“ Botanical energy”:

a naturalistic way
for skin-care ?

Introduction to
Chemistry of Cosmetics
Botanical Cosmetic Ingredients
Dr. CHAN, H W Dennis ©2019

Botanical / herbal ingredients

 Are cosmetic ingredients sitting in your
backyard?
 The wide variety of chemical constituents
found in plants have been used as a
biochemical resource by mankind. Many of
them have highly complex chemical
structures.
 In cosmetics, extraction of the biologically-
active compound increases the
bioavailability of the compound to the skin.
Many types of extraction processes are used
commercially to produce botanical extracts.
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Dr. CHAN, H W Dennis ©2019

Volatile Botanical ingredients

 What is a perfume? Substances  Examples:
that emits and diffuses a fragrant  eau
de parfum,
odor, especially a volatile liquid,  eau de toilette,
for applying to the skin and
clothing, putting in cleaners and  eau de Cologne
cosmetics, or scenting the air.  How to get them?

[Latin] per fume = “through smoke”

[French] la toilette = “vêtements ou accessoires
destinés à parer ” i.e. clothes and accessories that
aimed at beautifying / adorning.
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Nigel Groom, The New Perfume Handbook (2nd ed.), London: Blacke Academic & Professional ©1997.
Dr. CHAN, H W Dennis ©2019

Volatile Botanical ingredients

 Deodorant Property
 no perfume will smell exactly the same on any two people!

 The scent in pure perfume oils are far too concentrated to

smell pleasant.

 The most common solvent for dilution, is ethanol or a

mixture of ethanol and water; also can be diluted by
neutral-smelling lipids, e.g. jojoba oil or soybean oil.

ethanol triglycerides 4
 Dr. CHAN, H W Dennis ©2019

Volatile Botanical Extracts

Perfume types Concentration of
aromatic substances
Perfume (Parfum) 22% on average (up to 30%)

Eau de Parfum (EdP) 15-18%

Eau de Toilette (EdT) 5-8%

Eau de Cologne (EdC) 3-5%

Eau Fraîche < 3%

YSATIS Givenchy
CHANEL No5 CHANEL No19
Eau de Toilette
Parfum Eau de Parfum
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Dr. CHAN, H W Dennis ©2019

Expression
 also called cold press
 Oily skin of fruit is squeezed by hand, limonene
or in a press. It is manually or
mechanically pressed until all the oil
is squeezed out , e.g. orange oil,
lemon oil, bergamot oil

Citrus aurantium (orange)

Citrus grandis
(pamelo)

 This process is still used in obtaining

citrus oils from the rind, the fruit or Citrus limonum Citrus bergamia
plant. (lemon), (bergamot)
Citrus aurantifolia 6
(lime)
Dr. CHAN, H W Dennis ©2019

Expression
 Anatomy of a citrus fruit:

Peel (rind)
Segments flavedo
albedo
Juice sacs

Locular seeds
membrane pulp
central axis 7

Ref: Domingo J. Iglesias et al “Physiology of citrus fruiting” Brazilian Journal of Plant Physiology
2007, 19(4), 333-362.
Dr. CHAN, H W Dennis ©2019

Steam distillation
Linalool

 Process:
 Steam is passed through plant material held in a
still, whereby the essential oil turns to gas. It is
then passed through tubes, cooled, and liquefied. water
 Making use of the steam to get the volatile
components at a lower temperature (~100 ºC)
 e.g. lavender flowers/leaves, camphor tree stems heat 8
Dr. CHAN, H W Dennis ©2019

Steam distillation = Hydro-distillation

 An alternative: Oils can also be extracted by boiling botanical
substances (e.g. petals) in water instead of steaming them.
 higher possibility for causing :
 (i) decomposition
 (ii) resulting in tar

water

9
heat
Dr. CHAN, H W Dennis ©2019

Steam distillation

retort
Condenser
coils

10

Essencier
Dr. CHAN, H W Dennis ©2019

Solvent extraction
 Process
 Botanical materials are put into large tanks or drums
with mechanical agitation
 A solvent is poured over the botanical material
 The molecular ingredients dissolve in the solvents

Then, heat is supplied to evaporate the solvent


 a higher concentration of the perfume oil at the
bottom was left over and the essential oil obtained
this way is usually called spirits.
 Characteristics
 Wide range in selection of temperature / pressure
 Various solvent choices – volatile solvents (e.g.
benzene, hexane, or ethanol) 11
 Dr. CHAN, H W Dennis ©2019

Chemical synthesis
 Identifying molecular targets by fragrance analysis
 Expression
 Solvent Extraction
 Steam Distillation
 Headspace collection

rose furan

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1. Ohloff, Günther Scent and Fragrances, The fascination of odors and their chemical perspectives, Berlin: Springer-Verlag. ©1994, pp. 154-158.
2. R. Clery “12. Natural Product Analysis in the Fragrance Industry" in Charles S. Sell (Editors), The Chemistry of Fragrances (2nd edition) , Royal Society of Chemistry
Publishing. ©2006, pp. 214-228.
Dr. CHAN, H W Dennis ©2019

Chemical synthesis

rose oxide damascenone

farnesol 13
linalool -ionone
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Rose odor:
Rose-odor:
Rosefuran
Geraniol

Roses
Rosa centifolia /
Rosa damascena

Violet / Rose odor:

Garden Violets -ionone
Violet odor:
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(Viola Odorata) -isomethylionone
Dr. CHAN, H W Dennis ©2019

MOLECULAR COMPONENTS IN ESSENTIAL OIL OF ROSE (ROSA DAMASCENA)

Component % of Oil Threshold in p.p.b.
Citronellol 38 40
Paraffin oil (C14-C16) 16 -
Geraniol 14 75
Nerol 7 300
Phenethyl alcohol 2.8 750
Eugenol methyl ether 2.4 820
Eugenol 1.2 30
Farnesol 1.2 20
Linalool 1.4 6
Rose oxide 0.46 0.5
Carvone 0.41 50
Rose furan 0.16 200
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-Damascenone 0.14 0.009
-Ionone 0.03 0.007
Dr. CHAN, H W Dennis ©2019
Chemical synthesis
 from lemongrass aroma to rose aroma?

Catalysis by Catalysis
Hydrogen ion by acid -ionone
citral Scavenger, e.g. e.g. phosphoric and
calcium oxide acid
(from lemongrass)
(quicklime)
y-ionone
(pseudo-ionone)
-ionone

water
acetone
• Construct molecules from “building blocks”
• novel strategy to obtain botanical ingredients (totally identical to natural
botanical molecules)
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• Which is/are reactant(s)? Product(s)? By-product(s)?
1. Noda, C. et al "Aldol Condensation of Citral with Acetone on Basic Solid Catalysts". Braz. J. Chem. Eng. 1998, 15 (2).
2. Alfred Russell and R. L. Kenyon. "Pseudoionone". Organic Syntheses, Coll. Vol. 3, 23: 78.
Dr. CHAN, H W Dennis ©2019

CHEMICAL CHANGE - MECHANISM

 For advanced learners:

or

-ionone -ionone

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Dr. CHAN, H W Dennis ©2019

Non-volatile Botanical ingredients

 Botanicals aren’t just for fragrance. Many
plant extracts have provided important
source for pharmaceuticals.
 important analgesic drugs: e.g. morphine and
codeine. They are isolated from poppy (Papaver
somniferum).
Morphine

Codeine 18

Papaver somniferum
 Dr. CHAN, H W Dennis ©2019

Non-volatile Botanical ingredients

 important anti-cancer drugs: e.g.
 paclitaxel from the Pacific yew tree (Taxus brevifolia) Pacific yew tree
 vinblastine from Madagascar periwinkle
(Catharanthus roseus, a common garden flower).
They originally were identified from plants.

Paclitaxel

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Vinblastine

Madagascar periwinkle
Dr. CHAN, H W Dennis ©2019

EXPRESSION
 Vitis vinifera (Grape) seed extract
 Vitis vinifera seed oil
Procyanidin
 Procyanidin
 Tocopherol
 Tocotrienol

Tocopherol

Tocotrienol

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Dr. CHAN, H W Dennis ©2019
rhamnose
Citrus limonum extract or Citrus glucose

aurantium extract
 What is the plant?
 Citrus limonum / Citrus aurantium
 What does it contain?
 Hesperidin which is classified as a
“flavonoid glycoside”
 is a unique component found abundantly in
citrus fruit peel (mainly in albedo).
 Function:
Hesperidin
 reduced symptoms of capillary fragility and thus
contributes to the integrity of the blood vessels. They have
been shown to protect collagen (which is important
components of capillary walls.)
 anti-inflammatory effects.
 can neutralize ROS
 inhibit the tyrosinase activity in melanogenesis 21
 is a botanical humectant
Dr. CHAN, H W Dennis ©2019

Scutellaria baicalensis
Root extract
 What is the plant?
 Scutellaria Baicalensis (common name:
Baikal Skullcap)
 one of the common traditional Chinese
medicinal plants called “Huang-qin”
 What does it contain? Glucuronic

 Baicalin which is classified as a

acid Baicalin
“flavonoid glycoside”
 Function:
 anti-inflammatory effects
 antibacterial and antiviral
 can neutralize ROS
 inhibit the tyrosinase activity in
melanogenesis 22
 is a botanical humectant
Dr. CHAN, H W Dennis ©2019

Solvent Extraction Addition of

Botanical material
from botanical material
 Extraction procedures of flavonoid Addition of
glycosides, E.g. baicalin from Scutellaria Extraction solvent
Baicalensis (or hesperidin from citrus
limonum/citrus aurantium) Adjust temp /
 Soaked with 60% ethanol with mechanical pressure
stirring
Filtration
 Heated up to 80 °C for 1~2 hr
 Filtration: to remove residual botanical material Evaporation
(concentration)
 Concentration by evaporation of solvent
 Other methods: e.g. extraction with boiling
water, and/or assisting with ultrasonication for
extracting baicalin from Scutellaria baicalensis
(or hesperidin from citrus limonum/citrus 23
aurantium)
Dr. CHAN, H W Dennis ©2019

Example
• KANEBO® HADABISEI Clear White Essence
 Ingredients:
 Water, Glycerin, Alcohol, Cyclomethicone, Diglycerin,
Sorbitol, Ascorbyl Glucoside, Dipropylene Glycol, PEG-60
Hydrogenated Castor oil, Potassium Hydroxide, Carbomer,
Panthenol, Phenyl Trimethicone, Methyl Gluceth-20,
Polysorbate-20, Dipotassium Glycyrrhizate, Xanthan Gum,
Niacinamide, Sodium Citrate, Butylene Glycol, Disodium
EDTA, Citric Acid, Citrus limonum Extract, Soluble
Collagen, Methylparaben.
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Dr. CHAN, H W Dennis ©2019

Example
OLAY® WHITE RADIANCE RESTORING EMULSION
 Ingredients:
 Magnesium Ascorbyl Phosphate, Water, Glycerin, Isohexadecane,
Dimethicone, Dimethiconol, Isopropyl Isostearate, Sucrose
Polycottonseedate, Sodium Hydroxide, Cetearyl Glucoside, Cetearyl
Alcohol, PEG-100 Stearate, Stearic Acid, Carbomer, Stearyl Alcohol,
Cetyl Alcohol, Behenyl Alcohol, Propylparaben, Ethylparaben, Benzyl
Alcohol, Disodium EDTA, Niacinamide, Tocopheryl Acetate, Panthenol,
Morus Alba Root Extract, Pyridoxine Dipalmitate, Ginkgo Biloba Leaf
Extract, C10-18 Triglycerides, Panax Ginseng Root Extract, Helianthus
Annuus Seed Oil, Hesperidin, Perfume, Angelica Acutiloba Extract,
Lonicera Japonica Flower Extract, Lilium Candidum Flower Extract,
Yellow No. 5, Red No. 40, Blue No. 1 25
Dr. CHAN, H W Dennis ©2019 Example
REVLON®
AGE DEFYING MAKE UP WITH BOTAFIRM SPF 20
 Ingredients:
 Water, Cyclomethicone, Dimethicone, Propylene Glycol,
Titanium Dioxide, Zinc Oxide, Cetyl PEG/PPG-10/1
Dimethicone, Polyglyceryl-4 Isostearate, Magnesium Sulfate,
Methyldihydrojasmonate, Boron Nitride, Acetyl Hexapeptide-3,
Nylon-12, Stearic Acid, Polyglyceryl-6 Polyricinoleate,
PEG/PPG-18/18 Dimethicone, Triethoxycaprylylsilane,
Aluminum Hydroxide, Alumina, Soybean Protein, Retinyl
Palmitate, Tocopheryl Acetate, Panthenol, Hydrolyzed
Glycosaminoglycans, Sodium Ascorbyl Phosphate, Aloe
Barbadensis Leaf Juice, Salicylic Acid, Hydrolyzed Soy Protein,
Macrocystis Pyrifera Extract, Hydrolyzed Wheat Protein, PVP,
Mushroom Extract, Anthemis Nobilis Flower Extract, Saxifraga
Sarmentosa Extract, Grape Fruit Extract, Morus Bombycis Root
Extract, Scutellaria Baicalensis Root Extract,
Methoxypropylgluconamide, Laureth-7, Glycerin, Silica,
Methicone, PEG/PPG-20/15 Dimethicone, Dimethiconol,
Tribehenin, PEG-10 Dimethicone, Butylene Glycol, Sodium
Hyaluronate, Tetrasodium EDTA, Methylparaben, 26
Propylparaben, Mica, Iron Oxides (CI77491/CI77492/CI77499)
Dr. CHAN, H W Dennis ©2019

FURTHER READINGS:
1.Tracy Cornuelle; Jan Lephart “18. Topical Botanicals” in Zoe Diana Draelos,
Lauren A. Thaman (ed.) Cosmetic formulation of skin care products, New
York: Taylor & Francis, © 2006.
2.Cindy K. Angerhofer; Daniel Maes; Paolo U. Giacomoni “10. The Use of
Natural Compounds and Botanicals in the Development of Anti-Aging
Skin Care Products” in Nava Dayan (ed.), Skin Aging Handbook: An
Integrated Approach to Biochemistry and Product Development, New York:
William Andrew Inc. © 2008.
3.Anne-Dominique Fortineau, “Chemistry Perfumes Your Daily Life”,
Journal of Chemical Education 2004 , Vol. 81 (1), 45-50.
[ http://pubs.acs.org/doi/abs/10.1021/ed081p45 ]
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