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 The Metabolite Map for Identifying Probabilities and Olfactory Analysis As A Supplement to GCMS Analysis  Murray Hunter
1. Olfactory Evaluation 2. Using CGMS in Forensic Fragrance Construction 3. Using CGMS in Identifying Essential oil constituents 4. Using CGMS in Quality Assurance of Flavours & fragrances
What are essential oils?
   Essential Oil A volatile oil obtained from a  wide variety of plant, scrub,  and tree species and from  various parts of the plant  anatomy, such as the roots,  rhizomes, wood bark, leaves,  stems, fruit, flowers and seeds.  Usually extracted by hydro or  steam distillation, expression  or effleurage  - Hunter 1996
Concretes and Absolutes Volatiles and waxes extracted from plant material with hydrocarbon solvents (usually benzene and hexane) through washing and removal of the volatile solvent with distillation. A waxy aromatic substance remaining is called a concrete. The concrete is washed with alcohol to remove the volatile materials and ethanol removed through vacuum distillation to leave an absolute.
The Natural Aromatic Product Family
Olfactory Evaluation
? The Olfactory System & Odour Classification
The Human Olfactory System Odour molecules pass through the olfactory organ
Olfactory epithelium Olfactory mucosa Mucus! High in nasal cavity Site of transduction Contains olfactory receptor neurons (ORN)
11 Nose hair: Olfactory cilia ORN have cilia Cilia contain olfactory receptor proteins Similar to visual pigment Transduction Odorants bind to ORs Change shape of protein Ion flow across OR Electricity
Transmission Olfactory Receptors Olfactory Cells line the Olfactory Epithelium which is responsible for olfaction 	Each cell has cilia where receptor sites are located 	Replaced every month 	Axons of the olfactory receptors carry information to the olfactory bulb 	Olfactory bulb sends axons to several specific parts of the cortex with precise connections  	From the cortex, information is sent to other areas that control feeding & reproduction Olfactory Disorder Anosmia: the general lack of olfaction 	Specific Anosmia: the inability to smell a specific chemical
13 How many receptor types are there? 1000 different kinds of olfactory receptors (OR) 10 million OR neurons 10,000 of each type of OR Each OR neuron has only one type of receptor 1000 neuronal chemical detectors Potential to differentiate between 5,000-10,000 different odours
Olfactory Bulbs An outcropping of the brain Its like a snail in your brain! Electrical responses in cilia passed through olfactory nerve to OB
The hedonic primacy of olfaction Sensory and emotional experience Not the same for vision/audition Seeing and feeling more distinct More intertwined in the chemical senses Why? Orbitofrontal cortex Plays multiple roles Critical for emotional  experience Secondary sensory  cortex for olfaction Also centre of creativity and imagination
The olfactory interpretation process                           from input to response
Nobel Prize ,[object Object],[object Object]
Classification of Odours Curtis & Williams (1994)
Floral Family Descriptions
Woody Family Descriptions Animalic Family Descriptions
Balsamic Family Descriptions Herbaceous Family Descriptions Agrestic Family Descriptions
Green Family Descriptions Minty Family Descriptions Coniferous Family Description
Marine Family Descriptions Aldehydic Family Descriptions Medicated Family Descriptions
Fruity Family Descriptions Sub-Class (Citrus)
Spicy Family Description Miscellaneous Notes
Odour Characteristics Additional Characteristics
Fragrance Description Workshop
Performance Test GC-MS A Fragrance Development Lab A trained human more accurate than a GC-MS
Sample of a Flavour Chart
Using CGMS in Forensic                               Fragrance Construction From This To This
Apples aren't the same Sweet, sour, green, red, sharp, fresh, wholesome, etc. This means different aromatic chemicals play a role in fragrance
Discovered in 1937, the First Publication on  Raspberry Ketone appears in 1961
1964 – Introduction of Furaneol® 1965 – First publications on isolation of Furaneol® from strawberry and pineapple
1965-66 – α- & β-Sinensal isolated from orange oil
1960’s – Nootkatone First isolated in 1962, it’s importance to citrus flavor was unknown until it’s isolation from grapefruit by Mcleod in 1964. In 1966, Coca-Cola introduced Fresca. By 1970, Nootkatone was GRAS and became a key ingredient in Fresca. Coca-Cola manufactured Nootkatone for many years and soon made it available to the flavor industry. (+)-Nootkatone strong grapefruit odor,  bitter in taste  (-)-Nootkatone weak woody (vetiver note);  no grapefruit character;  virtually no taste Threshold:     60,000 ppb			  800 ppb
1970’s-80’s – Other Furanones Sotolon (caramel furanone) & Maple furanone identified in cane sugar – powerful caramel maple notes Maple Furanone (Abhexone) Sotolon Threshold:   0.003 ppb		          0.00005 ppb Sotolon – key flavorant of fenugreek, sake, sherry wine
1968 – Pfizer patents Ethyl maltol Ethyl maltol (Veltol Plus®) was touted to be about 6X stronger than maltol and an important substitute for  Coumarin. Well, at least it is stronger than maltol.
1975 - Introduction of α-Damascone and β-Damascone 1982 – Introduction of Damascenone 1970 – Discovery Damascenone & β-Damascone
1974 – Thiomenthones identified in Buchu oil Key component for black currant and  the “fuzzy” peach skin note
1980 – Patent on Oxane® 1977 - Winter identifies 2-methyl-4-propyl-1,3-oxathiane as a character impact compound in Passionfruit 1984 – Pickenhagen determines that (-)- cis- 2-methyl-4-propyl-1,3-oxathiane is the important diastereomer (-)-(2R,4S)-2-methyl-4-propyl-1,3-oxathiane ,[object Object]
 Threshold: 2 ppb(+)-(2S,4R)-2-methyl-4-propyl-1,3-oxathiane ,[object Object],             floral, less sulfury ,[object Object],[object Object]
Coumarinic p-Menthane Lactones Dihydromintlactone (1995) Wine lactone (1996) Mintlactone (1983) GRAS No.       --			   3764		             4032 Odor:	Vinous, lactonic	          Minty, coumarinic,      	    Coumarinic, hay,  	(coconut)                          tenacious		     lactonic, tonka Flavor:	Lactonic, sweet, herbal   Coumarinic, fatty, 	     Coumarinic, 				           herbal 		     lactonic, coconut Threshold*: 0.0000016ppb	           0.00012 ppb	     	     0.000039 ppb *In air Ref: Frerot, et. al., FlavourFragr. J., 2002; 17: 218–226; Gaudin, Tetrahedron,  2000, 56: 4769-4776
1962 – First publications appear on Methyl Jasmonate & Methyl Dihydrojasmonate   1R,2R-(-)-Z-methyl jasmonate               1S,2S-(+)-Z-methyl jasmonate   1R,2S-(+)-Z-methyl epijasmonate               1S,2R-(-)-Z-methyl epijasmonate Methyl Jasmonate – odorant, insect pheromone, plant growth regulator
Advances in Flavoring Materials Chirality & Odor - Methyl Jasmonate & Methyl Dihydrojasmonate ConfigurationOdor DescriptionOdor Threshold (in PPB) Methyl jasmonates 1R,2R-(-)-		Weak odor			          >70* 1S,2S-(+)-		Odorless				        Odorless 1S,2R-(-)-epi-		Odorless				        Odorless 1R,2S-(+)-epi-		Strong odor; floral, true jasmin-like	              3* Ref: T.E. Acree et. al., J.Agric.Food.Chem. 1985 Methyl dihydrojasmonates 1R,2R-(-)-		Floral, sweet, jasminelike		             240** 1S,2S-(+)-		Floral, fatty, cis-jasmone, hay character,         15,360** 			tea note, slightly lemon peellike (weak) 1S,2R-(-)-epi-		Herbal, fatty, tea-like, tobacco,	        12,500** 			β-damascone, cis-jasmone 1R,2S-(+)-epi-		Intensely floral, jasmine-like, bright, cis-          15** 			jasmone, slightly fatty, woody,  			β-ionone-like, extremely long lasting Ref: Werkhoff, P., et. al., Food Reviews International, 2002 * detection threshold **recognition threshold
                             Advances in Flavoring Materials 2001 – Takasago’s Professor RyojiNoyori wins  the 2001 Nobel Prize for Chemistry
Individual Aromatic Chemicals Probable Constituents of an essential oil
GC-MS Analysis of a Meat Flavor ,[object Object],Peak Identified as FurfurylMercaptan Powerful Coffee Aroma  1.6e+07  1.4e+07 Peaks are 2-Methyl-2,3-dihydrofuran-3-thiol isomers Powerful meat-like aroma  1.2e+07    1e+07 8000000 6000000 4000000 2000000 0 12.00 14.00 16.00 18.00 20.00 22.00 24.00 26.00 28.00 30.00 32.00 34.00 36.00 Time-->
Basic Fragrance Types ,[object Object]
  Chypre
  FougereCitrus Floral Aldehydic Spicy
[object Object],Citrus + Floral ,[object Object],Natural : Lemon Oil, Bergamote, Lime…. Chemical  : Citral, Dihydo Myrcenol….   Eau Savage Bergamot Lemon Orange  ,[object Object],O de Lancome (1975. Lancome) Bulgari Eau Parfume (1992. Bulgari) CK one (1994. C.Klein)  Eau Savage (1966.C.Dior) Rose  Jasmine Lily of Valley Oakmoss Ambergris Civet
[object Object],CK One Bergamot Lemon Mandarin Dihydro Myrcenol  Citrus Green Floral Jasmin Muguet Amber Musk Sandalwood Amber Woody Musk
[object Object],Floral + Floral JOY ,[object Object],Natural : Jamine Abs, Ylang Ylang, Rose Abs.  Tuberose …. Chemical  : Hedion, Benzyl Acetate…. Green  Green  ,[object Object],Joy (1935. Jean Patou) Diorssimo (1956.C.Dior) Anais Anais (1979. Cacharel) Paris (1983. YSL) Beautiful (1985. E. Lauder) Jasmine Rose  Ylang Ylang Violet Muguet Floral  Musk Sandalwood Powdery Musk Woody Powdery
Chanel No. 5 Aldehyd 10 Muguet Ylang-Ylang  Floral Jasmine Rose Carnation Aldehyde C-11 Aldehyde C-12 Aldehyddic Woody Powder Vanilla Sandalwood Musk ,[object Object],Floral + Aldehydic ,[object Object],Natural     : Not available  Chemical  : Aldehyde C-11, Aldehyde C-12..…. ,[object Object],Chanel No. 5 (1921. Chanel) Calandre (1969. 1969. Rabanne) First (1976. Van Cleef & Arpels)
L'Air du temps Bergamot Ylang Ylang  Floral Carnation Jasmine Rose Iris Spicy Floral Sandalwood Cedarwood Musk Woody Musk ,[object Object],Floral + Spicy ,[object Object],Natural     : Clove Buds oil, Pepper oil, Cinnamon oil.                      Carnation…….  Chemical  : Eugenol, Cinnamic Aldehyde  ..…. ,[object Object],L’air du Temps (1948. Nina Ricci) Fidji  (1966. Guy Laroche) Egoist (1990. Chanel)
[object Object],Natural     : Oak moss Abs. Vertiver, Patchouli oil                      Galbanum Cederwood, Sandalwood Chemical  : Veramoss, Iso E Super..…. Citrus  Green  Aldehyde ,[object Object],Mitsouko (1919. Guerlain) Miss Dior (1947. Christian Dior) Coco  (1984. Chanel) Ysatis (1984. Givenchy) Floral (Jasmine,  Rose, Ylang…) Woody Mossy Patchouli What is Chypre….? ,[object Object],[object Object]
Citrus  Mandarin Lemon Spicy(cinamon..) Floral Vanilla Abs. Sweet Balsam What is Oriental….? ,[object Object]
Representative IngredientsNatural     : Vanilla, Tolu Balsam, Mandarin, Cinnamon  Chemical  : Vanillin, Galaxolide..…. ,[object Object],Shalimar (1925. Guelain) Obsession (1984. Calvin Klein) Opium (1977. YSL) Samsara (1989. Guelain) Jean Paul Gaultier (1993. J.P.Gaultier)
[object Object],Bergamot Lavendin Clove Spearmint Herbacious Drakkar Noir Muguet Geranium Carnation Floral Woody Powdery Powdery Mossy Cederwood
Using CGMS in Identifying  Essential oil constituents
Ylang Ylang (Cananga odorata) benzyl acetate (ca. 25 %), p-cresyl methyl ether (ca. 20 %),  methyl benzoate (ca. 5 %), methyl salicylate, cinnamyl acetate,  (-)-linalool (ca. 15 %), geranyl acetate (ca. 10 %), farnesyl acetate (ca. 3 %),  as well as a number of other sesquiterpenes and their oxygenated  derivatives, e.g. muurolol T (ca. 2 %) Extraction Method: Steam distillation of the flowers Origin: Indonesia, Madagascar
Patchouli Oil (Pogostemon cablin) There are no synthetic  equivalents of the  patchouli scent. Main Constituents: (-)-patchoulol  (30-40 %). However, it is maintained  that norpatchoulenol, present in only  0.3-0.4 %, is playing a principal part  in the overall odour picture. (-)-patchoulol andnorpatchoulenol Obtained by steam  distillation under  pressure or CO2- extraction of the  dried leaves Patchouli is mostly  grown in Indonesia
Pandanus Oil (Pandanus odoratissimus) phenethyl methyl etherpandanol phenethyl methyl ether ( pandanol) (38 %), together  with terpinen-4-ol (19 %),  alpha-terpineol (8 %) and  phenethyl alcohol (7 %) [79].  Phenethyl alcohol and its  derivatives are common  odorants in flowers The flowers are hydro-distilled to yield a 'kewda attar Origin: native of South East Asia and is much  cultivated on the Indian East Coast
Backhousia citriodora (Lemon Myrtle) High Investment to Expand Industry in Australia Strong Demand as an Ingredient for tea Good Crop to Grow in Most Parts of Thailand Citral (geranial 51.43 % and neral 42.12 % )
Important New Compounds ,[object Object],Concentration Odor Unit = Odor Threshold
Different Major Chemical and Olfactory Profiles of Five Basil Oils
Harvest Timing Critical for Some Crops (Mentha piperata)
1959 – Bain & Webb – Turpentine into Fragrance & Flavor beta-Pinene Linalool Linalyl Acetate Menthol Myrcene Geraniol Citronellol Citronellal
1959 – Roche Process for Linalool & Citral via Acetylene
Points to Remember The highest probability is not necessarily the correct one Check back to see if that chemical could physically be present You will have to add new materials to your database (Both NIST & Wiley databases) Is it an artifact?  Confirm your analysis with other supportive data
Using CGMS in Quality Assurance of Flavours & fragrances
QC lab. in the days before the concept of ‘Health & Safety at Work’ – note lighted cigarettes dangling from lips of staff!
Gas Chromatography – Mass Spectrometry Detective work GC-MS analysis Looking at metabolite paths Olfactory analysis of living plants
Third Nobel Prize in this field ,[object Object]
Helps elucidate many of the C10H16 group terpene structures present in essential oils utilizing common reagents such as hydrogen chloride and hydrogen bromide. In 1909 he published the results of his extensive studies in the book Terpene und Campher, a volume of 600 pages dedicated to his pupils.beta-Pinene alpha-Pinene Camphene Camphor

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GCMS presentation - natural products

  • 1. The Metabolite Map for Identifying Probabilities and Olfactory Analysis As A Supplement to GCMS Analysis Murray Hunter
  • 2. 1. Olfactory Evaluation 2. Using CGMS in Forensic Fragrance Construction 3. Using CGMS in Identifying Essential oil constituents 4. Using CGMS in Quality Assurance of Flavours & fragrances
  • 4. Essential Oil A volatile oil obtained from a wide variety of plant, scrub, and tree species and from various parts of the plant anatomy, such as the roots, rhizomes, wood bark, leaves, stems, fruit, flowers and seeds. Usually extracted by hydro or steam distillation, expression or effleurage - Hunter 1996
  • 5. Concretes and Absolutes Volatiles and waxes extracted from plant material with hydrocarbon solvents (usually benzene and hexane) through washing and removal of the volatile solvent with distillation. A waxy aromatic substance remaining is called a concrete. The concrete is washed with alcohol to remove the volatile materials and ethanol removed through vacuum distillation to leave an absolute.
  • 6. The Natural Aromatic Product Family
  • 8. ? The Olfactory System & Odour Classification
  • 9. The Human Olfactory System Odour molecules pass through the olfactory organ
  • 10. Olfactory epithelium Olfactory mucosa Mucus! High in nasal cavity Site of transduction Contains olfactory receptor neurons (ORN)
  • 11. 11 Nose hair: Olfactory cilia ORN have cilia Cilia contain olfactory receptor proteins Similar to visual pigment Transduction Odorants bind to ORs Change shape of protein Ion flow across OR Electricity
  • 12. Transmission Olfactory Receptors Olfactory Cells line the Olfactory Epithelium which is responsible for olfaction Each cell has cilia where receptor sites are located Replaced every month Axons of the olfactory receptors carry information to the olfactory bulb Olfactory bulb sends axons to several specific parts of the cortex with precise connections From the cortex, information is sent to other areas that control feeding & reproduction Olfactory Disorder Anosmia: the general lack of olfaction Specific Anosmia: the inability to smell a specific chemical
  • 13. 13 How many receptor types are there? 1000 different kinds of olfactory receptors (OR) 10 million OR neurons 10,000 of each type of OR Each OR neuron has only one type of receptor 1000 neuronal chemical detectors Potential to differentiate between 5,000-10,000 different odours
  • 14. Olfactory Bulbs An outcropping of the brain Its like a snail in your brain! Electrical responses in cilia passed through olfactory nerve to OB
  • 15. The hedonic primacy of olfaction Sensory and emotional experience Not the same for vision/audition Seeing and feeling more distinct More intertwined in the chemical senses Why? Orbitofrontal cortex Plays multiple roles Critical for emotional experience Secondary sensory cortex for olfaction Also centre of creativity and imagination
  • 16. The olfactory interpretation process from input to response
  • 17.
  • 18. Classification of Odours Curtis & Williams (1994)
  • 20. Woody Family Descriptions Animalic Family Descriptions
  • 21. Balsamic Family Descriptions Herbaceous Family Descriptions Agrestic Family Descriptions
  • 22. Green Family Descriptions Minty Family Descriptions Coniferous Family Description
  • 23. Marine Family Descriptions Aldehydic Family Descriptions Medicated Family Descriptions
  • 24. Fruity Family Descriptions Sub-Class (Citrus)
  • 25. Spicy Family Description Miscellaneous Notes
  • 28.
  • 29.
  • 30. Performance Test GC-MS A Fragrance Development Lab A trained human more accurate than a GC-MS
  • 31. Sample of a Flavour Chart
  • 32.
  • 33. Using CGMS in Forensic Fragrance Construction From This To This
  • 34.
  • 35.
  • 36. Apples aren't the same Sweet, sour, green, red, sharp, fresh, wholesome, etc. This means different aromatic chemicals play a role in fragrance
  • 37.
  • 38. Discovered in 1937, the First Publication on Raspberry Ketone appears in 1961
  • 39. 1964 – Introduction of Furaneol® 1965 – First publications on isolation of Furaneol® from strawberry and pineapple
  • 40. 1965-66 – α- & β-Sinensal isolated from orange oil
  • 41. 1960’s – Nootkatone First isolated in 1962, it’s importance to citrus flavor was unknown until it’s isolation from grapefruit by Mcleod in 1964. In 1966, Coca-Cola introduced Fresca. By 1970, Nootkatone was GRAS and became a key ingredient in Fresca. Coca-Cola manufactured Nootkatone for many years and soon made it available to the flavor industry. (+)-Nootkatone strong grapefruit odor, bitter in taste (-)-Nootkatone weak woody (vetiver note); no grapefruit character; virtually no taste Threshold: 60,000 ppb 800 ppb
  • 42. 1970’s-80’s – Other Furanones Sotolon (caramel furanone) & Maple furanone identified in cane sugar – powerful caramel maple notes Maple Furanone (Abhexone) Sotolon Threshold: 0.003 ppb 0.00005 ppb Sotolon – key flavorant of fenugreek, sake, sherry wine
  • 43. 1968 – Pfizer patents Ethyl maltol Ethyl maltol (Veltol Plus®) was touted to be about 6X stronger than maltol and an important substitute for Coumarin. Well, at least it is stronger than maltol.
  • 44. 1975 - Introduction of α-Damascone and β-Damascone 1982 – Introduction of Damascenone 1970 – Discovery Damascenone & β-Damascone
  • 45. 1974 – Thiomenthones identified in Buchu oil Key component for black currant and the “fuzzy” peach skin note
  • 46.
  • 47.
  • 48. Coumarinic p-Menthane Lactones Dihydromintlactone (1995) Wine lactone (1996) Mintlactone (1983) GRAS No. -- 3764 4032 Odor: Vinous, lactonic Minty, coumarinic, Coumarinic, hay, (coconut) tenacious lactonic, tonka Flavor: Lactonic, sweet, herbal Coumarinic, fatty, Coumarinic, herbal lactonic, coconut Threshold*: 0.0000016ppb 0.00012 ppb 0.000039 ppb *In air Ref: Frerot, et. al., FlavourFragr. J., 2002; 17: 218–226; Gaudin, Tetrahedron, 2000, 56: 4769-4776
  • 49. 1962 – First publications appear on Methyl Jasmonate & Methyl Dihydrojasmonate   1R,2R-(-)-Z-methyl jasmonate 1S,2S-(+)-Z-methyl jasmonate   1R,2S-(+)-Z-methyl epijasmonate 1S,2R-(-)-Z-methyl epijasmonate Methyl Jasmonate – odorant, insect pheromone, plant growth regulator
  • 50. Advances in Flavoring Materials Chirality & Odor - Methyl Jasmonate & Methyl Dihydrojasmonate ConfigurationOdor DescriptionOdor Threshold (in PPB) Methyl jasmonates 1R,2R-(-)- Weak odor >70* 1S,2S-(+)- Odorless Odorless 1S,2R-(-)-epi- Odorless Odorless 1R,2S-(+)-epi- Strong odor; floral, true jasmin-like 3* Ref: T.E. Acree et. al., J.Agric.Food.Chem. 1985 Methyl dihydrojasmonates 1R,2R-(-)- Floral, sweet, jasminelike 240** 1S,2S-(+)- Floral, fatty, cis-jasmone, hay character, 15,360** tea note, slightly lemon peellike (weak) 1S,2R-(-)-epi- Herbal, fatty, tea-like, tobacco, 12,500** β-damascone, cis-jasmone 1R,2S-(+)-epi- Intensely floral, jasmine-like, bright, cis- 15** jasmone, slightly fatty, woody, β-ionone-like, extremely long lasting Ref: Werkhoff, P., et. al., Food Reviews International, 2002 * detection threshold **recognition threshold
  • 51.                              Advances in Flavoring Materials 2001 – Takasago’s Professor RyojiNoyori wins the 2001 Nobel Prize for Chemistry
  • 52.
  • 53.
  • 54. Individual Aromatic Chemicals Probable Constituents of an essential oil
  • 55.
  • 56.
  • 58. FougereCitrus Floral Aldehydic Spicy
  • 59.
  • 60.
  • 61.
  • 62.
  • 63.
  • 64.
  • 65.
  • 66.
  • 67.
  • 68.
  • 69. Using CGMS in Identifying Essential oil constituents
  • 70.
  • 71.
  • 72.
  • 73.
  • 74. Ylang Ylang (Cananga odorata) benzyl acetate (ca. 25 %), p-cresyl methyl ether (ca. 20 %), methyl benzoate (ca. 5 %), methyl salicylate, cinnamyl acetate, (-)-linalool (ca. 15 %), geranyl acetate (ca. 10 %), farnesyl acetate (ca. 3 %), as well as a number of other sesquiterpenes and their oxygenated derivatives, e.g. muurolol T (ca. 2 %) Extraction Method: Steam distillation of the flowers Origin: Indonesia, Madagascar
  • 75. Patchouli Oil (Pogostemon cablin) There are no synthetic equivalents of the patchouli scent. Main Constituents: (-)-patchoulol (30-40 %). However, it is maintained that norpatchoulenol, present in only 0.3-0.4 %, is playing a principal part in the overall odour picture. (-)-patchoulol andnorpatchoulenol Obtained by steam distillation under pressure or CO2- extraction of the dried leaves Patchouli is mostly grown in Indonesia
  • 76. Pandanus Oil (Pandanus odoratissimus) phenethyl methyl etherpandanol phenethyl methyl ether ( pandanol) (38 %), together with terpinen-4-ol (19 %), alpha-terpineol (8 %) and phenethyl alcohol (7 %) [79]. Phenethyl alcohol and its derivatives are common odorants in flowers The flowers are hydro-distilled to yield a 'kewda attar Origin: native of South East Asia and is much cultivated on the Indian East Coast
  • 77. Backhousia citriodora (Lemon Myrtle) High Investment to Expand Industry in Australia Strong Demand as an Ingredient for tea Good Crop to Grow in Most Parts of Thailand Citral (geranial 51.43 % and neral 42.12 % )
  • 78.
  • 79.
  • 80.
  • 81.
  • 82.
  • 83.
  • 84.
  • 85.
  • 86.
  • 87.
  • 88. Different Major Chemical and Olfactory Profiles of Five Basil Oils
  • 89.
  • 90.
  • 91.
  • 92.
  • 93. Harvest Timing Critical for Some Crops (Mentha piperata)
  • 94. 1959 – Bain & Webb – Turpentine into Fragrance & Flavor beta-Pinene Linalool Linalyl Acetate Menthol Myrcene Geraniol Citronellol Citronellal
  • 95. 1959 – Roche Process for Linalool & Citral via Acetylene
  • 96. Points to Remember The highest probability is not necessarily the correct one Check back to see if that chemical could physically be present You will have to add new materials to your database (Both NIST & Wiley databases) Is it an artifact? Confirm your analysis with other supportive data
  • 97.
  • 98. Using CGMS in Quality Assurance of Flavours & fragrances
  • 99. QC lab. in the days before the concept of ‘Health & Safety at Work’ – note lighted cigarettes dangling from lips of staff!
  • 100.
  • 101. Gas Chromatography – Mass Spectrometry Detective work GC-MS analysis Looking at metabolite paths Olfactory analysis of living plants
  • 102.
  • 103. Helps elucidate many of the C10H16 group terpene structures present in essential oils utilizing common reagents such as hydrogen chloride and hydrogen bromide. In 1909 he published the results of his extensive studies in the book Terpene und Campher, a volume of 600 pages dedicated to his pupils.beta-Pinene alpha-Pinene Camphene Camphor
  • 104.
  • 105.
  • 106. Elucidated the structures of the naturally occurring musk perfumes, civetone and muscone thus replacing scents prized since antiquity – but only available from endangered species. Civetone Muscone Musk Deer Moschusmoschiferus L. Civet Cat Viverracivetta
  • 107. Have fun with your new toy Thank You