Terpenes and

Terpenoids

Terpenes - class of >20,000 compounds

containing carbon atoms in multiples of five
Terpenoids - oxygen-containing terpenes
(alcohols, ketones, aldehydes)
The name "terpene" is derived from the word "turpentine"

(terebentin-reineden

elde edilir)

Terpenes and terpenoids are the primary constituents of theessential oils

of many types of plants and flowers.Essential oils : bitkilerdeki sellloz ve
niasta dndaki ou kez uucu olan belli bir tad/kokuya sahip bileikler)

rose oil

(zence
fil)

(kereviz)
1

The basic molecular formulae of terpenes are multiples of that, (C 5H8)nwhere

n is the number of linked isoprene -Isoprene - 2-methyl-1,3-butadieneunits. This is called theisoprene ruleor theC5 rule.
Compounds containing carbon atoms in multiples of 5 suggest a C 5 building
block - isoprene units linked in a head-to-tail fashion
Ancak unutulmamaldr ki molekller byyp halkalatka
biyosentezler bakalamalara yol aabilirler. Retrosentezlerle baa
gidilir.

2-methyl-1,3-butadiene

Head - branched end of isoprene

Tail - unbranched end of isoprene

Finding the isoprene building block - cyclic compounds

Finding the isoprene building block sesquiterpenes (C15)

Finding the isoprene building block triterpenes (C30) -

Squalene has a natural and vital part in the synthesis of all plant and animal
sterols, including cholesterol, steroid hormones, and vitamin D in the human body

Finding the isoprene building block - tetraterpenes

(C40)

Lycopene's eleven conjugated double bonds give it its deep red color and are responsible for its antioxidant activity.

Lycopene is responsible for the red color in tomatoes and watermelon

-carotene is the compound that causes carrots and apricots to be

Biosynthesis of Terpenes
Biological isoprene - isopentenyl pyrophosphate (3-methyl-3-butenylpyrophosphate).
Enzimlerle izomerizasyona urar. zomerizasyon rn yeni bir isopentenilpirofosfat ile
reaksiyonda monoterpen ieren pirofosfat trevi oluturur. Bu son trev doal koullarda ester
hidrolizine urar ve bir terpenoid olan geraniol verir.

Aldol cond

S N2

Enzimle hid.
Tioesterden alkole

Isopentenyl pyrophosphate is only one of the necessary reagents for the biosynthesis of terpenes
dimethylallyl pyrophosphate, a C5 isomer, is also necessary:

Add. of H+

elimination of a proton

RULE - isopentenyl pyrophosphate and dimethylallyl pyrophosphate are the C 5 building blocks for the
biosynthesis of terpenes

Elimination of a proton from a carbocation intermediate generates a double bond (E1 reaction)
Geranyl pyrophosphate - C10 building block for many biological monoterpenes
Geranyl pyrophospate ester hid ile geraniol verir.

humulene
found in theessential oilsofHumulus lupulus

Hemiterpenesconsist ofa single isopreneunit. Isoprene itself is considered the

only hemiterpene, but oxygen-containing derivatives are hemiterpenoids such as
prenol(found in citrus fruits, cranberry, grapes, raspberry, blackberry, tomato, white bread) and
isovaleric acid(found in inessential oils).
Monoterpenes consist oftwo isopreneunits and have the molecular formula
C10H16. Examples of monoterpenes are:geraniol,limoneneand terpineol.
Sesquiterpenes consist ofthree isopreneunits and have the molecular formula
C15H24. Examples of sesquiterpenes are:humulene,farnesenes, farnesol.

limonene

a strong smell of oranges

Prenol

isovaleric acid

terpineo

found in pine o
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Diterpenes are composed offour isopreneunits and have the molecular formula
C20H32. Examples arecafestol,kahweol,cembreneandtaxadiene(precursor oftaxol).
Diterpenes also form the basis for biologically important compounds such asretinol,
retinal, andphytol. They are known to be antimicrobial and antiinflammatory.

Retinol is one of the forms ofvitamin

Taxadiene from enzymestaxol used incancer chemotherapy
Pasifik porsuk aac kabuklarndan

Sesterterpenes, terpenes having 25 carbons andfive isopreneunits, are rare

relative to the other sizes. An example of a sesterterpene isgeranylfarnesol.
Triterpenes consist ofsix isopreneunits and have the molecular formula C30H48. The
linear triterpenesqualene, the major constituent ofshark liver oil.
Tetraterpenescontaineight isopreneunits and have the molecular formula C40H64.
Biologically important tetraterpenes include the acycliclycopene, the monocyclic
gamma-carotene, and the bicyclicalpha-andbeta-carotenes.
Polyterpenesconsist of long chains ofmany isopreneunits. Naturalrubberconsists
of polyisoprene in which the double bonds arecis.
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Terpenler HALKA SAYISINA gre de snflandrlabilirler:

Asiklik, monosiklik, bisiklik, trisiklik (2Z)-3,7-dimethyl-2,6-octadien-1-ol
Terpenlerde isimlendirme: IUPAC kurallar yansra zel okumalar
da sz konusudur.

8
7

Asiklik terpen rnekleri:

8

CH2OH
4

Kuyruk
4

ba

7-methyl-3-methyleneocta-1,6diene

(trans)-3,7-Dimethyl-2,6-octadien-1-ol
Ald turevi citral-a

(2Z)-3,7-dimethyl-2,6octadien-1-ol
Ald turevi citral-b

Mirisen
from parsley..

Monosiklik Monoterpen rnekleri: menthol

Thymol

menthol
Carvone
Kimyon ya

Bisiklik terpenlerin IUPAC okunmas:

1
4

6
3,7,7-trimethylbicyclo[4.1.0]hepta-3-ene

1-metil-7-metiliden-4-izopropiliden bisiklo[4.4.0]dekan

2,6,6-trimethylbicyclo[3.1.1]hepta-2-ene

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