basic fragrance chem1 - mae fah luang...

Nattaya Lourith, Ph.D. 1

Basic fragrance chemistry I

2

Objectives:

• Basic element• Chemical functional group of aroma

compounds

3

Contents:

• Introduction • Functional group

4

Flower and Chemistry

• Smell a Flower– The Fragrance is Chemistry

• See a Flower– The Colour is Chemistry

• Touch a Flower– The Structure is Chemistry

5

Carnation

• Flower • Eugenol• Perfume & Cosmetics

6

Vanilla• Seed• Vanillin• Perfume


7

O

OH

Lilial® Florol®Excital®

Orriniff®

Karanal®

Lyral®

Cedramber®

Boisambrebe®

Mayol®

Aldron®8

Functional groups with therapeutic actions

Anti-infectious, immunostimulantsAnti-infectious, immunostimulantsAnti-infectious, immunostimulantsEstrogen-like activityAnti-infections, calming, litholiticBalancing, calmingAntispasmodic, calmingBalancing, calmingCicatrizing (wound healing), mucolitic, litholitic, calmingExpectorant, antispasmodicAnti0infectious, immunostimulantsAnti-infectious, antispasmodicAnti-infectious, cortisone-like activityAntihistamines, anti-allergic

Acids Aromatics aldehydesC10 AlcoholsC15 & 20 AlcoholsAldehydesCoumarinsEstersLactonesKetones

OxidesPhenols Phenyl methyl ethersC10 TerpenesC15 Terpenes

Actions Functional group

9

Chemistry/Biology/Physiology/Psychology- Organic Chemistry – Synthetic, Molecular structure,

Biochemistry, Molecular Biology, Genomics,Anatomy, Neuroscience, Bioinformatics

- Analytical Chemistry – GC-MS analysis, Quality Assurance

- Physical Chemistry – Emulsions, Light scattering, etc.- Psychological aspects of perception – other influences

Computer Science – for all of the above +

OLFACTION & GUSTATIONMultidisciplinary Fields

10

Organic Chemistry

Organic synthesis

11

Analytical Chemistry

GC-MS analysis Volatiles from a living flower 12

Physical Chemistry


13

Artificial nose

14

15 16

Elements for Life• C : Carbon• H : Hydrogen• N : Nitrogen• O : Oxygen• P : Phosphorus• S : Sulfur

Living organisms composed of the 6 elements in 99.9% w/w

And trace 17 elements

17 18

Pork fired rice

Cheese pizza


19

hemoglobin isbright redcontainingIron (Fe)

20

Organic and Inorganic substances

• Organic– C, H, N, O, P, S

• Inorganic– Metal– Salt

21

Weight & Number

0Shell -1Electron

1Nucleus 0Neutron

1Nucleus+1Proton

MassLocation ChargeParticle

Atomic weight = Proton + Neutron

Atomic number = Proton

22

Structure

23

Chemical bonds : Octet rule

24

Chemical bonds : Electronegativity


25

Chemical bonds

Two or more elements combine to form compound

- Covalent bonds

- Ionic bonds

- Hydrogen bonds

26Covalent bonds

27Ionic bonds 28

Hydrogen bonds

29

Fragrance and Chemical functional group

- Hydrocarbon- Oxygen compounds- Nitrogen compounds- Sulfur compounds- Heterocyclic compounds- Halogen compounds

30

Fragrance compound name

DecNonOctHepHexPentButPropEthMethPrefix

10987654321C

Start with Prefix and end up with Suffix

-ate-ic-one-al-ol-yle-ene-aneSuffix

Functional group


31 32

Structure writing

33

Isomers

34

Isomers

Cis or Z Trans or E

35

Isomers

R, S or (+), (-) or d, l36

Hydrocarbon

Aliphaticalkane : single bond : CnH2n+2

alkene : double bond : CnH2n

alkyne : triple bond : CnH2n-2

cycloalkane : CnH2n

alicyclic : aliphatic cyclicAromatic


37

Alkane- 1C to 4C are colorless and odorless, flammable gases at ambient temp. & press.- 5C to 14C are colorless, flammable liquids, uninteresting odor- >15C are colorless, odorless, waxy solid

Hydrocarbon : Aliphatic

Lower alkanes are of no interest in perfumery, needed to remove as the extraction solvent from the extract

38

Hydrocarbon : AliphaticAlkene

- unsaturated hydrocarbon- geometric isomers- molecular parent of terpene

buta-1,3-diene

methylbuta-1,3-diene

Alkane posses odor rather similar to the corresponding alkane but more odor strength due to double bond. Simple alkanes are not used as perfume ingredients.

39

Terpene


Isoprene40

myrcene

Terpenemomoterpene : C10H16

sesquiterpene : C15H24(one and a half)

limonene α-pinene


farnesene

41

Alkyne

- unpleasant, petroleum-like odor- no application in perfumery

But its derivative recently used as perfume ingredient give powerful green character


42


cycloalkane CnH2n

alicyclic : aliphatic cyclic

Similar odor of those alkanehaving the same number of carbon


43

Hydrocarbon : Aromatic-Benzene is the prototype of aromatic compounds

1865 Friedrich August Kekulé

- Bezenoid compound posses sweet and pleasant odorDimethylbenzene or Xylene

1,2-dimethylbenzeneortho-dimethylbenzeneo-dimethylbenzene

1,3-dimethylbenzenemeta-dimethylbenzenem-dimethylbenzene

1,4-dimethylbenzenepara-dimethylbenzenep-dimethylbenzene 44

Alcohols & Phenols : R-OHEthers : R-O-RAldehydes : R-CHOAcetals : R-C(OR)2Ketones : R-CORCarboxylic acids : R-COOHEsters : R-COORLactones : O

O

Oxygen compounds

O O

45

Substitute group : R

C

H

H

C

H

H

C

H

H

C

H

H

H HC

H

H

C

H

H

C

H

H

C

H

H

C

H

H

H C

H

H

PentylPentane

46

Alcohols & PhenolsSome alcohol of interest to perfumer

NACreamy mushroom3-octen-2-ol1.2 ppb (H2O)Powerful mushroom1-octen-3-ol1550 ppb (H2O)Green, grassy and leafyE-3-hexen-1-ol70 ppb (H2O)Herbaceous, green, grassyZ-3-hexen-1-ol400 ppb (H2O)Green, leafyE-2-hexanolNAFresh green, leafyZ-2-hexanol

Odor detection threshold

OrganolepticsAlcohol

47

Pure phenol is colorless crystal with clean and antiseptic odor

Phenol was the first antiseptic ever usedPure phenol is very dangerous cause extremely

painful skin burn

OH

Alcohols & Phenols

O

OH

OHEugenol

Thymol

Glucoside form in oil of cloves, pale yellow liquid, strong odor. Antibacterial, antifungal

Perfumes, Soaps, Cosmetic

Thyme and ajowanoil, white solid, thyme odor

48

AldehydesAldehyde = alcohol dehydrogenatum Latin

= dehydrogenated alcohol English

3.0 ppb (H2O)Vinous fruity, coarse, very powerful

CH3(CH2)5CHOHeptanal4.5 ppb (H2O)Fruity green, very powerfulCH3(CH2)4CHOHexanal12.0 ppb (H2O)Choking, pungent, fruity, oilyCH3(CH2)3CHOPentanal

0.7 ppb (H2O)Orange peel, fatty, very powerfulCH3(CH2)6CHOOctanal

9.0 ppb (H2O)Choking, pungent, fruityCH3(CH2)2CHOButanal

9.5 ppb (H2O)Choking, suffocating, fruityCH3CH2CHOPropanal8.7 ppb (H2O)Choking, vinous, fruityCH3CHOAcetaldehyde


OrganolepticsFormula Aldehydes

Important aldehyde in perfumery = C8-C13

Perfume industry tends to speak of aldehyde C12 rather than dodecanal


49

Acetals

RO

R

OH

RO

R

OR

OO

Hemi-acetal Acetal

- Acetal posses interesting and useful odor- Acetal is alkali stable

PADMA = phenyl-acetaldehyde dimethyl acetal

O

O

acetaldehyde di-cis-3-hexenyl acetal

Perfume, green relates to hyacinth and watercress

Sweet and Green 50

Ketones

Acetone (aketon German) rose to ketoneAcetone has a rather harsh, etheral and unpleasant odor

used as a simple and inexpensive nail varnish remover

Fruity, orange like, floralCH3CO(CH2)7CH3DecanoneFruity, floral, herbaceousCH3CO(CH2)6CH3Nonanone

Floral, green fruity, herbaceous

CH3CO(CH2)5CH3OctanoneSweet, fruity, spearmintCH3CO(CH2)4CH3HeptanoneEthereal, fruityCH3CO(CH2)3CH3Hexanone

Fruity, orange like, waxy, floralCH3CO(CH2)8CH3Undecanone

Ethereal, not unpleasantCH3CO(CH2)2CH3PentanoneEthereal, not unpleasantCH3COCH2CH3ButanoneHarsh, etherealCH3COCH3PropanoneOrganolepticsFormula Ketones

51

Esters

1.0 ppb (H2O)Ethereal, fruity, butteryEtOOC(CH2)2CH3Ethyl butyrate1.5 ppb (H2O)Strong, fruity, appleEtOOC(CH2)3CH3Ethyl valerate1.0 ppb (H2O)Strong, fruity, wine, apple,

banana, pineappleEtOOC(CH2)4CH3Ethyl hexanoate

2.2 ppb (H2O)Strong, fruity, wine, cognacEtOOC(CH2)5CH3Ethyl heptanoate

15.0 ppb (H2O)Fruity, wine, sweet, cognac-apricot

EtOOC(CH2)6CH3Ethyl octanoate

850.0 ppb (H2O)

Fatty, oily, cognac, nutEtOOC(CH2)7CH3Ethyl nonanoate

10.0 ppb (H2O)Strong, ethereal, fruity, rumEtOOCEtEthyl propionate

5000.0 ppb (H2O)

Ethereal, sharp, wine-brandy like

EtOAcEthyl acetate


OrganolepticsFormula Esters

52

Cinnamon• Bark• Cinnamaldehyde• Perfume

53

Cinnamon

• Leaf• Eugenol• Vanillin raw material

54

Citronella• Leaf• Citronellol• Soap & Cosmetics


55

Clove

• Bud• Eugenol• Perfume

56

Cumin• Seed• Cuminaldehyde• Perfume

57

Eucalyptus

• Leaf• Cineole• Fixative

58

Fennel• Seed• Anethole• Oral care

59

Geranium

• Stem & Leaf• Geraniol• Perfume

60

Hyacinth• Flower• Benzyl acetate• Fragrant


61

Jasmine• Flower• Benzyl acetate• Floral perfume

62

Lavender• Flower• Linalool• Perfume & Soap

63

Lemongrass• Leaf• Citral• Soap & Detergent

64

Nutmeg

• Seed coat• i-Camphene• Oral care

65

Orange• Fruit peel• d-Limonene• Perfume & Lipstick

66

Orange

• Flower• Linalool• Perfume & Cosmetics


67

Patchouli• Leaf• (-)-Patchoulol• Perfume

68

Pennyroyal• Stem• d-Pulegone• Soap

69

Peppermint• Leaf• i-Menthol • Oral care

70

Rose

• Flower• i-Citronellol• Perfume

71

Sandalwood• Wood & Root• Santalol• Fixative

72

Spearmint• Leaf• i-Carvone• Oral care


73

Star anise

• Fruit• Anethole• Perfume

74

Thyme• Leaf & Flower• Thymol• Soap

75

Wintergreen• Leaf• Methyl salicylate• Oral care

76

Ylang ylang• Flower• Benzyl acetate• Perfume

77

References1. Butler H, editor. Poucher’s Perfume, Cosmetics and

Soaps. 10th ed. Dordrecht: Kluwer; 2000.2. Curtis T, William DG. Introduction to Perfumery. 2nd ed.

Trowbridge: Micelle Press; 2001.3. Arctander S. Perfume and Flavor Chemicals (Aroma

Chemicals). V. 1. Illinois: Allured; 1994. 4. Gimelli SP. Aroma Science. New York: Micelle Press;

2001. 5. Nattaya L. Fragrance Chemistry in Aromatic Science

1701351 [Lecture handout]. Chiangrai: MFU.6. Ellena C. Perfume formulation: words and chats. Chem.

Biodiv. 5: 1147-1153, 2008.7. Laudamiel C., Hornetz C., Mookherjee BD., Patel S. From

virgin education to real education. Chem. Biodiv. 5: 1159-1169, 2008.

78

Thank you for your attention

basic fragrance chem1 - mae fah luang...

Documents