Perfumes – Apiacea Or Carrot/Parsley Family

Home , Abelmoschus moschatus, Bay leaf, Boswellia papyrifera, Choisya ternata, Commiphora myrrha, Curry tree

Contact with new cultures changed the drinking, eating, recreational habits of Europeans From Asia came tea, from Africa (Arabia) coffee and from America (Holland) cacao While beer is the unrefined drink of primitive, happy people, distillation was learned from the Moors ( Al Cohol). With it came alcoholism, addiction; then smoking, tobacco, gold and syphilis from America. Crusading is a bad idea, isolationism is good.

The 3 temptations of foreign lands: alcohol + coffee (moor), tea + opium (asian) + smoking (american) Medically active substances in Plants Although medical action of plants like Aloe was known already to Cleopatra. However, the reduction of the effect to one or a few substances adds to our understanding of larger connection Anthraquinones: contract gut muscle Rheum, Cassia senna, also important red pigments Aloe, Rhamnus Mucilage: protect sensitive mucous Ulmus, Linum usit., membranes in throat, stomach & guts Verbascum, Tussilago Anthocyanins: important pigments, Rubus, Vaccinium, UV protectants & antioxidants Vitus vinifera Flavonoids: antioxidants, UV protect, Fagopyrum (rutin), antioxidants anti-inflamm, capillaries Vacc. leaves, lemon p Tannins: antibacterial, antifeedants, Quercus, Vitus vin., bind with proteins & alkaloids Rhus, Acacia catechu Coumarins: Blood thinner (anticoag.), Apium grav., Gallium relaxant, furanoco are photosensitizers Mellilotus off., Ammi Glucosinolates: skin inflammants, Rhaphanus (reddish), increase cap. Blood flow, red. Thymus Sinapis a, Brassica ni Medically active substances in Plants Plants are the biochemically most versatile & advanced kingdom of life, followed by fungi …. Vitamines: Compound (also ess AA Nasturtium off (Vit E) & FA) that cannot be prod. by humans Rosa can hips (Vit C) Essential oils/ Terpenes/Resins:olfact Melaleuca tee tree, perception coupled with emot memory Draceana, Thymus Cardiac Glycosides: off toxin Digitalis Maianthenu Cyanogenic Glycosides: in low doses Prunus serotina relaxant (cough), higher cyanide Sambucus, Linum usi Alkaloids: multiple inc narcotic action Solanaceae, Asterace Bitters: Di- & triterpenes, alkaloids Artemisia, Achillea, stimulate digestion Gentium, Humulus Fiber: polymeric substances that Avena, Platanum, accelerate passage through GI tract Malus, Saponins: Triterpene sapogenines + Glycyrrhiza,Solanum steroid s., hormonal, hemolytic action tubers, Saponaria … we might fairly gauge the future of biological sciences, centuries ahead by estimating the time it will take to reach a complete comprehensive understanding of odor Lewis Thomas The chemical concept: enzymes + receptors are protein bodies made to recognize a certain molecule

1% of human genes is for immune system –proteins that recognize old enemies & also adopt to new ones (virus identification + destruction takes days) 1% of human genes are dedicated to the olfactory system – but there is no adaptation but instant recognition of a smell.

Ref: Chandler Burr (2002) The Emperor of Scent, Random house , N.Y. Sensing of primary odors

after Moore et al. 1964 The stereochemical theory of odor, American scientist

Primary odor Chemicals Examples

Camphoraceous camphor moth repellent Musky pentadecanolactone Angelica root Floral phenylmethylethyl carbinol roses flowery Trans-alpha-ionone Viola sp. Peppermint menthone, menthol mint candy Ethereal ethylene dichloride dry-cleaning fluid Pungent formic/ acetic acids vinegar Putrid butyl mercaptan foul eggs An electronic Nose ?

When a polymer film is exposed to a gaseous vapor, some of the vapor gets into the film and causes the film to swell. The vapor-induced film swelling produces an increase in the electrical resistance of the film because the swelling decreases the number of connected pathways of the conducting component of the composite material. The detector films are made from an insulating organic polymer that swells plus an inorganic conductor such as carbon black, Au, Ag, etc .. The electrical resistance of the film is then read using simple, low power electronics. Arrays of chemically sensitive conducting polymer films. that individually respond with resistance changes to vapors can produce a distinguishable response patterns like mammalian olfactory senses flavors and fragrances Plant names referring to scent & taste Agathosmus = aromaticus = fragrans = odoratus = fragrant blandus = mild, pleasing citriodorus = lemon-scented deliciosus = delicious dulcis = sweet foetidus = evil-smelling glycyrrhizus = like licorice graveolens = heavy scented inodorus = scentless meliodorus = honey-scented oxycarpus = with sour fruit phu = rotten saccharatus = sugary sweet salsillus = salty suaveolens = sweet smell fragrant horticulture plants: Daphne odora (spring air), Galium odoratum (woodruff), Lathyrus odoratus (sweet pea), Myrrhis odorata (sweet cicely), Nymphea odorata (sweet lotus), Reseda odorata (mignonette), Viola odorata (sweet violet)

Plant names explained. Botanical terms & their meaning. Bastyr Library QK. P63. 2005 Horticulture Publications, Boston MA USA 2005 No doctrine but signatures Î “Plants have glands” Clear giveaways = signatures = anatomical clues that plants have sequestered lots of active compounds Î glandular trichomes, lacticifers, idioblasts, resin canals, floral & extrafloral nectaries Spices and perfumes – Apiacea or carrot/parsley family

Umbelliferae: umbel as inflorescense; flat-topped clusters of flowers Parsley (Petrosselinum crispum) leaf; dill (Anethum graveolens) leaf; cilantro (Coriandrum sativum) leaf and fruit (coriander spice) Spices and perfumes – Labiatea or mint family Mints have asymmetric, bilabiate (two-lipped) flowers, often in in axial nodes, square stems and opposite, fragrant leaves Rosemary (Rosmarinus officinalis), Thyme (Thymus vulgaris) antiseptic; Oregano (Origanum vulgare), Majoram (Origanum sp); Basil (Ocimum basilicum) Chatreuse; Sage (Salvia officinalis) stuffing, Peppermint (Mentha piperita); spearmint (Mentha spicata)

Picture of leaf glands Citrus family Pressurized vacuoles with essential oils protect citrus fruits. Interior of these fruits is isolated by thick cuticle and pectin layer. The Smell of Spring is here:

Daphne odora: earliest strong smelling flowers on Bastyr and UW Campus

Daphne x Burkwoodii: showy & fragrant spring flowers Allspice Calycanthus californica both flowers a& rubbed leaves have wonderful smell Syringa : lilac flowers strong aromatic smell in spring Choisya ternata Mexican orange scented spring flowers Buddleia davidii: distinct fragrance in summer flowers Hamamelis mollis: Witchhazel spicy-scented winter flowers Jasminum nudiflorum: gentle smell of winter flowers Gardenia jasminoides smell of Hawaii spring/summer flower Winter jasmin Lonicera Honeysuckle : familiar sweet smell in flowers Scented Flowers are fine, Scented Leaves are divine Aloysia triphylla Lemon Verbena: lemon- scented foliage Allspice or Sweetshrub Calycanthus floridus rubbed leaves have smell Labrador tea Ledum groenlandicum : leaves used for tea Lindera benzoin Spicebush crushed leaves with citrus scent Rosmarinus officinalis: desinfecting stron smell of this herb Sage Salvia officinalis: Sage S fructicosa used in cooking Sassafras officinalis: root, bark & leaves strongly scented Thymus vulgaris scented herb is actually a shrub Ruta graveolens Rue : strong scent in foliage Scent of foliage vs scent of flowers (Kerner’s rule)

ÎKerner von Marilaun (1904) Kerner’s rule:

Scent of foliage is mostly insect repellent while Scent of flowers is mostly insect attractant

Alliums (e.g. garlic) honey-smelling flowers, smelling foliage Conium maculatum (hemlock) honey-smelling flower, but repulsive smell of mice for the rest

•Exceptions to the rule Î same odor in flower and vegetation Primula auricula, Viola odorata, Gaultheria procumbens (wintergreen), woodruff (Galium odoratum), Lavendula vera etc. Scents as a Defense? Polemonium viscosum has blue to purple flowers. Some of them have a sweet scent (esters or terpenes) others have a skunky smell (amines). The pollinator of the Polemonium is the bumblebee Bombus kirbyellus, which prefers sweet smelling flowers without consideration for color. Îa lot of questions like “ was there another pollinator before ? or “do the skunky flowers deter pollen robbers like ants?” If so it is an example for smell as defense What about Kerner’s rule: Scent of foliage is mostly insect repellent while Scent of flowers is mostly insect attractant

William Agosta “ Thieves, deceivers and killers. Tales of chemistry in nature”, Princeton University Press 2001 5 groups of flower odors according to Kerner von Marilaun (1904) Kerner’s rule: Scent of foliage is mostly insect repellent while Scent of flowers is mostly insect attractant Alliums (e.g. garlic) honey-smelling flowers, negi smelling foliage Conium maculatum (hemlock) honey-smelling flower, repulsive smell of mice for the rest • Exceptions to the rule (same odor in flower and vegetation): Primula auricula, Viola odorata, Gaultheria procumbens (wintergreen), woodruff (Galium odoratum), Lavendula vera etc.

vanillin discovered as the first natural flavor in vanilla pods in 1872 Odors – volatile compounds matching olfactory receptors (1) Aldehydes: acetaldehyde is a pungent volatile imparting odor of super-ripe fruits, cinnamon aldehyde is giving away (2) Esters of organic acids: oil of wintergreen is not an oil but an ester made from salicylic acid and methanol, pine apple odor is ehtylbutyrate (3) Terpenes (as in essential oils, resins etc.): Steam-distillate pine needles which are available in huge amounts and give you essential oils that contain pinene etc. (4) Amines: Stinking goosefoot Chenopodium has amines that can be extracted with Na carbonate or NaOH Î trimethylamine that stinks like fish, try this with skunk cabbage (5) Sulfur-containing compounds: buthanethiole as in skunks, diallyl disulfide –odor of wounded garlic, allyl propyl disulfide –odor of onions (6) Phenolic volatiles: e.g. Coumarins – the “fresh hay” smell from woodruff, Vanilla leaf and sweet clover, gum benzoin etc. Flavour – phytochemcials with special meaning to humans Flavours principles: one has to differentiate between substances that have been isolated from a spice or that simulate one! apple ethyl-2-methylbutyrate banana amylacetate & eugenol coconut @-nona-lactone lemon citral (limonene= smell peach undeca-lactone vanilla vanillin celery apiole, myristicine mushrooms lenthionine onion Dipropyl disulphide, propanethiol lachrymator

Esters : amylacetate ethyl-methyl butyrate banana apple Harborne JB (1988) Introduction to Ecological Biochemistry, Academic Press London 5 groups of flower odors according to Kerner von Marilaun (1904) Kerner’s rule: Scent of foliage is mostly insect repellent while Scent of flowers is mostly insect attractant Alliums (e.g. garlic) honey-smelling flowers, negi smelling foliage Conium maculatum (hemlock) honey-smelling flower, repulsive smell of mice for the rest • Exceptions to the rule (same odor in flower and vegetation): Primula auricula, Viola odorata, Gaultheria procumbens (wintergreen), woodruff (Galium odoratum), Lavendula vera etc.

1. Indols: indol and skatol with the smell of corpses and excrements (repulsive to Pongo sapiens, decay products of proteins) • in red to brown flowers and reddish veins of • Aristolochia (dutchmen’s pipe, shape and smell of decaying tobacco in a. gigas), Asarum caudatum (wild ginger), Rafflesia species 2 Aminoids: trimethylamine (TMA) smells like herring brine, occur in in flowers of : • Spiraea, hawthorn (Cretaegus), pear, Mountain ash (Sorbus), dogwood (Cornus) • Elder berry (Sambucus racemosa), Barberry (Berberis or Mahonia), Chestnut (Castanea), Horse chestnut (Aesculus hippocastanum), Ash (Fraxinus), Primrose (Oenothera), Ivy (Hedera), tree of heavens (Ailanthus) Benzoloids/ Phenolics: pleasant smell of Lilac (Syringa vulgaris), similar smell in the laurels Daphne striata & odorata (indicates similar pollinators) Lily of the valley (Convallaria majalis) Narcissess (Narcissus poeticus) Vanillin smell in Heliotrope, twin flower (Linnea borealis), Daphne alpina, Nardosmia fragrans carnations (eugenol), sweet woodruff Galium/ Asperula odorata (coumarin), spicebush Lindera benzoin, Calicanthis (all spice bush) Choysia (Mexican orange) (bay laurel) Kaimonia Umbellaria (Californiua bay leaf/laurel) Paulownia, Lonicera (honey suckle) Meadowsweet (salicylic aldehyde, ) oil of wintergreen Gaultheria procumbens (methyl salicylate- a relative Paraffins: flowers of roses (Pelargonic acid), valerian (valerianic acid in Valeriana offcinalis) vine (Vitis vinifera, enanthic acid) thorn-apple (Datura stramonium) Petunia flowers, Paeonia flowers elderberry (Sambucus nigra), tobacco, tomato and other nightshades honey-scent in flowers of apricot, cherry, almond, Rhamnus, forget-me-not (Myosotis alpestris) Phlox (Phlox paniculata) willows (Salix), Angelica etc. Terpenes (isoprenoids): lavender (Lavendula), citrus, orange flowers (Citrus limon) same scent also in Gardenias, in some magnolia flowers and thyme (Thymus citriodorus) mints etc., Violets (alpha-ionon), banana oil (isopentenyl acetate), Many plants reek but there is one that can smell Cuscuta (Dodder) is a genus of about 100-170 species of yellow, orange or red (rarely green) parasitic plants. Formerly treated as the only genus in the family Cuscutaceae, recent genetic research placed it in the morning glory family, Convolvulaceae Dodder can be identified by its thin stems appearing leafless, with the leaves reduced to minute scales. It has very low levels of chlorophyll. The dodder's stem elongates quickly and waves slowly in the air, checking for odors from other plants. Science (Vol 313; Sept. 29, 2006) by Runyon, Mescher, and De Moraes at Penn State demonstrates that dodder use airborne (volatile) chemical cues to locate their host plants. Seedlings of Cuscuta pentagona exhibit positive growth responses to volatiles released by tomato and other species of host plants. When given a choice between volatiles released by the preferred tomato and the non- host wheat, the parasite exhibited preferential growth toward the former. Odors – volatile compounds matching olfactory receptors (1) Aldehydes: acetaldehyde is a pungent volatile imparting odor of super-ripe fruits, cinnamon aldehyde is giving away (2) Esters of organic acids: oil of wintergreen is not an oil but an ester made from salicylic acid and methanol, pine apple odor is ehtylbutyrate (3) Terpenes (as in essential oils, resins etc.): Steam-distillate pine needles which are available in huge amounts and give you essential oils that contain pinene etc. (4) Amines: Stinking goosefoot Chenopodium has amines that can be extracted with Na carbonate or NaOH Î trimethylamine that stinks like fish, try this with skunk cabbage (5) Sulfur-containing compounds: buthanethiole as in skunks, diallyl disulfide –odor of wounded garlic, allyl propyl disulfide –odor of onions (6) Phenolic volatiles: e.g. Coumarins – the “fresh hay” smell from woodruff, Vanilla leaf and sweet clover, gum benzoin etc. Leaf alcohol = cis-3 hexenol from leaves of Mentha arvinca or tomato has smell of cut grass.

This alcohol is frequently used in floral fragrances , in fruity flavors and green tea flavors. cis-3-Hexenol gives a fresh green effect although it is purely synthetic Synthetic Odorants

Benzonitrile PhCN synthetic Smells like KIWI shoe polish aromatic organic abbreviated PhCN. colourless, with a sweet almond odour. It is prepared by reaction of sodium cyanide with bromobenzene. Typical smell of cyanogenic compounds. Ref: Chandler Burr (2002) The Emperor of Scent, Random house , N.Y. 6. Esters of organic acids are highly unstable. Essential (ethereal) oils last (perfumes), esters hydrolyze during sweating and stink.

Apple smell is imitated by methyl butyric acid, butyric acid itself smells like rancid butter and is the give-away odor of perspiring humans (traceable by most animals)

Isoamyl acetate is an ingredient of banana ice cream, but it is also the attack pheromone for honeybees, you design your own catastrophic experiment. isopentenyl acetate has no natural occurrence but it is “the juicy fruit principle” in artificially flavored drinks

Many/most flowers exude a mixture of odors from different groups: jasmine, lilly of the valley etc. But insect attraction is not limited to one sense, but often a combination of odors, color and display Esters as odoriferous signals

Esters easily hydrolyze during sweating or with bases & acids. Therefore not used in perfumes. Apple smell is imitated by methyl butyric acid (when demethylating to butyric acid it will smell like rancid butter (attack of fem mosquitos) isoamylacetate is aroma of bananas & also attack signal for honeybees isopentenyl acetate is artificial fruit aroma, isobutyl propionate is art. rum aroma, benzyl acetate art peach aroma ethyl phenylacetate resembles the aroma of honey Fragrances Fragrance chemistry is an extremely complex science and art.. There are over 5000 chemicals and materials used in the fragrance industry. A fragrance formula may contain as few as 10 or as many as several hundred & up to 600 different ingredients. 5. Now let’s make synthetic esters using the following formulas: acid alcohol sulfuric acid fragrance 1 gram salicyclic acid 2 mL methanol 8 -10 drops wintergreen 3 mL acetic acid 2 mL octyl alcohol 10 -15 drops orange 4 mL formic acid 2 mL ethanol 20 drops rum 2 mL butyric acid 2 mL ethyl alcohol 15 -20 drops pineapple

2 mL butyric acid 2 mL methanol 15 -20 drops apple 1. Prepare hot water bath with a 400 mL beaker water on a hot plate, to slightly boiling. 2. Add the acid & alcohol ingredients to a test tube. 3. Into that solution you add the catalyst sulphuric acid. 4. place the test tubes into the hot water bath for about one minute. 5. Notice the essence. 6. Bastyr is fragrance-free environment! flavors and fragrances Plant smells Î Esters Pittosporum tobira (Pittosporaceae) Tobira, is a dense, rounded, evergreen shrub native to Japan, China, & Korea. The odor of the small flowers is somewhat reminiscent of orange flowers (neroli). The main component of the flower oil of tobira is the ester benzyl acetate

Asparagus officinalis (Liliaceae) has strongly reduced leaves. Asparagus sap is rich in the amino acid L-asparagine which contributes ot the taste-enhancing umami character. It was the first amino acid to be isolated in 1806 from asparagus. Most people observe a distinct odor from their urine shortly after eaten asparagus. This is caused by organic sulphur compounds: like methanethiol, dimethyl sulfide, dimethyl disulfide etc. Terpenes (isoprenoids) 1887 Otto Wallach: isoprene rule: all terpenes are made of C5 units synthesis starts not from AAs but from AcCoA Î isopentenenyl PP Hemiterpenes 5C, pure isoprene reported to be released from leaves of many plants, also tiglic + angelic acid, all are volatile Monoterpenes 10C, volatile & hence major constituents of essential oils . . acyclic MT: myrcene (Laurus nobilis), geraniol geranium Pelargonium), linalol (major ingr of Coriandrum sativum . . . . cyclic MT: menthol (Mentha sp), camphor pinene (major ingredient of turpentine), limonene, carvone (Carum carvycaraway seeds), thujone (convulsant blocks GABA Cl channels), @ ionone (viola, Channel#6 Simple monocyclic terpenoids – simple pleasures Monocyclic terpenoids are known by their smell Lemongrass Cymbopogon Lemongrass is a tall perennial grass, native to India. It is widely used as a herb in Asian cuisine. It has a citrus smell and can be dried and powdered.

Citronella Grass (Cymbopogon nardus) grows to 2 m and is used for the production of citronella oil, which is used in soaps, as a mosquito repellent in insect sprays and candles, and also in aromatherapy,

Principal chemical constituents of citronella: geraniol and citronellol are antiseptics, hence their use in household disinfectants and soaps. Sesquiterpenes - volatile (smell!) or bitter (taste!) Sesquiterpenes 15C aliphatic & cyclic artemisinin b antimalaria drug cardinene (juniper & cedar tree) santonin is anti-thelmic of wormwood Artemisia maritima Acorone is smell of sweetflag Acorum calamus Caryophyllene major ingr in clove oil Eugenia (not eugenol) Abscisic acid dormancy-inducin hormon of buds & seeds Tetrahydroidentin is bitter in dandelion Taraxacum officinale humulene bitter in Pilsner beer gentianin bitter in Gentium liqu Diterpenes - volatile (smell!) or bitter (taste!) Diterpenes 20C: aliphatic, cyclic but no longer volatile Î resins Gibberellins are plant hormones taxol yew tree taxus, antimitotic podolactone from Podocarpus (evergreen conifer Gondwanaland) with antileukemic activity Marrubiin from horehound Marrubium vulgare vasorelaxant Clerodanes from Ajuga, Salvia, Teucrium have antifeedant char. zoapatanol from Mexican Zoapatle plant Montanoa toment. abortifacient Bizarre Plants :Dictamnus The burning bush Dictamnus albus is a member of the Rutaeceae. Many plants of dry locations are known to increase production of terpenes to cool leaf surfaces by terpene transpiration. Dictam, however, produces so much that it can undergo self-ignition (see burning bush stories in Bible & Koran) .

It is thought that droplet formation in the leaf focuses sunlight to a temperature that ignites terpenes which burn like a gas grill using the stomates as valves. Plant smells CloverTrifolium spp (Fabaceae) smell Cinnamon tree bark is dominated by acetophenone (24 %), methyl dominated by c aldehyde cinnamate (11 %), 1-phenylethanol (8 %),

cinemaldehyde Clary sage Salvia sclarea (Labiatae) Essential oil made by steam distillation of the flowering tops has main constituents (-)-linalyl acetate (67 %) and (-)-linalool (16 %). Ambergris-like nuances are due to oxidative degradation products of the diterpene sclareol Î (-)-ambrox. Sclareol is the main constituent (> 70 %) of the essential oil (concrete) made by extraction.

The fragrant clove buds contain 20 % essential oil. Eugenol (ca. 80 %), eugenyl acetate and caryophyllene are main constituents. Allelopathy of the air –volatile terpenes against grasses Californian chaparral has shrubs Salvia leucophylla & Artemisia tridentata that create bare circles of soil with a diameter of 1-2 m, beyond there are some herbs and then start grasslands with Avena, Bromus, Festuca species The substances that are released a volatile terpenes that compose a cloud around the plants and accumulate in dry soil around the roots. The terpenes are in Salvia l. sagebrush: 1,8-cineole and camphor . in Artemisia tr sagebrush: same + pinene + camphene, The volatiles of the Apiaceae The volatiles and hence smell of carrot family plants is a complex mixture of terpenes & phenols. Apiol is a diuretic & the major constituent of the oil of parley seeds Petrosillium , trans-Anethole determines smell & taste of of anise seeds Pimpinella anisum. Phenyl propanoids are water-insoluble phenolics with three-carbon side chains; anethole and myristicin are determining the semll of nutmeg. Eugenol is a dental analgesic from oil of cloves but occurs in many plants. Caffeic & coumaric acid give aroma to coffea beans, raw or roasted.

Monoterpenes: Carvone is major component of Caraway Carum carvi, linalool is principle const of coriander Coriandrum sativum Scents as Life’s Elixir? The bee’s way to extract essential oils We know that the fragrance of flowers is a signal to guide insect & bat pollinators to the flowers where they are rewarded by food donations in the form of either pollen or nectar However, some plants do not offer food, e.g. orchids. They offer either illusion of sex (bee orchid), violence (hammer orchid) or a selection of fine fragrance (bee o) Euglossine bees are the pollinators of bee orchids, which reward them with scents generated by glands in the orchid flowers producing about 60 various scents. The male bees exude some lipid solvent to their front feet & mop the scents up to finally collect them in slit- opening bags of the hind feet. Bees show intoxication & falls into a bucket that leads to the anther where a pollen packet (pollinarium) is glued to its head; funny looks Î This orchid fragrance Î extends the life span of the male euglossine bees! Plants produce specific insect poisons, hormones and sexual attractants

Mutualism (+ +) or Commesalism (+ 0) ??? Wound-induced airborne volatiles as SOS signals: insect regurgitant volicitin (amine) triggers synthesis of volatile terpenoids as wasp attractants in maize through methyl jasmonate in cotton

Through terpenoid trans-2- hexenal in Phaseolus No-man’s land made by allelopathic plants – Ambrosia artemisifolia – infamous ragweed volatile communication Stick insects throw brown, shiny hard-shelled eggs with an detachable appendage rich in lipids – they mimic seeds ants transport them to the safety of their nest, severe the appendage and dump them now far away from home.

Many plants are as sedentary as the stick and need the same help in propagating their species. Bloodroot (Sanguinaria canadensis), castor bean (Ricinus officinalis) and many other seeds have oilbodies that attract ants that store them safely in their nests undergound, severe the elaiosome and let them germinate on their well fertilized garbage dump.

Æ Cape of South Africa invaded by foreign ants and many plants disappeared 1.signal is oleic acid which also signifies a dead ant Î impulse to get it to exit. oleic acid is one of the principal unsaturarted fatty acids of plants: 2. signal is 1,2- diolein, insect fat smelling like ant brood Insects mimicking Plant Seeds We know that passion flowers mimic the deposition of eggs on their leaves in order to deter the pregnant butterfly to deposit her eggs next to their cannibalistic cousins. Stick insect But there are insects who mimic plant seeds, in particular the Stick Insect – a slow moving leaf eater mimicking a branch. Unlike most soft insect eggs, these have a shell hardened by Ca salts and take a brown, shiny appearance of a seed. More important is appearance of a capitulum rich in fats & resembling seed elaiosomes, that bloodroot are detached by foraging ants without damage to the egg.

The ants transport the eggs like seeds to their nests, detach the fat bodies to feed their larvae and deposit the rest on their junk pile an ideal breeding ground for plant seeds and a protected place from predating wasps and plant eaters A famous plant in S Africa depends on ant propagation: red stump or Mimetes cucullatus. Introduced Argentine ants do not transport the seeds & where they rule, the plants rapidly disappear PAL + blue light Î Phenolics The plants’ blue-light switch to the synthesis of phenolic metabolites Plant smells CloverTrifolium spp (Fabaceae) smell Cinnamon tree bark is dominated by acetophenone (24 %), methyl dominated by c aldehyde cinnamate (11 %), 1-phenylethanol (8 %),

The fragrant clove buds contain 20 % essential oil. Eugenol (ca. 80 %), eugenyl acetate and caryophyllene are main constituents. Synthesis of Phenolic compounds starts from AAs

Synthesis of phenolics (also called phenylpropanoids starts from the aromatic amino acids Phenylalanine & Tyrosine,but not from Tryptophan Cinnamic acid is a spice plus a Phenylalanine Cinnamic acid strong antifungal & allelopathic Simple Phenolics or phenylpropanoids

Vanillin, first synthesized in 1872

Salicylic acid, Methyl Salicylic acid =wintergreen; volatile signal) Ferulic acid, Caffeic acid simple phenols

Methyl salicylate is the so-called “oil” of wintergreen

release of volatile methyl salicylate by leaves of tobacco is also an important signal for some wasp to attack predating caterpillars Cinnamonic aldehyde is fragrant Cinnamon trees are native to South East Asia, but its origin was mysterious in Europe until the sixteenth century. Due to the presence of coumarin, European warned against consuming large amounts of Cassia which cause liver and kidney damage in high concentrations. Ceylon cinnamon has negligible amounts of coumarin.

Cinnamaldehyde gives cinnamon its Cinnamonum zeylanicum flavor and odor. A pale yellow viscous liquid from the bark of cinnamon trees and other species of the genus Cinnamomum The essential oil of cinnamon bark is about 90% cinnamaldehyde. from the cinnomon tree Cinnamomum zeylandicum by steam distillation of the bark. Camphor Camphor is a waxy, white solid with a strong, aromatic odor found in wood of the camphor laurel (Cinnamomum camphora), an evergreen tree found in Asia. can also be synthetically made from oil of turpentine. It is used for its scent, as an ingredient in cooking (mainly in India), embalming fluid

Chinese Camphor from the tree Cinnamonum camphora Cinnamomum camphora has poor quality Borneo camphor comes from tree Dryobalanops aromatica (after the city Baros on Borneo. To get camphor you make incision in the tree and get several buckets of Camphory juice. Later you repeat the same halfway down the tree. After that the tree dies…. The Curry Tree & the Curry plant The curry tree (Murraya koenigii) is a tropical tree in the Rutaceae, which is native to India. The leaves are fragrant and used used in curries ("curry leaves“ or "sweet neem leaves." as unavoidable content of curries in South India, Not related to Curry Plant, Helichrysum ital.

Helichrysum italicum – the curry plant is a flowering plant of the daisy family Asteraceae native to the Mediterranean. It is called the curry plant because of the strong thyme-like smell of its leaves. It has nothing whatsoever to do with the mixture of spices used in Indian cooking, nor with the curry tree (Murraya koenigii). Choysia ternata Mexican Orange Choysia ternata is a member of the Rutaecea (Citrus family) . Mexican orange is a small and compact evergreen broadleaf shrub that gets about 6-8 ft (1.8-2.4 m) tall.

The leaves are opposite and palmately compound with three elliptic leaflets, each about 2-3 in (5-8 cm) long. When bruised they give off a strong and pungent smell.

The white 4 or 5-petaled flowers are about 1 in (2.5 cm) across and deliciously fragrant. They stand in clusters of above the foliage. Mock-orange (Philadelphus lewesii, are shrubs from 1 to 6 m tall, native to North America, They are named "mock-orange" since their flowers are similar to those of oranges and lemons (Citrus) But Philadelphus is a asterid, not related to Citrus (advanced rosids). Phenols as flavors

4% of the beans

catechins Phenolics Î Coumarins

Characterized by the lactone double ring, volatile with smell of mawn hay, reduces capillary permeability & edemic swelling

Sources: Apium graveolens (celery seeds radix), leaves, Angelica, Gallium odorata = woodruff Melilotus officinalis (sweet clover) Achlys triphyllum Vanilla leaf Tonka beans Liatis odoratissima = deer tongue Phenolics Î the bloody DiCoumarins Coumarin is water-insoluble but in alkaline solution 4-hydroxy coumarin can be soluble. It is not an anticoagulant but it does fluoresce. Dicoumarol is an anticoagulant that functions as a Vitamin K antagonist (similar to warfarin, for which it was the inspiration). Dicoumarol is a natural chemical substance when coumarin is transformed in mouldy feeds or silages by a fungi, into dicoumarol. Dicoumarol in silaged wet sweetclover hay, was the cause of bleeding disease in cattle (identified in WI, USA in 1940) Mechanism: prevents formation of prothrombin Natural Coumarins can kill sheep Natural Coumarins can kill sheep Phenolic protect wood for ages

Lebanon cedar was the pride of the Phoenician fleet. It was not attacked by fungi or mussels. However this was also the cause of the deforestation of North Africa Phenolic odors Coumarin benzopyrone; toxin found in many plants, notably in tonka bean, vanilla leaf, vanilla grass woodruff Galium odoratum, mullein Verbascum, bison grass, sweet clover Melilotus cassia bark, one of the cinnamon species: 1 teaspoon of cinnamon powder contains 5.8 to 12.1 mg of coumarin, a sweet scent of newly- mown hay, has been used in perfumes since 1882. Banned in foods, not drinks Plant smells Î Coumarins Melilotus albus (Fabaceae) White sweetclover Coumarins are found in many plants - sweetgrass, vernal grass, sweetclover, woodruff, Vanilla leaf, lavender, tonka beans, etc. In the fresh, living plants coumarin is mostly present as a glycoside (e.g. melilotoside in sweetclover). When the plants are injured or wither, the glycosides are split by enzymes. Hence the term “sweet after-death” used for the smell pf the pillows stuffed by the pioneer women.

coumarine

Couman Coumane ®, a cyclopropane analogue of coumarin from Flexitral, has just received FEMA GRAS status for use as a flavor. Tonka (Dipteryx odorata) beans – or the smell of coumarin The tonka bean is the seed of Dipteryx odorata, the cumaru legume tree The seed is black and wrinkled in appearance, with a smooth brown interior. It is known mostly for its fragrance, which is reminiscent of vanilla, almonds, cinnamon, and clove Î used in perfume & tobacco before being banned in some countries.

The seed contains coumarin, which can be lethal Î use in food is banned in the US by the FDA. Prescription drugs use more powerful forms of coumarin.

Tonka is legal in the EU & a fashion ingredient in French cuisine (mostly in desserts &stews). The plant originates from South America (Guyana, Orinoco region) Vetiver - oil of tranquility Vetiver is oil of tranquility distilled from the rootlets of Vetiveria zizanoides or Khus-Khus grass, imported from Haiti. It has a heavy, woodsy, earthy-sweet scent. Some traditional uses: for muscular aches, to increase circulation, to relieve melancholy and nervous tension, for restful sleep. Emotional profile: for fears, obsessions, scattered thoughts, anger and hurt, unworthiness, neurotic behavior, addiction. Blends with: sandalwood, ylang ylang, clary sage, lavender, patchouli, Oil of tranquility Vetiver roots jasmine and rose. Primary metabolites: L-amino acids H2N- in @ position to -COOH, 23 AAs essential in all organisms Secondary metabolites: >200 non-proteinogenic AA, many synthesized by plants of the legume family: poisonous for most herbis: D-AAs Decarboxylation of AAs ---> amines, - COOH ---> -H Examples for simple amines (can be isolated with cation exchange resin )

Lysin ---> cadaverin H2N(CH2)5NH2 (MO, seeds, flowers) Ornithine ---> putrescine

H2N(CH2)4NH2 (stinking, MO, flowers) HO-Tryptophan ---> auxin, Histidine ----> Histamine Volatile Amines stink While phenolic compounds derive from aromatic Amino Acids by de- amination, amines derive by decarboxylation (e.g. histidine to histamine) Decarboxylations of AAs occur naturally in plants and also after death in animals, especially rapid in fish (methylamine, trimethyl amine). Especially bad is the smell of putrescine and cadaverine. Plants realized that these amines attract dung flies as pollinators.

trimethylamine

Putrescine & cadaverine follow this Bizarre Plants Monstrous + stinky (amines): Amorphophallus titanum, Rafflesia arnoldii, Aristolochia grandiflora (Humboldt), Welwitschia mirabilis, Victoria amazonica, Aztecs’ handflower tree Cheirostemon platanoides (related to Cocoa tree, Humboldt), Baobab (sausage) trees Adansonia, boogam trees Idria columnaris (desert in Baja California), elephant or skunk tree Bursera microphylla (Baja California; tug on leaf & it burps out a foul smelling, fetid spray over a distance of 50 cm), squirting cucumber Ecballium elaterum shoots fruit as a rocket over 3 m distance, slimy mucilage with seeds sticks to the one who touched the fruit

WB Emboden(1974): Bizarre Plants; magical, monstrous, mythical. MacMillan P. NY Stinking Plants Corps Flower Titan arum. with sharp points at the pollen surface. One plant produces a billion grains of pollen that can stay airborne for days spreading over an area of many miles. Affects 75 % of all allergy sufferers. Rafflesia arnoldii. Rafflesia was found in the Indonesian rain forest by an Indonesian guide working for Dr. Joseph Arnold in 1818, & named after Sir Thomas Raffles, leader of the expedition

Stinking Iris Iris foetissima. It is known as "stinking" because some people find the smell of its leaves unpleasant when crushed or bruised, an odour that has been described as "beefy"

Stinking Hellebore Helleborus foetidus, known variously as stinking hellebore, dungwort, and bear's foot, is in Ranunculaceae, native of the mountainous regions of Central and Southern Europe

Skunk cabbage Symphocarpus foetidus is one of the many stinky plants in its family the Araeceae. The burping skunk tree is a member of the Burseraceae, related to frankincense (Boswellia) and myrrh (Commiphora) but unlike them it stinks (skunk tree).

The elephant tree Bursera microphylla is native to Northern Mexico, Southern California and Arizona, especially desert regions. It reaches 5 m in height. The foliage is made up of long, legume-like leaves which are composed of paired leaflets. It flowers in rounded yellow buds which open into small, star-shaped white or cream flowers

When you tug on a leaf it burps and emits a fine spray over 50 cmm distance that is foul fetid smelling caused by amines Scents as a Defense?

Polemonium viscosum has blue to purple flowers. Some of them have a sweet scent (esters or terpenes) others have a skunky smell (amines).

The pollinator of the Polemonium is the bumblebee Bombus kirbyellus, which prefers sweet smelling flowers without consideration for color.

Îa lot of questions like “ was there another pollinator before ? or “do the skunky flowers deter pollen robbers like ants?” If so it is an example for smell as defense

William Agosta “ Thieves, deceivers and killers. Tales of chemistry in nature”, Princeton University Press 2001 Stinky plants: the Durian fruit

The Durian is the fruit of trees from the genus Durio and has been known and consumed in southeastern Asia since prehistoric times, but has only been known to the western world for about 600 years. This is a fruit, which smells like a rotting corpse, and has actually been banned in some hotels Sulfides, e.g. garlic Allium sativum Sulfides (except for AA cysteine, methionine) restricted to few families characterized by obnoxious odor, simple HC sulfides in Allium species including lachrymators, in Brassica, radish, onions glucosinolates or mustard oils, thiophenes in Asteracea in association with polyacetylens. 6000 a ago Egypt, garlic produces lots of sulfur-containing volatiles that repel insects & other herbivores. Inside the vacuoles there is a colorless, odorless compound called alliin. The cytosolic enzyme allinase converts alliin into sulfenic acid + ammonia. Two sulfenic acid molecules combine to allicin – smelly & fiery tasting compound that breaks down to diallyl disulfide –smelly & a powerful insecticide!!!! = = 1. 3.ÎÎ ÎÎ In vacuole 2. 4. from plants to war: cotton to gun cotton 1846 Swiss chemist Christian Schonbein in Basel was doing some chemical experiments in the kitchen of his home. He spilled a flask containing nitric + sulfuric acid (konigswasser – a solution that cleans all glass & mopped it up with his wife’s cotton apron. After this he hung it over the hot oven for a quick dry. Unfortunately for his Nitrocellulose (also: cellulose marriage the entire apron flared up & nitrate, flash paper) is a disappeared. highly flammable compound formed by nitrating cellulose This was the invention of smokeless through exposure to nitric acid powder or gun cotton. Nitrocellulose or another powerful nitrating plasticized by camphor was used by agent. When used as a Kodak, as a film base in X-ray films propellant or slow explosive, it is also known as guncotton. Plant smells Î sulfur compounds The most notorious feature of skunks is their anal scent glands, which produce a mixture of sulfur-containing chemicals such as methyl and butyl thiols traditionally called mercaptans, which have a highly offensive smell strong enough to ward off bears.

Asparagus officinalis (Liliaceae) has strongly reduced leaves. Asparagus sap is rich in the amino acid L-asparagine which contributes ot the taste-enhancing umami character. It was the first amino acid to be isolated in 1806 from asparagus. Most people observe a distinct odor from their urine shortly after eaten asparagus. This is caused by organic sulphur compounds: like methanethiol, dimethyl sulfide, dimethyl disulfide etc. Lab exercise: something to behold for the eye: onion When onions are sliced or eaten, cells are broken, allowing the enzyme alliinase to break down amino acid sulphoxides and generate sulphenic acids. A specific sulfenic acid, 1-propenesulfenic acid, is rapidly rearranged by a second enzyme, to syn-propanethial-S-oxide, a volatile gas known as the onion lachrymatory factor or LF.The gas diffuses through the air and Task1: eventually reaches the eye, where it activates 1. Cut onion while partner holds a sensory neurons, creating a stinging sensation. large sheeth of pH (or yellow red Tear glands produce tears to dilute and flush beet) paper to catch flares of sulfenic out the irritant. Similar Chemicals are known as acid. lachrymatory agents 2. Test for active lachrimatory cutting onions under running water or factor by cutting an onion + bringing submerged in a basin of water. Another way to it near your partner’s head reduce irritation is by freezing, or by not cutting off the root of the onion which has a higher 3. Cut onion under slightly alkaline concentration of enzymes water pH 9-10 and test again. Muscone Muscone is an oily liquid that is found naturally as the (-)-enantiomer, but synthetic material is typically a racemate. It is very slightly soluble in water and miscible with alcohol. Muscone is the primary contributor to the odor of musk. muscone The chemical structure was first elucidated by Lavoslav Ružička. It is a 15-membered ring ketone with a methyl group in the 3-position

Natural muscone is obtained from the glandular secretion of the unfortunate musk deer, which has been abused for perfumery and medicine for thousands of years. Since obtaining natural musk required killing the civetone endangered animal, nearly all muscone used in perfumery today is synthetic.

Female dear & humans are very sensitive to musk smell during ovulation Plant Smells resemble Animals In mammals the males use musks as pheromones. Examples are musk deer, musk ox, civet and the musk rat producing macrocyclic ketones as well as lactones. Musk lactones – however - are also found in some plants Musk odorants in plants are always macrocyclic lactones. In animals, using musk pheromones can be ketones as well as lactones,. Angelica seeds have several macrocyclic musks, e.g 15-pentadecanolide

Ambrette seeds contain an oil with a musky- to-ambery odour. It's major component istetradecen-14-olide .

Ambrette seeds Abelmoschus moschatus (Malvaceae) come from a tropical hibiscus. The seeds contain an oil with a fatty-musky, slightly ambery odour: 5(Z)-tetradecen-14-olide & 7(Z)-hexadecen-16-olide, also called ambrettolide. Now it is largely replaced by synthetic musks, eg. the isomer 9-hexadecen-16- olide is made by the Swiss company Givaudan. Ambrette Seeds Abelmoschus moschatus (Abelmosk, Ambrette seeds, Annual hibiscus, Bamia Moschata, Galu Gasturi, Muskdana, Musk mallow, Musk okra, Musk seeds, Tropical jewel hibiscus, Yorka okra; syn Hibiscus abelmoschus is an aromatic and medicinal plant in the Malvaceae native to India Musk mallow seed oil was once frequently used as a substitute for animal musk; however this use is now mostly replaced by various synthetic musks due to costs. The seeds are added to coffee; unripe pods ("musk okra"), leaves and new shoots are eaten as vegetables. considered an insecticide & aphrodisiac Ambrette seeds Abelmoschus moschatus (Malvaceae) come from a tropical hibiscus. The seeds contain an oil with a fatty-musky, slightly ambery odour: 5(Z)-tetradecen-14-olide & 7(Z)-hexadecen-16-olide, also called ambrettolide. Now it is largely replaced by synthetic musks, eg. the isomer 9-hexadecen-16- olide is made by the Swiss company Givaudan. flavors and fragrances limonene in citrus fruits and menthol in the labiatae

vanillin discovered as the first natural flavor in vanilla pods in 1872 Human Odors Human odors are produced by the skin's apocrine sebaceous or sweat glands, developing during puberty These glands are located in 6 areas1: 1) axillae (underarm pits) 2) nipples of both sexes2 3) The pubic, genital, and circumanal regions 5) The eyelids 6) The outer ear This would be called part of a pheromonal system in any other mammal. humans who smell only the bacterial breakdown products of glandular secretions. Sebaceous secretions themselves consist mostly of lipids such as squalene and other esters. When degraded free fatty acids result, that smell unpleasant. The most prominent examples of hircine fatty acids have the general formula (CH3(CH2)nCOOH) and are called butyric acid (n=2), caproic acid (n=4), and caprylic acid (n=6). While women's have an acute ability to smell musk , the musky odors of civetone (civet cat), or exaltolide (a synthetic musk), men are relatively insensitive to these substances. Moreover, women's sensitivity to these substances varies as a function of their menstrual cycle. Women on the pill, women who have had ovarectomies, pregnant women, and post-menopausal women are as insensitive as men. Sexual “Chemistry” – myth or suppressed reality? Mate selection is a highly complex process & we are consciously aware of only part of it; the rest is either unpredictable or operates outside our awareness, Certainly, there is nonverbal communication between people: eye contact, smiles, general body language, pheromones, clothes outward appearances: Female: low waist-to-hip ratio, full lips, facial features, Male: broad shoulders, clear skin, masculine facial features Smell: Women’s preferences for certain male scents and other male features change over their cycle. Near ovulation, they prefer masculine traits and musky smells ; at other phases they prefer stability.

After sex, the brain releases oxytocin, which results in companionable feeling of love & social bondage. Sex on a whim can lead to feelings for a person who is wrong for you.

J. Fast M. Bernstein: “Sexual Chemistry: What is it. How to use it.” Pocket Books , N. Y. 1983 Pheromone perfumes – are they the missing link in sexual chemistry? Although humans generally rate olfaction as their least important sensory modality, they spend billions of dollars, years of their effort to modify the way they smell

In humans the main odor-producing Pherone Formula M-11 organ is the skin. Odors are largely Pheromone produced by the skin's apocrine Cologne for Men to Attract sebaceous glands, which develop during Women, with puberty & are associated with sweat 5mg of Human glands and tufts of hair. Pheromones Perfumes - mimicking undiscovered pheromones? Perfumes were made in India & Egypt more than 5000 a ago. Chinese & Japanese made scent clocks burning different odors for the times of day! Perfumes were royal gifts (see Jesus birth) Since “per fume” = through air you need fixatives (balsams & resins) to prevent rapid exhaustion of volatile substances called odorants: 1. Concretes (alcoholic extract with removed of alcohol), 2. absolutes, 3. distilled oils, 4. expressed oils, 5. Tinctures (civet, castoreum, musk)

Perfume = costliest fragrance with 22% essential oils. Eau de Parfum between 15 and 22% essential oils. Eau de Toilette (EDT) with 8 to 15% oils. Eau de Cologne has just 4% essential oils. Eau Fraiche has 1 to 3% essential oils, is the lightest plants include anise, bay leaf, bergamot, cardamom, cedar wood, rose, eucalyptus, frankincense, gardenia, geranium, iris, jasmine, lavender, lemon, lilac, lily, lily of the valley, magnolia, moss, neroli, orange, orris, patchouli, pine, raspberry, sage, sandalwood, tuberose, vanilla, violet and ylang-ylang. animal products include musk from the male musk deer, ambergris from sperm whales, castoreum a secretion of the beaver and civet from the civet cat. All are used as fixatives & add mystery to smell Famous Perfumes Ernest Beaux created Chanel No. 5 for Coco Chanel in 1921. It has a floral top note of ylang-ylang and neroli, with a heart of blends of jasmine and rose all above a woody base of sandalwood and vetiver. Guerlain's Shalimar launched first in 1925 & relaunched in 2001. It's a refined oriental feminine fragrance with iris, vanilla, and rose - a truly sense hitting perfume 1944 saw the introduction of Femme by Rochas. In 1947 Dior launched the ever popular Miss Dior. Max Factor's Hypnotique and Primitif were popular in 1950s 4711 Eau de Cologne, with its 4711 roll on stick was especially popular for summer heat perspiration 1977 Yves St. Laurent put 'Opium' perfume in production huge success with women- a perfume for sultry evenings. in the 80s blatant erotic advertising led to the success of the 1985 Obsession from Calvin Klein. Obsession with its heavy smell of vanilla was dominant in the market. Human Pheromones –sure! Q. Is there any evidence to show that Pheromones are effective in attracting women? A: There is plenty of evidence. With the advances in science, the evidence that pheromones are effective in attracting women is growing rapidly. Pherlure commercial

"and this pretty sales person walked up and asked if i need anything and i said just looking and the next thing i know shes asking me what my phone number was and what i was doing later tonight...... WOW!!!!!!!!!!! this stuff is great." RJ, IL Spices and perfumes – driving forces of human history In ancient Near Eastern cultures fragrances and spices were used to preserve meat including human corpses. Also Egyptian girls used fragrant perfume cones (animal grease) to have a short- distance effect on the Old Egyptian male. Together with the dress it was devastating. Perfumes Î tradition or requirement? Perfume is a mixture of fragrant essential oils and other odorants, fixatives, and solvents used to give the human body, animals, objects, and living spaces a pleasant smell. History: The word perfume derives from Latin "per fumum", meaning through smoke. Art of making perfumes began in ancient Mesopotamia, Egypt, Rome &Persia. Ancient East Asian fragrances were more incense based. The world's oldest perfumery was in Pyrgos (Cyprus) 4,000 years old perfumes, 60 stills, mixing bowls, funnels and perfume bottles. The Persian Muslim doctor & chemist Avicenna ( Ibn Sina) first described the process of extracting oils from flowers by means of distillation. He discovered liquid perfumes as mixtures of oil and crushed herbs or petals. Hungary water was the first European, alcohol-based perfume, made by court alchemists in the late 1300s from distilling fresh rosemary (and possibly thyme) with strong brandy, later additions were lavender, mint, sage, marjoram, costus, lemon. Aromas & Aromatherapy 1732 Farina in French-occupied Cologne made blend of neroli, bergamot, lavender & rosemary in grape distil. Î Eau de Cologne – Napoleon used several bottles a day 1939 Dr. Jean Valnet of the French Army used thyume , clove & lemon oil for wound treatment & later for psychological treatment Î the re-birth of the cure by fragrances (which indeed are a carrier of emotional memory, easy for induced Pavlov reflexes) Substances in essential oils: lipophilic terpenes, phenols, esters, aldehydes etc. Example: Thyme oil: principal constituents are thymol (antiseptic) , carvacrol (antiseptic to toxic), cymene, terpinene, camphene, borneol, linalol, menthone, citral, geraniol, thujanol used in mouthwash like Listerine brand , make your own: (3 drops of thymol oil into one ounce of water plus tincture of Oregon grape! Or other astringents like menthol) Hydrosols – holograms of plant essence? * Watery solution, also hydrolate (water milk french), floral water = condensate water produced during distillation of plant material for aromatherapy - a form of phytotherapy Plant materials used to extract essential oils

Flowers: roses, carnations, orange, violets, lavender Shoots: mints, rosemary, geranium, citronella, lemon gr Seeds/fruits: oranges, lemons, nutmeg Roots: sassafras Wood: cedar, sandalwood, pine Gums: balsam, myrrh Bark: cinnamon, cassia

* Catty, S. “Hydrosols; the next aromatherapy” Healing Arts Press Rochester Vermont, 2001 What the smell of Essential Oils reveals about the ingredients An essential oil is a mixture of many terpenes plus other volatile substances turn into gas molecules at room temperature & ar easily distilled Aniseeed Pimpinella anisum = trans anethole (75-90 %) Basil Ocimum basilicum = linalol (50%), methyl chavicol (25%) etc. Bay laurel Laurus nobilis = cineol (40 %), pinene, linalol, meth eugenol Benzoin Styrax benzoin = coniferyl cinnamate, benzoate, cinnamic ac Calamus Acorus calamus = beta-asarone (80 %), oral toxin Camphor Cinnamonum camphora = cineole (75-95 %), pinene, Caraway Carum carvi carvone (60 %), limonene (40%) cinnamon Cinnamonum zeylandicum eugenol 95% Wormwood Artemisia absinthium = 71 % thujone, azulene, terpenes Ylang-ylang Cananga odorata = methyl & acetyl benzoate, methyl salicylate, eugenol, geraniol, linalol, terpenes: pinene, cadimene Some essential oils are not oils at all esters “oil of Wintergreen” Gaultherai procumbens = methyl salicylate 98 %) oil of tonka beans Dipteryx odorata = 99 % coumarins = phenolic compounds garlic Allium sativum allicin, allyl propyl disulphide, citral, linalol Essential = Fragrant Oils are healing mind & body Aromatic plants are easily recognized & are used by animals and people for millions of years. They were soon part of rituals: juniper sprigs are burnt in Tibetan Temples, frankincense in Roman Catholic Church, Gum Benzoin in Greek & Russian Orthodox Church.

Essential oils are the key components for aroma, taste and flavor in perfumes, spices, & condiments. Essential ( misleading term = not like essential amino acids or fatty acids; i.e. a substance we absolutely require for health but cannot produce) from the distilled alchemical essence of plants), volatile, fragrant oils. Lipophilic substances taken up through nose & skin with twofold action: psychological and physiological effects. Î Aromatherapy is healing mind & body : fragrant oils provide more than aroma

Essential oils are products of steam distillation, mechanical processing of citrus rinds or dry distillation of natural materials. Essential oils are physically separated from the water phase. Aromatherapy: established by Rene-Maurice Gattefosse in 1920s, popularized by Dr. Jean Valnet 1964 with strong reductionist emphasis on pharmacological ingredients, 1978 Paul Belaiche Î 3 volumes on Clinical Use of Aromatherapy for infections etc. : oils for medicinal use must be genuine ( = unchanged) & authentic (from one plant) Julia Lawless (1992) The encyclopedia of essential oils. Barnes & Noble BooksN.Y. Roszak, Theodore (1994) Eco-psychology – voice of the earth. Stuttgart Antibacterial effects of Fragrant Oils As Gattefosse demonstrated already during WWI: Fragrant oils are antibiotica as strong as penicillin – a remedy developed during WW II. Geraniol: effective against Candida yeast Thymol: knocks out Micrococcus flavus Staphylococcus aureus, epidermitis E. coli, Bacillus subtilis Geraniol, thymol & many other ingredients are found in thyme oil etc. Paul Belaiche (1978) Phytotherapie et d’Aromatherapie (3 volumes). Paris Antimicrobial effects of Fragrant Oils Bactericidal components in essential oils: Monoterpenes in oils of Tea tree, Niaouli, Eucalyptus radiata, Ravensare aromatica Phenols in oils of Thyme, Oregano, Mountain savory Fungicidal components in essential oils: Esters in oils of Lavender, Roman chamomile, Geranium, aldehyde from Cinnamon Mucolytic components in essential oils: Ketones in oils of Eucalyptus dives, Rosemary, Lactones in Inula graveolens brochodilatory components in essential oils: Terpenes in oils of Pine, Cypress, Hazelnut , rubbed on chest for relieve

Paul Belaiche (1978) Phytotherapie et d’Aromatherapie (3 volumes). Paris Resins –purifying incenses of old Mastic is the resin Pistacia lentiscus growing in only a few villages of the island of Chios. Wounded Pistachio trees have resin flow in August. is chewed like chewing gum. Î word masticate, trad. Greece Gum Benzoin is resin produced by the tall Styrax trees (S. benzoin & S. tonkinense) native to Indochina, also called the Java incense trees growing no taller than a person. Gum benzoin was used in Chinese perfumes due to its stable aroma, also in massage oil. The wounded bark fills with yellow fluid that hardens into a reddish mass. Gum guggul myrrh –like resin from the Iranina thorn tree Commiphora mukul, native to western Iran and Eastern India, perfume of Persian women at the time of Alexander’s conquest.. Balsam of Gilead, Balm of Mecca. Resin from 3 m tall trees of Commiphora opobalsamum native to Southern Yemen, kingdom of Saba (queen of Sheba’s gift to Solomon), later planted from Egypt to Palestine, remedy for ringworm + skin diseases. B of Gilead from N. American Populus candicans Î Resins –purifying incenses of old Sandalwood: from wood and root of parasitic trees Santalum album, wounding causes gum to flow Î pure native to Indonesia and India. 1000 BC use in India as incense, perfume to enhance sexual attraction (sandalwood resembles male pheromone) and in oil paste applied as UV-protecting sunscreen! Red Sandalwood gives red powder like Santalum but lacks aroma. derived from different trees Pterocarpus santalina that form forests in Madagascar. Decorative wood for pagodas, statues etc. , spice in marzipan & biscuits. Aloeswood resin from tree Aquilaria mallantis native to Eastern has black hard dense wood. Muslim kingdom of Champa (South Vietn) Chinese med. uses it for nervousness, Ayurveda for mental illness. Myrrh reddish-brown resin from dried sap of tree Commiphora myrrha, native to Yemen & Somalia (Punt). Unlike other resins, myrrh expands and "blooms" when burned instead of melting or liquefying .not related to Myrrhis odorata = sweet cicely Asafoetida – the ersatz Silphium of Greek antiquity Asafoetida = Europe’s forgotten spice? from Iran – a repulsively smelling resin from the Iranian Fennel Ferula asafoetida often adulterated with F. persica & F. galbanum – all tall stout umbellifers The secret of it was first discovered by German botanist Engelbert Kaempfer who travelled in Iran & Turkey under cover and wrote 1712 “Five studies of exoticwonders, political, scientific and medical” How to make Incense! Incense (incendere, "to burn") is composed of aromatic biotic materials, which release fragrant smoke when burned. Many religious ceremonies employ incense, preparing a clean air for the gods. Making Incense needs four basic ingredients: - an aromatic substance: any herb with a pleasant smell - a bonding agent to hold cones and cylinders together (base) - a solvent for the bonding agent - a substance that supports controlled burning of the cone Combustible base The combustible base of a direct burning incense mixture not only binds the fragrant material together but also allows the produced incense to burn with a self-sustained ember, which propagates slowly and evenly through an entire piece of incense with such regularity that it can be used to mark time. The base is chosen such that it does not produce a perceptible smell. Commercially, two types of incense base predominate: •Fuel and oxidizer mixtures: Charcoal or wood powder forms the fuel for the combustion. Gums such as Gum Arabic or Gum Tragacanth are used to bind the mixture together while an oxidizer such as Sodium nitrate or Potassium nitrate sustains the burning of the incense. Fragrant materials are combined into the base prior to formation as in the case of powdered incense materials or after formation How to make Incense! Making Incense needs four basic ingredients: - an aromatic substance: any herb with a pleasant smell - a bonding agent to hold cones and cylinders together (base) - a solvent for the bonding agent - a substance that supports controlled burning of the cone Common raw incense making materials Makko powder (Machilus thunbergii), Borneol camphor(Dryobalanops aromatica), Sumatra Benzoin (Styrax benzoin), Omani frankincense (Boswellia sacra), Guggul (Commiphora wightii), Golden Frankincense (Boswellia papyrifera), Tolu balsam (Myroxylon toluifera), Somalian myrrh (Commiphora myrrha), Labdanum (Cistus villosus), Opoponax (Commiphora opoponax), white Indian sandalwood powder (Santalum album)