SCS Summer School Fragrance

With ‘nose’ Marianne Martin

• To inspire your interest in fragrance

• To develop an understanding of the process to select the perfect fragrance for a personal care product

• To help prepare you for the SCS distance learning diploma examination

2 Learner Outcomes by the end of the session learners will be able to: • Describe at least one extraction techniques for fragrance ingredients of natural origin • Select personal care fragrances against various parameters • Use a smelling blotter

3 Finding out about each other and our sense of smell In groups of 3 to 5 people find out:

1. Each other’s name/s 2. What are each other’s most favourite and/or least favourite smells 3. Any strong memories related to scent 4. Can you identify some of the botanicals? 5. If not describe their odour 6. Explore their odour today even if you believe they are familiar 7. They all contain essential oils in tiny sacs. You can only see the oil sacs with the naked eye in one of the botanicals. Can you see which one? Finding out about each other and our sense of smell In groups of 3 or 5 people:

7. All the botanicals contain essential oils in tiny sacs. You can only see the oil sacs with the naked eye in one of the botanicals. Can you see which one? 8. Choose a spokesperson to relate the most interesting observation or anecdote from your group discussion. Lemon Citrus Medica Limonum • Citrus fruit • Grown in Sicily • Essential oil sacs 0.4-0.6mm diameter • Cold extraction techniques

6 Cold pressed or expressed oil production

7 Lemon Citrus Medica Limonum

• The odour of the fresh essential oil is mouth wateringly close to the original • Citrus oils are prone to oxidation and deteriorate quickly • How would you store a citrus oil to improve its shelf life?

8 Rosemary Rosmarinus Officinalis • Herb • Reputed to aid memory • In ancient Greece students would rub rosemary on their foreheads before exams to help them remember

9 Rosemary Rosmarinus Officinalis • Alpha and beta wave patterns in the brain are affected by rosemary • Most people feel more alert but calm when smelling rosemary

10 Rosemary Rosmarinus Officinalis • Rosemary oil contains camphor • Camphor is found in medicated products such as Vick’s vapour rub • In perfumery we use the term camphoraceous meaning smells camphor like

camphor 11 Some academic studies confirming the effects of rosemary oil and lavender EEG activity, alertness, and mood were assessed in 40 adults given 3 minutes of aromatherapy using two aromas, lavender (considered a relaxing odor) or rosemary (considered a stimulating odor). Participants were also given simple math computations before and after the therapy. The lavender group showed increased beta power, suggesting increased drowsiness, they had less depressed mood (POMS) and reported feeling more relaxed and performed the math computations faster and more accurately following aromatherapy. The rosemary group, on the other hand, showed decreased frontal alpha and beta power, suggesting increased alertness. They also had lower state anxiety scores, reported feeling more relaxed and alert and they were only faster, not more accurate, at completing the math computations after the aromatherapy session. Diego et al, (1998), Aromatherapy Positively Affects Mood, Eeg Patterns of Alertness and Math Computations, International Journal of Neuroscience A study with 140 participants looked at the effects on memory of lavender oil, rosemary oil and no odour (the control group). The rosemary group showed overall improved quality of memory but with an impairment of speed compared to the control. Moss et al, (2003), Aromas of Rosemary and lavender essential oils differentially affect cognition and mood in healthy adults, International Journal of Neuroscience 12 Clove Buds eugenol Eugenia Caryophyllus • Spice • Contains 75-80% eugenol • What problems might occur in personal care products containing clove oil?

Photographs by Tony Burfield

13 Clove Buds Eugenia Caryophyllus eugenol • Spice • Contains 75-80% eugenol • Eugenol is one of the commonly reported EU allergens • How could the addition of clove oil affect the INCI label of a personal care product? Photographs by Tony Burfield

14 Distillation invented in Arabia

• The Arabs invented the alembic still • Distillation is mentioned around 200 – 300 CE but the alembic still with a more efficient condensing system is invented around the 11th or 12th century CE • Words beginning with al- are derived from Arabic

• “al” is the article or “the” in Arabic manuscript held in Arabic the British Library showing an alembic still

15 Distillation invented in Arabia

Translation of the text in the manuscript by LCF students: To my son, You should know that if your flame is too strong the water will rise yellow to where collected and will be ruined. When your flame is utilized in the proper way, you will obtain what you need, having the will and support of God. The Arabic manuscript held in distillate should be kept away the British Library from sunlight until needed; showing an alembic still then take the oil from the water. 16 Stem Distillation

17 Steam Distillation The process

• The distillation vessel is loaded or “charged” with the botanical • Steam is passed up through the botanical • The oil sacs are ruptured and the volatile essential vapour is carried with the steam into the “Goose neck” outlet • The essential oil and steam condense in the condenser • Depending on the density of the oil, it either floats or sinks in the collection vessel or “Florentine” flask (the majority of essential oils float) • The oil can be tapped off

18 Fragrances including Clove oil

Old Spice, Shulton, 1938 Opium, Yves St Laurent, 1977 19 Frankincense or Olibanum resin Boswellia Carterii

• Frankincense oozes from the stems of a bush and hardens in the sun • The bushes grow in arid regions of Yemen and Southern Arabia • In ancient times there was an incense trade route • Wars were fought over the control of frankincense trade

Censer 3rd century BC Shabwa, Yemen 20 British museum collection Photo by Muhammad Al Shanfari 21 Frankincense or Olibanum resin Boswellia Carterii

• Olibanum is processed by steam distillation to make the essential oil • Olibanum is also extracted using hydrocarbon solvents to make the resinoid • In which products can the sticky resinoids cause problems?

22 Fragrances containing Frankincense or Olibanum resin Boswellia Carterii

2MAN Comme des Garçons 2004

23 Fragrances with Frankincense or Olibanum resin Boswellia Carterii

2 Man, Comme des Garçons, 2004

Rei Kawkubo designer 24 Japanese Perfumery

• The Tale of Genji written around 1000 AD has numerous references to fragrance • A chapter dedicated to perfume creation competitions

2 Man, Comme des Garçons, 2004 25 Benzoin

INCI name Styrax Benzoin Botanical name Styrax Tonkinensis Geographic Origins Thailand, Indonesia, Philippines Botanical part Exudate from tree trunk

Extract Resinoid

Odour family Balsamic

26 Fragrances containing benzoin

Shalimar, Guerlain, 1925 Jicky, Prada Candy, Guerlain, 1898 Prada, 2011 27 Benzoin Balsamic Family

• Balsams are odorous resinous exudates from shrubs found in the desert • They are sweet smelling and warm so vanilla is included in the balsamic odour family although it is from a dried bean • Balsams and balsamic notes include: Olibanum

Benzoin Myrrh Frankincense or Olibanum in the perfumery trade Myrrh Opoponax Peru Balsam Tolu Balsam Cistus Labdanum Vanilla

28Vanilla Pink Pepper Shinus Molle

• Relatively new perfumery material (1990s onwards) • Extraction method uses

• liquid CO2 • under high pressure • in costly equipment • made of 20mm thick stainless steel

29 CO2 Extraction

Extraction columns charged with Condenser – Evaporator botanical Containing heat exchangers

Liquid CO2 Sump collecting crude storage tank extraction product

30 CO2 Extraction

• CO2 is compressed to a liquid and passed through the charge in a series of vessels • The resultant liquid passes to the evaporator • The CO2 evaporates to a gas and is passed back into the condenser and used again • The extract is collected

• Some manufacturers use subcritical liquid CO2 • Some manufacturers use supercritical liquid CO2

31 Fragrances including Pink Pepper

Pleasures, Estée Lauder, 1995 32 Fragrances including Pink Pepper

Eau des Merveilles, Hermes, 2004

33 Tonka bean Dipteryx odorata

The tree that yields tonka beans is from central America especially Venezuala

34 Tonka bean Dipteryx odorata

Tonka beans contain coumarin

35 The first synthetic used in perfumery

Coumarin

IUPAC name Chromen-2-one

Functional group Lactone Fougère Royale, Houbigant, Occurrence Found in nature 1882 contained about 50% e.g. Tonka beans of the recently synthesised Odour note Powdery chemical coumarin

Perfumery uses Part of the bottom note accord Blends well with moss, balsamic notes and other lactones

36 The First “Modern” Perfume The father of fragrance for men • Fougère Royale, Houbigant, 1882 contained about 50% of the then recently synthesised chemical coumarin

• Fougère means fern in French • Ferns have little or no odour • Houbigant said in his marketing: “If God had created an odour for fern it would be Fougere Royale”

37 The First “Modern” Perfume The father of fragrance for men

• We still use the term Fougère to describe the family of male fine fragrance started by Fougère Royale

38 THE FOUGÈRE ACCORD

Fougère Paco Rabanne Drakkar Noir pour homme Hugo Mr Burberry Houbigant Guy Laroche Paco Rabanne Hugo Boss Burberry 1882 1982 1973 1995 2016

1964 1988 2016 Brut Coolwater Boy Shulton Davidoff Chanel

39 Variation in Odour Perception LCF Student Odour Recognition Journal entries for Calone

a) Watermelon; fresh, sweet; reminds me of a summer picnic with watermelon to eat

b) Whenever I eat salmon my mum makes a bowl of sliced cucumbers dowsed in vinegar. Calone reminds me of that

c) Fresh ozonic; reminds me of sea shore, shells, fish, marine life

d) Ocean, salty, fishy; matt, wet; reminds me of a smelly beach, not pleasant

40 Variation in Odour Perception LCF Student Odour Recognition Journal entries for Calone

Watermelon; fresh, sweet; reminds me of a summer picnic with watermelon to eat

Reminds me of watermelon juice I always drink at dinners in Malaysia

41 Influence of Synthetics in 20th Century Perfumery

Calone

IUPAC name 7-Methylbenzo(1,4)dioxepin-3-one

Functional group Cyclic diether and ketone

Occurrence Not found in nature

Odour Family Aquatic

Perfumery uses Fresh ozonic, marine note and water melon. Calone is evident throughout the fragrance profile Trend setter Calone was patented in 1966 but waited until the 1990s to create a new fashion in fragrance:

New West for him, Aramis, 1988

42 Influence of Synthetics in 20th Century Perfumery and beyond Calone

New West for him Acqua di Giò Boss Pure Aramis 1988 Giorgio Armani 1996 Hugo Boss 2008

Escape for women L’Eau d’Issey L’Eau par Kenzo pour Homme CK2 Calvin Klein 1991 Issey Miyake 1992 Kenzo 1999 Calvin Klein 2016

43 Find out about fragrance on the web

• www.osMoz.com • www.fragrantica.com • www.basenotes.net

44 Fragrance Exam Question 2013 a) Answer all parts: Part 1 State which extraction technique would be used in each of the following scenarios to produce ingredients for the fragrance industry and briefly give your reasons: a) Scenario 1: You are a poor farmer trying to supplement your income with a 2 marks cash crop. You grow vetivert to create terracing on your land. How would you process the vetivert root with limited capital resources? b) Scenario 2: Jasmin is a delicate flower the odour is destroyed at high 2 marks temperatures. With fellow farmers and the aid of a fragrance raw material producer you create a cooperative to process jasmin flowers. What extraction method/s would you use to make a product that can be used in alcoholic perfumery? c) Scenario 3: You are a flavour/fragrance raw materials producer. There is a 2 marks huge demand for natural vanilla flavours. What equipment might you invest in to produce a vanilla extract eligible for natural accreditation by COSMOS or Ecocert? Part 2 9 marks Describe in detail the extraction techniques used in scenario 2 above.

45 Vetivert oil

INCI name Vetiveria Zizanoides Geographic Origins Indonesia, Haiti, Bourbon, India Botanical part Root Extract Oil Vetivert root Odour family Woody

Vetivert bundles

Vetivert Distillation 46 Vetivert oil

INCI name Vetiveria Zizanoides Geographic Origins Indonesia, Haiti, Bourbon, India Botanical part Root Extract Oil Odour family Woody Perfumery uses Widely used in men’s fine fragrance Long lasting base note

Vetivert is a grass above ground with a deep odorous root system

Vetivert being planted for terracing Vetivert is used here to help protect the more delicate crop basil 47 Fragrance Exam Question 2013 a) Answer all parts: Part 1 State which extraction technique would be used in each of the following scenarios to produce ingredients for the fragrance industry and briefly give your reasons: a) Scenario 1: You are a poor farmer trying to supplement your income with a 2 marks cash crop. You grow vetivert to create terracing on your land. How would you process the vetivert root with limited capital resources? b) Scenario 2: Jasmin is a delicate flower the odour is destroyed at high 2 marks temperatures. With fellow farmers and the aid of a fragrance raw material producer you create a cooperative to process jasmin flowers. What extraction method/s would you use to make a product that can be used in alcoholic perfumery? c) Scenario 3: You are a flavour/fragrance raw materials producer. There is a 2 marks huge demand for natural vanilla flavours. What equipment might you invest in to produce a vanilla extract eligible for natural accreditation by COSMOS or Ecocert? Part 2 9 marks Describe in detail the extraction techniques used in scenario 2 above.

48 Jasmine

Botanical name Jasminum grandiflorum INCI name Jasminum officinale Geographic Origins Egypt, India, Morocco, China, (historically France) Botanical part Flower Extract Concrete, Absolute Flowers are too delicate to steam distil , essential oil is not made Yield Around 0.3% Odour family Floral

49 Solvent Extraction

Concrètes

• The hydrocarbon solvent extracts non-odorous materials from the botanical as well as the odorous materials • The non-odorous materials are mainly waxes and colours • Concrètes are insoluble in alcohol (ethanol) or water based systems • They can be used directly in soap perfumery and non- aqueous balms • Concrètes are the starting point for further extraction with ethanol to produce absolutes

50 Solvent Extraction

Absolutes

• An absolute is made by mixing ethanol with the concrète • Tapping off the ethanol solution from the waxes • Distilling off the alcohol under vacuum • Absolutes are soluble in alcohol (ethanol) but still contain colour

51 Is this jasmine concrete or jasmine absolute?

52 Solvent Extraction Why not just extract with alcohol in one step?

• Most botanicals contain too much water to make direct alcohol extraction possible • More unwanted non-odorous materials would be removed in the aqueous alcohol system and some of the hydrophobic aroma chemicals would not be extracted efficiently

53 Fragrance Exam Question 2013 a) Answer all parts: Part 1 State which extraction technique would be used in each of the following scenarios to produce ingredients for the fragrance industry and briefly give your reasons: a) Scenario 1: You are a poor farmer trying to supplement your income with a 2 marks cash crop. You grow vetivert to create terracing on your land. How would you process the vetivert root with limited capital resources? b) Scenario 2: Jasmin is a delicate flower the odour is destroyed at high 2 marks temperatures. With fellow farmers and the aid of a fragrance raw material producer you create a cooperative to process jasmin flowers. What extraction method/s would you use to make a product that can be used in alcoholic perfumery? c) Scenario 3: You are a flavour/fragrance raw materials producer. There is a 2 marks huge demand for natural vanilla flavours. What equipment might you invest in to produce a vanilla extract eligible for natural accreditation by COSMOS or Ecocert? Part 2 9 marks Describe in detail the extraction techniques used in scenario 2 above.

54 CO2 Extraction

Extraction columns charged with Condenser – Evaporator botanical Containing heat exchangers

Liquid CO2 Sump collecting crude storage tank extraction product

55 CO2 Extraction

• Some manufacturers use subcritical liquid CO2 • Some manufacturers use supercritical liquid CO2

56 57 Below are some of the botanicals extracted

using CO2

Vanilla Coffee

Green tea Pink Pepper 58 Comparison of extraction techniques

Extract Temp of Hydrolysis Protein Contains Contains Capital Certified process degradation waxes colour investment Natural by “stilly”odours for COSMOS equipment Cold Pressed Ambient Sometimes if X Low to essential oil from there is contact ✓ ✓ Medium ✓ with juice citrus fruit

100°C (less if dry Low levels Low Essential oil steam used) X (lower if ✓ (Higher for ✓ by vacuum and dry Steam distillation vacuum applied) steam) Concrete ca 30°C X X ✓ High levels Medium X

Absolute ca 30°C X X X High levels Medium X

CO2 extract Sub critical 10-20°C X X X Medium Very high ✓ typical Super critical 31°C+ X X X Medium Very high ✓ 59 Evaluation/Attribute Analysis Exercise

• There are 5 submissions to smell A-E • Allow every member of your group to smell the fragranced product before anyone speaks • Match each fragrance to one of the following simple odour descriptions/odour families: Evaluation exercise Odour families Jar letter

1 Balsamic, fruity, floral, chypre

2 Citrus, lemon

3 Ozonic/marine

4 Aldehydic, floral

5 Green Evaluation exercise Odour families Jar letter

1 Sweet, fruity, floral, chypre

2 Citrus, lemon

3 Ozonic/marine

4 Aldehydic, floral

5 Green u Fragrance and colour are intimately related Decide whichPink fragrance/s match/es each colour way

Green

Purple Name Jar letter/s

Sea salt and kelp

Meadow fresh with star flower

Invigorating wakeup call

Sensual moments

Sunflower and sunshine

Powder fresh Star flower

Borago Officinalis Tangible Product Benefit Jar letter/s

Cleanliness

Hair shine

Moisturising

Hair volume

? Intangible benefit Jar letter/s

The user feels fresh

The user feels sensual

The user feels that they care for themselves

The user feels that they care for the environment

? Signal Attribute Jar letter/s The onlooker feels that the user cares for themselves The buyer feels the product signals they care for their family The onlooker feels that the user has a vibrant personality The onlooker feels that the user is safe and dependable

The user feels the product signals a sporty life style

? Aims

• To inspire your interest in fragrance

• To develop an understanding of the process to select the perfect fragrance for a personal care product

• To help prepare you for the SCS distance learning diploma examination

69 Learner Outcomes by the end of the session learners will be able to: • Describe at least one extraction techniques for fragrance ingredients of natural origin • Select personal care fragrances against various parameters • Use a smelling blotter

70 • Good luck with your studies • The average person: takes about 3 million breaths a year • Enjoy your sense of smell

Thank you