Volatile oils & Resins

Nichakan Peerakam, Ph.D.

http://www.gatain.com/wp-content/uploads/2015/11/chamomile_oil.jpg https://cdn.shopify.com/s/files/1/1326/5735/products/Frankisence_resin_grande.jpg?v=14731
 วัตถุประสงค์
• เข้าใจความหมาย สามารถอธิบาย ลักษณะ คุณสมบัติ การใช้
ประโยชน์ในทางเภสัชกรรมของ volatile oil และ resins ได้
• บอกชนิดของ volatile oil และ resins ได้
• อธิบายกระบวนการสกัดเพื่อให้ได้มาซึ่ง volatile oils และ
resin ได้
 Contents
Volatile oils Resins
o Introduction o Classifications of resins
o The Physical properties o Characteristic components of
o Advantages resins
o Sources of volatile oils o The physical properties of
o Major categories of volatile oils resins
o Classification of volatile oils
: Hydrocarbons References
: Oxygenated hydrocarbons
o Volatile oil extraction

https://www.organicfacts.net/wp-content/uploads/2013/05/sageessentialoil2.jpg
http://www.dentistryiq.com/content/dam/diq/online-articles/2015/04/essential-oil-bottles.jpg
Introduction
 Volatile oils are the organic compounds
generated from plants and animals.
 Uniqueness of the odor
 Sometimes called “Essential oil”
 ภาษาไทยเรียก “นา้ มันหอมระเหย”
 Large number of biological activities
Plants are able to synthesize two kind of oils.
• Fixed oils: consist of esters of glycerol and fatty
acid (triglycerides).
• Essential oils: the mixtures of volatile, organic
compounds originating from a single botanical
source, and contribute to the flavor and fragrance
of plants.

https://www.sks-bottle.com/images/aroma_dropbtlsLRG.jpg
 Volatile oils are stimulated in many parts of the
plant and stored in plant cells such as glands,
glandular hairs, oil ducts or resin ducts.
Some plants produce the volatile oils by stimuli
from fungus.

https://static1.squarespace.com/static/54bd6f5ce4b032b48e8edb6b/54bd7 https://lifethymebotanicals.com/wp- https://3.imimg.com/data3/EW/BG/MY-

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The physical properties
 Colorless or slightly yellow
 Reacts due to exposure to light and air
 Less dense than water
 High refractive index
 Optical rotation
 Soluble in usual organic solvent
(ether, chloroform, alcohol ) and fat

http://cdn.dontmesswithmama.com/wp-content/uploads/2014/10/Top- http://sedonaaromatherapie.com/blog/wp-
50-Homemade-Holiday-Gifts-Ideas-with-Essential-Oils.jpg content/uploads/2015/12/Christmas-Scents-lisa870-Fotolia.j
Advantage
In nature;
• In nature many single chemical constituents found in essential oils
are used for insect communication. >>>>”insect pheromones”

Humans;
• Used as therapeutic agent
• Used as flavoring agent in food industry
• Used in perfume and cosmetic industries
• Used as material for synthesis of other compounds.

http://www.homesbydeonnalinsky. http://www.hulala.my/photos/deals/17714/main/main-w-4-hours-full-body- http://www.naturalkelley.com/uploads/5/7/3/0/57308603/

com/images/industry-spice.png traditional-aromatherapy-massage-aroma-phyto-facial.jpg s695003123253507793_p24_i2_w413.jpeg
 Effect of essential to the human
body system

• Relevant to the olfactory system

: Olfactory epithelium
- Olfactory receptor
: Limbic system
- Hypothalamus, amygdala and hippocampus

https://blackchicken.com.au/blogs/news/8-
things-know-inhaling-pure-essential-oils
• Relevant to Gastrointestinal tract
: Relieve and treatment the symptom
- carminative, flatulence
- digestion
- nausea, vomit
- antispasmodic
- stimulate liver function

http://www.essentialoilspedia.com/ib
• Relevant to Respiratory system
- mucolytic
- cold and stuffy nose

https://www.thehippyhomemaker.com/the-science-of-
smell-in-aromatherapy-how-smelling-essential-oils-works/
 Sources of volatile oils
 Plants that produce essential oils belong to many
different botanical species.
 There are found throughout the globe.
 5% of aromatic plants found from 350,000 plant
species estimated globally.
 More than 400 of these are commercially processed
for their aromatic raw material.
 About 50% being cultivated.

https://s-media-cache- https://jennscents.com/wp-content/uploads/2016/08/holistic- https://s-media-cache- http://www.reflexionofsole.co

ak0.pinimg.com/originalsb.jpg ak0.pinimg.com/originals/4a.jpg m/files/4769/323211.jpg
 Sources of volatile oils (cont.)
 Apiaceae (Umbelliferae) o วงศ์ ผักชี
 Asteraceae (Compositae) o วงศ์ ทานตะวัน/ วงศ์ ดาวเรื อง
 Lamiaceae (Labiatae) o วงศ์ กระเพรา
 Lauraceae o วงศ์ อบเชย
 Myrtaceae o วงศ์ ชมพู่ เช่ น กานพลู ยูคาลิปตัส
 Piperaceae o วงศ์ พริกไทย
 Pinaceae o วงศ์ สนเขา
 Rutaceae o วงศ์ ส้ ม
 Zingiberaceae o วงศ์ ขิง-ข่ า
http://baringtheaegis.blogspot.com http://seedspadensword.ning.com
 Plant families that provide large
Lamiaceae
quantities of volatile oils Zingiberaceae
Piperaceae Rutaceae
Apiaceae Pinaceae

Glandular hairs Rhizomes

ของต้ นและใบ Modified Schizogenous passages
Vittae Schizogenous
parenchyma cell ของเปลือกผล petals
ของ pericarp passages
ของทั้งต้ น
http://www.botany.hawai http://www.ucmp.berkeley.ed https://www.pinterest.c http://www.aphotoflora.co https://hiveminer.com/Ta http://pro-natura.ro/wp-
i.edu/faculty/carr/lami.ht u/anthophyta/paleoherbs/pipe om/noreshen/carrot- m/arb_pinaceae_pine_famil gs/philippinelime/Timeli content/uploads/2014/05/Cur
m rales.html family-apiaceae/ y.html ne cuma-Curcuma-longa-30.jpg
Major categories of volatile oils
• Terpenoids
They are constructed from a series of
isoprene unit (2-methylbuta-1,3-diene)
linked together in head to tail fashion
which is usually found in monoterpenoids
(C-10) and sesquiterpenoids (C-15).
: Synthesis from Isoprenoid pathways
such as limonene, citral, geraniol, menthol
and camphor etc.
• Phenylpropanoids
These compounds contain a benzene ring
structure with an attached propane (C3) side chain.
Eugenol
The most common precursor is cinnamic acid, a
derivative of the shikimic acid pathway.
Exp. Eugenol, anethol

Anethol

• กลุ่มอื่น ๆ
ได้แก่สารในกลุ่ม coumarins, sulfur compounds, hydrocarbons
เช่น n-heptane เป็ นต้น
Classification of volatile oils

1.Hydrocarbons
 Essential oils contain simple hydrocarbons in the form of
terpene.
 Terpenes make up the largest chemical group of natural products
with over 30,000 known terpene compounds.
 It is according to the number of isoprene units that their
molecules contain.
 In the structure of hydrocarbon volatile oils, alkenes are common
constituents of essential oils. A carbon-carbon double bond has special
chemical properties because of its electron density, and can be considered in
a similar way to heteroatom-containing functional groups.

Exocyclic double bond

Endocyclic double bond

 Monoterpene hydrocarbons
 Unsaturated hydrocarbons formed by the joining of two
isoprene units and have ten carbon atoms.
 Colorless
 Highly volatile
 Insoluble in water
 Low boiling points
 Prone to oxidation
General therapeutic actions of monotepenes
including:
 Antiseptic; antibacterial; antiviral
 Chemopreventive
 Stimulating; energizing
 Mild expectorants/ decongestants (specifically needle oils, such as pine)
 Drying/dehydrating effect on skin and mucous membranes

Note:
All terpene compounds react easily to oxygen and can degrade quickly.
It can make certain essential oils potential irritants and/or sensitizers.
Example of monoterpene hydrocarbons
Chemical compounds Source of plants
Citrus fruits, e.g. Lemon, Tangerine, Bitter and Sweet
Limonene
orange, Neroli, Caraway, Dill, Fir, Mint, Pine
Myrcene Pine, Juniper and many other oils
-pinene, -pinene Pine and many other oils
-ocimene Basil
d-limonene Begamot, Citronella, Lemongrass, Palmarosa
Terpinolene Eucalyptus, Tea tree
-phellandrene Dill, Fennel, Black pepper
-phellandrene Angelica seed, Dill, Pine, Fir, Cypress
Marjoram, Cardamon, Lemon and some Ocimum species
-terpinene
(Basil)
(-)-car-3-ene Pine, Black pepper
 Sesquiterpene hydrocarbons
 Fifteen carbon atoms and based upon the joining of
three isoprene units.
 Colorless (except chamazulene, which is blue)
 Insoluble in water
 More aromatic
 Less volatile
 Higher boiling points than monoterpenes
 Non polar compound and oxidizes slower than
monoterpenes
General therapeutic actions of sesquiterpenes are:

 Antiseptic
 Antibacterial
 Powerful anti-inflammatory
 Antispasmodic
 Calming and soothing to the nervous system
Example of alkene hydrocarbons
contained in volatile
-cadinene, -cedrene, chamazulene,
Endocyclic
-copaene, -gurjunene, -humulene,
alkenes -phellandrene, -pinene, -thujene
(E)-and (Z)-anethole, apiole (dill and Eugenol
Exocyclic parsley), (-)-aromadendrene, (-)-
alkenes camphene, eugenol, longifolene, -
pinene, safrole, -santalene

Acyclic -farnesene, -myrcene, -ocimene

alkene
Turpentine oil (นา้ มันสน) Leech lime (มะกรูด)
 Distilled from Pinus palustris, Pineceae  The pill fruit of Citrus hystrix, Rutaceae
family family
 -pinene and -pinene are the major  -pinene and limonene are the major
components. components.
 Used for counterirritant  Used as spice and fragrance

(-)-pinene (-)-pinene

http://www.conifers.org/pi/P http://www.carolinanatur https://www.daleysfruit.com.au/buy/kaffi http://www.planfor.fr/achat,

inus_palustris.php e.com/trees/pipa.html r-lime-tree.htm combava,1273,FR
 2. Oxygenated Hydrocarbons
 The construction is hydrocarbons with the addition of
oxygen.
 The oxygenated hydrocarbons are governed by a functional
group that provides the family with general physical and
chemical attribute.

A functional group is an atom or group of atoms that

imparts specific chemical and physical properties to a
molecule such as alcohol has the function of –OH.
Alcohols
 The organic compounds that contain hydroxyl group (-OH).
 Polar molecules and a higher boiling point than terpenes of similar
molecular weigh.
 They typically have pleasant aromas and are slightly soluble in water.

The essential oils rich in alcohols are considered to be generally

nontoxic, safe for children and the elderly, and are typically used for skin
care applications

“Alcohol compound have names that end in –ol”

o Monoterpene alcohols
 Strong antimicrobial
 Antibacterial and antiviral
 Gentle to the skin
 Immune system support Chemical
Source of plants
compounds
Bornenol Spike Lavender, Rosemary, Thyme
Citronellol Rose, Geranium, Eucalyptus citriodora
Geraniol Palmarosa, Citronella, Lemongrass, Geranium
Lavandulol Lavender
Linalool Lavender, Bergamot, Orange, Rosewood
(Note: Linalool has sedative properties.)
Menthol Peppermint
Nerol Neroli, Bergamot, Petitgrain, Rose
Terpin-4-ol Tea tree, Juniper berry

https://www.aromatherapy-essential-oils.com.au/geranium-essential-oil.html http://www.thehealthcure.org/lavender-tea.html
o Sesquiterpene alcohols
 Anti- inflammatory
 Immune supportive

Chemical
Source of plants
compounds
-bisabolol German chamomile
Carotol Carrot seed
Daucol Carrot seed
Farnesol Rose
-santalol and - santalol Sandalwood
Zingiberol Ginger
http://theabundantlifeonline.com/traditional-
medicine/plants/german-chamomile-flower/ http://bunny-bites.netlify.com/img/carrot-seed.jpg http://www.cadima.com/photos_produits/Rosa-damascena5.jpg
 Borneol, Borneol camphor (พิมเสน)
 Can be found in Dipterocarpaceae family
such as Dryobalanops aromatica
 White solid crystal
 Not sublimate at room temperature
 Bitter and spicy
 Used for carminative, antiseptic, anti-
inflammation and antispasmodic

http://www.natureloveyou.sg/Dryobalanops%20aromatica/ http://www.potbot.com/potbot- http://www.thaicrudedrug.com/main.php?action

Main.html md/terpenes/borneol =viewpage&pid=93
 Peppermint oil (นา้ มันสาระแหน่ )
 Distillated from peppermint (Mentha piperita),
Labiatae family
 Menthol is the major component (40-60%)
colorless and solid properties
 Used for topical antipruritic, antiseptic,
counterirritant (0.1-2% in recipe)
 Peppermint oil used as flavoring, carminative,
counterirritant

Mehtha arvensis var. piperescens Mentha piperita

http://www.koop-phyto.org/en/medicinal-plants/mint.php https://www.herbalfire.com/peppermint-mentha-piperita.html
 Rose oil (นา้ มันกุหลาบ) Coriander oil (นา้ มันลูกผักชี)
 Extracted from Rose spp., Rosaceae  Distillated from seed of
family Coriandrum sativum, Apiaceae
family
 Contained in alcohol classification
70-75% such as geraniol,  Linalool is the major component
citronellol, nerol, farnesol etc. (60-70%)
 Great importance in perfumery  Use as favoring, carminative,
antiseptic and antispasmodic

http://insideoutwellnesscoach.co https://www.freespiritgroup.com.a http://store.labo- http://www.onlyfoods.net/coriander-

m/product/rose-oil/ u/rose-adore-products/ hevea.com/_imgs/00320_coriander_bio.jpg seeds-coriandrum-sativum.html
 Phenol
 The structure contains an –OH group attached to the carbon of
benzene ring.
 The –OH group attachment to the benzene ring make phenols
more reactive.
 Phenol are polar compounds, higher boiling points, and are
somewhat more water soluble than alcohols.

“The names of phenol compounds, like alcohols. end in –ol”

https://commons.wikimedia.org/wiki/Linalool
 General therapeutic actions of phenols:
 Strong antibacterial and antimicrobial activities
 Stimulant to the immune system
 Strengthening yet stimulating to the nervous system

Chemical
Source of plants
compounds

Carvacrol Wild marjoram, Oregano, Thyme

Thymol Thyme

Eugenol Clove bud, Cinnamon

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content/uploads/2015/11/shutterstock_249009754-e1447445801427.jpg ages/foodfacts/thyme-fb.jpg content/uploads/2013/05/clove-for-toothache.png
 Thyme oil Clove oil (นา้ มันกานพลู)
 Distillated from Thymus vulgaris,  Main source of clove oil is flower buds
Labiatae family of Syzygium aromaticum, Myrtaceae
 Thymol is the major component family
(20-30%) and includes carvacrol  Yields 14-21% essential oil and the
 Biological activities are antimicrobial, density is greater than water
expectorant, antispasmodic and  Eugenol (70-90%) as the major
carminative component
 It is local anesthetic, anti-analgesic,
antiseptic, antispasmodic and
carminative

https://plants.ces.ncsu.edu/media/imag http://medicalplants.persiangig.com/i http://www.bigmamma.in/photo/ http://www.herbal-supplement-resource.com/wp-

es/Thymus_vulgaris.jpg mage/Avishan/Avishan%20(3).jpg cloves_laung-750x750.jpg content/uploads/2015/05/cloves-flower-buds-herb.jpg
 Betel vine (พลู)
 Leaves of Piper betel, Piperaceae
family are sources of this essential oil
 Chavicol and eugenol are the majority
components
 The biological activities are local
anesthetic, anti-analgesic, antiseptic,
antispasmodic, antimicrobial,
antipruritic and carminative
http://www.thaiarcheep.com/.html
Creosote
 Destructive distillation from Pinenaceae,
Cupressaceae, Betulaceae, Fagaceae
families such as Pinus palustris, Fragus
grandiflora
 Guaiacol and creosol are the main
compounds
 The bioactivities are antiseptic,
expectorant
 Guaiphenesin (glyceryl guaiacolate)
synthesized from guaiacol shown
expectorant activity
http://wiki.ggc.usg.edu/images/d/de/LongleafPine.jpg
Aldehyde
 The compound structure contains the –CHO functional
group.
 May be considered as partially oxidized primary alcohols.
 Slightly fruity odor when smelled on their own.
 Are mildly polar compounds and have a lower boiling point
and slightly more soluble in water than alcohols.
 They often cause skin irritation and allergic reactions.

“The names of aldehyde end in –al or aldehyde”

 General therapeutic actions of aldehyde:
 Strongly antiviral, antimicrobial activities
 Calming and sedative to CNS
 Anti-inflammatory
Chemical
 Skin irritants Source of plants
compounds
Citral Lemongrass, Lemon verbena

Citronella, Eucalyptus citriodora,

Citronellal
Melissa

Geranial Lemon, Lemongrass, Lime, Melissa

Neral Ginger, Lemon, Lemongrass, Melissa

Other aldehydes: acetaldehyde, benzaldehyde, cuminic

aldehyde, nonanal, perillaldehyde, piperonal
https://essentiallyaustralia.com.au/shop/eucalyptus-lemon-scented-gum-essential-oil/ http://lifegreen.vn/data/upload_file/Image/tinh-dau-sa/cay-sa-chanh.png
 Cinnamon oil (นา้ มันอบเชย)
 Distilled from leaves, branches, bark and young shoots of Cinnamomum ssp.
 tran-Cinnamic aldehyde is main component of cinnamon oil.
 Used as antiseptic, carminative, flavoring agent.

Three species of Cinnamomum spp. used as ingredients in pharmaceutical

production.
- C. loureini (Saigon Cinnamon, อบเชยญวน) yields 2-6% of essential oil
- C. zeylamicum (Ceylon Cinnamon, อบเชยเทศ) yields 0.5-1% of essential oil
- C. cassia (Cassia Cinnamon, อบเชยจีน) yields 0.5-1.5% of essential oil
http://www.aromaoilstore.com/files/product/small/Cinnamon%20Bark%20Essential%20Oil.jpg
http://www.kingarthurflour.com/item-img/1748CINOIL_01_05_2016__09_11_04_456
Pharmacopoeia
Crude drug
Cinnamon BP : Bark of C. zeylamicum (อบเชยเทศ)
Cinnamon NF : Bark of C. loureirii (อบเชยญวน)
Essential oil
Cinnamon oil BP : the essential oil from
C. zeylamicum
Cinnamon oil USP : the essential oil from
C. cassia (อบเชยจีน)

https://www.chemipan.com/home/images/black-coffee-
http://www.irpinianews.it/wp-content/uploads/cannella.jpg https://medthai.com/wp-content/uploads/2014/07
cinnamon_www-thetrentonline-com.jpg
 Lemon oil (นา้ มันผิวมะนาว)
 Distilled from yellow peels of Citrus lemon, Rutaceae.
 The essential oil contains limonene 70-80% as the major
component.
 Citral (3.4-3.6%) is an odorous compound (mixed of geranial :
neral, 3:1)
 Under acidic conditions, citral can be changed to p-cymene by
an enzyme from the albedo of fruit.

http://www.trustedhealthproducts.com/health-resources/wp-content/uploads/lemon-oil3.jpg http://www.medicalnewstoday.com/content//images/articles/283/283476/lemons.jpg
 Lemongrass oil Citronella oil
(นา้ มันตะไคร้ ) (นา้ มันตะไคร้ หอม)
 Distillate from leaves and stem of  Distillate from leaves and stem of
Cymbopogon citratus, Gramineae Ceylon citronella (Cymbopogon
family nadus) and Java citronella (C.
winterianus), Gramineae family
 Citral (53-85%) is the major component
 Used as a flavoring agent in cosmetic  Citronellal (32-45%) as main
production and soap compound
 More sesquiterpene found in Java
citronella than Ceylon citronella
but less quantity of monoterpene
hydrocarbon
 Used as insect repellent

https://i0.wp.com/www.ootyhub.com/wp- http://timesofindia.indiatime http://naturalmosquitorepellents.net/wp-

content/uploads/lemongrass-oil-benefits.jpg?resize=352%2C230 s.com/photo/56006410.cms content/uploads/2010/07/Citronella-oil-insect-repellent.jpg
 Cumin oil (นา้ มันยีห
่ ร่ า) Leech lime (นา้ มันมะกรูด)
 Distillate from seed of Cuminum  Distillate from leaves and peel of
cyminum, Apiaceae family Citrus hystrix, Rutaceae family
 The major component is  Citronellal as the major component
cuminaldehyde 25-35%
 Used as a spice
 Biological activities are antimicrobial
and antispasmodic
 Used as a flavoring agent and as an
ingredient in animal medication

https://www.thegivingtown.com/593-home_default/nature- http://www.naturalremedies.org/images
http://www.essentialoil.in/images/detailed/2/Cumin-oil-20-ml-1.jpg
inspired-kaffir-lime-scalp-serum.jpg /kaffir-lime.jpg
Bitter almond oil
 Obtained from compression of kernels of Prunus
amygdalus var. amara, Rosaceae family
 The percentage of yield is about 1%
 Benzaldehyde is the majority compound of bitter
almond oil
 Used as food favoring and base carrier oil

http://hjopc.com/wp- http://www.beckysbathsalts.com/images/source/ http://aetherwelt.at/bittermandel/ https://pimg.tradeindia.com/02044786/b/1

content/themes/hjopc/images/b19.jpg Flowers_and_Plants/Almond_Image.jpg /Bitter-Almond-Oil.jpg
Ketones
 Ketones are similar to aldehyde with the exception that carbon is
directly attached to carbonyl group (–C=O).
 They are moderately polar compounds and are considered to be stable.
 Not prone to oxidation.
 Lower boiling point than alcohol but higher than hydrocarbon
molecules.
 Slightly more soluble in water than alcohol.

“Ketone compounds have names that end in –one,

except for camphor”
 General therapeutic actions of ketones:
Chemical  Strong mucolytic
Source of plants
compounds
Rosemary ct camphor, Spike lavender,  Promotes skin/ tissue regeneration
Camphor
Lavendula stoecha, Camphor oil, Sage
 Wound healing agents
d- Carvone Caraway, Dill

l- Carvone Spearmint
 Calming to nervous system, sedative
Fenchone Fennel, Lavender, Thuja

Menthone Peppermint oil and other Mentha species

Nootkatone Grapefruit

Piperitone Peppermint, Eucalyptus polybractea

Pulegone Pennyroyal oils, Peppermint

Thujone Thuja, Sage, Wormwood

Verbenone Rosemary ct verbenone

http://www.gardensonline.com.au/Uploads/Plant/1786/LavandulaStoechasBMs800.jpg https://www.oldethompson.com/client_assets/spice_images/large_images/Caraway.jpg
http://img1.liveinternet.ru/images/attach/c/3/121/794/121794265_102437728_large_202002700.jpg http://www.onlyfoods.net/wp-content/uploads/2011/11/Spearmint-Photos.jpg
 Camphor (การบูร) Spearmint oil
 Distillate from leaves or bark of  Distillate from the areal part of
Cinnamomum camphora, Lauraceae Mentha spicata, Labiatae family
family  0.5-1% volatile oil yield
 Fragrant, spicy first then followed by  (-)-carvone (45-60%) as the major
cool tingle component
 Sublimate at room temperature  Used for flavoring agent in toothpaste
 It is topical antipruritic, rubefacient, and mouthwash
antiseptic  Carminative

http://keys.lucidcentral.org/keys/v3/eafrinet/weeds/key/weeds/Media/Html/images/Cin http://2.wlimg.com/product_images/bc-full/dir_8/238134/spearmint-oil-1371488.jpg
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 Caraway oil Dill seed oil
 Distillate from dried seed of Carum  Distillate from seed of Anethum
carvi, Apiaceae family graveolens, Apiaceae family
 3-7% yield of the oil and (+)-carvone  The yield of volatile oil is about
(50-60%) as the main compound 3-4%
 Carminative and antispasmodic  (+)-carvone (50%) as the major
component
 Used as a flavoring agent
 Used as carminative for an infants
and also showed antispasmodic
activity

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Siamese cardamom
Camphor seed (กระวาน) Musk (ชะมดเชียง)
 Distillate from seeds of Amomum  Obtained from glandular secretion of
cardamomum (A. krevanh), Musk deer (Moschus moschiferus)
Zingiberaceae family
 They yield 1.4% of essential oil after
 Camphor and borneol camphor are the distillation
major components
 Muscone is the major component
 Carminative
 Used as fixative in fragrance industry

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Ethers
 An oxygen atom in the molecule is bonded to two carbon atoms.
 It’s not often found in volatile oils.
 Ethers exist in cyclic forms, where an oxygen atom forms part of
a ring.
 Fairly unstable and oxidizes rapidly on exposure to air or water.
 These ethers are also know as oxide.
 The major oxide to be found within essential oils is 1,8-cineole.

“Oxide compound have names that end in –ole or -oxide”

 General therapeutic actions of oxides:
 Antiviral Example of ethers and oxides
 Expectorant Ethers Oxides
 Respiratory stimulate (E)-Anethole -Bisabolol oxide A
Dill apiole -Bisabolone oxide A
-Asarone -Caryophellene oxide
p-Cresyl methyl ether 1,8-Cineole
Elemicin Geranyl oxide
Estragole Linalool oxide A
Methyleugenol (2R)-Nerol oxide
(Z)-O-Methyl isoeugenol (-)-cis-Rose oxide
Phenylethyl methyl ether Sclareol oxide
Myristicin
Safrole
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 Eucalyptus oil Cajuput oil (นา้ มันเขียว)
 Distillate from fresh leaves of  Distillate from fresh leave of
Eucalyptus spp., Myrtaceae family Melaleuca leucadendron, Myrtaceae
such as E. globulus, E. polybractea, E. family
smithii, E. Australiana
 The major component is 1,8-cineole
 Good eucalyptus oil yields more than about 50-65%
70% of 1,8-ceneole
 Used as carminative, diaphoretic and
 Biological activities are antiseptic, antiseptic
bactericide, counterirritant, anti-
bronchitis, anesthetic, diaphoretic etc.

https://australianseed.com/persistent/catalogue_ima https://aromaticstudies.com/main/wp- http://www.tovarnaorganika.si/files/507a47762fb29abf05826b44b72

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 Tea tree oil Galanga oil (นา้ มันข่ า)
 Distillate from branch and fresh leaves
of Melaleuca altemifolia., Myrtaceae  Distillate from rhizome of Alpinia
family. galanga, Zingiberaceae family.
 1,8-ceneole and terpinen-4-ol are the  The major component is 1,8-cineole .
major components.
 Antifungal and antibacterial
 Used as antiseptic, healing, anti- activities.
inflamatory, antibacterial and antifungal
and is used in low concentrations in
cosmetics and skin washes.

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 Cardamom (กระวานเทศ)
 Distillate from seeds of Elettaria cardamomum., Zingiberaceae.
 1,8-ceneole and -terpinyl acetate are the major components.
 Used as carminative and antispasmodic.

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 Phenolic ether volatile oils

Anise oil and star anise oil

 Anise oil (2-3%) extracted from dried seeds of

Pimpinella anisum, Umbeliferae family and
star anise oil (2.5-5%) distillated from dried
fruits of Illicium verum, Illiciaceae.
 Anethole (80-90%) is the main chemical
constituent.
 Used for an ingredient in cough syrup ,
carminative, expectorant.

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 Fennel oil Sweet basil (โหรพา)
 Distillate from dried seeds of  Distillated from leaves and stems of
Foeniculum vulgare , Umbelliferae Ocimum basilicum, Labiatae.
family.
 The major components are methyl
 The major component is anethole chavicol and methyl cinnamate.
60-90%
 Used as spices.
 Used as a flavoring agent,
carminative, antiseptic and
antitussis.

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 Nutmeg oil or Myristica oil (นา้ มันจันทน์ เทศ)
 Distillate from dried kernels of Myristica fragrans, Myristicaceae.
 The significant compounds are myristicin (4%) and elemicin (2%) and
other major chemicals such pinene, camphene, sabinene (60-80%).
 Used as a flavoring agent and a carminative.

*Myristicin and Elemicin are the hallucinogenic agents*

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 Calamus oil (นา้ มันว่ านนา้ ) Holy basil (กระเพรา)
 Extracted from rhizome of Acorus  Distillate from leaves and stems of
calamus, Araceae. Ocimum sanctum (O. tenuiflorum),
Labiatae.
 The significant components are
acorone and -asarone.  The major component is methyl
eugenol.
 Used as a carminative, antispasmodic
and in the fragrance industry.  Used as a spice.

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Esters
 Esters are the product of a chemical reaction that occurs between an
alcohol and an organic acid .

 Organic acids have a terminal carbon that shares electrons with both
a carbonyl group (COOH) and a hydroxyl group.

 Mildly polar compounds with characteristically intense fruity aroma.

 They have a similar boiling point as alcohols or ketones of similar

molecular weight and are somewhat soluble in water.

“Esters have names that end in –ate or ester”

 General therapeutic actions of esters:
 Relaxing to the central nervous system (CNS)
 Balances body and mind Chemical
Source of plants
 Antispasmodic compounds

 Nervous system tonic Bornyl acetate

Pine and fir species, Rosemary,
Thyme
 Soothing to dermal inflammations
Geranium (leave), Lemon, Rose,
Geranyl acetate
Lavender, Marjoram

Lavender, Bergamot, Clary sage,

Linalyl acetate
Petitgrain, Neroli

Menthyl acetate Peppermint and other mint species

Methyl salicylate Wintergreen, Birch

Thymol acetate Thyme

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 Other carboxylic esters
Benzyl acetate Benzyl benzoate
Eugenyl acetate Benzyl cinnamate
Sabinyl acetate Benzyl salicylate
Citronellyl acetate (-)-Borneol acetate
Lavandulyl acetate Butyl angelate
Terineol acetate cis-Sabinyl acetate
Citronellyl bytyrate -Terpinyl acetate
Methyl benzoate Neryl acetate
Veriverol acetate Eugenyl acetate
 Wintergreen oil
(นา้ มันระกา) Birch oil
 Extracted from leaves of Gaultheria  Distillate from bark of Betula pendula
procumbens, Ericaceae family. Roth., Butalaceae family.
 Contains methyl salicylate 85-98% as  Methyl salicylate is the major
the major component. components.
 Used as a food flavoring, added to  Anti-inflammatory, antibacterial,
gum and toothpastes, helps to relax antifungal, antirheumatic,
and also antirheumatic, antispasmodic, diaphoretic.
antiseptic, antimicrobial activities.

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Peroxides

 Two atoms of oxygen form a link between two carbon atoms.

 Highly reactive chemicals that decompose easily at high

temperatures and on prolonged exposure to air or water.

 A typical example is the toxic ascaridole found in wormseed oil.

Chenopodium oil
 Distillate from aerial part while flowering and fruiting of
Chenopodium ambrosioides var. anthelminticum, Chenopodiaceae.
 The significant compound is ascaridole 60-70%
 Used as anthelmintic for ascaris and hookworm.

http://science.halleyhosting.com/nature/gorge/5petal/goosefoot/chenopodium/ambrosioides.html
Glycoside derived volatile oils
They are volatile oils that are prepared differently
than the usual method because they contain glycoside or
sugar in the structure.

Examples: Wintergreen oil, Mustard oil and Vanillin

 Mustard oil
 Compressed from seeds of Brassica nigra,
Cruciferae.
 Fixed oil from the compressed seeds is macerated
with warm water, then sinigrin in fixed oil will
change to allyl isothiocyanate by enzyme myrosin,
then distillated.
 Used as seasoning, local irritant, emetic, rubefacient.

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 Vanillin
 Extracted from Vanilla planifolia pods, Orchidaceae.
 Usually fresh vanilla pods contain glycoside gluco-
vanillin and gluco-vanillic alcohol after harvest, slow
drying of the pods changes the chemicals to vanillin.
 Used as a flavoring agent.

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 Volatile oil extraction
o Two methods of volatile extraction include:
>> Expression  produces citrus oils
>> Distillation  produces essential oils and hydrosols.

o Other methods used to produce other aromatic products

include:
>> Solvent extraction  produces absolute
>> Enfleurage  produces absolute
>> CO2 extraction  produce CO2 extraction

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 Expression
The method of extraction specific to citrus
essential oils, such as tangerine, lemon, bergamot,
sweet orange and lime.
 It was done in the form of sponge pressing
which is literally accomplished by hand.
 The citrus rinds will first be soaked in
warm water.
 Then it will be pressed with a sponge.
(breaking the glandular essential oil)
 The liquid extract will flow over to a
container and is allowed to separate.
 The essential oil is then removed.
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 Distillation
Water distillation:
The plant material comes into direct contact with the water.

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 Water and steam distillation:
The water remains below the plant material, which has been
placed on a grate.

http://www.union-nature.com/img/distillation_ANG.jpg
  Steam distillation:
This method mostly commonly used. The process, steam is
injected into the still at slightly higher pressures and temperature.

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 Solvent extraction
This method uses a solvent such as hexane, petroleum ether, ethanol or
methanol to extract the lipophilic material from plant material. The solvent
also pulls the chlorophyll and other plant tissue resulting in color and
thick/viscous extract known as a concrete.
Then a concrete is mixed with ethanol to extract the aromatic
compound of the material.

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 Enfleurage
It is a cold-fat extraction process that is based upon the principles
that fat possesses a high power of absorption. The fat used must be
relatively stable against rancidity. Grass continues to employ
enfleurage as a method of extraction.

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CO2 extraction
(Supercritical fluid extraction)
• This technique combines the best
aspects of steam distillation and
solvent extraction.
• When carbon dioxide is put under
high-pressure of at least 72.9
atmospheres of pressure at a
temperature as low as 31.1°C (the
“critical point”),
• It becomes a supercritical fluid with
the permeation properties of a gas but
the solvation properties of a liquid.

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 Advantage VS disadvantage of extraction
Extraction Advantage Disadvantage
Economical Time consuming
Simple apparatus Changing constituents
Distillation
Large quantity scale
Little labor
Simple apparatus Oxidizes quickly
Expression
No heat Only citrus peel oil
Low temperature needed Time consuming
Enfleurage
Solvent residue left Labor intensive
No heat Expensive
CO2 extraction Pure product
Long lasting product
Solvent extraction Consistent product Solvent residue
 Quality control
The essential oil quality control followed by International Standard
Organization (ISO) including:
 Physical and chemical properties
>> appearance, color, odor, taste, relative density, refractive
index, optical rotation, miscibility soluble, ester value, acid
value and viscosity
 Chemical constituent
>> Quality and Quantity (GCMS)

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 RESINS

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 Resins are solid, amorphous products of a
complex chemical nature. It is a brittle substance
secreted by plants into special ducts. They are often as a
response to damage to the plant by wounding, wind
damage, etc.
They are the mixture of resin acid, resin alcohol,
resin phenol (resinotanmols), esters and resene. Some
believe it was be oxidative product of terpene resins.
It is usually found in schizogenous or
schizolysigenous ducts or cavities of plants.
“Specific gravity of resins are 0.90-1.25”

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 Classification of Resins
 Oleoresins  Resins + Volatile oils
 Oleo-gum-resins  Resins + Volatile oils + Gums
 Balsams  Resinous mixtures mixed balsamic acid
(cinnamic acid and benzoic acid) or
esters from balsamic acids
 Gum-resin  Gums + Resins
 Resin acids  Diterpenoid acids
 Resinotaninols  Complex alcohols
 Glycoresins  Sugars + resin acids
Characteristic component of Resins
o Resin acid was found as independent forms and esters forms which
dissolve in an alkaline solution such as abietic acid in pine resins.
o Resin alcohols (Resinol) was found in the independent form and ester
form as well, and some resinols are complex structures called
resinotannols that can be reactive with Fe3+ similar to tannin such as
aloeresinotannol.
o Resene is the complex neutral substances which will not transform to salt
or esters, can not dissolve and does not hydrolyze with alkaline.
The physical properties of Resins
 Insoluble in water but soluble in alcohol and fixed oil.
 Heavier than water and volatile oils.
 High boiling points.
 Translucent and burns with a characteristic smoky flame
(their use in incense).
 Fixative actions, making them useful ingredients in crafts
and industry.
Resins
Podophyllin
 It is derived from dried rhizomes and roots of Podophyllum
peltatum (Berberidaceae) which originates in the forests of
central and eastern United States.
 The plants contain 3.5-6% podophyllin resin consisting of
podophyllotoxin 20%, -peltatin 10%, -peltatin 5% and
lignan glycoside.
 They are a powder with a peculiar bitter taste.
 It is irritating to mucous membranes, especially of the eyes.
 Its caustic nature is utilized in the form of topical applications
for warts and condylomas.
 It can stops cell divisions and is sometime used in leukaemia,
but problems with side effects limits its use.
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 podophyllotoxin
-peltatin

-peltatin

Podophyllum peltatum

Podophyllum hexandrum
(Indiant podophyllin) https://upload.wikimedia.org/wikipedia/commons/t
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 Etoposide Teniposide

Small lung cancer, testicular

Paediatric neuroblastoma and
cancer, lymphoma and acute
lymphoma
lymphocytic leukemia
Indian Hemp or Cannabis resin
 It is derived from the dried flowering tops of pistillate
plants of Cannabis sativa and C. indica (Cannabidaceae).
 The plants contain 15-20% resin consisting mainly of
tetrahydrocannabinols (8-THC and 9-THC) and also other
cannabinoids such as cannabinol, cannabidiol,
cannabidiol-carboxylic acid (cannabidiolic acid) and
cannabichromene.
 THC is a lipophilic compound and responsible for most of
the pharmacologic actions of cannabis.
 It is used as a euphoric, sedative, anti-nauseant, appetite
stimulant, bronchodilator and reduces intraocular pressure
in glaucoma.
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cannabinol 9-THC 8-THC

cannabidiol cannabidiolic acid cannabichromene

 9-THC

Nabilone

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 Lac (ครั่ง)
Aleuritic acid  It is resin cultivated from insects namely Laccifer
lacca.
 Lac insect colonize the branches of the host trees
and secrete the resinous pigment.
 “Shellac Lac” is obtained from resin which is
extracted with a dilute soda solution then dried.
After that it was precipitated with sulfuric acid
and filtrate.
 Shellac Lac are the polymer compositing between
Terpenic acid terpenic acid and aleuritic acid including laccaic
acids which gives it a red color.
 Laccaic acids are used to coat pills in the
pharmaceutical industry and for the furniture
Shellac
industry.
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Oleoresins
It can found in many kind of spice such as pepper.
The methods to extract oleoresins are as follows:
1) Single-stage process: the extraction using suitable solvents
such as acetone and hexane, then the extracted sample was
evaporated to obtain oleoresins.
2) Double-stage process: It is extraction by using steam
distillation which obtains the essential oil. Then the sample
is dried and extracted with appropriate solvent to obtain
resin. After that, the essential oil and resin are mixed
together to be oleoresins.
Turpentine (ยางสน)
 Obtained from Pinus palustis and other Pinus spp. in the family Pinaceae.
 In Thailand, P. merkusii (สนสองใบ) gives the higher quantity resin than P. kesiya.
(สนสามใบ).
 Turpentine prepared by scraping the stem of the terpentine tree then spraying
50% sulfuric acid to make fasting flow resin. Then the resin was distillated by
steam distillation to obtain turpentine oil (15-30%) and resin or colophony.
 The resin is amber and brittle which contains resin acid 90% and other
components.
 The amount of resin depends on many factor such as cultivation, preparation, age
of the plant and harvesting.
 Resin acid is an isomeric diterpene acid form which is (+)-pimaric acid and (-)-
pimaric acid before distillation. In the process of distillation, unstable (-)-pimaric
acid will decompose to become abietic acid.
 Currently, turpentine is used less in pharmaceutical industry-typically for
preparing zinc oxide, adhesive plasters and other ointments- usually it is used in
varnishes and the toner industry.
 (+)-Pimaric acid (-)-Pimaric acid Abietic acid

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Ginger (ขิง)
 Oleoresin from ginger derived from rhizomes
[6]-Gingerol
(essential oil 1-2% and resin 5-8%).
 Gingerols in ginger gives a spicy taste
consisting of [6]-gingerol as major component.
Shogaol  With long storage gingerol will lose molecules
of water and changes to become shogaol and
zingerone which is spicier than gingerols.
Zingerone
 Usually used as carminative, anti-nausea.
 The biological activities of gingerol are anti-
inflammatory, febrifuge, anti-nausea and
antitussis.
 Pharmacological activity, shogaol and zingerone
are anti-inflamatoy.

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 Phlai (ไพล)
 Obtained from rhizome of Zingerber montanum (Z. cassumunar),
Zingiberaceae.
 The major component in the essential oil is and orther curcuminoids
and compound D ((E)-4-(3’,4’-dimethoxyphenyl)but-3-en-1-ol).
 Compound D showed bronchial muscle activity.
 Used as a liniment.

Compound D

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 Turmeric (ขมิน
้ ชัน) ar-Turmerone

 Obtained from rhizome of Curcuma longa (C. domestica), Zingiberaceae.

 The major component is turmerone and other curcuminoids the main
types are curcumin, monodesmethoxycurcumin and
bisdesmethoxycurcumin.
 Used to treat gastric ulcer, anti-inflammatory, antibacterial and used to
prepare turmeric paper used for borax test..
Curcumin R1 = R2 = OCH3
Monodesmethoxy R1 = OCH3 R2 = H
curcumin
Bisdesmethoxycurcumin R1 = R2 = H

R1 R2

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Capsicum, Chilies (พริก)
 Derived from dried fruits of Capsicum frutescens and C. annuum,
Solanaceae.
 Major component is capsaicin 1.5% usually found at the dissepiment.
 Capsaicin are hot and spicy and are analgesic, anti-inflammatory, anti-
neuralgia, neurotoxic
 Used as ingredient in stomachic tonic, appetite stimulant, ointments or
plasters.

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Pepper (พริกไทย) Long pepper (ดีปลี)
 Obtained from pepper fruits of Piper  Obtained from fruits of Piper
nigrum, Piperaceae. retrofractum, Piperaceae.
 They contain volatile oil 2-4% and  They are spicier than pepper but
piperine (5-9%) as the main
compound. contain less volatile oil and piperine.

 Pharmacological activity of piperine  Use as a carminative, antitussis and

are antiepileptic, press CNS, expectorant.
analgesic, anti-inflammatory,
febrifuge and insecticide.
 Use as a carminative and diaphoretic.

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กฤษณา Mastic (กายานจีน)
 Obtained from heartwood of Aquilaria  Obtained from Pistacia lentiscus,
crassna and A. malaccensis, Anacardiaceae.
Thymelaeaceae.
 Oleoresin are solid in form and yellow
 Oleoresins of this plant are consisting gray in color.
of sesquiterpenes.
 Used to fill teeth, as an antitussis,
 Used as a traditional cardiotonic, and expectorant and used with cetyl alcohol
to treat symptoms of nausea, dizziness in enteric pill-coating.
and vomiting.
 Currently used in perfume industry.

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Hops
 It is widely cultivated in north America and Europe.
 Hops consisted of volatile oil 0.3-1% and resin 3-
12%.
Humulone  The major components are -bitter acid (such as
humulone) and -bitter acid (such as lupulone) and
other compounds.
 Humulone and lupulone have antimicrobial
activity.
 The extracts of this plant are spasmolytic, hypnotic,
sedative.
 The traditional medicine used as tea for micturate,
anodyne, nervous diarrhea, insomnia, restlessness,
internal cramps and inappetence.
Lupulone
 In the present, Hope used in beverage industry for
bitter flavor and preservative.
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Oleo-Gum-Resins
Myrrh (Aravian or Somali Myrrh)
 It is oleo-gum-resins obtained from the stem of various species of Commiphora
such as Commiphora molmol and Commiphora spp.(Burseraceae) growing in north-
east Africa and Arabia.
 The secretion is obtained by spontaneous exudation form the cracks and fissures
which commonly form in the bark and some is obtained from incisions.
 The yellowish-white, viscous fluid soon hardens in the great heat to reddish-
brown masses.
 It contains 7-17% volatile oil, 25-40% resin, 57-61% gum and 3-4% impurities.
 They are stimulants, antiseptic and astringent
 Used as a stomach tonic and as an ingredient in mouthwash.

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 Asafoetida (มหาหิงค์ุ)
 Obtained from rhizome and roots of the shrub
Ferula assa-foetida (Apiaceae).
 Rich oleo-gum-resin is made up of 6-17% volatile
oils which is a disulfide compound similar to
those in garlic, 40-64% resin and 7-25% gum.
 The resins consists of farnesiferols, ferulic acid
and asaresinatannols.
 Asafoetida are antispasmodic and expectorant.
 Used as tincture (drug for external use) for
carminative.

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Balsams
Storax (liquid storax, styrax)
Two kind of storaxs are:
1. Levant (Asiatic) Storax obtained from stem of Liquidamber orientalis,
Hammamelidaceae.
 Beaten plants in early summer season for stimulate and aggregate
balsams in the bark
 Harvest in autumn by compression and is boiled and compressed
again to obtain levant storax (viscous semi-solid)
2. American storax (Sweet gum), it generated by nature between bark and
heartwood of Liquidambar styraciflua a native plant distributed in central
and northern regions of America.
 Official in USP
 Storax composed of free cinnamic acid 5-15%, cinnamyl cinnamate
(styracin) 5-10%, phenylpropyl cinnamate 10% and lesser amount of benzoic
acid.
o They are an antiseptic agent and used as an ingredient in
compound benzoin tincture for bedsores and benzoin inhalation
for treatment of bronchitis.

cinnamic acid phenylpropyl cinnamate

cinnamyl cinnamate

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 Benzoin
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 It is a balsamic resin derived from the bark of
Styrax benzoin tree (Styraceae) in Southeast
Asia.
 It contains cinnamic acid, benzoic acid, and
triterpene acid.
 Its action is antiseptic, stimulant, expectorant,
diuretic and antifungal.
 It is used as a food preservative and also an
ingredient in pharmaceutical preparation such as
Whitfield’s Ointment (with salicylic acid) for
ringworm and athlete’s foot.
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Gum-Resins
Gamboge (รงทอง, รง)
 It is derived from a vessel in the bark of Garcinia hanburyii, Guttiferae.
 It is solid orange brown .
 Gamboge is composed of gum (arabin 15-20%) and resin (gambogic acid
65-75%).
 It is strong purgative.
 Used for vermifuge in cows.
References
1. Evans, W.C. Trease and Evans Pharmacognosy. 16th Edition. Edinburgh London New York
Philadelphia St Louis Sydney Toronto. 2009.
2. Tisserand, R. and Young, R. Essential Oil Safety: A guide for health care professionals. 2nd
Edition. Edinburgh London New York Philadelphia St Louis Sydney Toronto. 2014.
3. Shutes, j. and Weaver, C. Aromatheraphy for Bodyworkers. Upper Saddle River, New Jersey
07458. 2008.
4. Pengelly, A. The Constituents of Medicinal Plants. Allen & Unwin. Australia and New Zeland.
2004.
5. Dhawan, B.N. and Rostogi, R.P. in Wijesekera, R.O.B. (edits.) The medicinal plant industry.
CRC Press, U.S.A. pp. 185-208. 1991
6. Duke, J.A. Handbook of biologically active phytochemicals and their activity. CRC Press. U.S.A.
1992.
7. Hornok, L. Cultivation and processing of medicinal plants. John Wiley & Sons, Chichester, UK.
1992.
8. Leung, A.Y. and Foster, S. Encyclopedia of common natural ingredients used in food, drugs, and
cosmetics. 2nd Edition. John Wiley & Son, New York. 1996
9. Mandal S.C., Mandal, V. and Das, A.K. Essentials of Botanical Extract. Elsevier Inc. USA.2015.
10. สานักหอสมุดและศูนย์ สารสนเทศวิทยาศาสตร์ และเทคโนโลยี. นา้ มันหอมระเหยและสุ คนธบาบัด. กรมวิทยาศาสตร์ บริการ
กระทรวงวิทยาศาสตร์ และเทคโนโลยี. กรกฏาคม 2553.
11. วีณาจิรัจฉริยากูล. ยาและผลิตภัณฑ์ ธรรมชชาติ. ภาควิชาเภสั ชวินิจฉัย คณะเภสั ชศาตร์ มหาวิทยาลัยมหิดล.กรุ งเทพฯ. 2534.
“Education is the most powerful
weapon which you can use to
change the world”

-Nelson Mandela-