Pharmacognosy 生藥學

Volatile oils (揮發油)

School of Pharmacy Hsun-Shuo Chang

藥學系張訓碩

第一教學大樓7樓 藥用植物學科室 (N724)

07-3121101 ext. 2664
hschang@kmu.edu.tw
1
 Aim of study
◆ Introduction of volatile oils
◆ Classification of volatile oils

• Robbers JE, Speedie MK, Tyler VE. Pharmacognosy and Pharmacobiotechnology. Williams
& Wilkins, Baltimore, 1996.
• W. C. Evans. Trease and Evans Pharmacognosy. 15th edition, W. B. Saunders, London, 2002.
• W. C. Evans. Trease and Evans Pharmacognosy. 16th edition, W. B. Saunders, London, 2009.
• Concise Traditional Chinese Herbal Medicine, 2nd Edition. The Pharmaceutical Society of
Taiwan Pharmacognosy group, Taipei, 2019. 2
Volatile oils (揮發油)

3
 Volatile oils
◆ also called ethereal oils or essential oils: represent the
“essences” or odoriferous constituents of the plants
◆ evaporate when exposed to the air at ordinary
temperatures
◆ Spices are dried, fragrant, aromatic, or pungent plant
parts that contain a volatile oil and are used primarily in
food as a seasoning rather than for nutrition

4
Table 1-1 Representative volatile oils and spices 3,11,16

Name Part used Botanical Origin Production Important Use

Areas Constituents
Anise The dried, The annual herb, Spain, France, 1-3 % volatile oil Flavor
(aniseed) ripe fruit Pimpinella anisum Egypt containing 80-90 %
(Apiaceae) (E)-anethole, 10-15
% chavicol
Caraway The dried, The biennial herb, Carum Netherlands, 3-6 % volatile oil Flavor
ripe fruit carvi (Apiaceae) Poland, Russia, containing 50-85 %
northern Africa, (+)-carvone, 40-50 %
India, Pakistan (+)-limonene

Citronella oil Volatile oil The grass, Sri Lanka, 5-55 % (+)- Perfume,
distilled with Cymbopogon winterianus Indonesia, citronellol, 25-40 % insect
steam from (Poaceae) China, Taiwan, geraniol, 11-15 % repellant
freshly cut or Argentina, (+)-citronellol
partially dried Brazil, India
leaves
Eucalyptus oil The dried, The tree Eucalyptus Australia, Brazil, 70-85 % cineole, Antiseptic,
scythe globulus and other Spain, Portugal, 5-15 % α-pinene mild
shaped leaf species of Eucalyptus Angola, South anesthetic,
(Myrtaceae) Africa, China, stimulating
India expectorant
5
 Table 1-2 Representative volatile oils and spices 7,8,12,23

Name Part used Botanical Origin Production Areas Important Use

Constituents
Fennel The dried, ripe fruit The perennial Spain, Russia, volatile oil containing Flavor,
herb Foeniculum Bulgaria, Italy 65-70 % (E)-anethole, carminative
vulgare 10-15 % limonene,
(Apiaceae) 6-7 % fenchone,
4 % methyl chavicol

Lavender oil Volatile oil distilled The dwarf shrub, France, Bulgaria, 30-60 % (-)-linalyl Perfume
with steam from the Lavandula Russia, Australia acetate, (-)-linalool,
fresh flowering tops angustifolia cineole, terpinen-4-ol
(Lamiaceae)

Lemon oil Volatile oil obtained The small Spain, Italy, 70-80 % (+)-limonene, Flavor,
by expression evergreen tree California, Florida, 8-10 % b-pinene, perfume
without the aid of Citrus limon Argentina, Cyprus, 8-10 % g-terpinene, 2-
heat, from the fresh (Rutaceae) Brazil, Israel, 4 % citral
peel Australia, Ivory
Coast, Greece

Orange oil Volatile oil obtained The tree, Citrus California, Florida, 1-2 % decanal, Flavor
by expression from sinensis Brazil, Italy, Israel more than 90%
the fresh peel of the (Rutaceae) limonene
ripe fruit 6
Table 1-3 Representative volatile oils and spices 17

Name Part used Botanical Origin Production Important Use

Areas Constituents
Pine oil Volatile oil obtained The tree, Pinus Southeastern 65 % α-terpineol, Disinfectant
by extraction and palustris and other United States 10 % methyl chavicol deodorant
fractionation or by species of Pinus and related phenol
steam distillation of (Pinaceae) ethers, 9 % borneol,
the wood 8 % fenchol,
4 % menthols

Rose oil Volatile oil distilled Perennial herbs or Bulgaria, geraniol, Perfume
(otto of rose) with steam from shrubs, Rosa southern (-)-citronellil,
the fresh flowering gallica, R. France, Turkey, nerol,
damascene, R. alba, Morocco, 2-phenylethanol
R. centifolia, and Russia
varieties of these
species (Rosaceae)

Spearmint oil Volatile oil distilled The perennial herb Washington, 45-60 % (-)-carvone, Flavor,
with steam from Mentha spicata or Idaho, (-)-limonene, carminative
the fresh, M. cardiac Wisconsin, cineole
overground parts of (Lamiaceae) Michigan,
the flowering plant Indiana, China
7
Table 1-4 Representative volatile oils and spices 22,24

Name Part used Botanical Origin Production Important Use

Areas Constituents
Thyme The dried An evergreen Spain, Italy, Volatile oil Flavor
leaves and herbaceous shrub, France, containing
flowering tops Thymus vulgaris, T. Greece thymol,
Zygis, and its variety carvacril,
gracilis (Lamiaceae) p-cymen,
a-terpinene,
g-terpinene

Turpentine oil Volatile oil The tree Pinus Southeastern 65 % α-pinene, Counterirritant
distilled from palustris and other United States 30 % β-pinene
the oleoresin species of Pinus
(Pinaceae)

Wintergreen oil Volatile oil The leaves of the Eastern 98 % methyl Flavor,
(gautheria oil, distilled with shrublike perennial United States salicylate Counterirritant,
betula oil, steam from Gaultheria procumbens and Canada anti-inflammatory
sweet birch oil) the dried plant (Ericaceae) or the bark
material of the tree Betula
lenta (Betulaceae)

8
 分泌組織 (secretory tissue)
◆ 外部分泌組織 (external
secretory):

▬ 腺毛(glandular hair)
表皮毛的一種，由表皮
細胞向外引伸生長而成，
含分泌物:精油或黏液

▬ 蜜腺(nectary)︰
蟲媒花常具蜜腺，外壁
薄，不具角質層，分泌
花蜜
http://digitalbotanicgarden.blogspot.tw/2011/12/solanum-lycopersicum-tomato-solanaceae.html
http://en.wikipedia.org/wiki/Trichome 9
http://abugblog.blogspot.tw/2010/05/ants-helping-plants-extrafloral.html
 分泌組織 (secretory tissue)
◆ 內部分泌組織 (internal
secretory):
▬ 分泌細胞(secretory cell)
單個散生具有分泌能力的細
胞，細胞充滿分泌物後，即
成為死亡的儲存細胞
a. 具揮發油，油細胞，例如:
肉桂、薑、菖蒲
b. 具黏液質，黏液細胞，例
如:白及、半夏、知母
其他含樹脂、鞣質等 http://distillingherbs.blogspot.tw/2011/02/plant-secretory-structures.html
c.
10
 分泌組織 (secretory tissue)
◆ 內部分泌組織 (internal
secretory):
▬ 分泌腔(secretory cavity)
a. 離生分泌組織 (schizogenous
secretory tissue):分泌細胞中
層裂開，細胞間隙擴大形成
腔隙，四周分泌細胞較完整，
例如:當歸
b. 溶生分泌組織(lysigenous
secretory tissue):分泌細胞本 http://www.yourarticlelibrary.com/biology/types-of-intercellular-spaces-schizogenous-lysigenous-

身溶解而形成腔室，腔室周 spaces/3837/

圍細胞不完整，例如:橘皮
11
 分泌組織 (secretory tissue)
◆ 內部分泌組織 (internal
secretory):
▬ 分泌道(secretory canal)
上皮細胞產生的分泌物處存
在腔道中
a. 樹脂道(resin canal):
松樹樹幹-貯存油脂
b. 油管(vittae):
小茴香果實-貯存揮發油
c. 黏液道(slime canal)或黏液
管(slime duct):
美人蕉和椴樹-貯存黏液 http://taxusbaccata.hubpages.com/hub/The-Incredible-Uses-of-Resin-From-the-
Ancient-Egyptian-Mummies-to-the-Swan-Lake-Ballerinas
http://www.chinabaike.com/article/396/tujie/2007/20070917517170.html 12
 分泌組織 (secretory tissue)
◆ 內部分泌組織 (internal secretory):
▬ 乳汁管(laticifer)：
分泌乳汁的管狀組織，多
核的活細胞
a. 單乳管(無節乳管) (non-
articulated laticifer)︰
由一個細胞構成，壁薄多
分枝(杜仲、吊鐘花)
b. 連合乳管(有節乳管)︰
(articulated laticifer) 由許多
細胞構成，連接處隔膜消
失，分枝或不分枝(蒲公英) Trends in Plant Sci. 2008; 13: 631-639. 13
 Volatile oils 5,10,13,14

◆ specialized secretory structures:

▬ Lamiaceae: glandular hairs (腺毛)
▬ Piperaceae: modified parenchymal cells (變異柔細胞)
▬ Apiaceae: oil-tubes called vittae (油室)
▬ Pinaceae, Rutaceae: in lysigenous passages (溶生通道)
or schizogenous passages (離生通道)
◆ formed directly by the protoplasm, by decomposition of the
resinogenous layer of the cell wall, or by the hydrolysis of
certain glycosides
14
 Volatile oils 2

◆ Conifers: volatile oils may occur in all tissues

◆ Rose: only in the petals (appreciable quantities)
◆ Cinnamon: only in the bark and the leaves
◆ Apiaceous fruits: only in the pericarp
◆ Mints: only in the glandular hairs of the stems and leaves
◆ Orange: one kind of oil occurs only in the flower petals
and another kind only in the rind
◆ the particular plant organ that contains the volatile oil such
as the bark, buds, bulbs, flowers, fruit, leaves, rhizomes,
roots, seeds, or in some cases the entire plant tops 15
 Volatile oils
◆ Chemical constituents of volatile oils and spices based
on their biosynthetic origin

▬ terpenoid derivatives formed

(via the acetate-mevalonic acid pathway)

▬ aromatic compounds formed

(via the shikimic acid-phenylpropanoid route)

16
 Volatile oils
◆ Although volatile oils differ greatly in their chemical
constitution, they have a number of physical properties in
common:
▬ characteristic odors
▬ high refractive indices
▬ most of them are optically active
▬ specific rotation is often a valuable diagnostic property
▬ immiscible with water
▬ soluble in ether, alcohol, and most organic solvents
17
 Volatile oils
◆ volatile oils are differentiation from fixed oils:
▬ volatile oils can be distilled from their natural sources
▬ do not consist of glyceryl esters of fatty acids
▬ do not leave a permanent grease spot on paper
▬ cannot be saponified with alkalies
▬ do not become rancid as do the fixed oils
▬ on exposure to light and air, they oxidize and resinify

18
 Volatile oils
◆ practically all volatile oils consist of chemical mixtures
that are often quite complex
◆ almost any type of organic compound may be found in
volatile oils: hydrocarbons, alcohols, ketones, aldehydes,
ethers, oxides, esters, and others
◆ only a few possess a single component in a high
percentage (clove oil contains not less than 85 % of
phenolic substances, chiefly eugenol)

19
 Volatile oils
◆ it is not uncommon for a volatile oil to contain over 200
components, and often the trace constituents are essential
to the odor and flavor
◆ the absence of even one component may change the
aroma
◆ plants of the same species grown in different parts of the
world usually have the same components, but the
percentages that are present may differ

20
 4,9

peppermint 薄荷
steam distillation spearmint 綠薄荷
(蒸餾法)
clove oil 丁香油

lemon oil 檸檬油

expression orange oil 柑桔油
(壓榨法) citrus oil 柑桔油
Methods of obtaining (ecuelle method)
volatile oils

enfleurage rose oil 玫瑰油

extraction
(抽提法)
21
 Methods of obtaining volatile oils
◆ direct steam distillation: applicable to fresh plant drugs
(peppermint, spearmint)
▬ steam is forced through the fresh herb and carries the oil
droplets through a vapor pipe attached at the top of the tank to
the condensing chamber
▬ certain components of a volatile oil tend to hydrolyze, whereas
other constituents are decomposed by the high temperatures
▬ ideal distillation methods:
➢ provide for the the highest possible diffusion rate of steam
and water through plant membranes
➢ keep the hydrolysis and decomposition at a minimum
22
 Methods of obtaining volatile oils
◆ expression (lemon oil, orange oil): some volatile oils
cannot be distilled without decomposition
◆ citrus oil (柑橘油): ecuelle method
◆ a pressing action on the fruit removes the oil from the
glands, and a fine spray of water washes the oil from the
mashed peel while the juice is extracted through a center
tube that cores the fruit
◆ the resulting oil-water emulsion is separated by
centrifugation

23
 Methods of obtaining volatile oils 19

◆ enfleurage (flower petals): the volatile oil content of

fresh plant parts (flower petals) is so small that oil
removal is not commercially feasible
▬ an odorless, bland, fixed oil or fat is spread in a thin layer
on glass plates
▬ flower petals are placed on the fat for a few hours; then,
repeatedly, the old petals are removed, and a new layer of
petals is introduced
▬ the oil may be removed by extraction with alcohol
▬ formerly used extensively in the perfumes and pomades

24
 Methods of obtaining volatile oils
◆ extraction: using solvent systems based on such volatile
solvents as petroleum ether or benzene
▬ the chief advantage: uniform temperature (usually 50°C)
▬ extracted oils have a more natural odor that is unmatched
by distilled oils, which may have undergone altered
chemical constitution by the high temperatures
▬ this feature is of considerable importance to the perfume
industry
▬ distillation method is a low-cost operation compared to
the cost of the extraction process

25
 Medicinal and commercial uses
◆ spices and condiments (anise, clove, nutmeg)
◆ carminative action (eucalyptus oil, wintergreen oil)
◆ flavors for food and confection and in the spices,
perfume, and cosmetic trades
◆ perfumery materials such as volatile oils are used
directly not only for perfumes and cosmetics but also are
essential for the manufacture of soaps, toiletries, and
deodorizers and for masking or providing odor to
household cleaners, polishes, and insecticides

26
 Chemistry of volatile oils 6

◆ many volatile oils and spices consist largely of :

CHO
▬ monoterpenoids COOCH3

▬ phenylpropanoids OH

(C6 phenyl ring with H3CO

an attached C3 OH
Methyl salicylate (C6-C1) Vanillin (C6-C1)
propane side chain) (甲基水楊酸) (香蘭素)

O H2C CH CH2
HC CH CH3
H3CO O CH CH CHO

H3CO

H2C CH CH2 OH
OCH3
Anethole Myristicin Cinnamaldehyde Eugenol
(茴香腦) 27
(肉荳蔻醚) (肉桂醛) (丁香酚)
 Chemistry of volatile oils
◆ the stereochemistry of the constituents of volatile oils
markedly determines the type of olfactory response evoked
by the compounds
◆ geometric isomers, whether ortho/meta/para or cis/trans,
are in most cases readily distinguished both as to quality and
strength of odor
◆ monoterpenes: the (+) and (–) enantiomeric from in
different species: limonene, α-fenchol, borneol, menthone,
carvone, and linalool
◆ the racemic mixture: limonene, α-terpinol, α-fenchol,
carvone, and camphor
28
 Chemistry of volatile oils
◆ (+)-carvone has an odor and flavor of caraway, whereas (–)-
carvone produces a spearmint odor and flavor
◆ the stereochemical theory of olfactory: different kinds of
olfactory receptor sites are in the nose
◆ odorant molecules could lodge on these sites and would have
shapes and sizes (varying stereochemistry) that were
complementary to the shape and size of the particular
receptor
◆ a proper fit at the receptor would be required to initiate a
nerve impulse that would register in the brain the perception
of the odor
29
 Cinnamon 肉桂
◆ Cinnamon or Saigon cinnamon is the dried bark of
Cinnamomum loureirii Nees (Lauraceae)
◆ Ceylon cinnamon, the dried inner bark of shoots of coppiced
trees of C. zeylanicum Nees (Lauraceae)
◆ Cassia cinnamon is the dried bark of C. cassia (Nees) Nees
ex Blume (Lauraceae)
◆ commercial cinnamon from cultivated trees in Sri Lanka
(Ceylon), southwestern China, Vietnam, Laos, Indonesia, the
West Indies, the Seychelles, Madagascar, and many other
localities
◆ however, cinnamon from southeastern Asia and adjacent
island is superior in quality 30
 Cinnamon 肉桂
◆ volatile oil:
▬ Saigon cinnamon yields from 2 to 6 %
▬ Cassia cinnamon yields from 0.5 to 1.5 %
▬ Ceylon cinnamon yields from 0.5 to 1 %
◆ other constituents are mannitol, which causes the
sweetness of the bark, and tannin, which is abundant in
Cassia cinnamon
◆ Saigon, Ceylon, and Cassia cinnamon are carminatives
and flavors
31
 Cinnamon oil 桂皮油 25

◆ Cinnamon oil (cassia oil) from the leaves and twigs of

Cinnamomum cassia (Nees) Nees ex Blume (Lauraceae)
◆ Cinnamon oil is a yellowish to brownish liquid that becomes
darker and thicker by age or by exposure to air; it possesses
the characteristic odor and taste of Cassia cinnamon
◆ cinnamic aldehyde, 80 to 95 %;
the remainder consists of terpenes, such as
limonene, p-cymene, (–)-linalool, and β-caryophyllene,
and other compounds such as eugenol
◆ flavoring agent, carminative and pungent aromatic, antiseptic
properties
32
 Clove 丁香 [Latin: clavus (nail)]
◆ the dried flower bud of Eugenia caryophyllus (Sprengel)
Bullock et Harrison (E. caryophyllata Thunberg) (Myrtaceae)
◆ the buds are gathered when they change from green to
crimson and are carefully dried in the sun
◆ the best cloves from Tanzania (4/5 of the world’s supply)
◆ 65 % of the world’s supply of cloves is ground and mixed
with tobacco in cigarettes and consequently smoked
◆ a volatile oil (14 to 20 %), gallotannic acid (10 to 13 %),
oleanolic acid, vanillin, and the chromone, eugenin
◆ Clove is a carminative and a flavor
33
 Clove oil 丁香油 1

◆ volatile oil distilled with steam from the dried flower buds
of Syzygium aromaticum (L.) Merr. et L.M. Perry.
◆ contains not less than 85 %, by volume, of total phenolic
substances, chiefly eugenol
◆ the oil contains free eugenol (70 to 95 %), eugenol acetate,
and 5 to 8 % β-caryophyllene
◆ above constituents constitute about 99 % of the oil, but they
do not account for the characteristic, fresh, fruity note of
clove oil. This is produced by several minor constituents,
O
especially methyl-n-amyl ketone
34
 Clove oil 丁香油
OH
◆ Eugenol or 4-allyl-2-methoxyphenol is a phenol OCH3

obtained from clove oil and from other sources

◆ clove oil shaking with a 10 % solution of sodium

hydroxide → sodium eugenolate → washed with ether
→ decomposed with sulfuric acid → the eugenol is
separated by steam distillation

◆ a colorless or pale yellow, thin liquid that has a strongly

aromatic odor of clove and a pungent spicy taste

35
 Clove oil 丁香油 1,18

◆ clove oil is classed as a flavor

◆ antiseptic, counterirritant, and carminative properties

◆ oils with a particularly high content of eugenol are

OH
used in commercial production of vanillin OCH3

◆ Eugenol is classed as a dental analgesic vanillin

CHO

◆ Eugenol is applied topically to dental cavities and often

mixed with zinc oxide as a temporary dental filling

36
 Nutmeg (Myristica) 肉豆蔻
◆ the dried, ripe seed of Myristica fragrans Houttuyn
(Myristicaceae) deprived of its seed coat and arillode and
with or without a thin coating of lime
◆ indigenous to the Molucca; cultivated in other tropical
regions, including the West Indies
◆ the commercial supply is largely derived from the Malay
Archipelago
◆ with the exception of those from Penang, nutmegs are
partially coated with lime to product them from attack by
insects
37
 Nutmeg (Myristica)肉豆蔻
◆ fixed oil (25 to 40 %) is solid at ordinary temperatures,
sometimes occurs in prismatic crystal, and known as
‘‘nutmeg butter’’ O O
O OCH3 O
◆ volatile oil (8 to 15 %) contains
myristicin and safrole
◆ proteins and starch
in considerable amounts myristicin safrole

◆ a flavor and a condiment, a hallucinogenic agent: the large

amount (up to 15 g): desired intoxication also produces
flushing of the skin, tachycardia, absence of salivation, and
other undesirable side effects 38
 Nutmeg oil (Myristica oil )肉豆蔻油
20
◆ Nutmeg oil or Myristica oil is the volatile oil distilled
with steam from the dried kernels of the ripe seed of
Myristica fragrans Houttuyn (Myristicaceae)

◆ 10 to 30 % α-pinene, 10 to 20 % β-pinene,
15 to 30 % sabinene, 5 to 12 % myristicin,
2 to 7 % (±)-limonene, 3 to 6% γ-terpinene,
and 1 to 2 % safrole

◆ a flavoring agent, carminative properties

39
 Peppermint 薄荷
◆ Peppermint consists of the dried leaf and flowering top
of Mentha piperita L. (Lamiaceae)

◆ indigenous to Europe; naturalized in the northern United

States and Canada; cultivated in areas where the fertile
soil has high water holding capacity

◆ American peppermint oil: M. piperita

◆ Japanese peppermint oil: M. arvensis L. var. piperascens

◆ contains volatile oil (about 1 %), resin, and tannin

40
 Peppermint oil 薄荷油
◆ Peppermint oil from the fresh overground parts of the
flowering plant of Mentha piperita
◆ not less than 5 % of esters, calculated as methyl acetate,
and not less than 50 % of total menthol, free and as esters
◆ a colorless or pale yellow liquid that has a strong,
penetrating odor of peppermint and a pungent taste that is
followed a sensation of cold when air is drawn into the
mouth
◆ a pharmaceutic aid (flavor) (chewing gum), a carminative,
a stimulant, and a counterirritant
41
 Peppermint oil 薄荷油
◆ American peppermint oil contains from 50 to 78 % of
free (–)-menthol and from 5 to 20 % combined in
various esters such as the acetate

◆ also contains (+)-menthone, (–)-menthone, cineole, (+)-

isomenthone, (+)-neomenthone, and (+)-menthofuran

◆ in the genus Mentha of which there are approximately 25

species, an equal number of hybrids, and a larger number
of intraspecific chemical races or chemotypes

42
 Peppermint oil 薄荷油
◆ a gene encoding a key enzyme (4S-limonene synthase)
of the pathway has been isolated, sequenced, and
functionally expressed in a bacterial host

◆ (–)-(4S)-limonene, the first cyclic monoterpenoid to arise

from the common intermediate geranyl pyrophosphate

◆ hydroxylated at C-3 to yield (–)-trans-isopiperitenol (in

peppermint-type species) or at C-6 to afford (–)-trans-
carveol (in spearmint-type species)

43
 CH3

CH3 CH3 H 3C CH2

(–)- trans-Carveol (–)- Carvone (–)-Dihydrocarvone
OPP CH3
CH3

H 3C CH3 H3C CH2 OH

O
Geranyl (–)- (4S)-Limonene
pyrophosphate H3C CH3
H 3C
(+)- Menthofuran (+)- Neomenthol
CH3 CH3 CH3 CH3 CH3 CH3

OH O O O O OH

H3C CH2 H 3C CH2 H 3C CH2 H 3C CH3 H 3C CH3 H3C CH3

(–)- trans-Isopiperitenol (–)- Isopiperitenone (+)- cis-Isopulegone (+)- Pulegone (–)- Menthone (–)- Menthol
CH3 CH3

Fig. Pathway of monoterpenoid biosynthesis in Mentha species

O OH

H 3C CH3 H3C CH3

(+)- Isomenthone (+)- Isomenthol
 Peppermint 薄荷
◆ the long days of northern latitudes: oil contains
relatively small amounts of menthone and menthofuran
and large amounts of menthol

◆ short-day illumination: an oil that contains small

amounts of menthol and relatively large amounts of
menthofuran

◆ high concentrations (up to 30 % in some cases) of

menthofuran in such oils impart a disagreeable cloying
odor to products in which they be incorporated

45
 Summary

◆ Classification of volatile oils

◆ Methods of obtaining volatile oils

◆ Medicinal and commercial uses

◆ Cinnamon, Clove, Nutmeg, Peppermint

46
 國考題
1. 下列有關clove oil之敘述，何者錯誤? (101/2)
(A)主要萃取方式為有機溶劑萃取 (B)萃取部位為花苞
(C)主成分為eugenol，為製造vanillin的原料 (D)可用於治療牙痛

2. 玫瑰的揮發油（Volatile oils）含在植物的何種部位中? (101/2)

(A) 花瓣 (B) 果實 (C) 樹皮 (D) 種子

3. 下列何者之生合成屬於 mevalonic acid pathway ? (102/2)

(A) Methyl salicylate (B) Anethole (C) Eugenol (D) Citronellol

4. 下列何種精油通常用ecuelle method方法萃取? (103/2)

(A) 松油(pine oil) (B) 小茴香油(fennel) (C) 柑橘油(citrus oil) (D) 玫瑰油(rose oil)

5. 薄荷之揮發油（volatile oils）存在於下列那一種分泌組織中? (103/2)

(A)腺毛(glandular hairs) (B)變異的柔細胞(modified parenchymal cells)
(C)油管(vittae) (D)離生道(lysigenous passage)
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6. 揮發油及香料主要之組成有那類成分? (103/7)
① Phenylpropanoids ② Flavonoids ③ Monoterpenoids ④ Triterpenoids
(A)①② (B)①③ (C)②③ (D)③④

7. Fennel是下列何種植物之成熟果實? (104/7)
(A) Eucalyptus globulus (B) Foeniculum vulgare
(C) Citrus sinensis (D) Lavandula angustifolia

8. 檸檬油（lemon oil）之製備方法及主成分之配對為：(105/2)
(A)壓榨法－limonene (B)壓榨法－citral (C)蒸餾法－citral (D)溶媒抽取法－limonene

9. Enfleurage常用於提取下列那一類成分? (105/2)
(A) protein (B) lignin (C) volatile oil (D) alkaloids

10. 下列那一科別之植物的精油主要藏於glandular hair中? (105/2)

(A) Apiaceae (B) Lamiaceae (C) Leguminosae (D) Pinaceae
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11. 下列關於精油與其主成分之配對，何者錯誤? (105/7)
(A)桂皮油(cinnamon oil)-cinnamic aldehyde (B)丁香油(clove oil)-eugenol
(C)大茴香油(anise oil)-carvone (D)薄荷油(peppermint oil)-menthol

12. Anethole主含於下列何者? (106/2)

(A) Pinus palustris (B) Cinnamomum cassia (C) Rosa gallica (D) Foeniculum vulgare

13. 下列植物科別與其精油（volatile oils）分泌結構之配對，何者錯誤? (107/2)

(A) Labiatae－glandular hairs
(B) Piperaceae－modified parenchymal cells
(C) Rubiaceae－lysigenous or schizogenous passages
(D) Apiaceae－oil tubes

14. 下列何種植物之揮發油主要存於腺毛（glandular hairs）? (107/7)

(A) Pinus palustris (B) Pimpinella anisum (C) Citrus sinensis (D) Mentha spicata

15. 下列何者不屬於精油(volatile oils)? (107/7)

(A) eucalyptus oil (B) pine oil (C) fennel (D) sesame oil 49
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16. d-Carvone可由下列何者提取? (107/7)
(A) caraway (B) fennel (C) lavender oil (D) eucalyptus oil

17. Spearmint oil中主要含下列何種成分? (108/2)

(A) d-citronellol (B) l-citronellol (C) d-carvone (D) l-carvone

18. 有關丁香之敘述，下列何者錯誤? (108/7)

(A)基原植物之科名為Myricaceae (B)使用部位為乾燥花蕾
(C) clove來自拉丁文clavus釘子的字意 (D)主成分為eugenol，可作牙科鎮痛劑

19. 下列何者為製備揮發油之油脂吸附法? (109/7)

(A) direct steam distillation (B) expression (C) enfleurage (D) ecuelle

20. 下列何者為nutmeg oil之製備方法? (110/2)

(A) steam distillation (B) expression (C) enfleurage (D) ecuelle

21. 下列生藥成分，何者具有兩個五碳環結構? (110/7)

(A) d-camphor (B) α-pinene (C) l-thujone (D) l-menthol 50
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22. 下列何者之使用部位與另三者不同? (111/2)
(A) anise (B) caraway (C) fennel (D) thyme

23. 下列生藥之基原植物，何者不屬於繖形科? (111/2)

(A) Lavandula angustifolia (B) Carum carvi
(C) Pimpinella anisum (D) Foeniculum vulgare

24. 下列何者為Betula lenta樹皮之主成分? (111/7)

(A) methyl salicylate (B) pinene (C) thymol (D) eugenol

25. 精油、基原植物與其所屬科別之配對，下列何者正確? (111/7)

(A) Cinnamon oil－Cinnamomum cassia－Lauraceae
(B) Fennel oil－Foeniculum vulgare－Araliaceae
(C) Peppermint oil－Mentha piperita－Piperaceae
(D) Turpentine oil－Pinus palustris－Taxaceae

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