Perfumes• Earliest use of plant fragrance lost in history

• Perfume (burning plants) may have been first use

• Egyptians using scented oils at least 5000 years ago

• Egyptian men would put solid cone of perfume on the head, let it melt

• Greeks used various scents for different body parts– mint, marjorum,

thyme, etc

• Romans scented clothes, houses, bedding and bath oil, as well as their bodies

• Japanese and Chinese used incense as clocks

http://www.nawcc.org/museum/nwcm/galleries/asian/incense.htm

Traditional methods of extracting essences

• Not usually water soluble

• Macerate (chop) plant parts in hot oil, then extract with alcohol

• Enfleurage – flowers placed on layer of

purified fat or oil– they are replaced every

couple of weeks– yields outstanding scents,

very expensivehttp://www.museesdegrasse.com

• Popularity of perfume waned in Europe after the fall of the Roman empire, returned with the crusaders

• Distillation of essential oils

• Attributed to Avicenna, Arab, late 900’s

Distillation of natural fragrances

• Plant parts are exposed to steam• Volatile oils are carried out in steam• Steam is cooled, oil floats and can be

skimmed• 5-6 tons of roses needed to get one kilo of

essential rose oil• Fractional distillation allows collection of

substances with different volatility

Attars (steam distillates) being prepared in India

Perfumes in 18th century Europe

• More flowery as opposed to heavier scents

• Numerous ways to use perfumes, elaborate containers

• Vinaigrettes• Pommanders go out of

style with availability of liquid perfume

Eau de Cologne

• Germany, invented an 1709 by an Italian barber

• Rosemary, orange flower, and bergamot oils distilled in grape spirits

• Non-greasy• Napolean decreed the

formula must be public in 1810

Grasse, in Provence, France

• Started with tannery perfumes– for scenting gloves?

• A local company got a patent on the distillation system

• 1720’s become a local industry

• Good sources for jasmine, rose, orange

• Modern perfume industry started here

Perfume odorant types today

• Concretes– purest, soft plant parts are placed in solvent

• Absolutes– concretes concentrated in alcohol

• Resinoids– extracted like concretes, from plant secretions

• Tinctures– direct extraction with ethanol

• Distilled essential oils– most common modern methods

Perfume anatomy

• Top notes– immediately perceived, highly volatile, bright,

often citrus, ginger

• Middle notes– a minute to an hour; often rose, lavender

• Bottom notes– often animal, resin scents, perhaps vanilla,

sandlewood

Types of fragances

• Perfume (22% essential oils)

• Eau de Parfum (15-22%)

• Eau de Toilette (8-15%)

• Eau de Cologne (4%)

Business of scents (perfumes)

• 10-20 billion dollar industry

• Only a few companies are doing smell R & D

• They work for two main client groups; household products companies, and perfume companies

• Lots of secrecy

Lavender

• Mint family• Sterile hybrid of two species

(L. angustifolia and L. latifolia) most often used today

• Obtained by steam distillation• More than 300 components,

linalool important• In many men’s fragrances (fern

note)

Rose• Rosa centifolia and

damascena

• Petals extracted with steam or solvents

• Used in many perfumes, foods

Geranium • Pelargonium graveolens• Oils distilled from leaves and

stems• Much cheaper than rose,

similar fragrance in some types

• Essence from Reunion island especially fruity

• Also in drinks, insect repellent

Geraniol and related compounds

• Found in a variety of plants

• Also produced synthetically

Jasmine• Jasminum grandiflorum• Volatile solvents now

used, used to be enfleurage• A ton of flowers to yield a

kilo of essence• Extremely expensive• Wide range of

“jasmonoid” compounds, biosynthesis perhaps similar to prostaglandins

• Benzyl acetate and related compounds common

Tuberose

• Polyanthes tuberosa• Amaryllis relative• Expensive, low yield to

extract, done by enfleurage until relatively recently

• Many fragrance compounds (eugenols, nerol) also some weird tuberose lactones

Orange

• Citrus species

• Flowers, leaves, fruits, even bark all used

• Distillation or solvents used

• Wide range of compounds isolated, including linalool

Bergamot

• Citrus bergamia• Zests from unripe fruits

used• Harmonious with many

other compounds; contains linalool, limonene does not dominate in this as it does in orange oil

• Coumarins removed from essence (photosensitizing)

• In Earl Grey tea, as well as perfumes, soaps

• Eau de Colognes

Iris of Florence

• Iris pallida• Violet-scented rhizomes

(orris root) used to produce a concrete with iron in myristic acid (called a butter)

• In perfume with heavy, woody notes

ylang-ylang

• Cananga odorata, related plants

• From SE Asia (?)• Annonaceae• Very floral scent• Several common

compounds (eugenols, linalool) also

• p-Cresyl methyl ether – stinks by itself, but blends

well

Patchouli

• Shrub in the mint family• Pogostemon cablin • Distilled dried leaves

yield several important fragrances

• Distinctive strong odor, but also mixes well

Vanilla• Native to Mexico, much

now grown in Madagascar• More than 200 compounds

have been identified• Extract used in small

amounts in perfumes; it’s very strong

• Lots of synthetic vanillin relatives used

vanillin

Vanillin analogs, some with carnation, cocoa butter overtones

Oakmoss

• Evernia prunastri

• A lichen found in much of Europe

• Some constituents now synthesized

Olibanum (incense tree)

• Resin from a Boswellia tree

• Resinous, woody smell

• Used in some perfumes (Opium, Jicky)

Fixatives

• Various animal products– Ambergis, musk, castoreum, civet– synthetics often used now– e.g. ambergris compound from

sage

Others

• Ginger, cardamom, pepper (Piper nigrum), clove

• Many more…

Perfume themes

• Floral

• Chypre (bergamot, jasmine, oakmoss)

• Aldehydic (most famous is Chanel No.5, described as piquant)

• Fougerè (lavender, coumarin, oakmoss), often in men’s products

• Woody (sandlewood, patchouli, cedar)

• Oriental (includes vanilla, ambergris)

Synthetic vs natural: what are the issues?

• “The truth about fragrance oils”– www.earthmamaangelbaby.com/fragrance_oils.html

– “Each essential oil comes from just one source, a living plant.  There are no chemicals involved.”

• Remember, they are all chemicals!• We may actually know more about the synthetic

mixtures than the natural ones

Concerns

• Toxicity to people?

• Allergens?

• Increasing asthma incidence?

• Unknown compounds in the mix?

• Persistence in the environment?– Example: synthetic musk

Synthetic musk

• May accumulate in some organisms (e.g. mussels), prevents removal of other toxins