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biol 439 > monoterpenoids > Flashcards

monoterpenoids Flashcards

1
Q

monoterpenoids have _____(#) of isoprene units

A

2

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2
Q

via ______ to ________ condensaiton of ______ + _______ yields C_____ (#) GPP

A

tail to head
DMAPP + IPP
C10

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3
Q

C10 GPP is the source of _____________-

A

monoterpenoids

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4
Q

monoterpenoids divided into 5 groups:

A

acyclics
monocyclics
bicyclics
iridoids
irregular/mixed

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5
Q

monoterpenoids economic importance

A

flavours, perfumes, solvents

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6
Q

monoterpenoids functions in plants:

A

competition with other plants (herbicides)
insect attractants and repellants
insect pheromones

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7
Q

physical characteristics of monoterpenoids

A

colourless (usually), lipid soluble, volatile, fragrant, easily separated by chromatography

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8
Q

difficulty extracting MT because they’re…

A

volatile

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9
Q

acyclic MT are from ____ + ____

A

IPP + DMAPP

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10
Q

examples of acyclic MT’s

A

aldehydes, citral, nerol

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11
Q

nerol is an _______ MT (class) and found in ___________

A

acyclic MT
orange blossum

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12
Q

aldehydes are ________ MT (class) and with a strong lemon scent. they are found in ______ and _______ oils

A

acyclic
rose and lemongrass

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13
Q

cyclicization of MT’s via __________

A

resonance

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14
Q

basis of monocyclic MT’s/skeleton:

A

1-methyl-4-isopropyl cyclohexane

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15
Q

cyclic MT’s derived from _________

A

Neryl-PP (neryl diphosphate)

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16
Q

most monocyclic MT’s have a _____-______ skeleton

A

para-methane

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17
Q

NPP folded such that cyclicization favored final products from ___________ and ______________

A

modification
adding functional groups

18
Q

examples of monocyclic mono-terpenoids (x2)

A

limonene, thymol

19
Q

limonene is a _________ MT. (class)
has a _______ bond.
in ________ oils.

A

monocyclic
double bond
citrus oils

20
Q

thymol is a _________ MT (class)
is a _________ with a ________ functional group
source: __________
effect on animals: __________
effect in plants: __________

A

monocyclic
phenol with a alcohol FG
thyme
midly toxic
fungicide

21
Q

some bicyclic MTs are derived from

A

limonene

22
Q

___-pinene is more favorable structure
___-pinene is less favorable structure

A

alpha
beta

23
Q

common bicyclic MT is alpha-pinene. found in many _______ tree species

A

pine

24
Q

camphor is a __________ MT (class)
source:
makes:
used in:
commercially derived from:

A

bicyclic
camphor tree
plastics
explosives, antiseptics
pinene

25
Q

cineole is a ________ MT (class)
seen in ________ oil
used to treat:

A

bicyclic
eucalyptus
respiratory diseases

26
Q

ascaridole is a ___________ MT (class)
used by humans as a _______ to expel _______
used by plants as a natural _________

A

bicyclic
laxitive, intestine worms
insecticide

27
Q

synthesis of alpha/beta-pinene (bicyclic) MT’s:

________ -> _________ -> __________
it has a _________ intermediate

A

NPP (acyclic) -> mono -> bicyclic

carbocation

28
Q

the carbocation of forming the pinene is, __________, __________

A

short lived, stabilized by enzymse

29
Q

forming pinene uses a carbocation. transition state intermediates aren’t proven because the enzymes are ____________

A

very low concentration, so it’s hard to tell

30
Q

iridoids have a __(#)___-member _________ ring fuzed to a ____________

A

6
lactose
5-membered ring

31
Q

iridoids found in _____-

A

ants

32
Q

iridoids derived from ______
______ soluble
plants make it for _________ against _________
progenitor of iridane family:

A

NPP
water soluble
protection against disease and insects
Loganin

33
Q

secioridoids structure: ___-member _____ ring attached to a ___-member ______ ring

A

6, lactose
6, lactose

34
Q

which two MT’s have similar properties? and what are the properties

A

iridoids and secoiridoids
insecticide

35
Q

secoiridoids found in

A

ginger root

36
Q

irregular and mixed MT group have _________ distribution

A

restricted

37
Q

2 examples of irregular and mixed

A

camphene and pyrethrins

38
Q

camphene looks bicyclic MT but not from _______. instead it has a ___________ skeleton that comes from linkage of _____ ________

A

NPP
lavandul skeleton
x2 DMAPPs

note: the cyclic (a, mono, bi) come from IPP + DMAPP

39
Q

pyrethrins is in the catagory of

A

mixed MT’s

40
Q

pyrethrins are from __________________
_________ to fish and insects
_________ to plants and mammals
used as an insecticide but not near a _________

A

chrysanthemum flowers
toxic
non-toxic
water source

41
Q

pyrethrins used to treat

A

fish parasites

biol 439 (12 decks)

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