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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_158_библиотеки_им_акад_М_И_Перельмана
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1
2 3
4
5
6
24
Pulegone
67.17
C
l0
H
l6
O
152
0.16
25
a-Caryophyllene
69.10
С15Й24
204
0.29
26
2-Octadienal,
3,7-dimethyl-,
(Z)-
69.89
CioHleO
152
0.22
27
3-Cyclohexene-
1
-methanol-a,a-4-
trimethyle
71.40
CioHieO
154
35.84
28
Naphthalene,
1,2,34,4A,5,6,8A-
octahydro-7-methyl
72.74
C
15
H
2
4
204
0.11
29
2,6-Octadien-
1
-ol,
3,7-dimethyl-,
acetate,
(Z)-
73.14
С|
2
н
2
оо
2
196
0.10
30
2,6-Octadienal,
3,7-dimethyl-,
(E)-
74.06
СюН
16
О
152
2.06
31
2,6-Octadien-
1
-ol,
3
,7-dimethyl-,
acetate,
(E)-
75.57
C12H20O2
196
1.31
32
2,6-Octadienal,
3,7-dimethyl-,
(Z)-
78.86
CioHjeO
152
0.80
33
2,6-Octadien-l-ol,
3,7-dimethyl-,
(E)-
82.50
CioHigO
154
0.91
34
Benzenemethanol,
a,
a-
4-trimethyl-
82.87
СюНыО
150
0.12
35
Cis-Z-a-bisabolene
epoxide
89.47
C
I5
H
2
4O
220
0.32
36
Trans-Z-a-bisabolene
epoxide
89.76
C15H24O
220
0.12
37
Caryophyllene
oxide
94.18
С15Н24О
220
1.23
38
12-Oxabicyclo[9.1.0]dodeca-3,7-diene,
1,5,5,8-tetramethyl
98.20
С|
5
Н
24
О
220
0.05
39
Cuminol
101.6
С|5Н
]4
О
150
0.71
40
Thymol
107.0
Ci
0
H
14
O
150
0.62
41
Tau-muurolol
107.8
C1
5
H
26
O
222
0.15
42
a-Famesene
108.4
C15H24
204
0.02
43
Phenol,
2-methyl-5-(l
-methylethyl)-
109.0
C10H14O
150
0.27
44
a-Cadinol
110.8
C
15
H
26
O
222
0.39
45
Tetracyclo[6.3.2.0(2,5).0(l,8)]tridecan-
9-ol,
4,4-dimethyl
115.3
C|
5
H
24
O
220
0.21
46
1
H-3
A,7-methanoazulene,
octahydro-
1
,4,9,9-tetramethyl
117.6
C|
5
H
26
206
0.08
47
Aromadendrene
oxide-(2)
120.2
C15H24O
220
0.23
Problems
1
.
Definition:
What
is
terpenoid,
show
structures,
and
make
short
statements
on
some
important
terpenoids.
2.
Classifications
of
terpens,
detail
discuss
and
write
related
structures
of
each
type.
https://t.me/med1917
3.
Extraction
and
isolation
of
terpens
from
plant
resources,
and
to
draw
block
scheme,
indicate
the
applied
solvents
and
methods.
4.
Please
describe
the
methods
of
obtaining
essential
oil
from
plant
resources
Make
short
statements
for
each
method.
5.
Describe
the
classification
of
sesquiterpene,
write
structures
of
some
important
sesquiterpens
and
biological
activities.
6.
Definition:
Diterpenoids,
explain
with
biosynthesis,
structure
and
properties.
7.
Structures
of
abietic
type
of
terpen,
distribution
in
plant
material,
anil
biological
activities.
8.
Definition:
Triteipenoids,
explain
with
biosynthesis,
structure
and
properties.
9.
Distribution
of
ursolic
acid
and
oleanolic
acid
in
plant
material,
they
belong
to
which
class
of
natural
products,
structure,
and
biological
activities.
10.
Compare
the
carotenoids
with
other
terpen
compounds,
show
their
structure,
and
explain
about
properties.
https://t.me/med1917
5.
LABORATORY
WORKS
FOR
THE
COURSE
OF
CHEMISTRY
OF
NATURAL
COMPOUNDS
Laboratory
work
1
Obtaining
pectin
from
citrus
fruits
Pectin
is
found
in
the
cell
walls
of
plants
and
often
rich
found
in
fruits
and
vegetables.
When
it
is
heated
with
acid
and
sugar
then
taken
jelly-like
mass.
Jelly
properties
of
pectin
used
in
food
industry
as
marmalade,
jam,
and
other
manufacture
of
products.
As
raw
material
for
pectin
are
apples,
citrus
fruit
peel,
sunflower
heads,
etc.
is
used.Pectin
is
a
high
molecular
compound
(molecular
weight
200,000).
Its
structural
basis
of
methyl
alcohol
installments
esterified
poligalakturon
acid.
ОН
СООСНз
OH
COOH
On
the
basis
pectin
with
araban
and
galactan
polysaccharides
and
partially
can
be
linked
with
phosphoric
acid.
By
repeated
deposition
of
pectin
with
Alcohol,
all
the
impurities
can
be
removed.
The
necessary
reagents
and
materials'.
Peel
of
citrus
fruit
..................
50
g
Hydrochloric
acid
(0.03N)
....
200
ml
Alcohol
...................................
500ml
Lead
acetate,
ammonia,
sugar,
citric
acid.
Orange,
lemon
or
tangerine
skin
cut
off
with
meat
cutter,
put
in
https://t.me/med1917
fabric,
and
deposition
in
glass
with
alcohol,
for
cleaning
compound
of
essential
oils,
pigments,
etc.
closing
glass
to
60-70°C
and
boiled
in
water
bath
for
1
hour.
Then
Buchner
squeeze
the
fabric
Buchner
funnel,
pour
alcohol
again.
This
operation,
alcoholic
extracts
repeated
until
the
color
turns
very
pale
yellow.
Washed
mass
putted
to
500
ml
flask
and
pour
200
ml
of
0.03
N
hydrochloric
acid,
heat
in
boiling
water
bath
for
1
hour.
Hot
solution
filtrate
through
the
cotton,
wash
waste
filter
with
hot
water
twice.
Cooled
(indicator
litmus)
neutralize
with
ammonia,
and
then
evaporate
water
to
steam
in
60-80
ml.
Add
the
remaining
syrup
two
volume
of
alcohol.
Then
centrifuge
of
resulting
crude
pectin.
If
necessary
to
take
very
clean
product,
dissolve
the
pectin
with
a
small
amount
of
warm
water,
alcohols
settle
again
and
over
the
sediment
to
hour
glass,
and
air
dry.
After
sharing
of
alcohol,
measure
the
sediment
and
calculates
the
output.
Qualitative
reactions:
Galakturon
acid
test
(by
Ehrlich).
Dissolve
in
3-4
ml
of
water
pectin
(on
the
edge
of
a
spatula),
add
a
few
drops
of
10%
of
basic
lead
acetate,
and
heated
in
boiling
water
bath.
If
the
precipitate
formed
at
the
beginning,
turns
orange
over
time,
then
there
are
acid.
Testing
pectin
’
s
jelly-like
properties.
Add
to
the
pectin
50
ml
of
water,
filled
with
porcelain
plate,
for
a
certain
time
due
to
swelling.
After
adding
25
g
of
powdered
sugar,
sand
bath
for
10-15
minutes
thoroughly
heated.
Boiled
with
1
m
L
of
40%
citric
acid
to
the
mixture,
pour
the
mix
into
the
porcelain
or
plastic
forms.
Take
2-3
hours
after
the
jelly
is
ready
to
taste.
Questions:
1.
Technique
experiment:
what
will
you
learn?
2.
What
conclusions
will
you
reach?
Explain.
3.
Please
making
discussion
about
chemical
and
biological
properties
of
pectin.
Laboratory
work
2
Qualitative
analysis
of
polyphenols
of
plantmaterials
Measure
on
the
scale
of
100
g
of
raw
plantmaterials;
add
80%
aqueous-alcoholic
solution,
left
for
a
day.
Filter
the
solution
and
https://t.me/med1917
repeat
the
method
on.
Joint
extract
divided
into
three:
one
chat
extract
used
for
qualitative
analysis
of
polyphenols
with
paper
chromatography
(extract
1),
the
remaining
two
(2
and
3
extract)
used
to
study
the
acid
phenol.
OH
OH
()
14>>c<«iechui
3
RalklefbCG)
(-)
l.py.*lkx-4UxhiB
3
gal1a*c(li<XXi)
COOH
QH
Gallic
acid
(GA)
1-
extract
is
concentrated
under
vacuum
at
40°C.
The
solvent
system
for
paper
chromatography:
1.
n-Butanol:
Acetic
acid:
Water
(BAW,
40:
12.5:
29);
2.
15%
sulfuric
acid.
Identification
phenols
by
using
the
following
reaction:
1.
Complex
formation
with
1%
aqueous
solution
of
ammonium
iron
alum
(IAK).
Phenols
with
ortho-dihydroxyl
groups
are
colored
green,
and
three
rows
of
hydroxyl
groups
in
blue.
2.
The
reaction
of
nitrogen
(azo)
addition,
leading
to
the
formation
of
dyed
nitrogen
(azo)
additives.
A)
Reaction
with
dinitro
sulfanyl
acid.
Before
use,
add
0.3%
sulfanyl
acid
solution
of
8%
hydrochloric
acid
solution,
several
drops
of
a
5%
solution
of
sodium
nitride
and
stir.
Chromatogram
sprinkle
this
solution
and
then
20%
sodium
carbonate
solution.
B)
Diazote
n-nitroaniline.
Mix
1.5
ml
of
0.5%
n-nitroaniline
rastora
in
2N
HC1
and
0.5
ml
of
an
aqueous
solution
of
sodium
nitride.
Chromatogram
sprinkle
this
solution
and
then
with
15%
aqueous
sodium
carbonate
solution.
3.
Solution
of
1%
vanillin
in
concentrated
hydrochloric
acid.
Meta-dioxy
group
(resorcinol,
phloroglucinol)
in
phenols
are
painted
in
red.
4.
The
oxidation
reaction
of
silver
oxide.
Stir
in
the
ratio
1:1
solution
of
0.1N
silver
in
nitric
acid,
5N
aqueous
ammonia
https://t.me/med1917
solution.
Chromatogram
sprinkle
this
solution
and
then
dried
in
an
oven
at
105°C
for
3-5
minutes.
Phenols
are
defined
spots.
The
procedure
for
determining
the
chromatogram:
after
drying
in
air
chromatogram
(under
the
hood),
its
viewing
under
UV
light,
tag
number
and
the
light
of
certain
things.
Then,
one
determines
the
chromatogram
of
1%
sodium
IAK
tick
certain
color
patches
determined
diazo
chromatogram
second
reagent,
the
third
solution
of
silver
in
nitric
acid
to
ammonia.
5.
Ammonia
solution
flavones,
flavonols,
flavanonols
painted
in
yellow
color,
and
change
in
the
orange
or
red
when
heated.
Chaicones
and
aurons
are
colored
red
or
purple
color.
Net
catechins
not
colored.
Anthocyanins
with
ammonia
or
sodium
carbonate
are
painted
in
blue
or
purple.
6.
1%
solution
of
vanillin
in
concentrated
hydrochloric
acid,
catechins
are
painted
in
red-strawberry
color
(phloroglucinol
and
resorcinol).
This
reagent
proanthocyanidins
(flavan-3,
4-diol;
dimers
in
the
A
and
В
groups
are
painted
in
the
color
of
a
strawberry.
Flavones,
flavonols
and
their
glycosides
are
painted
in
bright
yellow
color.
Preparation
of
acid
phenol.
2
extract
was
concentrated
to
a
small
residue
is
then
added
in
the
same
volume
of
5%
aqueous
sodium
bicarbonate
solution.
Phenol
acid
form
salts
are
readily
soluble
in
water.
Phenols
extradited
ethyl
acetate.
The
aqueous
portion
was
oxidized
to
the
acid
environment
and
extradited
phenol
acid
ethyl
acetate.
Washed
several
times
in
an
isolation
flask
to
separate
minerals
ethyl
acetate
extract.
Evaporate
the
ethyl
acetate
extract
to
minimum
volume
and
the
residue
examined
by
paper
chromatography.
To
determine
the
phenol
acids
by
paper
chromatography
is
used
(including
listed
above,
the
system
of
solventsto
phenols)
Parts
1
and
2
(two
systemic
chromatography)
and
3
(solvent
system):
1.
benzene:
acetic
acid:
water
(6:
7:
3
the
organic
phase)
2.
Sodium
formate:
formic
acid:
water
(10:
1:
200)
3.
1
-Butanol:
acetic
acid:
water
(CCU
8:
2:
2)
Determination.
1.
The
chromatogram
browsing
the
UV
light.
All
oxykorich
acid
reflected
in
blue.
https://t.me/med1917
2.
The
chromatogram
splash
JACQUES
solution.
Acid
with
a
hydroxyl-colored
in
green
and
blue
three
color
hydroxyl.
3.
Sprinkles
diazo
sulfanyl
acid
and
n-nitroaniline
diazote.
Questions:
1.
Do
your
results
agree
with
your
expectations?
explain!
2.
Discuss
how
the
presence
of
different
functional
groups
impact
R
f
(why
do
some
compounds
move
further
up
the
plate
than
others?)
3.
Look
up
the
compound
structures,
consider
what
factors
influence
move
ment
on
Paper
chromatography
or
a
TLC
plate?
solvent
polarity
or
inter-
molecular
forces.
Laboratory
-work
3
Isolation
and
identification
catechine
from
green
tea
The
tea
leaves
contain
catechins
and
their
galloesters.
Major
impurity
components:
L
-
epicatechin,
L
-
gallocatechin,
their
esters
with
acids
gal.
For
example,
a
composition
tanids
Ceylon
tea
leaves:
L
-
epicatechin
6.5%,
gallocatechin
24.2%,
epicatechingallat
9%,
49%
gallocatechingallat.
Tannin
contents
are
22-24%in
green
tea,
14-17%
in
black
tea.
(+)-Catechin
3-O-gallate
(
1
)(+)-Catechin
3,5-di-O-gallate
(2)
(1)
Cathchin
С|
5
Н|
4
О
6
,
M/W
290
g/mol,
(2)
Gallocatechin
C
2
2H|
8
O|
0
,
M/W
442g/mol.
Tea
catechins
are
not
hydrolyzed.
When
heated
with
dilute
acids
are
converted
to
insoluble
solids,
called
flobafens.
They
are
active
as
https://t.me/med1917
vitamin
P,
i.e.
are
the
drugs
strengthen
capillaries
and
also
help
to
absorb
ascorbic
acid
in
the
body.
The
Materials
and
Reagents:
Green
tea
.........................
100
g
Ethylacetate
.....................
60
ml
Lead
acetate,
iron
chloride
solutions,
vanillin
sulfuric
acid.
In
a
500
ml
flask
was
put
not
fermented
green
tea,
add
300
ml
of
hot
water
and
heat
to
reflux
for
about
one
hour.
Cotton
to
filter
the
solution
in
the
funnel,
the
residue
treated
with
water
a
second
time.
Add
to
associate
lead
acetate
solution
until
complete
precipitation
of
lead
tanate.
Filter
the
resulting
solution
was
saturated
color.
Add
a
1%
solution
of
sulfuric
acid
to
give
an
acidic
medium.
Filter
the
resulting
white
precipitate.
Extradited
filtrate
3
times
with
ethyl
acetate
in
20
ml.
The
ethyl
acetate
portion
pour
in
a
porcelain
dish
in
advance
by
measuring
its
weight,
and
dry
in
the
bath
to
dry.
The
resulting
tannin
crumble,
and
measure
the
weight.Yield
should
be
about3-4
g
Tannin,
obtained
from
green
tea,
soluble
in
water
and
alcohol,
amorphous
powder.
Qualitative
reactions:
dissolve
a
portion
of
tannin
in
the
water,
pour
into
3
tubes
and
analyzed
by
qualitative
reactions
to
determine
catechines
contents.
1.
Iron
salts
(1%
or
FAK
or
1%
FeCl
3
)
-
painted
in
black
and
green.
2.
1%
vanillin
dissolved
in
concentrated
hydrochloric
acid
-
red
color.
Questions:
1.
Do
your
findings
agree
with
your
expectations?
Explain.
2.
What
is
catechin
and
its
role
in
plants?
Laboratory
work
4
Isolation
rutin
and
quercetin
from
buckwheat
’
s
leaves
Rutin
is
a
citrus
flavonoid
glycoside
found
in
many
plants
including
buckwheat,
the
leaves
and
petioles
of
Rheum
species,
and
asparagus.
Rutin
has
biological
activity
as
P
vitamin,
if
it
is
https://t.me/med1917
insufficient,
blood
roots
became
weak
and
capillaries
are
flow
faster.
Quercetin
When
it
is
hydrolyzed
in
comfortable
conditions,
i.e.
by
rhamnodiastaza
or
10%
of
acetic
acid,
rutin
aglycone
is
decomposed
to
quercetin
or
rarely
occurring
disaccharide
-
rutinose.
When
rutin
is
hydrolytically
decomposed
by
mineral
acids,
disaccharide
is
resolved
to
D-glucose
and
L-rhamnose.
Quercetin
was
found
out
in
many
plants
’
peel.
The
reagents
and
materials'.
Dry
leaves
of
buckwheat
....................
20g
Ethyl
alcohol
........................................
1
50ml
Ether
......................................................
20ml
20g
of
buckwheat
is
occupied
to
the
250ml
graduated
flask
and
add
150ml
of
70%
of
alcohol,
during
1
hour
to
hold
reflux
condenser
under
water
bath
and
heat
it.
Then
solution
is
separated
by
Buhner
funnel,
and
to
be
washed
by
10ml
of
ether
two
times.
Taken
products
are
analyzed
by
paper
chromatogram
in
one
system
with
standards.
Paper
chromatogram
is
filled
to
buthanol-1;
acetic
acid;
water
(BAW,
40:12,5;29)
solutions
system.
Yield
0.3-0.4
g.
From
water,
rutin
trihydrate
is
crystallized,
m.p
is
192°C.
Rutin
is
precipitated
by
absolute
methyl
alcohol,
m.p.
is
198°C.
Rutin
is
poorly
soluble
in
water
and
acetone,
not
soluble
in
benzene,
ester
and
chloroform.
Quercetine
or
3,5,7,3,4-pentaoxiflavone
dissolves
0.4g
of
rutin
in
2
ml
alcohol,
then
add
20ml
1%
of
HC1.
After
30-40
min,
quercetin
is
precipitate,
due
to
water
and
alcohol
it
’
s
crystallized
in
hydrate
form.
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Identification
reactions:
1.
Rutin
and
quercetin
give
green
color
with
iron
chloride
solution.
2.
With
concentrated
sulfur
acid
give
green
fluorescence
yellow
color.
Questions:
1.
What
is
the
experiment
about?
What
will
you
learn?
2.
Biological
properties
of
rutin
and
quercetin?
What
differences
and
relations
between
them?
Laboratory
work
5
Isolation
nicotine
from
a
cigarette
(tobacco)
Nicotine
3-(l
-
methyl
-
2-pirrolidinil)pyridine
-
the
main
alkaloid
of
tobacco
and
shag,
meets
in
the
form
of
citrate.
As
a
nicotine
is
especially
poisonous
it
do
not
use
in
medicine.
In
agriculture
it
is
used
as
an
insecticide.
And
also
is
the
main
material
for
receiving
niacin
and
its
derivate.
The
reagents
and
materials'.
Shag
or
cigarette,
g
.....
100
Ether,
ml
.................................
100
Hydrated
lime,
g
....................
15
Oxalic
acid,
g
.........................
20-30
Sodium
hydroxide,
hydrochloric
acid,
2%
solution
of
silicon
tungsten
acid,
methyl
iodine,
methanol,
picric
acid,
acetic
acid,
n-
butyl
alcohol,
Dragendorff
reagent.
On
the
mortar
thoroughly
pulverized
tobacco
with
slaked
lime.
The
mixture
was
transferred
into
a
flask
and
make
steam
distillation
(until
stopped
to
form
a
precipitate
with
2%
solution
of
silicon
tungsten
acid).
To
the
taken
distillate
add
oxalic
acid
(powder)
to
form
an
acidic
medium
(checked
with
Congo
indicator).
The
solution
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