monoterpenoids Flashcards
monoterpenoids have _____(#) of isoprene units
2
via ______ to ________ condensaiton of ______ + _______ yields C_____ (#) GPP
tail to head
DMAPP + IPP
C10
C10 GPP is the source of _____________-
monoterpenoids
monoterpenoids divided into 5 groups:
acyclics
monocyclics
bicyclics
iridoids
irregular/mixed
monoterpenoids economic importance
flavours, perfumes, solvents
monoterpenoids functions in plants:
competition with other plants (herbicides)
insect attractants and repellants
insect pheromones
physical characteristics of monoterpenoids
colourless (usually), lipid soluble, volatile, fragrant, easily separated by chromatography
difficulty extracting MT because they’re…
volatile
acyclic MT are from ____ + ____
IPP + DMAPP
examples of acyclic MT’s
aldehydes, citral, nerol
nerol is an _______ MT (class) and found in ___________
acyclic MT
orange blossum
aldehydes are ________ MT (class) and with a strong lemon scent. they are found in ______ and _______ oils
acyclic
rose and lemongrass
cyclicization of MT’s via __________
resonance
basis of monocyclic MT’s/skeleton:
1-methyl-4-isopropyl cyclohexane
cyclic MT’s derived from _________
Neryl-PP (neryl diphosphate)
most monocyclic MT’s have a _____-______ skeleton
para-methane
NPP folded such that cyclicization favored final products from ___________ and ______________
modification
adding functional groups
examples of monocyclic mono-terpenoids (x2)
limonene, thymol
limonene is a _________ MT. (class)
has a _______ bond.
in ________ oils.
monocyclic
double bond
citrus oils
thymol is a _________ MT (class)
is a _________ with a ________ functional group
source: __________
effect on animals: __________
effect in plants: __________
monocyclic
phenol with a alcohol FG
thyme
midly toxic
fungicide
some bicyclic MTs are derived from
limonene
___-pinene is more favorable structure
___-pinene is less favorable structure
alpha
beta
common bicyclic MT is alpha-pinene. found in many _______ tree species
pine
camphor is a __________ MT (class)
source:
makes:
used in:
commercially derived from:
bicyclic
camphor tree
plastics
explosives, antiseptics
pinene
cineole is a ________ MT (class)
seen in ________ oil
used to treat:
bicyclic
eucalyptus
respiratory diseases
ascaridole is a ___________ MT (class)
used by humans as a _______ to expel _______
used by plants as a natural _________
bicyclic
laxitive, intestine worms
insecticide
synthesis of alpha/beta-pinene (bicyclic) MT’s:
________ -> _________ -> __________
it has a _________ intermediate
NPP (acyclic) -> mono -> bicyclic
carbocation
the carbocation of forming the pinene is, __________, __________
short lived, stabilized by enzymse
forming pinene uses a carbocation. transition state intermediates aren’t proven because the enzymes are ____________
very low concentration, so it’s hard to tell
iridoids have a __(#)___-member _________ ring fuzed to a ____________
6
lactose
5-membered ring
iridoids found in _____-
ants
iridoids derived from ______
______ soluble
plants make it for _________ against _________
progenitor of iridane family:
NPP
water soluble
protection against disease and insects
Loganin
secioridoids structure: ___-member _____ ring attached to a ___-member ______ ring
6, lactose
6, lactose
which two MT’s have similar properties? and what are the properties
iridoids and secoiridoids
insecticide
secoiridoids found in
ginger root
irregular and mixed MT group have _________ distribution
restricted
2 examples of irregular and mixed
camphene and pyrethrins
camphene looks bicyclic MT but not from _______. instead it has a ___________ skeleton that comes from linkage of _____ ________
NPP
lavandul skeleton
x2 DMAPPs
note: the cyclic (a, mono, bi) come from IPP + DMAPP
pyrethrins is in the catagory of
mixed MT’s
pyrethrins are from __________________
_________ to fish and insects
_________ to plants and mammals
used as an insecticide but not near a _________
chrysanthemum flowers
toxic
non-toxic
water source
pyrethrins used to treat
fish parasites
