Perfumes and Essential Oils. David S. Seigler Department of Plant Biology University of Illinois...

Perfumes and Essential Oils

David S. Seigler Department of Plant Biology

University of IllinoisUrbana, Illinois 61801 USA

seigler@life.illinois.eduhttp://www.life.illinois.edu/seigler

Perfumes and Essential Oils: Outline

ImportanceHistoricalEconomic Esthetic

Manufacture

Types of perfumery ingredients + Odorants + Concretes + Absolutes

+ Tinctures+ Distilled oils+ Expressed Oils

+ Fixatives + Extenders

o Methods of isolation + Enfleurage:Pomade, soapImportant oils prepared by enfleurage: Rose, jasmine,violet + Steam Distillation + Fractional Distillation:Important oils prepared by distillation: Ylang-ylang, patchouly, oil neroli, lavender, lemon grass oil, citronella oil

+ Expression Important oils by

expression: lemon, lime

+ Extraction Important oils by extraction

• Question: Why is one method preferred over another?

• 1. Cost• 2. Quality of product• 3. Availability of product

• Commercial essential oils:UsesPropertiesSources

Reading

• CHAPTER 8 IN THE TEXT

The origin of perfumes

• It is difficult to know when people first started to use perfumes. The Egyptians had become skilled perfumers over 5000 years ago.

• The Hebrews learned from them. Recipes for perfumes and incenses are found in the Torah or Jewish law.

• Perfumes also showed up very early in the Orient. The Japanese and Chinese both developed perfumes and incenses as well.

A perfume market in Sudan

Courtesy Dr. Dorothea Bedigian

• Perfumery reached its pinnacle during the Roman Empire. They perfumed everything. After the fall of the Roman Empire, perfumery in Europe just about disappeared.

• The Arabs maintained these skills and improved them.

• At the time of the Crusades, the crusaders not only discovered spices, but also perfumes.

• The French developed the art of perfumery even more.

• There is a lot of folklore associated with perfumery. Many of the recipes for the best perfumes are guarded trade secrets.

• In the last few years, all major perfumers have a staff of organic chemists and perfume compounding is no longer an art, but a science.

How perfumes are made

• All perfumes originally came from plants (or animals). The material could be used directly (as frankincense and myrrh) or extracted in some way. The challenge was (and is) how to remove the essential oils from the plant material without changing the composition.

• Other materials known as fixatives retard and modify the evaporation of volatile essential oils.

• Odorants give the perfumes characteristic odor.

• There are five types:– concretes– absolutes– distilled and fractionally distilled oils

– expressed oils– tinctures.

http://www.fragonard.com/@en-us/Default.asp

• Many factors determine which method is used. Among these are cost, quality of essence, and use of the product.

• Concretes are the purest of the natural odorants. They are obtained by using a hydrocarbon solvent to dissolve the essential oils out of the plant.

• The solvent is then removed under vacuum by mild heating.

Concretes

Absolutes

• Absolutes are extracted from the non-volatile materials with alcohol.

• The alcohol is removed under vacuum• The alcohol is recovered and used in colognes and lotions.

• Enfleurage is a special method for making concretes and absolutes. The petals are pressed onto a coating of pure lard and changed often.

• After several days, the lard has dissolved the released essential oils.

• The essential oils are then removed from the lard with alcohol.

• The residual lard is pomade.• After extraction, the lard is used to make soaps etc.

Enfleurage

Tray of lard with jasmine flowers used for

enfleurage

Pomade from enfleurage

• It is possible to make exceedingly fine fragrances in this way, but it is also very expensive.

• This process today is seldom carried out in France, but more commonly in the Balkans and the Near East where labor is much cheaper.

• Grasse in Provence used to be the center for this industry.

Grasse, Provence, France

• Rose oil or attar of roses (also otto). The best quality oils (absolutes) sell for as much as $10,000 per kilogram.

• From Rosa damascena (or R. alba and R. centifolia) in the late bud stage. These are small shrubs with not too showy flowers. Done from April to July. One g from about 2000 g of flowers.

• The oil is about 40-65% citronellol but many minor components that are essential for good rose quality.

• In fact, some are quite important at less than 0.1% of the citronellol content.

• Rose oils are usually extended before marketing.

Rosa damascena, Rosaceae

Rose petals

National Geographic

Jasmine (Jasminum grandiflorum, Oleaceae)

• Jasmine (Jasminum grandiflorum, Oleaceae) is also grown in southern France. From July to October.

• 5000 flowers makes about 1 lb of flowers.

• More than 300 lbs. of flowers are required to make 1 lb. of oil.

• The flowers are picked at daybreak for best odor.

• Today this oil is mostly obtained by solvent extraction because of price.

Jasmine, Jasminum officionale,

Oleaceae

Violet (Viola odorata, Violaceae)

• Violet (Viola odorata, Violaceae) is also from Grasse, Toulouse and from the Taggia valley in Italy. Grown under shaded conditions. January to April.

• The flowers are picked at night or early morning. 1000 lbs. of flowers gives 1 lb. of oil.

Violet, Viola odorata, ViolaceaeCourtesy Dr. Anita

Brinker

Codistillation with water

• Steam distillation (or codistillation with water) is another gentle and widely used process.

• Much less expensive than enfleurage.• The oils are insoluble and when the steam-oil mixture is condensed, the oil can be removed. The most volatile compounds come over first and some fractionation is observed.

• Fractional distillation (without water) separates the components by boiling point (the explanation in the text is not quite accurate).

• Both steam distillation and fractional distillation of essential oils are much cheaper than enfleurage, but different mixtures of compounds are obtained and heat causes some rearrangements and changes in structure of the essential oil components.

Fractional distillation

Oil ylang-ylang (Cananga odorata, Annonaceae) is widely used in perfumes and is

relatively expensive.

Steam distilling ylang ylang, Cananga odorata National Geographic

Essential oil from Acacia dealbata

Patchouly oil (Pogostemon cablin, Lamiaceae or Labiatae)

• Patchouly oil was brought from India to England by the British East India Company.

• This perfume became the mark of dissolute women. Used in heavy perfumes and soaps as a fixative.

• Isolated by distillation. The foliage is 2-3% oil.

• Now produced in the Seychelles and Indonesia.

• Oil neroli (from orange blossoms) (Citrus aurantium) is also isolated by distillation.

• From Italy, Spain, Portugal, Provence. May.

Lavender (Lavendula

officinalis or L. vera)

(Lamiaceae or Labiatae) also important from

Provence.

• Lemon grass oil (Cymbopogon citratus, Poaceae or Gramineae) is widely used as a substitute for expressed lemon oil.

• It is used in soaps, perfumes, food products, and in mosquito repellents.

Bentley and Trimen, Medicinal Plants

Citronella oil (Cymbopogon nardus),

Poaceae, used to be widely used as a mosquito

repellent in the South.

Expressed oils

• Expression is useful for things like lemon and lime peels.

• For most plants, the oils are contaminated with too many other undesirable compounds to make the method practical.

• The compounds are not changed by heat, however, and in some instances are better quality than steam distilled or fractionally distilled.

Citrus fruits.

Carolina Biological Supply Co.

Tinctures

• Tinctures (or alcoholic extracts) are widely used. They are cheap, but they are sometimes contaminated with other undesirable products as well.

• Today, many perfumes are purely synthetic, but the best quality perfumes still come from plants.

• In laundry soap, this is probably not too critical. For good quality perfume, it's obviously more a concern.

• In some cases, the plants are so inexpensive, that synthetic products are not competitive.

• Not only the isolation of the essential oil, but also the compounding of the perfume is complex and critical.

Types of perfumery ingredients

OdorantsConcretesAbsolutesTinctures

FixativesExtenders

• The balance of essential oils, fixatives, and extenders is all involved. This stage is often highly empirical.

• Most perfume companies have a "nose" to evaluate the products.

A “nose”

National Geographic

Orris root, Iris florentina, Iridaceae

National Geographic

Orris root National Geographic

Extenders

Some essential oils, such as rose, jasmine, or neroli are very expensive.

When used in a blend it is important that their fragrance is not wasted.

Natural extenders are the oils used with the most expensive oils to make the blends affordable while at the same time respecting the notes of the precious oils.

• The major components of essential oils are terpenes, phenylpropanoids, and metabolized fatty acids. They are found in all different parts of plants and the essential oils from the different plant parts differ in composition. They often differ with stage of development as well.

Commercial essential oils

An alembic or still

• Essential oils are used in: soaps, deodorants, toilet preparations, flavoring food and beverages, tobacco, antiseptics, solvents (e.g., turpentine), insecticides and insect repellents (as oil of citronella), and plasticizers in plastics.

Camphor tree, Cinnamomum camphora,

Lauraceae

Eucalyptus, Eucalyptus globulis, Myrtaceae

Sassafras, Sassafras albidum, Lauraceae

Juniper or cedar, Juniperus

virginiana, Cupressaceae