multi-functional products from palm oil
TRANSCRIPT
Dr.Hanaa M. Soliman National Research Centre
Multi-Functional Products from Palm oil
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 NH
HN
HN
O
S
4A
4B
R
NH
HN N
O
SHRR = CH3(CH2)14
Synthesis of triazole thiadiazole derivatives
4
H2SO4KOH
65A5B
NH
HN
HN
O
S
NN
S NH
PhNN
NSH
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.
EtON
NH
ArO
Cl
13
9
ab
C6H5-ClpC6H5-CH3p
13 Ar
NN
S
NH
NO
Ar
4
NH
HN
HN
O
SR
R
COOEt
15
ab
C6H6C6H5-Cl-p
Ar15
C6H5-CH3-pd
Ph-HN N NH
ArO
Cl10NN
SNH
N
OAr
R CONHPh
16
R' N NH
ArO
Cl11NN
SNH
N
OAr
R COR'
ab
C6H6C6H5-Br-m
Ar16
C6H5-CH3-pc
R'
CH3
CH3
CH3PhPhd
R = CH3(CH2)14
Thiadiazines
arteriosclerosis treatment, antiprotozoal, antibacterial,
and antifungal
4
NH
HN
HN
O
SR
R = CH3(CH2)14
NH
N
SR'
HN
Ph
O
R
R'Br
O
22
21
ab OCH2CH3
CH3
22 R'
ArBr
O
17NH
N
SAr
HN
Ph
O
20
ab C6H5-Cl-p
C6H5-CH3-p
Ar
c
C6H6
20
R
Cl CN
NH
N
SHN
PhNC
26
23R
oxadiazolethione, thiadiazolthione
KOH / EtOH NH
NH
SO
SK
O
NNH
S
28
HCl / EtOHH2SO4 / ice
S
NNH
S
29
NHNH2
O
2
CS2
27
R R
RR
R = CH3(CH2)14
Cl OEt
O
NH
NH
ClO
O
O
NNH
OO
NN
OH
NH
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
NNH
X
28 or 31
H2N Y N
NNH
YN
NN
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
NN
S
N
R
N
NN
S
N
35
NN
N
NH2
SH
33b
POCl3
R
R
HCOOH POCl3
NN
N
N
S
36
R
R = CH3(CH2)14
O
NNH
O
31
N
N
N
O
O
38
NH2OH
O
R
R
NH2
OH
ON O
NN
O
39
R
NH2
NH2NHN
NN
40
R
R = CH3(CH2)14
NH
O
2NH
N
NNH2
NH2 NH2
S
41
NH2Hg(OAc)2
RR
N
N
N
N CN
C17H35 CN
O N(CH3)2
C17H35
42R
N
HN
N
N O
CH349
CH3 OEt
O O
47R
51
Ar BrO
50
ab
C6H6C6H5-Cl-p
Ar51
C6H5-CH3-pd
N N
NR
NAr
48
N
HN
N
N O
54
NCOEt
O
NH2
R52
R = CH3(CH2)14
N
NNH
NH2
N
NNH
N2NO2
41 55
HNO3
NaNO2
CN
CN
R R
N
NN
N NCN
NH2R
57
NN
N
N
N
NH261
N
NH2
CN
R
CN
CN
H2N
NC 58
62
NN
N
N
N
NH2
N N
N NH2
NH2
R
H2N NH2
O
N
N
N
N
N
N N
NH2
NH2R
H2N NH2
O
N
N
N
N
N
NH2
NH2
NOH
N
N
N
N
N
N
NH2
HN
65
NH2OH
64
R
R
63
R = CH3(CH2)14
N
NNH
NH2
N
NNH
N2NO2
41 55
HNO3
NaNO2R R
H3C R'
OO
N
N
N
N
N
R'
CH3
O
68
a
b OCH2CH3
CH3
68 R
R
55
RN
N
N
NO
R' R'73
a
b CH3
R'H
73
OO
R' R'
ArCN
O
N
N
N
N
N
CN
Ar76
74
ab C6H5-CH3-p
ArC6H6
76
R
R = CH3(CH2)14
Diazoles
are used for preventing the nephrotoxicity induced by cisplatin
NN CH3
O
HO
NN CH3
O
O
NH
NH2
O
2
79A 79BR
O
EtO
O
RR
NN 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.
0
5
10
15
20
25
control TBHQ P-N
indu
ctio
n ti
me
(h)
oxidation stability oxidation stability
Total antioxidant activity (%)
80
85
90
95
100
105
110
0 10 20 30 40 50 60
Tota
l ant
ioxi
dant
act
ivit
y (
%)
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
DP
PH
sca
veng
ing
acti
vity
(%
)
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
AB
TS˙+
sca
veng
ing
acti
vity
(%
)
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
Sup
erox
ide
anio
n ra
dica
l(O˙̄ 2
)
scav
engi
ng a
ctiv
ity
(%)
Hydrogen peroxide scavenging activity(%)
0
10
20
30
40
50
60
N P-N BHA BHT
Hyd
roge
n pe
roxi
de s
cave
ngin
g ac
tivi
ty (
%)
Ferrous ions (Fe2+) chelating activity (%)
0
10
20
30
40
50
60
70
80
N P_N BHT BHA
Ferr
ous
ions
(Fe
2+)
chel
atin
g ac
tivi
ty (
%)
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.
