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Scent chemistry blaženka čiško anić eng

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Scent chemistry blaženka čiško anić eng

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Overwiew of scent chemistry adapted from croatian original presentation

Overwiew of scent chemistry adapted from croatian original presentation

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Scent chemistry blaženka čiško anić eng

  1. 1. Author: Blaženka Ćiško-AnićAuthor: Blaženka Ćiško-Anić Saponija d.d. Osijek, CroatiaSaponija d.d. Osijek, Croatia SCENTSCENT CHEMISTRYCHEMISTRY ModifiedModified byby MscMsc Miro MeleMiro Mele dipl.ing.dipl.ing. Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 11
  2. 2. History of scentHistory of scent  Awareness of scent is so old as human race.Awareness of scent is so old as human race.  Knowledge about scented materials is known from allKnowledge about scented materials is known from all written history from 5000 years as before troughwritten history from 5000 years as before trough unwritten communication.unwritten communication.  Our ancestors noticed a pleasent odour of flowers ndOur ancestors noticed a pleasent odour of flowers nd also other plant and animal materials. That was a pointalso other plant and animal materials. That was a point for aromatizing everyday food.for aromatizing everyday food.  A word perfume comes from latin “per fumum” meaninA word perfume comes from latin “per fumum” meanin “with help of smoke”“with help of smoke” Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 22
  3. 3. History of scentHistory of scent Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 33  Picture 1.Picture 1. One of oldest found stone wessels (height 7,4 cm), where use for scented oilOne of oldest found stone wessels (height 7,4 cm), where use for scented oil storage is pressumptied. Found in Iranian mountains Presumption taht is from era 2750-2350storage is pressumptied. Found in Iranian mountains Presumption taht is from era 2750-2350 b.C. (Source:: Edwin T. Morris,b.C. (Source:: Edwin T. Morris, Scents of TimeScents of Time, The Metropolitan Museum, The Metropolitan Museum of Art, New York,of Art, New York, 1999, str.16)1999, str.16)
  4. 4. Origin of scent industryOrigin of scent industry  Flourishing of chemistry in 19 century inFlourishing of chemistry in 19 century in Germany and United Kingdom madeGermany and United Kingdom made foundation for development of scent andfoundation for development of scent and aroma industry we know today.aroma industry we know today.  Globally scent and aroma industry isGlobally scent and aroma industry is grown to business at more than 20 billiongrown to business at more than 20 billion dollars annually.dollars annually. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 44
  5. 5. Scent raw materialsScent raw materials  Natural (essential oils andNatural (essential oils and extracts)extracts)  Synthetic moleculesSynthetic molecules Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 55
  6. 6. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 66 Production of natural scentProduction of natural scent ngredients:ngredients:  ExpressionExpression  DistillationDistillation • dry distillationdry distillation • steam distillationsteam distillation • waterdiffusionwaterdiffusion  Extraction (different solvents and CO2)Extraction (different solvents and CO2)
  7. 7. NATURAL SOURCE CONCRETECONCRETE (REZINOID)(REZINOID) Ethanol extraction Solvent extraction Enfleurage POMMADEPOMMADE TINKTURETINKTURE ABSOLUTEABSOLUTEESSENTIAL OILESSENTIAL OIL Terpeneless oilTerpeneless oil Ethanol exstryctionEthanol extraction Deterpening DISTILLATION Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 77
  8. 8. Proces of natural scenting raw materials vary widely, then they are dependent on seasonal variations. Variations can be Compensated by long term contracts and on site organization of growing. For production of 1 kg jasmine extract about 7 000 000 flowers picked by hand in early morning are needed. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 88
  9. 9. Synthetic scent ingredientsSynthetic scent ingredients Chemistry of scent compounds is alsoChemistry of scent compounds is also Interesting for ability of synthesis chemistInteresting for ability of synthesis chemist to investignate realtion between structure ofto investignate realtion between structure of molecule and its activitymolecule and its activity (structure – activity(structure – activity relaationships)relaationships); just smelling is enough for; just smelling is enough for Estimation of new substance.Estimation of new substance. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 99
  10. 10. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1010 Ernest Beaux, creator of historically famous perfumeErnest Beaux, creator of historically famous perfume Chanel No. 5 said:Chanel No. 5 said: «We'll have to count on chemists to find new substances, if«We'll have to count on chemists to find new substances, if we are to make new and original notes. Yes, the future ofwe are to make new and original notes. Yes, the future of perfumery is in the hand of chemistry.»*perfumery is in the hand of chemistry.»* *Classification des Parfums et Terminologie, Comité Française du Parfum, Paris, (1998) str. 36-37
  11. 11. CoumarinCoumarin • synthetized year 1868, available onsynthetized year 1868, available on market from 1876 was a turning pointmarket from 1876 was a turning point and is looked as milestone of modernand is looked as milestone of modern perfumeryperfumery • Jean-François Houbigant createdJean-François Houbigant created perfumeperfume Fougère RoyaleFougère Royale 1882.1882. O O Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1111
  12. 12. Historically relevant molecules for creating trends in creation of scents O O CHO HO CH3O CHO 4 O OHHO OCH3 O O O 3 Kumarin (1868.) Vanilin (1876.) γ-undekalakton(1908.)Evernyl® (1898.)α-ionon(1898.) Aldehid C12 (1880.) Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1212
  13. 13. O H H O CO2CH3 OH O O O O OH α-damaskon (1969.)Galaxolide ® (1967.) Dihidromircenol (1960.)Hedione ® (1960.)Ambrox® (1950.) Etilmaltol (1969.) Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1313
  14. 14. Classification of scents according to type of scent:Classification of scents according to type of scent:  citrus (lemon, orange, bergamot, grapefruit)citrus (lemon, orange, bergamot, grapefruit)  greengreen  aldehydealdehyde  plantplant  green (bluebell, jasmin, lilly of the valley,green (bluebell, jasmin, lilly of the valley, orange flower, iris, violet, rose, tuberose, freesia)orange flower, iris, violet, rose, tuberose, freesia)  fruitfruit  amberamber  food likefood like  woodywoody  moshusmoshus Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1414
  15. 15. Ingredient Scent Approx. usage (ton/year) Ambrox® Ambric 6 L-Karvon Spearmint 600 Citronelol and its esters Rose 6000 Dihidromyrcenol Lemon, flower 2000 Geraniol/nerol and their esters Rose 6000 Hidroksicitronellal Lilly of the valley 1000 Borneol/izoborneol and acetates Conifera 2000 Linalool Flower woody 4000 Linalil-acetat Flower fruity 3000 Mentol Like Mentha Piperita 5000 (Metil)iononi Violet 2000 α-Terpineol i acetati Conifera 3000 Acetilated ceddar oil woody 500 Table 1. Mayor terpene derived scent inredients. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1515
  16. 16. Classification of scents according to funktionalClassification of scents according to funktional groups:groups: 1.1.Compounds only with C, H, OCompounds only with C, H, O • AlcoholesAlcoholes • EstersEsters • AldehydesAldehydes • KetonsKetons • CarbohydratesCarbohydrates 2.2.Heterocyclic compoundsHeterocyclic compounds 1.1.Compounds with sulphurCompounds with sulphur Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1616
  17. 17. AlcoholsAlcohols • etanol, dipropyilene-glycoletanol, dipropyilene-glycol • cis-3-heksenol (scent of fresh mawned grass)cis-3-heksenol (scent of fresh mawned grass) • geraniol, linalool, dihidromyrcenol, citronellolgeraniol, linalool, dihidromyrcenol, citronellol • menthol, terpineolmenthol, terpineol • benzyl alcohol, 2-feniletanol (fenil-etil-alcohol)benzyl alcohol, 2-feniletanol (fenil-etil-alcohol) Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1717
  18. 18. EstersEsters • ethyl esters – ethyl-acetate, triethyil-citratethyl esters – ethyl-acetate, triethyil-citrat • allyil-cikloheksilpropanoat – scnet of ananasaallyil-cikloheksilpropanoat – scnet of ananasa • benzyl-acetate, fenilethyl-acetate, benzyl-benzoatebenzyl-acetate, fenilethyl-acetate, benzyl-benzoate • methyl-salicilate, heksyl-salicilate, benzyl-salicilatemethyl-salicilate, heksyl-salicilate, benzyl-salicilate • lactones –lactones – γγ-undecalactone (Peach aldehyde),-undecalactone (Peach aldehyde), γγ-nona--nona- lakton (Coconut aldehyde)lakton (Coconut aldehyde) • metil-dihydrojasmonatmetil-dihydrojasmonatModified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1818
  19. 19. AldehydesAldehydes • lauril aldehid (Aldehid C12),lauril aldehid (Aldehid C12), 2-metilundecanal (Aldehid C12 MNA )2-metilundecanal (Aldehid C12 MNA ) • 3-(4-3-(4-terttert-butylfenil)-2-methylbutanal (Lilial-butylfenil)-2-methylbutanal (Lilial®® ),), 3-(4-isopropilfenyl)-2-methylbutanal (Cyclamen3-(4-isopropilfenyl)-2-methylbutanal (Cyclamen aldehid)aldehid) • vannilin, etil-vannilinvannilin, etil-vannilin Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 1919
  20. 20. KetonesKetones • 4-hidroksiphenyl-2-butanon (Raspberry Ketone)4-hidroksiphenyl-2-butanon (Raspberry Ketone) • cis-3-metil-2-(2-pentenil)-2-ciklopenten-1-oncis-3-metil-2-(2-pentenil)-2-ciklopenten-1-on (cis-Jasmone)(cis-Jasmone) • iononi (iononi (αα--ionon,ionon, ββ--ionon)ionon) • damasconesdamascones Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2020
  21. 21. Carbon hidratesCarbon hidrates • d-limonene,d-limonene, αα-pinene,-pinene, ββ-pinene-pinene Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2121
  22. 22. Heterocyclic compoundsHeterocyclic compounds • maltol • coumarine • indol Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2222
  23. 23. Compounds with moshus like scentCompounds with moshus like scent CH3H3C NO2O2N C(CH3)3 NO2 CH3 NO2O2N OMe C(CH3)3 CH3H3C NO2O2N C(CH3)3 CH3O Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2323 Musk xylol Musk ketone Musk ambrette Nitro-moshus
  24. 24. Policylic moshus O CH3 H3C CH3 H3C CH3H3C O H3C CH3 CH3H3C H3C CH3H3C CH3H3C CH3 CH3 O Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2424 Galaxolide® Cashmeran® Versalide®
  25. 25. Nirvanolide® Exaltolide® Makrocyclic moshus OH3C O O O Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2525 Nirvanolide® Exaltolide®
  26. 26. Compounds with flower scent:Compounds with flower scent: FlorhidralFlorhidral®® H3C CH3 H OCH3 H3C CH3 H OCH3 R S Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2626 Enantiomers of Florhidrala® Flower, watery green scent Fresh flower green scent of Lilly of the valley
  27. 27. O CH3 COOMe O CH3 COOMe Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2727 (1(1RR, 2, 2RR)-methyl-jasmonat)-methyl-jasmonat IUPAC: metil-{(1R,2R)-3-okso- 2-[(2Z)-pent-2-en-1-il]-ciklopentil} -acetat (1(1RR, 2, 2SS)-methyl-jasmonat)-methyl-jasmonat IUPAC: metil-{(1R,2S)-3-okso- 2-[(2Z)-pent-2-en-1-il]-ciklopentil} -acetat Compounds with flower scentCompounds with flower scent - metil-jasmonat: gives character to jasmine scent (- metil-jasmonat: gives character to jasmine scent (Jasminum grandiflorum L.Jasminum grandiflorum L.))
  28. 28. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2828 Compunds with amber woody scentCompunds with amber woody scent H3CCH3H CH3CH2CH3OHCH3 OHCrO3AcOHH3CCH3H CH3 CH3 OO H3CCH3H CH3 CH3 OO +LiAlH4 H3CCH3H CH3CH3OHOH H3CC H3H CH3CH3O H3CCH3H CH3CH3O+ (-)-A mbrox TsOH MeNO2,30°C H3C CH3 H CH3 CH2 CH3 OH CH3 OH CrO3 AcOH H3C CH3 H CH3 CH3 O O H3C CH3 H CH3 CH3 O O + LiAlH4 H3C CH3 H CH3 CH3 OH OH H3C CH3 H CH3 CH3 O H3C CH3 H CH3 CH3 O + (-)-Ambrox TsOH MeNO2, 30 °C
  29. 29. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 2929 Iso E SuperIso E Super®® - main woody component H3C CH3 CH2 CH2 H3C H3C CH3 O H3C CH3 CH3 CH3 O H3C CH3 CH3 CH3 O H3C CH3 CH3 CH3 O CH3 H (AlCl3) H2SO4 + ca. 5 % 500 ng/L 5 pg/L prag osjetljivosti prag osjetljivosti
  30. 30. Process of smelling – chiralic identification ofProcess of smelling – chiralic identification of compoundscompounds CH3 O C H CH3H2C Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3030 O CH3 H C CH2H3C L-karvon spearmint D-karvon Caraway, cumine
  31. 31. Ohloff, 1961: first reults about enentioselectivity of chiralOhloff, 1961: first reults about enentioselectivity of chiral scent substancesscent substances OH H3C CH3 (S)-(-)-citronelol CH3 Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3131 (R)-(+)-citronelol OH H3C CH3 CH3
  32. 32. Differences in scent of some enantiomeres ofDifferences in scent of some enantiomeres of chiral substanceschiral substances MATERAL DESCRIPTION OF SCENT (+)-ENANTIOMER (-)-ENANTIOMER Hidroksicitronelal Lilly of the valley green peppermint Sweet lilly of the valley Linalool Sweet petitgraine Woody lavandin Karvon Scent of caraway Scent of spearmint Nootkaton Scent of grapefruit Woody spicy scent Nerol oksid Green flower scent Green spicy sccent with geranium note Mentol Fresh peppermint Strong cold effect Plant less peppermint Weak cold effect Limonen Orange Turpentine Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3232
  33. 33. You don’t taste with your mouth or your nose; you taste with your brain. Mark Friedman, Monell Chemical Senses Center, SAD Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3333
  34. 34. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3434  many aspects are still unexplained  scent forms together with taste chemical sensorial apparatus – CHEMORECEPTION (ability of perception of chemical signals)  Chemoreception is probably a first sensorial signal of living organisms Present achievments about olfaction process
  35. 35. Theory of olfaction  Dominating is a thesys that molecules of scenting inghredient are coming into contact with receptors and they transmite electricalsignal trough nervs.  Contact between receptor and scented molecule is realized trough olfactory epitel licated on top od nose hole. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3535
  36. 36. Results of scent perception research  By inhalation of pleasent scents gtested persons gave better notes about look of people on photos. Casino visitors spent to 45% more in pleasent odoured environment  Hair shampoo initially graded as worst in effect of hair washing efficiency, was graded much higher after correction of scent Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3636
  37. 37. Modified by Miro MeleModified by Miro Mele Parfummele d.o.o. SloveniaParfummele d.o.o. Slovenia 3737 Thank You!

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