The Chemistry of Fragrances

Perfumes and More

28 March 2019
 The Chemistry of Fragrances
Perfumes and More

28 March 2019

1. Brief History
 The Chemistry of Fragrances
Perfumes and More

28 March 2019

1. Brief History
2. Nobel Prize (2004)
 The Chemistry of Fragrances
Perfumes and More

28 March 2019

1. Brief History
2. Nobel Prize (2004)
3. Catalytic Preparation of Fragrances
 The Chemistry of Fragrances
Perfumes and More

28 March 2019

1. Brief History
2. Nobel Prize (2004)
3. Catalytic Preparation of Fragrances
4. Industrial Organometallic Processes
 The Chemistry of Fragrances
Perfumes and More

28 March 2019

1. Brief History
2. Nobel Prize (2004)
3. Catalytic Preparation of Fragrances
4. Industrial Organometallic Processes
5. Toxicology Outline
 The Chemistry of Fragrances
Perfumes and More

28 March 2019

1. Brief History
2. Nobel Prize (2004)
3. Catalytic Preparation of Fragrances
4. Industrial Organometallic Processes
5. Toxicology Outline
6. Review of Flavor & Fragrance (2018)
 Brief History of Fragrances
• <1850: only the wealthiest could afford
fragrances and perfumes

• <1900: Perfumes were made of entirely natural

materials

• 2019: over 3000 fragrance ingredients are

available to consumers (>90% chemically
synthesized)

• Expected in everything from household cleaners to shampoo to processed

food and more!

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Brief History of Fragrances
• Use of fragranced materials dates back
thousands of years

• “Perfume” comes from Latin per fume meaning

“through smoke” as in the burning of incense

• Egyptians pressed, boiled, dried, powdered,

macerated in fat, and even distilled

• The early Crusades spread perfumes to Middle

Age Europe

• Alchemy turned into chemistry in the 19th century, and fragrance was at the
forefront

• 1882: Paul Parquet created Fougere Royale from synthetic coumarin,

oakmoss, geranium, and bergamont

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were
based on the analysis of natural sources:
• Plants (lavender, jasmine)
• Fruits (lemon, orange)
• Animal (musk, ambergris)

• Three main methods for acquiring

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were
based on the analysis of natural sources:
• Plants (lavender, jasmine)
• Fruits (lemon, orange)
• Animal (musk, ambergris)

• Three main methods for acquiring

Expression

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were
based on the analysis of natural sources:
• Plants (lavender, jasmine)
• Fruits (lemon, orange)
• Animal (musk, ambergris)

• Three main methods for acquiring

Steam Distillation

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Brief History of Fragrances
• Traditional discovery and development of new synthetic chemicals were
based on the analysis of natural sources:
• Plants (lavender, jasmine)
• Fruits (lemon, orange)
• Animal (musk, ambergris)

• Three main methods for acquiring

Solvent Extraction

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Brief History of Fragrances
• Chanel No5 was the first commercial perfume to use synthetic materials

• Synthetic materials are:

• Cheaper
• Less prone to degradation

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Brief History of Fragrances
• Much like medicinal chemistry,
derivatives are explored after
natural detection

Fortineau, A.-D., Chemistry Perfumes Your Daily Life. J. Chem. Educ. 2004, 81 (1), 45.
 Development of Types of Odors

Musk

Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
 Development of Types of Odors

Woody

Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
 Development of Types of Odors

‘Prodrug’ equivalence in perfumes

Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
 Development of Types of Odors

Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
 Development of Types of Odors

Gautschi, M.; Bajgrowicz, Ja. A.; Kraft, P. Flavours and Fragrances 2001, 55, 379-387
 2004 Nobel Prize in Medicine & Physiology
Linda B. Buck Richard Axel

Howard Hughes Medical Institute Howard Hughes Medical Institute

Fred Hutchinson Cancer Research Columbia University College of
Center Physicians and Surgeons

.
 2004 Nobel Prize in Medicine & Physiology
Two main questions:
• How do mammals detect so many different environmental chemicals?
• How does the brain translate those chemicals into diverse odor
perception and behaviors?

Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
 2004 Nobel Prize in Medicine & Physiology
Two main questions:
• How do mammals detect so many different environmental chemicals?
• How does the brain translate those chemicals into diverse odor
perception and behaviors?

Humans can sense 10,000 to 100,000 chemicals (small, volatile)

Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
 2004 Nobel Prize in Medicine & Physiology
Two main questions:
• How do mammals detect so many different environmental chemicals?
• How does the brain translate those chemicals into diverse odor
perception and behaviors?

Humans can sense 10,000 to 100,000 chemicals (small, volatile)

G-protein coupled receptors (GPCR) were discovered to be responsible for

odor detection

Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
 2004 Nobel Prize in Medicine & Physiology
Two main questions:
• How do mammals detect so many different environmental chemicals?
• How does the brain translate those chemicals into diverse odor
perception and behaviors?

Humans can sense 10,000 to 100,000 chemicals (small, volatile)

G-protein coupled receptors (GPCR) were discovered to be responsible for

odor detection

Odor receptors seem to be randomly distributed

Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
 2004 Nobel Prize in Medicine & Physiology
Two main questions:
• How do mammals detect so many different environmental chemicals?
• How does the brain translate those chemicals into diverse odor
perception and behaviors?

Humans can sense 10,000 to 100,000 chemicals (small, volatile)

G-protein coupled receptors (GPCR) were discovered to be responsible for

odor detection

Odor receptors seem to be randomly distributed

Different odorants can all trigger one type of

receptor neuron

Buck, L. B., Unraveling the Sense of Smell (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6128-6140.
 2004 Nobel Prize in Medicine & Physiology

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Why study smell?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Why study smell?
It’s a primal sense

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Why study smell?
It’s a primal sense

Can we study smell?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Why study smell?
It’s a primal sense

Can we study smell?

It’s difficult to
understand, but it
has tangible pieces
(molecules &
receptors)

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Why study smell?
It’s a primal sense

Can we study smell?

It’s difficult to
understand, but it
has tangible pieces
(molecules &
receptors)

What questions
should be asked?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Why study smell?
It’s a primal sense

Can we study smell?

It’s difficult to
understand, but it
has tangible pieces
(molecules &
receptors)

What questions
should be asked?
How do we smell?
How does the brain learn
and interpret these signals?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
• 1300 odor receptors in a mouse
Why study smell?
It’s a primal sense

Can we study smell?

It’s difficult to
understand, but it
has tangible pieces
(molecules &
receptors)

What questions
should be asked?
How do we smell?
How does the brain learn
and interpret these signals?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
• 1300 odor receptors in a mouse
Why study smell?
• 500 in a human
It’s a primal sense

Can we study smell?

It’s difficult to
understand, but it
has tangible pieces
(molecules &
receptors)

What questions
should be asked?
How do we smell?
How does the brain learn
and interpret these signals?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
• 1300 odor receptors in a mouse
Why study smell?
• 500 in a human
It’s a primal sense
• C. elegans have 302
neurons of which 16
are dedicated to odor
Can we study smell? representing a 1000
It’s difficult to odorant receptor
understand, but it genes
has tangible pieces
(molecules &
receptors)

What questions
should be asked?
How do we smell?
How does the brain learn
and interpret these signals?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
• 1300 odor receptors in a mouse
Why study smell?
• 500 in a human
It’s a primal sense
• C. elegans have 302
neurons of which 16
are dedicated to odor
Can we study smell? representing a 1000
It’s difficult to odorant receptor
understand, but it genes
has tangible pieces
(molecules &
receptors) Gene coding is
clearly important
for odor
What questions recognition
should be asked?
How do we smell?
How does the brain learn
and interpret these signals?

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Mapping brains/neurons when exposed to odors in mice & fruit flies

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 2004 Nobel Prize in Medicine & Physiology
Mapping brains/neurons when exposed to odors in mice & fruit flies

Clear relationship but get stuck at “ghost in the machine”

Axel, R., Scents and Sensibility: A Molecular Logic of Olfactory Perception (Nobel Lecture). Angew. Chem. Int. Ed. 2005, 44 (38), 6110-6127.
 Catalytic Preparation of Fragrances
Catalytic Hydrogenations

Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
 Catalytic Preparation of Fragrances

Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
 Catalytic Preparation of Fragrances
Catalytic Hydride Reduction

Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
 Catalytic Preparation of Fragrances
Catalytic Dehydrogenation

Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
 Catalytic Preparation of Fragrances
Catalytic C–C bond formation

Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
 Catalytic Preparation of Fragrances
Catalytic C–O bond formation/cleavage

Chapuis, C.; Jacoby, D., Catalysis in the preparation of fragrances and flavours. Applied Catalysis A: General 2001, 221 (1), 93-117.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Bovo, S.; Scrivanti, A.; Bertoldini, M.; Beghetto, V.; Matteoli, U., A New Enantioselective Catalytic Route to Florhydral®. Synthesis 2008, 16, 2547–2550.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
da Silva, J. G.; Vieira, C. G.; dos Santos, E. N.; Gusevskaya, E. V., Hydroformylation of endocyclic double bonds in para-menthenic terpenes under mild conditions. Applied Catalysis A:
General 2009, 365 (2), 231-236.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
da Silva, J. G.; Vieira, C. G.; dos Santos, E. N.; Gusevskaya, E. V., Hydroformylation of endocyclic double bonds in para-menthenic terpenes under mild conditions. Applied Catalysis A:
General 2009, 365 (2), 231-236.
 Synthesis of Fragrances with Organometallic Chemistry
Aldehydes are extremely common in synthetic perfumes

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Hydrogenation with Ruthenium Yields Synthetic Analogs

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
 Synthesis of Fragrances with Organometallic Chemistry
Hydrogenation with Ruthenium Yields Synthetic Analogs

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Christian C, Gautier A, Blanc P-A (1995) Eur. Pat. Appl. EP 643958 A2 (Firmenich SA)
 Synthesis of Fragrances with Organometallic Chemistry
Hydrogenation with Ruthenium Yields Synthetic Analogs

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Chapuis C (2004) Chem Biodivers 1:980-102
 Synthesis of Fragrances with Organometallic Chemistry
Hydrogenation with Ruthenium Yields Synthetic Analogs

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
 Synthesis of Fragrances with Organometallic Chemistry
Hydrogenation with Ruthenium Yields Synthetic Analogs

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
 Synthesis of Fragrances with Organometallic Chemistry
Hydrogenation with Ruthenium Yields Synthetic Analogs

Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
Beller, M.; Blaser, H.-U. Organometallics as Catalysts in the Fine Chemical Industry; 2012.
Schulte-Elte K-H, Pamingle H, Vial C (1998) Eur. Pat. Appl. EP 882697 A1 (Firmenich SA)
 Toxicology

Criteria 2 Document

©2019 Research Institute for Fragrance Materials

 Toxicology

©2019 Research Institute for Fragrance Materials

 Toxicology

#4
Data
Methods Generation

#3
Exposure
Threshold

#2
Read-
Across Data

#1
Data

©2019 Research Institute for Fragrance Materials

 Toxicology
How to analyze 3000 fragrance materials?

©2019 Research Institute for Fragrance Materials

 Toxicology
Fragrances

Clustering based on functional group

Nitrogen Oxygen Sulfur

Acids Alcohols Esters Aldehydes Ketones Hydrocarbons
containing containing containing

Clustering based on extended fragment

Saturated Unsaturated

Vinyl Vinylene Aromatic a,b unsaturated Heterocyclic

Cyclic Straight chain Branched Cyclic Conjugated Straight chain Branched

Spiro Bicyclo Macrocyclic

# C, LogKow # C, LogKow
Functional
group

Extended
fragment
©2019 Research Institute for Fragrance Materials
 Toxicology
How to analyze 3000 fragrance materials?

©2019 Research Institute for Fragrance Materials

 Toxicology
p-Methoxy
Cinnamaldehyde

Similar

o-Methoxy
Hetero Cinnamaldehyde
aromatic
Reactivity

Alpha alkyl
substituted
hetero aromatic
Cinnamaldehyde

Alkyl substituted
Beta alkyl aromatic
substituted

Dissimilar
Alpha alkyl Alpha aryl
substituted substituted

©2019 Research Institute for Fragrance Materials

 Toxicology

http://fragrancematerialsafetyresource.elsevier.com

©2019 Research Institute for Fragrance Materials

©2019 Research Institute for Fragrance Materials
.
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

.
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Tsutsui, Y.; Mizuno, J.; Sunada, K., Does the aroma of a patient’s preferred dental topical anaesthetic affect anxiety,
fear, and autonomic nervous system activity prior to dental local anaesthesia? A randomized trial. Flavour Fragrance
J. 2018, 33 (6), 405-410.

Hamakawa, M.; Okamoto, T., The effect of different emotional states on olfactory perception: A preliminary study. Flavour
Fragrance J. 2018, 33 (6), 420-427.

Anesthetic and fear

 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Tsutsui, Y.; Mizuno, J.; Sunada, K., Does the aroma of a patient’s preferred dental topical anaesthetic affect anxiety, fear, and
autonomic nervous system activity prior to dental local anaesthesia? A randomized trial. Flavour Fragrance J. 2018, 33 (6),
405-410.

Hamakawa, M.; Okamoto, T., The effect of different emotional states on olfactory perception: A preliminary study.
Flavour Fragrance J. 2018, 33 (6), 420-427.

Emotional states
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Lee, S. M.; Cho, A. R.; Yoo, S.-H.; Kim, Y.-S., Effects of maltodextrins with different dextrose-equivalent values. Flavour
Fragrance J. 2018, 33 (2), 153-159.

Apriceno, A.; Girelli, A. M.; Scuto, F. R.; Tarola, A. M., Determination of furanic compounds and acidity for Italian honey quality.
Flavour Fragrance J. 2018, 33 (6), 411-419.

Texier–Bonniot, T.; Berdagué, P.; Robins, R. J.; Remaud, G.; Lesot, P., Analytical contribution of deuterium 2D-NMR in oriented media
to 2H/1H isotopic characterization: the case of vanillin. Flavour Fragrance J. 2018, 33 (3), 217-229.

.
Analyzing biodegradation
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Lee, S. M.; Cho, A. R.; Yoo, S.-H.; Kim, Y.-S., Effects of maltodextrins with different dextrose-equivalent values. Flavour Fragrance J.
2018, 33 (2), 153-159.

Apriceno, A.; Girelli, A. M.; Scuto, F. R.; Tarola, A. M., Determination of furanic compounds and acidity for Italian honey
quality. Flavour Fragrance J. 2018, 33 (6), 411-419.

Texier–Bonniot, T.; Berdagué, P.; Robins, R. J.; Remaud, G.; Lesot, P., Analytical contribution of deuterium 2D-NMR in oriented media
to 2H/1H isotopic characterization: the case of vanillin. Flavour Fragrance J. 2018, 33 (3), 217-229.

.
Quality testing
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Lee, S. M.; Cho, A. R.; Yoo, S.-H.; Kim, Y.-S., Effects of maltodextrins with different dextrose-equivalent values. Flavour Fragrance J.
2018, 33 (2), 153-159.

Apriceno, A.; Girelli, A. M.; Scuto, F. R.; Tarola, A. M., Determination of furanic compounds and acidity for Italian honey quality.
Flavour Fragrance J. 2018, 33 (6), 411-419.

Texier–Bonniot, T.; Berdagué, P.; Robins, R. J.; Remaud, G.; Lesot, P., Analytical contribution of deuterium 2D-NMR in
oriented media to 2H/1H isotopic characterization: the case of vanillin. Flavour Fragrance J. 2018, 33 (3), 217-229.

.
2D-NMR probing technique
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Taiti, C.; Costa, C.; Figorilli, S.; Billi, M.; Caparrotta, S.; Comparini, D.; Mancuso, S., Volatome analysis approach for the
taxonomic classification of tree exudate collection using Proton Transfer Reaction Time of Flight Mass Spectrometry. Flavour
Fragrance J. 2018, 33 (3), 245-262.

Belhassen, E.; Bressanello, D.; Merle, P.; Raynaud, E.; Bicchi, C.; Chaintreau, A.; Cordero, C., Routine quantification of 54 allergens in
fragrances using comprehensive two-dimensional gas chromatography-quadrupole mass spectrometry with dual parallel secondary
columns. Part I: Method development. Flavour Fragrance J. 2018, 33 (1), 63-74.

.
Plant classification technique
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Taiti, C.; Costa, C.; Figorilli, S.; Billi, M.; Caparrotta, S.; Comparini, D.; Mancuso, S., Volatome analysis approach for the taxonomic
classification of tree exudate collection using Proton Transfer Reaction Time of Flight Mass Spectrometry. Flavour Fragrance J. 2018,
33 (3), 245-262.

Belhassen, E.; Bressanello, D.; Merle, P.; Raynaud, E.; Bicchi, C.; Chaintreau, A.; Cordero, C., Routine quantification of 54
allergens in fragrances using comprehensive two-dimensional gas chromatography-quadrupole mass spectrometry with dual
parallel secondary columns. Part I: Method development. Flavour Fragrance J. 2018, 33 (1), 63-74.

.
Allergen detection
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Jentzsch, P. V.; Gualpa, F.; Ramos, L. A.; Ciobotă, V., Adulteration of clove essential oil: Detection using a handheld Raman
spectrometer. Flavour Fragrance J. 2018, 33 (2), 184-190.

.
Purity testing
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Trytek, M.; Paduch, R.; Pięt, M.; Kozieł, A.; Kandefer-Szerszeń, M.; Szajnecki, Ł.; Gromada, A., Biological activity of

oxygenated pinene derivatives on human colon normal and carcinoma cells. Flavour Fragrance J. 2018, 33 (6), 428-437.

Nagai, K.; Horii, Y.; Fujisaki, Y.; Fuyuki, R.; Misonou, Y., Effects of olfactory stimulation with scents of grapefruit and
lavender essential oils on the skeletal muscle sympathetic nerve and muscle blood flow in rats. Flavour Fragrance J. 2018,
33 (2), 135-143.

Satou, T.; Hayakawa, M.; Goto, Y.; Masuo, Y.; Koike, K., Anxiolytic-like effects of essential oil from Thymus vulgaris was
increased during stress. Flavour Fragrance J. 2018, 33 (2), 191-195.

.
Cancer treatment
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Trytek, M.; Paduch, R.; Pięt, M.; Kozieł, A.; Kandefer-Szerszeń, M.; Szajnecki, Ł.; Gromada, A., Biological activity of
oxygenated pinene derivatives on human colon normal and carcinoma cells. Flavour Fragrance J. 2018, 33 (6), 428-437.

Nagai, K.; Horii, Y.; Fujisaki, Y.; Fuyuki, R.; Misonou, Y., Effects of olfactory stimulation with scents of grapefruit and

lavender essential oils on the skeletal muscle sympathetic nerve and muscle blood flow in rats. Flavour Fragrance J. 2018, 33 (2),

135-143.

Satou, T.; Hayakawa, M.; Goto, Y.; Masuo, Y.; Koike, K., Anxiolytic-like effects of essential oil from Thymus vulgaris was
increased during stress. Flavour Fragrance J. 2018, 33 (2), 191-195.

.
Blood flow
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Trytek, M.; Paduch, R.; Pięt, M.; Kozieł, A.; Kandefer-Szerszeń, M.; Szajnecki, Ł.; Gromada, A., Biological activity of
oxygenated pinene derivatives on human colon normal and carcinoma cells. Flavour Fragrance J. 2018, 33 (6), 428-437.

Nagai, K.; Horii, Y.; Fujisaki, Y.; Fuyuki, R.; Misonou, Y., Effects of olfactory stimulation with scents of grapefruit and
lavender essential oils on the skeletal muscle sympathetic nerve and muscle blood flow in rats. Flavour Fragrance J. 2018,
33 (2), 135-143.

Satou, T.; Hayakawa, M.; Goto, Y.; Masuo, Y.; Koike, K., Anxiolytic-like effects of essential oil from Thymus vulgaris
was increased during stress. Flavour Fragrance J. 2018, 33 (2), 191-195.

.
Stress reduction
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Satou, T.; Hanashima, Y.; Mizutani, I.; Koike, K., The effect of inhalation of essential oil from Rosmarinus officinalis
on scopolamine-induced Alzheimer's type dementia model mice. Flavour Fragrance J. 2018, 33 (3), 230-234.

Ambrosch, S.; Duliban, C.; Heger, H.; Moser, E.; Laistler, E.; Windischberger, C.; Heuberger, E., Effects of 1,8-Cineole and
(–)-Linalool on Functional Brain Activation in a Working Memory Task. Flavour Fragrance J. 2018, 33 (3), 235-244.

Natsch, A.; Kern, S.; Corbi, E.; Pérès, C.; Nägelin, M.; Leijs, H.; van Strien, M.; Calandra, M. J.; Wang, Y., Interlaboratory
evaluation of methods to quantify skin-sensitizing hydroperoxides of limonene and linalool (II): Analysis in cosmetic bases.
Flavour Fragrance J. 2018, 33 (4), 322-330.

.
Alzheimer’s treatment
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Satou, T.; Hanashima, Y.; Mizutani, I.; Koike, K., The effect of inhalation of essential oil from Rosmarinus officinalis on
scopolamine-induced Alzheimer's type dementia model mice. Flavour Fragrance J. 2018, 33 (3), 230-234.

Ambrosch, S.; Duliban, C.; Heger, H.; Moser, E.; Laistler, E.; Windischberger, C.; Heuberger, E., Effects of 1,8-Cineole and (–)-

Linalool on Functional Brain Activation in a Working Memory Task. Flavour Fragrance J. 2018, 33 (3), 235-244.

Natsch, A.; Kern, S.; Corbi, E.; Pérès, C.; Nägelin, M.; Leijs, H.; van Strien, M.; Calandra, M. J.; Wang, Y., Interlaboratory
evaluation of methods to quantify skin-sensitizing hydroperoxides of limonene and linalool (II): Analysis in cosmetic bases.
Flavour Fragrance J. 2018, 33 (4), 322-330.

.
Brain activity
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Satou, T.; Hanashima, Y.; Mizutani, I.; Koike, K., The effect of inhalation of essential oil from Rosmarinus officinalis on
scopolamine-induced Alzheimer's type dementia model mice. Flavour Fragrance J. 2018, 33 (3), 230-234.

Ambrosch, S.; Duliban, C.; Heger, H.; Moser, E.; Laistler, E.; Windischberger, C.; Heuberger, E., Effects of 1,8-Cineole and
(–)-Linalool on Functional Brain Activation in a Working Memory Task. Flavour Fragrance J. 2018, 33 (3), 235-244.

Natsch, A.; Kern, S.; Corbi, E.; Pérès, C.; Nägelin, M.; Leijs, H.; van Strien, M.; Calandra, M. J.; Wang, Y.,
Interlaboratory evaluation of methods to quantify skin-sensitizing hydroperoxides of limonene and linalool (II):
Analysis in cosmetic bases. Flavour Fragrance J. 2018, 33 (4), 322-330.

.
Cosmetic damages
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Swathy, J. S.; Mishra, P.; Thomas, J.; Mukherjee, A.; Chandrasekaran, N., Nanometric neem oil emulsification
through microfluidization, and its therapeutic potential against Aeromonas culicicola infection in Cyprinus carpio.
Flavour Fragrance J. 2018, 33 (5), 340-350.

.
Antibacterial effects
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Yi, Q.-y.; Yi, S.-w.; Qin, T.-f.; Li, C.-y., Using RAPD and ISSR Molecular Markers to Analyze the Genetic Diversity of
Rose scented Pelargonium Populations. Flavour Fragrance J. 2018, 33 (1), 75-81.

.
Genetic testing
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Starkenmann, C.; Niclass, Y.; Beaussoubre, P.; Zimmermann, J.; Cayeux, I.; Chappuis, C. J.-F.; Fieber, W., Use of
fecal and sawdust biochar as a new perfume delivery system. Flavour Fragrance J. 2018, 33 (1), 82-90.

Song, J.; Chen, H., Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium
bromide (TADAB) and its potential applications in cosmetics. Flavour Fragrance J. 2018, 33 (2), 160-165.

.
Fecal & Sawdust biochar for perfume delivery
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Starkenmann, C.; Niclass, Y.; Beaussoubre, P.; Zimmermann, J.; Cayeux, I.; Chappuis, C. J.-F.; Fieber, W., Use of fecal and
sawdust biochar as a new perfume delivery system. Flavour Fragrance J. 2018, 33 (1), 82-90.

Song, J.; Chen, H., Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium
bromide (TADAB) and its potential applications in cosmetics. Flavour Fragrance J. 2018, 33 (2), 160-165.

.
Alginate microcapsules
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Mohammadi, N.; Ehsani, M. R.; Bakhoda, H., Development of caffeine-encapsulated alginate-based matrix combined
with different natural biopolymers, and evaluation of release in simulated mouth conditions. Flavour Fragrance J.
2018, 33 (5), 357-366.

Horváth, B.; Pál, S.; Széchenyi, A., Preparation and in vitro diffusion study of essential oil Pickering emulsions stabilized by
silica nanoparticles. Flavour Fragrance J. 2018, 33 (6), 385-396.

.
Alginate encapsulation
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Mohammadi, N.; Ehsani, M. R.; Bakhoda, H., Development of caffeine-encapsulated alginate-based matrix combined with
different natural biopolymers, and evaluation of release in simulated mouth conditions. Flavour Fragrance J. 2018, 33 (5),
357-366.

Horváth, B.; Pál, S.; Széchenyi, A., Preparation and in vitro diffusion study of essential oil Pickering emulsions
stabilized by silica nanoparticles. Flavour Fragrance J. 2018, 33 (6), 385-396.

.
Nanoparticle stabilization
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems*
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Chappuis, C. J.-F.; Huber, R.; Niclass, Y.; Starkenmann, C., Simulating latrine conditions to assess perfume
performance against malodour. Flavour Fragrance J. 2018, 33 (4), 313-321.

.
Latrine models
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Romagny, S.; Coureaud, G.; Thomas-Danguin, T., Key odorants or key associations? Insights into elemental and
configural odour processing. Flavour Fragrance J. 2018, 33 (1), 97-105.

Bastiaan-Net, S.; van den Berg-Somhorst, D. B. P. M.; Ariëns, R. M. C.; Paques, M.; Mes, J. J., A novel functional screening
assay to monitor sweet taste receptor activation in vitro. Flavour Fragrance J. 2018, 33 (2), 173-183.

.
Odor and mental connections
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Romagny, S.; Coureaud, G.; Thomas-Danguin, T., Key odorants or key associations? Insights into elemental and configural
odour processing. Flavour Fragrance J. 2018, 33 (1), 97-105.

Bastiaan-Net, S.; van den Berg-Somhorst, D. B. P. M.; Ariëns, R. M. C.; Paques, M.; Mes, J. J., A novel functional
screening assay to monitor sweet taste receptor activation in vitro. Flavour Fragrance J. 2018, 33 (2), 173-183.

.
Monitoring sweet receptors
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Cicchetti, E.; Vasseur, C., Critical comparison of selected olfactometric methods for the determination of impact
odorants. Proposal of a new representation of olfactometric results. Flavour Fragrance J. 2018, 33 (2), 144-152.

.
Argument for bubble plots
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Larcinese-Hafner, V.; Tchakalova, V., Co-surfactant, co-solvent, and hydrotropic properties of some common cooling
agents. Flavour Fragrance J. 2018, 33 (4), 303-312.

Barzegar, H.; Mehrnia, M. A.; Nasehi, B.; Alipour, M., Fabrication of peppermint essential oil nanoemulsions by
spontaneous method: Effect of preparing conditions on droplet size. Flavour Fragrance J. 2018, 33 (5), 351-356.

.
Surfactant properties of cooling agents
 Some Topics Not Covered
• Emotional Response
• Analytical Testing
• Medicinal Testing
• Botany
• Flavor/Scent Delivery Systems
• Physical Response (biology)
• Categorization Methods for Data
• Physical Properties

Larcinese-Hafner, V.; Tchakalova, V., Co-surfactant, co-solvent, and hydrotropic properties of some common cooling agents.
Flavour Fragrance J. 2018, 33 (4), 303-312.

Barzegar, H.; Mehrnia, M. A.; Nasehi, B.; Alipour, M., Fabrication of peppermint essential oil nanoemulsions by
spontaneous method: Effect of preparing conditions on droplet size. Flavour Fragrance J. 2018, 33 (5), 351-356.

.
Nanoemulsions
 Enantioselective Syntheses and Sensory Properties of
2-Alken-4-olides

Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172.
 Enantioselective Syntheses and Sensory Properties of
2-Alken-4-olides

Sharpless
asymmetric
dihydroxylation

Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172.
.
 Enantioselective Syntheses and Sensory Properties of
2-Alken-4-olides
Sensory panel test:
5 healthy, non-smoking judges
2 male, 3 female
Ages 23 to 29

Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172.
.
 Enantioselective Syntheses and Sensory Properties of
2-Alken-4-olides
Sensory panel test:
5 healthy, non-smoking judges
2 male, 3 female
Ages 23 to 29

Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172.
.
 Enantioselective Syntheses and Sensory Properties of
2-Alken-4-olides
Sensory panel test:
5 healthy, non-smoking judges
2 male, 3 female
Ages 23 to 29

Retention Times
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172.
.
 Enantioselective Syntheses and Sensory Properties of
2-Alken-4-olides
Sensory panel test:
5 healthy, non-smoking judges
2 male, 3 female
Ages 23 to 29

Amount needed
for detection
Dai, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Enantioselective syntheses and sensory properties of 2‐Alken‐4‐olides. Flavour Fragrance J. 2018, 33 (2), 166-172.
.
 Multivariate statistical analysis of a large odorants
database aimed at revealing similarities and links
between odorants and odors
• Break up odors into “subjective” • Remove any descriptors with <5 related
categories compounds
• 150 odor notes • Kept ones like “fruity,” “floral”
• 1000-2000 odorants • Removed 63 odorants

• Use self-organizing maps (SOMs) to • Used AI to split odorants into similarity

relate odor with structure via Artificial “trees”; cut trees at 3 dimensions deep
Neural Network (ANN)

• Draw 3777 odorants from Flavor-Base

(a large library of compounds)

• Retain 3571 after removing compounds

activating retronasal stimuli

Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants
and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
 Multivariate statistical analysis of a large odorants
database aimed at revealing similarities and links
between odorants and odors

Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants
and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
 Multivariate statistical analysis of a large odorants
database aimed at revealing similarities and links
between odorants and odors

“Green Split”

Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants
and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
 Multivariate statistical analysis of a large odorants
database aimed at revealing similarities and links
between odorants and odors

Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants
and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
 Multivariate statistical analysis of a large odorants
database aimed at revealing similarities and links
between odorants and odors

Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants
and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
 Multivariate statistical analysis of a large odorants
database aimed at revealing similarities and links
between odorants and odors

• “Rose” can be related to “honey,” “metallic,” “geranium”

• “Honey” and “geranium” never exist in an odor description
together
• “Rose-honey” and “rose-geranium-metallic” are different
odors related to the perception of the flowers called “roses”

Tromelin, A.; Chabanet, C.; Audouze, K.; Koensgen, F.; Guichard, E., Multivariate statistical analysis of a large odorants database aimed at revealing similarities and links between odorants
and odors. Flavour Fragrance J. 2018, 33 (1), 106-126.
 Synthesis of butenolides by reactions of 3‐alkenoic
acids with diphenyl sulfoxide/oxalyl chloride

Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-
404.
Stamatopoulos, P.; Frérot, E.; Tempère, S.; Pons, A.; Darriet, P., Identification of a New Lactone Contributing to Overripe Orange Aroma in Bordeaux Dessert Wines via Perceptual Interaction
Phenomena. J. Agric. Food. Chem. 2014, 62 (12), 2469-2478.
Rajkumar, G.; Shanmugam, S.; Galvâo, M. d. S.; Dutra Sandes, R. D.; Leite Neta, M. T. S.; Narain, N.; Mujumdar, A. S., Comparative evaluation of physical properties and volatiles profile of
cabbages subjected to hot air and freeze drying. LWT 2017, 80, 501-509.
Shu, N.; Shen, H., Aroma‐impact compounds in Lysimachia foenum‐graecum extracts. Flavour Fragrance J. 2009, 24 (1), 1-6.
 Synthesis of butenolides by reactions of 3‐alkenoic
acids with diphenyl sulfoxide/oxalyl chloride

Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-
404.
 Synthesis of butenolides by reactions of 3‐alkenoic
acids with diphenyl sulfoxide/oxalyl chloride

Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-
404.
 Synthesis of butenolides by reactions of 3‐alkenoic
acids with diphenyl sulfoxide/oxalyl chloride

Ding, R.; Li, Y.; Liu, Y.; Sun, B.; Yang, S.; Tian, H., Synthesis of butenolides by reactions of 3-alkenoic acids with diphenyl sulfoxide/oxalyl chloride. Flavour Fragrance J. 2018, 33 (6), 397-
404.
 Application of natural deep eutectic solvents for the
“green” extraction of vanillin from vanilla pods
• 2000 to 3000 tons vanilla produced every year

• <1% of vanillin in the flavor market is from vanilla

• Most extracted with aqueous ethanol (50% v/v)

• Leaves potentially undesirable ethanol (up to 35% v/v)
• Only non-toxic option

• Natural deep eutectic solvents (NADES) might be an option

• Ionic liquids could be useful, but they are highly toxic

• Some natural liquid mixtures have been shown to be ionic

• Organic acids/bases
• Could explain biological phenomena
• Unlike lipids or water, can dissolve taxol, rutin, etc.

González, C. G.; Mustafa, N. R.; Wilson, E. G.; Verpoorte, R.; Choi, Y. H., Application of natural deep eutectic solvents for the “green”extraction of vanillin from vanilla pods. Flavour
Fragrance J. 2018, 33 (1), 91-96.
 Application of natural deep eutectic solvents for the
“green” extraction of vanillin from vanilla pods

González, C. G.; Mustafa, N. R.; Wilson, E. G.; Verpoorte, R.; Choi, Y. H., Application of natural deep eutectic solvents for the “green”extraction of vanillin from vanilla pods. Flavour
Fragrance J. 2018, 33 (1), 91-96.
 Application of natural deep eutectic solvents for the
“green” extraction of vanillin from vanilla pods

González, C. G.; Mustafa, N. R.; Wilson, E. G.; Verpoorte, R.; Choi, Y. H., Application of natural deep eutectic solvents for the “green”extraction of vanillin from vanilla pods. Flavour
Fragrance J. 2018, 33 (1), 91-96.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin

• Fragrance agent • Flavoring agent

• Antifungal activity
• BP: 248 °C • BP: 265 °C

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin

• Guest-Host technique for

separation

• β-cyclodextrin (CD) showed good

affinity for CAc in past reports

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
Using ROESY (Rotating frame Overhause Effect Spectroscopy) to probe
1H-1H coupling through space

Aromatic CAc
Protons

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
Using ROESY (Rotating frame Overhause Effect Spectroscopy) to probe
1H-1H coupling through space

Aromatic CA
Protons

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin
Using ROESY (Rotating frame Overhause Effect Spectroscopy) to probe
1H-1H coupling through space

Aromatic CA
Protons

Both show Ph-ring

deep in β-CD

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin

Similar new peaks

suggest complexes
are isostructural

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Facile separation of cinnamyl acetate and
cinnamaldehyde based on host–guest complexation
with β‐cyclodextrin

Chai, K.; Xu, Z.; Zheng, L.; Zhou, L.; Tong, Z.; Ji, H., Facile separation of cinnamyl acetate and cinnamaldehyde based on host–guest complexation with β-cyclodextrin. Flavour Fragrance J.
2018, 33 (4), 285-293.
 Identification of key aroma compounds in raw and
roasted lily bulbs (Bai He)
• Lily bulbs (‘Bai He’) are a popular ingredient in Chinese cooking

• Little is known about the odorants responsible for their distinct aroma

• Solvation followed by gas chromatography-olfactometry (GC/O) were

used to identify new aroma-active compounds

Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.
http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
 Identification of key aroma compounds in raw and
roasted lily bulbs (Bai He)

Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.
http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
 Identification of key aroma compounds in raw and
roasted lily bulbs (Bai He)
• They dilute each identified compound and rate how dilute they can still
smell it; this gives a flavor dilution (FD) factor
• Dilute 1:1 , 1:2, …, 1:1024

• Raw: 25 odorants detected in the FD range from 1 to 1024

• Roasted: 42 odorants detected in the FD range from 1 to 1024

Odorants with FD > 63 in Raw Lily Bulbs

Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.
http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
 Identification of key aroma compounds in raw and
roasted lily bulbs (Bai He)
Odorants with FD > 63 in Roasted Lily Bulbs

Chiang, N.; Ho, C. T.; Munafo Jr, J. P., Identification of key aroma compounds in raw and roasted lily bulbs (Bai He). Flavour Fragrance J. 2018, 33 (4), 294-302.
http://www.ingenieria-analitica.com/downloads/dl/file/id/1226/product/95/presentacion_sniffers.pdf
 Comparison of the aromatic profile of traditional and
modern types of Huang Jiu (Chinese rice wine) by
aroma extract dilution analysis and chemical analysis
• “Pure” microorganism fermentation changes aroma profile

• Huang Jiu is a good study

• 60% is from traditional techniques
• Open pottery jars
• 30 to 90 days
• 3 years of aging
• 40% is from modern techniques
• Fermentation tanks
• 20 to 30 days
• 1 year of aging

• Tested with GC-O and GC-MS

Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis.
Flavour Fragrance J. 2018, 33 (3), 263-271.
Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis.
Flavour Fragrance J. 2018, 33 (3), 263-271.
Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis.
Flavour Fragrance J. 2018, 33 (3), 263-271.
 Comparison of the aromatic profile of traditional and
modern types of Huang Jiu (Chinese rice wine) by
aroma extract dilution analysis and chemical analysis

Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis.
Flavour Fragrance J. 2018, 33 (3), 263-271.
 Synthesis of thiophene derivatives with long-lasting
citrusy type odour

Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
 Synthesis of thiophene derivatives with long-lasting
citrusy type odour

Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
 Synthesis of thiophene derivatives with long-lasting
citrusy type odour

Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
 Synthesis of thiophene derivatives with long-lasting
citrusy type odour

Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
 Synthesis of thiophene derivatives with long-lasting
citrusy type odour

Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
 Synthesis of thiophene derivatives with long-lasting
citrusy type odour

Determined by a
6-person panel
Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R., Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragrance J. 2018, 33 (4), 279-284.
 Chemistry Careers in Fragrance
Sensient Robertet Symrise
(Nice) Firmenich
(Milwaukee) (Holzminden)
(Geneva) T Hasegawa
(Tokyo)

Takasago
IFF (Tokyo)
(Mid-Atlantic)
Frutarom
(Haifa)
Givaudan Huabao
(Vernier) (Hong Kong)

Chen, S.; Xu, Y.; Qian, M. C., Comparison of the aromatic profile of traditional and modern types of Huang Jiu (Chinese rice wine) by aroma extract dilution analysis and chemical analysis.
Flavour Fragrance J. 2018, 33 (3), 263-271.