Flavor and Fragrance Materials of Natural Origin

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Alexina Johns
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1 Flavor and Fragrance Materials of Natural rigin

2 Expression

4 Enfleurage

5 Jasmine

6 Jasmine

7 Distillation

8 Steam Distillation $30 $300/kg tonnes/yr Steam/il vapor mixture Plant material H 2 out Condensor Still H 2 in Steam Essential oil Water of Cohobation

9 Lavendar

10 Sandalwood

13 Fractional Distillation Water condensor Water condensor Condensor/ Fractionating column

15 Extraction/Isolation ethanol extraction Natural Material Tincture distillation solvent extraction enfleurage Essential il distillation Concrete (Resinoid) ethanol extraction Pomade ethanol extraction Absolute

16 Gas Chromatography / Mass Spectrometry (GCMS)

18 Headspace analysis

21 GC-MS of Soft Soap

22 GC-MS of Multipurpose cleaner

23 GC-MS of Dishwashing detergent

25 Figure 1. Column A 160 I40 I G _I-/ TIME, PAINUTES Gas chromatogram of a concentrate of volatile constituents from roast beef drippings. Attenuation 256, sample size 0.3 p1,

26 Peak no Table I. Volatile Constituents of Roast Beef and Roast Beef Drippings Compd Sample Peak no. Compd Diethyl ether (solvent) M, D 23 It-Nonanal Ethyl acetate (solvent M, D 24 2-ctenal impurity) 25 1-Heptanol Ethanol (solvent impurity) 2-Methylbutanal M, D M, D 26 Benzaldehyde 2-n-Hept ylfuran 3-Met hylbutanal M, D Ca-benzene 2,3-Butanedione M 2,4-ctadienal (tent,) n-pentanal M, D 2,3-Butanediol n-nonane M, D 2-Decanone 1-Propanol 2,3-Pentanedione D M rz-tetradecane rz-decanal Toluene M, D 28 y-butyrolactone Dimethyl disulfide M 29 2-Nonenal n-hexanal M, D 30 1-ctanol n-decane M, D 31 2-n-ctylfuran n-butanol 1,4-DimethyIbenzene M, D M, D Butyric acid 6(?)-Methyltetradecane 1,ZDimethylbenzene 3-Heptanone M D 32 Phenylacetaldehyde 2-cten n-undecane M, D n-pentadecane 2-Heptanone M, D 34 2-Undecanone n-heptanal M, D y-hexalactone 2-Hexenal D n-undecanal 3-Hydroxy-2-butanone M, D 35 2-Decenal 1-Pentanol M, D 36 2,4-Nonadienal 2-n-Pentylfuran M, D 6-Valerolactone (tent.) Trimethylbenzene M y-heptalactone Methylethylbenzene M Dimethyl sulfone 3-ctanone M, D 2-Dodecanone Trimethylbenzene M, D n-hexadecane 4-Heptanol (tent.) D 39 2,4-Decadienal 3-Heptanol D n-dodecanal 2-ctanone M, D 40 2-Undecenal n-dodecane M, D 41 2,4-Decadienal 6-Heptalactone n-ctanal M, D n-heptadecane 2-Heptenal M, D Heptadecene 2,3-ctanedione M Acetylpyrrole Dieth ylbenzene M y-ctalactone 1-Hexanol M, D 43 2-Tridecanone Acetic acid D 12-Tridecanal 19 C8-benzene M 44 2-Dodecenal 20 2-n-Hexylfuran D 6-ctalactone n-butylbenzene M 45 2,4-Undecadienal Ca-benzene M n-ctadecane Dimethylpyrazine (tent.) D 47 y-nonalactone 4-ctanol (tent.) D 2-Tridecenal 3-ctanol D 2,4-Dodecadienal 2-n-butox yet hano M 6-Nonalactone 22 2-Nonanone M, D y-decalactone n-tridecane M, D 2-Pentadecanone a M: Compo lund was found in roast beef meat; D: Compound was found in roast beef drippings. D D M, D D D D D D

27 Volatile Composition of Some Brazilian Fruits: Umbu-caja (Spondias citherea), Camu-camu (Myrciaria dubia), Araça-boi (Eugenia stipitata), and Cupuaçu (Theobroma grandiflorum) Maria Regina B. Franco*, and Takayushi Shibamoto Faculdade de Engenharia de Alimentos, UNICAMP, Campinas-SP, CP 6121, CEP , Brazil, and Department of Environmental Toxicology, University of California, Davis, California J. Agric. Food Chem., Vol. 48, No. 4, 2000 Franco and Shibamoto Table 1. Volatile Composition of the Umbu-caja Sample compound Kovats index % area NI a ethyl acetate NI NI NI R-pinene NI ethyl butyrate toluene butyl acetate β-pinene β-myrcene d-limonene β-phellandrene 1192 tr c cis-β-ocimene trans-β-ocimene ethyl hexanoate hexyl acetate ,5,5,6-tetramethyl-1,3-cyclohexadiene b ethyl octanoate 1442 tr R-copaene β-caryophyllene R-caryophyllene β-selinene ,2,3,4,4a,5,6,8a-octahydro-4a, dimethylnaphthalene b δ-cadinene 0.32 Table 2. Volatile Composition of the Camu-camu Sample compound Kovats index % area ethyl acetate R-pinene R-fenchene ethyl butyrate camphene NI a 1065 tr b β-pinene car-3-ene 1142 tr β-myrcene R-phellandrene NI R-terpinene d-limonene β-phellandrene eucalyptol 1208 tr γ-terpinene p-cimene terpinolene fenchol 1554 tr β-caryophyllene terpineol 1574 tr humulene 1606 tr NI NI a NI, not identified. b Traces. There was an inversion in the order of elution of ethyl

28 GC-lfactory (GC-)

29 Infrared Spectroscopy

30 Limonene

31 Citronellol H

32 Carvone

33 Nuclear Magnetic Resonance (NMR)

34 2-D NMR

35 Biosynthesis

36 Cellulose Glucose Acetyl Coenzyme A Biosynthesis

37 Terpene Biosynthesis CoAS + CoAS Claisen condensation (substitution) CoAS Acetoacetyl-CoA

38 Terpene Biosynthesis CoAS + CoAS Claisen condensation (substitution) CoAS Acetoacetyl-CoA CoAS Acetoacetyl-CoA + SCoA Acetyl-CoA Aldol reaction (addition) CoAS H SCoA H 2 (hydrolysis) H H SCoA b-hydroxy-b-methyl-glutaryl-coa

39 Terpene Biosynthesis CoAS + CoAS Claisen condensation (substitution) CoAS Acetoacetyl-CoA CoAS Acetoacetyl-CoA + SCoA Acetyl-CoA Aldol reaction (addition) CoAS H SCoA H 2 (hydrolysis) H H SCoA b-hydroxy-b-methyl-glutaryl-coa H H SCoA NADPH + H + (reduction) H H H mevalonic acid ATP (convert to good leaving group) H H PP mevalonic acid diphosphate PP = P P H H H

40 Terpene Biosynthesis CoAS + CoAS Claisen condensation (substitution) CoAS Acetoacetyl-CoA CoAS Acetoacetyl-CoA + SCoA Acetyl-CoA Aldol reaction (addition) CoAS H SCoA H 2 (hydrolysis) H H SCoA b-hydroxy-b-methyl-glutaryl-coa H H SCoA NADPH + H + (reduction) H H H mevalonic acid ATP (convert to good leaving group) H H PP mevalonic acid diphosphate PP = P P H H H H H PP (decarboxylation) PP PP mevalonic acid diphosphate isopentyl-pyrophosphate dimethylallyl-pyrophosphate

41 Isoprene Units PP + PP PP PP prenyl pyrophosphate isopentyl pyrophosphate geranyl pyrophosphate farnesyl pyrophosphate PP H H Acyclic Monoterpenoids geranyl pyrophosphate geraniol (rose) H citral (lemon) H H citronellol (rose) citronellal (lemon/citrus) linalool (floral) geranyl acetate (floral)

42 Cyclic Monoterpenoids H limonene α-terpineol α-pinene (citrus) (lilac) (pine) β-pinene camphor H l-(-) menthol (mint) (S)-carvone d-(+) (R)-carvone l-(-)

43 Sesquiterpenoids H H α-bisabolol cedrol chamomile oil (anti-inflammatory) Virginian and Chinese cedarwood oil H PP farnesyl pyrophosphate H H patchouli alcohol patchouli oil α-santalol East Indian sandalwood oil zizinal vetiver oil

44 H H ambreine H H Ambergris dihydro-γ-ionone ambrinol H ambrox Moist, soft, creamy, persistent, warm, animalic, woody, amber

45 Australian beach, lb Ambergris = $750,000

46 Polyketide, Terpenoide or Shikimate? H CoA acetylcoenzyme A (polyketide) CoA PP PP prenyl pyrophosphate isopentyl pyrophosphate (terpenoid) H H H shikimic acid (shikimate) H 3 C ethyl everninate CH 3 methyl jasmonate Me Me Me β-asarone H H H H polyketide polyketide H H H H H shikimate

47 deodarone dehydrocostus lactone

CERTIFICATE OF ANALYSIS - GC PROFILING

Date : May 22, 2018 CERTIFICATE OF ANALYSIS - GC PROFILING SAMPLE IDENTIFICATION Internal code : 18E08-NAD2-1-CC Customer identification : Lemon Oil - Argentina - R122257-02 Type : Essential oil Source