perfumer uses to evaluate a scent as it develops. terpeneless - Complete or partial removal of monoterpenic or hydrocarbons by distillation of an essential oil to: a) improve solubility in diluted alcohol or food grade solvents. b) increase stability of the oil and prevent the appearance of rancid notes.

41 Basic flow of olfactory information in the brain Smell perception threshold Smell type vs concentration

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