Multi-Functional Products from Palm oil

Dr.Hanaa M. Soliman
National Research Centre
Multi-Functional Products from
Palm oil

Chemist_hanaa@hotmail.com
1. Introduction
2. Preparation of hetero cyclic compounds
5. Acknowledgment
3. Preparation of amphiphilic radical capture
4. Conclusion

Hot Tip
 Fatty acids have been reported for their various biological applications
such as antimicrobial, antifungal, Pesticidal activities.
 Palmitic acid found to comprise 21–30% (molar) of human adipose
tissue,(fat is loose).
 Heterocyclic compounds are well known by their pharmaceutical
importance. Derivatives of triazoles, thiadiazoles and thiadiazines have
played an important role in the medicinal chemistry. Where they
possess broad-spectrum antimicrobial activity. Also they have been
studied for a number of pathological conditions such as inflammation,
pain, and hypertension. Thus they can be used as antibacterial,
antimycobacterial , antifungal, antioxidant, and antidepressant agents.

Palm oil can be used as a non
expensive source for pure
palmitic acid hexadecanoic
acid (it can easily extracted by
a new simple technique), which
appended to triazole,
thiadiazole and thiadiazine
nucleus, in order to combine
the beneficial effects of both of
hetero cyclic nucleus and fatty
acid in a new single structure
of a certain biological activity
on human health.
.

 Moreover these compounds
are expected to have several
advantages over the parent
heterocyclic one, where they
can easily penetrate the
lipoprotein cell membrane,
they may be stored in liver
and skin as a lipid component
that can be used whenever
they needed, also the toxicity
and side effects of this new
compounds may be reduced
by the presence of the long
chain fatty acid residue which
circulate the hetero nucleus

Palmetic acid is a suitable starting material for the synthesis of a
variety of heterocyclic systems pendent to a long chain fatty acid
residue of biological potency.
Synthesis of phenyl isothiocyanate
CH3(CH2)14COOH N
H
H
N
H
N
O
S
4A
4B
R
N
H
H
N N
O
SH
RR = CH3(CH2)14

Synthesis of triazole thiadiazole
derivatives
4
H2SO4KOH
65A5B
N
H
H
N
H
N
O
S
NN
S
N
H
Ph
NN
N
SH
Ph
NHN
N
S
Ph
R R R
R
R = CH3(CH2)14

MeI/EtOH
5 7 8
R
NN
N
SH
Ph
R
NN
N
SMe
Ph
R
NN
N
NHNH2
Ph
NH2NH2
R = CH3(CH2)14
Triazoles
are usually used as antifungal, antiasthma and allergic drugs

Thaiadiazoles
can be used in antibiotic preparations,
antimicrobial,antiinflammatory, anticancer, anti convulsant,
antidepressant, antioxidant, and radio protective.
EtO
N
N
H
Ar
O
Cl
13
9
a
b
C6H5-Clp
C6H5-CH3p
13 Ar
N
N
S
N
H
N
O
Ar
4
N
H
H
N
H
N
O
S
R
R
COOEt
15
a
b
C6H6
C6H5-Cl-p
Ar15
C6H5-CH3-pd
Ph-HN
N
N
H
Ar
O
Cl
10
NN
SN
H
N
O
Ar
R CONHPh
16
R'
N
N
H
Ar
O
Cl11
NN
S
N
H
N
O
Ar
R COR'
a
b
C6H6
C6H5-Br-m
Ar16
C6H5-CH3-pc
R'
CH3
CH3
CH3
PhPhd
R = CH3(CH2)14

Thiadiazines
arteriosclerosis treatment, antiprotozoal, antibacterial,
and antifungal
4
N
H
H
N
H
N
O
S
R
R = CH3(CH2)14
N
H
N
S
R'
H
N
Ph
O
R
R'
Br
O
22
21
a
b OCH2CH3
CH3
22 R'
Ar
Br
O
17
N
H
N
S
Ar
H
N
Ph
O
20
a
b C6H5-Cl-p
C6H5-CH3-p
Ar
c
C6H6
20
R
Cl CN
N
H
N
S
H
N
Ph
NC
26
23R

oxadiazolethione, thiadiazolthione
KOH / EtOH N
H
NH
S
O
SK
O
N
NH
S
28
HCl / EtOHH2SO4 / ice
S
N
NH
S
29
NH
NH2
O
2
CS2
27
R
R
RR
R = CH3(CH2)14

Cl OEt
O
N
H
NH
Cl
O
O
O
N
NH
O
O
N
N
OH
N
H
NH2
O
2
30
31A 31B
R
RR
R
R = CH3(CH2)14
Oxadiazole
can be used as muscle relaxants, antibacterial anti-
inflammatory and antifungal

O
N
NH
X
28 or 31
H2N Y N
N
NH
Y
N
N
N
XHY
R
R R
32A, 33A 32B, 33B
a
b
O
S
X33
X
a
b C6H5-CH3-p
Ar
c
C6H6
C6H6
C6H5-CH3-pd
S
S
O
O
X32
Y= NH2, Ar
R = CH3(CH2)14

NN
N SCH3
NH2
34
MeI
R
COOH
COOH
N
N
N
S
N
R
N
N
N
S
N
35
NN
N
NH2
SH
33b
POCl3
R
R
HCOOH
POCl3
NN
N
N
S
36
R
R = CH3(CH2)14

O
N
NH
O
31
N
N
N
O
O
38
NH2
OH
O
R
R
NH2
OH
O
N O
NN
O
39
R
NH2
NH2
NHN
NN
40
R
R = CH3(CH2)14

NH
O
2
N
H
N
N
NH2
NH2 NH2
S
41
NH2
Hg(OAc)2
R
R
N
N
N
N CN
C17H35 CN
O N(CH3)2
C17H35
42
R
N
H
N
N
N O
CH349
CH3 OEt
O O
47
R
51
Ar
Br
O
50
a
b
C6H6
C6H5-Cl-p
Ar51
C6H5-CH3-pd
N
N
N
R
N
Ar
48
N
H
N
N
N O
54
NC
OEt
O
NH2
R52
R = CH3(CH2)14

N
N
NH
NH2
N
N
NH
N2NO2
41 55
HNO3
NaNO2
CN
CN
R R
N
N
N
N N
CN
NH2R
57
N
N
N
N
N
NH261
N
NH2
CN
R
CN
CN
H2N
NC 58
62
N
N
N
N
N
NH2
N N
N NH2
NH2
R
H2N NH2
O
N
N
N
N
N
N N
NH2
NH2
R
H2N NH2
O
N
N
N
N
N
NH2
NH2
N
OH
N
N
N
N
N
N
NH2
HN
65
NH2OH
64
R
R
63
R = CH3(CH2)14

N
N
NH
NH2
N
N
NH
N2NO2
41 55
HNO3
NaNO2
R R
H3C R'
OO
N
N
N
N
N
R'
CH3
O
68
a
b OCH2CH3
CH3
68 R
R
55
R
N
N
N
N
O
R' R'73
a
b CH3
R'
H
73
OO
R' R'
Ar
CN
O
N
N
N
N
N
CN
Ar
76
74
a
b C6H5-CH3-p
Ar
C6H6
76
R
R = CH3(CH2)14

Diazoles
are used for preventing the nephrotoxicity induced by cisplatin
N
N CH3
O
HO
N
N CH3
O
O
N
H
NH2
O
2
79A 79B
R
O
EtO
O
RR
N
N CH3
O
H3CO O
R
81
R = CH3(CH2)14

COMPOUNDS NO.
Inhibition Zone Diameter (IZD) (mm/mg
CompoundTested)
Gram + ve Gram - ve
Staphelococcus
Epiderm
Enterococus
fesalis
Enterobacter.
cloacae
Flavobacterium
CONTROL 0.0 0.0 0.0 0.0
4 + ve ++ ve -------- +++ ve
5 +++ ve + ve + ve --------
7 ++ ve +++ ve +++ ve +++ ve
15a ++ ve + ve + ve + ve
20a +++ ve +++ ve +++ ve + ve
26 ++ ve ++ ve +++ ve +++ ve
35 ++ ve -------- ++ ve --------
36 -------- +++ ve ++ ve ++ ve
39 ++ ve + ve ++ ve +++ ve
46 ++ ve ++ ve ++ ve +++ ve
57 + ve +++ ve ++ ve + ve
61 +++ ve + ve -------- ++ ve
62 ++ ve +++ ve +++ ve ++ ve
65 -------- + ve + ve + ve
76 +++ ve +++ ve +++ ve +++ ve
81 ++ ve ++ ve ++ ve ++ ve
Referances
Vacomycin –
rifampin
Penicillin G
Gentamycin –
cephpalosporin –
cefotaxime
Imipenem
Normal flora
Natpathegen

Palmitic acid can also
be appended to certain
naturally occurring
compounds, to produce
a new compound of
malti functions and
composed of 100%
natural products.

OH
OH
OH
OH OH OH
OH
OH
OH
OHOH
OH
OH
OH
OH
OH
OH
OH OH OH
OH
OH
OH
OH
OH
OH

OH
OH
OH
OH
OH
OH OH OH
OH
OH
OH
OH
OH
OH
OH
OH
OH OH
OH
OH
OH
OH
OH
OH
OH
OH

0
5
10
15
20
25
control TBHQ P-N
inductiontime(h)
oxidation
stabilityoxidation stability

Total antioxidant activity (%)
80
85
90
95
100
105
110
0 10 20 30 40 50 60
Totalantioxidantactivity(%)
time (h)
N
P-N
BHT
BHA

0
10
20
30
40
50
60
70
80
90
100
0 5 10 15 20 25 30 35 40 45
DPPHscavengingactivity(%)
Concentration (μg/mL)
BHA
N
P-N
BHT
DPPH scavenging activity (%)

ABTS+ scavenging activity (%)
0
20
40
60
80
100
120
0 5 10 15 20 25 30 35 40 45
ABTS˙+scavengingactivity(%)
Concentration (μg/mL)
BHA
P-N
N
BHT

Superoxide anion radical scavenging activity (%)
0
10
20
30
40
50
60
70
80
90
100
N-P N BHT BHA
Superoxideanionradical(O˙̄2)
scavengingactivity(%)

Hydrogen peroxide scavenging activity(%)
0
10
20
30
40
50
60
N P-N BHA BHT
Hydrogenperoxidescavenging
activity(%)

Ferrous ions (Fe2+) chelating activity (%)
0
10
20
30
40
50
60
70
80
N P_N BHT BHA
Ferrousions(Fe2+)chelating
activity(%)

This amphiphilic compound composed of 100% natural
products, Thus it can be used as:
Dietary supplements and diseases preventing
 Food additives in order to prevent oxidative degradation
of foods.
Hindrance of metal corrosion, vulcanization of rubber, and
polymerization of fuels in the fouling of internal combustion
engines
Emulsifiers.
Surfactants.
 Removal for heavy metals during water treatment.

I would like to express my respectful thanks and sincere
gratitude to Prof. Dr. Shaker Arafaat , Prof. Dr. Amany
Basuny, Prof. Dr. Ahmed Elsharkay and Prof. Dr.
Magdy Al-egami Professors at Food Technology Research
Institute, Agricultural Research Center, for their
continuous and valuable help, fruitful criticism and
encouragement during the execution of this work .
The author wishes to express her most sincere gratitude and
respectful thanks to Prof. Dr. Ferial Zaher, Prof. Dr.
Yosef El-shatory, Prof. Dr. Mahmoud El-mallah, Prof.
Dr. Hend El-noamany, Prof. Dr.Saadeya Mostafa and
Prof. Dr. Omayma El kinawe Professors at National
research centre, for their useful help, incessant effort, useful
suggestion and valuable support.

Multi-Functional Products from Palm oil

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