220
Chapter 12 · The Balm of the Trees - Terpenes
12
they usually have a trivial name in addition to
their IUPAC name. Terpenes are the main component of the essential oils produced in plants
and therefore belong to the class of secondary
ingredients. Terpenes perform a wide variety of
tasks, e.g. as pheromones, antimicrobial agents,
therapeutics, aromas or odorous substances.
Depending on their chain length, acyclic terpenes can be divided into different classes, which
are presented in . Table 12.1:
5 Hemiterpenes consist of only one C5 unit.
This class includes about 30 compounds, such
as prenol or angelic acid.
5 Monoterpenes are composed of two isoprene units, i.e. they are C10 compounds.
Since the isoprene molecule is asymmetric
and has a “head” (h) and a “tail” (t), different combinations are possible: hh, ht, th
or tt. Most monoterpenes from nature are
head-tail-linked. In total there are about 1000
monoterpenes.
5 Sesquiterpenes consist of three C5 building
blocks and thus have a C15 skeleton. About
8000 sesquiterpenes are known today.
5 The 3000 diterpenes known in nature are
C20 compounds.
Chapter Timetable
5 You get to know the different classes
of terpenes as well as their industrial
extraction
– The important class of acyclic and
cyclic monoterpenes
– The classes of higher terpenes, i.e.
sesqui-, di-, tri- and tetraterpenes.
12.1 Structure and Production
of Terpenes
Terpenes are chain-like or cyclic, natural substances whose carbon structures are formally
derived from isoprene (2-methyl-1,3-butadiene).
Originally only hydrocarbons were classified as
terpenes, but alcohols, aldehydes, ketones, ethers
and carboxylic acids as well as their esters also
belong to this compound class. The term terpenoids was chosen as a generic term covering
all functionalized compounds. The name isoprenoids is also familiar. More than 40,000 terpenoids are known today. Since many terpene
compounds have been known for a long time,
. Table 12.1 Structures of acyclic terpene compounds
C-number Name
Structure example
5
Hemiterpenes
h
t
10
Monoterpenes
15
Sesquiterpenes
20
Diterpenes
30
Triterpenes
t
t
n
Polyterpenes
n
Chapter 12 · The Balm of the Trees - Terpenes
12
they usually have a trivial name in addition to
their IUPAC name. Terpenes are the main component of the essential oils produced in plants
and therefore belong to the class of secondary
ingredients. Terpenes perform a wide variety of
tasks, e.g. as pheromones, antimicrobial agents,
therapeutics, aromas or odorous substances.
Depending on their chain length, acyclic terpenes can be divided into different classes, which
are presented in . Table 12.1:
5 Hemiterpenes consist of only one C5 unit.
This class includes about 30 compounds, such
as prenol or angelic acid.
5 Monoterpenes are composed of two isoprene units, i.e. they are C10 compounds.
Since the isoprene molecule is asymmetric
and has a “head” (h) and a “tail” (t), different combinations are possible: hh, ht, th
or tt. Most monoterpenes from nature are
head-tail-linked. In total there are about 1000
monoterpenes.
5 Sesquiterpenes consist of three C5 building
blocks and thus have a C15 skeleton. About
8000 sesquiterpenes are known today.
5 The 3000 diterpenes known in nature are
C20 compounds.
Chapter Timetable
5 You get to know the different classes
of terpenes as well as their industrial
extraction
– The important class of acyclic and
cyclic monoterpenes
– The classes of higher terpenes, i.e.
sesqui-, di-, tri- and tetraterpenes.
12.1 Structure and Production
of Terpenes
Terpenes are chain-like or cyclic, natural substances whose carbon structures are formally
derived from isoprene (2-methyl-1,3-butadiene).
Originally only hydrocarbons were classified as
terpenes, but alcohols, aldehydes, ketones, ethers
and carboxylic acids as well as their esters also
belong to this compound class. The term terpenoids was chosen as a generic term covering
all functionalized compounds. The name isoprenoids is also familiar. More than 40,000 terpenoids are known today. Since many terpene
compounds have been known for a long time,
. Table 12.1 Structures of acyclic terpene compounds
C-number Name
Structure example
5
Hemiterpenes
h
t
10
Monoterpenes
15
Sesquiterpenes
20
Diterpenes
30
Triterpenes
t
t
n
Polyterpenes
n