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UNIVERSITAS 17
AGUSTUS 1945
FAKULTAS FARMASI
FITOKIMIA 2
DAMERIA SIAHAAN 1343050006
ASTI EKA SAFITRI 1443050050
ACHMAD RIDHO 1443050054
SHINTA FEBRIYANTI 1443057055
TRI MULYANINGSIH 1443057056
SENDY PERMANA 1443057052
FEBRY DIAN LESTARYANA
1443057060
FEN
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DAFTAR PUSTAKA
JUDUL ............................................................................................................................ i
DAFTAR PUSTAKA ..................................................................................................... 1
BAB I
1.1 DEFINISI DAN STRUKTUR FENOL ............................................................... 2
1.2 TATA NAMA FENOL ........................................................................................ 3
1.3 KARAKTERISTIK FENOL ................................................................................ 4
1.4 KLASIFIKASI FENOLIK DAN TURUNAN SENYAWA ................................ 5
1.5 DETEKSI REAKSI WARNA SENYAWA FENOL ........................................... 10
1.5.1 CONTOH SENYAWA FENOL ......................................................... 15
1.6 BIOSINTESIS SENYAWA FENOL ................................................................... 24
1. DAFTAR PUSTAKA ........................................................................................... 34
BAB I
I. DEFINISI DAN STRUKTUR FENOL
FENOL 2016 1
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S!"#$%$ &!"'(i) *!+,-$)$" !"#$%$ #$"/ $"#$) i!*,)$" -$$
,*,$". F!"'(i) *!*i(i)i i"i" $+'*$i) $, $$, (!i /,/, i+')i OH
$" /,/, 7 /,/, ($i" -!"#!+$"#$. S!"#$%$ i"i i!+i "$*$ !+$$+)$" "$*$
!"#$%$ i",)"#$8 &!"'(. S!"#$%$ &!"'( )!$"#$))$" *!*i(i)i /,/, i+')i(
(!i $+i $, !i"//$ i!, polifenol. S!"#$%$ &!"'( *!(i-,i $"!)$ +$/$*
!"#$%$ #$"/ !+$$( $+i ,*,$" #$"/ *!*-,"#$i i+i $*$8 #$i, i"i"
$+'*$i) #$"/ *!"/$","/ $, $$, ,$ /,/, 9OH.
S!"#$%$ &!"'(i) i $($* !+$-$
$"/$ (,$8 *!*-,"#$i :$+i$i +,),+
#$"/ (,$8 *,$ i!*,)$" i !*,$ $"$*$"8 $,"8 ,"/$
$" ,$. Ri,$" !"#$%$ &!"'(i) $($* !($ i)!$,i +,),+"#$8 $"$+$ ($i"
&($:'"'i8 &!"'( *'"'i)(i) !!+$"$8 &!"i( -+'-$"'i8 -'(i&!"'( (i/"i"8 *!($"i"8
$""i"8 $" ),i"'" &!"'(i).
B$"#$) !"#$%$ &!"'(i) $($*i *!"/$","/ !),+$"/9),+$"/"#$ $, /,/,
i+')i( $" (!i $"#$) #$"/ *!*!",) !"#$%$ !!+8 !!+ $$, /(i')i$
$+i-$$ !"#$%$ !$"#$. S!"#$%$ !!+ $$, !!+ &!"'( !+!, *!*i(i)i
)!($+,$" #$"/ (!i !$+ $($* $i+ $+i-$$ !"#$%$ &!"'( $" !"#$%$
/(i')i$"#$.
D$($* )!$$$" *,+"i8 !"#$%$ &!"'( !+,-$ ;$ -$$ #$"/ i$) !+%$+"$8
!$-i
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Cl
OH
NO
2
OH
Br
OH4
Kl!r!" #$!
l%ρ-klor
ofen
ol)
2$&'r!"#$!l
%ο-nitro
feno
l)
3Br!(!"#$
!l% -ɱbro
of
enol
)
*!*!+(,)$" $$"#$ ,$, !"#$%$ #$"/ $-$ *!"'"'+)$" H. S!"#$%$ &!"'(i)
*!+,-$)$" '"' i!$( $+i !"#$%$ #$"/ *,$ *!"'"'+)$" $'* H.
II. TATA NA!A FENOL
M!",+, !&i"ii8 &!"'( $$($ i+')i!";!"$. F!"'( $$($ "$*$ ,*,*
,",) !"#$%$. N$*$ IUPAC (International Union of Pure and Applied
Chemistry) $$($ !";!"'(8 i,+,")$" $($* $+$ #$"/ $*$ !-!+i "$*$9"$*$
IUPAC ,",) $(''( $(i&$i). K!i)$ *'(!),( &!"'( i/$"i)$" !"/$" )!('*-')9
)!('*-') $*$$"8 $i) orto, meta, para #!* $$, i!* -!"'*'+$" $-$
i/,"$)$".
D$($* )!,$ )$,8
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III. KARAKTERISTIK SEN"A#A FENOLSi&$ 9i&$ $+i &!"'(8 $$($ >$. M!*-,"#$i /,/, i+')i !$-i ,)$" !+*$,) /'('"/$" $()''( $"
,)$" -,($ !+*$,) $$ .
. T!+*$,) $$* )$+'($ #$"/ !+i&$ $$* (!*$.
. Ti$) !+%$+"$ !"/$" %,
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I$. KLASIFIKASI FENOLIK DAN TURUNAN SEN"A#AK($i&i)$i F!"'(i) !+$/i $$ 4 *$$*8 #$i,>
%. Fenol &e'er(n
S!$+$ ,*,* !"#$%$ &!"'(i) !!+$"$ *!*i(i)i i&$ $)!+ii$(8
$"i!-i) $" $"i!(*i"i). S!"#$%$ $+i )!('*-') i"i $i( ,i,i /,/,
&!"'( $($* -'ii orto, meta dan -$+$. C'"' !"#$%$ &!"'(i) !!+$"$
#$"/ !+,i,i '(! ,$ $" $, /,/, 7OH !+,+, 7 ,+, $$($
floroglukinol 183859+ii+')i!";!"$ $" +!'+)i"'( 1839
ii+')i!";!"$.
*. A& fenolt
A$* &!"'($ $$($ ,+,"$" $+i /'('"/$" $$* i+')i i"$*$8 #$"/
*!*i(i)i )!(i*-$$" #$"/ i"//i $($* i"i"/ !( $"$*$". H$( i"i *!*,"/)i")$"
,",) $-$ *!*!+i)$" )!,","/$" #$"/ i/"i&i)$" i i$"/ )!!$$"8 )$+!"$
!"#$%$ $$* &!"'($ '"'"#$ $$* &!+,($ *!*i(i)i $)i:i$ $"i)$")!+ $"
$"i')i$". S!($i" i, 1. S!$/$i $"i')i$"8 $$* &!+,($ )!*,"/)i"$" *!"!+$()$" +$i)$( !$8
!-!+i spesies oksigen reaktif ROS. ROS )!*,"/)i"$" #$"/ *!"#!$)$"
DNA +,$) $" *!*-!+!-$ -!",$$". Ji)$ i$*$)$" -$$ $$* $)'+$
$" :i$*i" E8 $$* &!+,($ )!*,"/)i"$" $-$ *!"/,+$"/i +! ')i$i $"
-!*!",)$" i*!+ i*ii"! $($* ),(i #$"/ *!"!/$ -!",$$".
2. D!"/$" ,i -$$ !%$" $" ,i i" :i+'8 *!"/$+$)$" $%$ $$* &!+,($
)!*,"/)i"$" *!*i(i)i ,,"/$" !"/$" $)i:i$ $"i,*'+ -!+($%$"$" )$")!+
FENOL 2016 5
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-$#,$+$ $" )$")!+ $i. A$* &!+,($ *!*i(i)i )!*,"/)i"$" !$/$i
-!"!/$ )$")!+ #$"/ !&!)i&8 #$"/ i!$)$" '(! -$-$+$" !"#$%$
)$+i"'/!"i)8 !-!+i !";'-i+!"! $" 49"i+'G,i"'(i"! 19')i$. N$*," -!+(,
*!"
A$* &!"'($ $$($ !"#$%$ &!"'(i) #$"/ $-$ i$i()$" $($ $,"#$
i$($ !"/$" +!$)i )'"!"$i :$"i((i !"/$" $$* *$('"$.
A$-," +,*, $"/," $$* &!+,($ $$($ !$/$i>
=$*$+> R,*, $"/," $$* &!+,($
A$* &!"'($ i)!$,i $-$ *!"$i()$" $" *!*-!+),$ %$+"$ $"'i$"i".
C'"' $$* &!"'($ #$"/ $-$ !+-!+$" !$/$i )'9-i/*!"$i !+!, $$($
$$* i"$-$ $" $$* &!+,($. K'9-i/*!"+$i
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$$+ )$+'" #$"/ !+i+i $+i i"i" !";!"$ C6 #$"/ !+i)$ -$$ ,
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ii) ii 300C. A$* i"$*$ !+*$,) !"#$%$ &!"'( #$"/
i$i()$" $+i (i"$$" $$* i)i*$ $" +!$)i !+i),"#$.
B$$" $$+"#$ $$($ &!"i($($"i" $" i+'i" $*$ !-!+i $$*
)$&!$8 $$* -9),*$+$8 $" $$* &!+,($. K!!*-$ !"#$%$
!+!, -!"i"/ ,)$" )$+!"$ !+$-$ *!(i*-$ $($* !",)
$) !+i)$ !$8 *!($i")$" )$+!"$ *!+!)$ i,$ *!"
18245 /+*3. A$* i"$*$ *!"ii -$$ ,, 300 C8 52 F8 !"/$" ii)
(!(! 133 C8 21 F. D$-$ ($+, $($* $*-$i 500 */(i!+8 !"/$" )!$$*$"
-K$ 4844. A$* i"$*$ *!*-,"#$i ii) "#$($ -$$ ,, 100 C 212 F. A$*
i"$*$ i/,"$)$" !$/$i -!"#!$-8 i"i/' i"!i)8 $" -+',) &$+*$i !+!",.
K!/,"$$" ,$*$ i$($ $($* -!*,$$"*!i(8 !i( $" !";i( !!+ ,",)i i",+#
FENOL 2016 8
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*i"#$) %$"/i. A$* i"$*$ *!+,-$)$" -+!),+'+8 ;$ -!"$,(, ,",) -!*$"i
$-$+$* *!($(,i $*i"$i #$"/ i)$$(ii9!";i* *!"
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K,*$+i" $$($ ($)'" $$* '9i+')ii"$*$. K,*$+i" i$) !+%$+"$8
)+i$( -+i*$i)8 $" *!*-,"#$i )$+$)!+ii) $, #$"/ %$"/i $" +$$
-$i8 $+'*$i8 +$$ #$"/ -$"$8 ($+, $($* $()''(. K,*$+i"
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i"!)ii$. S!($i" i,8 (i/"$" *!+,-$)$" )'*-'"!" )i*i$ #$"/ $)i& $($*
,*,$" '$ !+!",. S$($ $, !"#$%$ /'('"/$" (i/"$"8 #$i, -''-#((''i"8
i)!$,i $-$ *!"/$*$ ,*'+. D$($* -!"/'$$" Ci"$8 (i/"$" $"#$) i-$)$i
,",) *!"/'$i -!"#$)i !-$ii $" *!(i","/i '+/$" $i.
d. Antosianin
A"'i$"i" *!+,-$)$" !"#$%$ !+%$+"$ )!$"#$)$" *!+$8 i+, $" ,"/, -$$
,$8 $#,+ $" $"$*$" i$. S+,),+ ,$*$"#$ i$"$i !"/$" $$"#$ 2 i"i"
!";!"$ C6H6 #$"/ i,,"/)$" !"/$" 3 $'* )$+'" #$"/ *!*!",) i"i".
S,i,i !+$-$ /,/, )i*i$ -$$ +$"/)$ $"'i$"i" $-$ *!*-!"/$+,i %$+"$
$" )!$i($" $"'i"i". P!"$*$$" /,/, /(i)'i$ $$, /,/, i+')i !$ -$$ i"i"
A *!"#!$)$" %$+"$ !"!+,"/ i+, $" +!($i& i$) $i(. S!$(i)"#$8 -!"$*$$"
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U
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+. Rek&i 'i4o
D!"/$" +!$)i Di$;'8 F!"'(
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i$ %$+"$ *!+$8 ')($8 $$"/ )'+!) $-i i, i!(,-)$" -$$ ($+. $ $($* HC( !"!+.
PAS9N$ > ),"i"/ *!+$ -!i&i)
O+'&'+* "!,> K!+, i'(!6. L$+,$" ;$ N$HCO3
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. AG. B+'* !+(!i > E"$-$" -,i
. R!$)i M'(i > $ !i)i $(''( 1 ($+,$" !"!+ /,($ !,8 ($(,
H2SO4 - 8
Di(i$ ($-i$" $%$"#$ > i"i" ,"/, .
@. KOH 50 !+(!i8 ($(, )('+'&'+* !+(!i > i+, .
$. %&!A NA!"#L1.
1. F!C(3
> ($+,$" -$"$8 i ,"/,8 $($* N$OH ,"/, ),$
3. M$+G,i > i $) !+%$+"$
6. L$+,$" ;$ N$HCO3
. R!$)i M'(i > $ !i)i $(''( 1 ($+,$" !"!+ /,($ !,8
($(, H2SO4 - 8 Di(i$ ($-i$" $%$"#$ > N!/$i&
@. KOH 50 !+(!i8 ($(, )('+'&'+* !+(!i > i+, .
'. R&S#RCN
1. K+i$( -,i $) !+%$+"$8 !",)
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$ R!'+i" =(#!+i" $$* ')$($ H2SO4 - 9999 :i'(!
F(,+'!"i > i Ji"//$ *!+$
MARUIS
MAYER
BOUCHARDAD L$+,$" $($* $i+ /$+$* H( "#$ !+!$)i $$* ),$ i)+'*$ )!(,$+
/$ CO2 .
0. R#2ALL#L
FENOL 2016 16
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OH
OH
OH
1. K+i$(8 $) !+%$+"$8 *!"/)i($- -($ $$, ,"/, 99999 ')!($
5. F!(i"/ > +!,)i -$$ ,, )$*$+
6. M$+G,i > M!+$8 -$"$)$" $" ii$*)$" > *!+$ ,$
. P9A!$ > +'$ *,$ $i
. S-' ! > ($+,$" ;$ $($* $i+ 25 $i+ +.- !,$ 30 *!"i >
-i")9 :i'(! .
3. NA2N
$. R$$ *,($9 *,($ !+$)$+8 ($(, $"$!!i . T.L 124 Q C 7 125 Q C$
. L$+, $($* $(''(8 !!+
. ! > !!9!! *i"#$)
!. HNO3 H2SO4 ! > ),"i"/ ($*$
&. F!C(3 > ,"/, ')!($
/. Di$*,"/)$" !"/$" N$OH ($(, i$$*)$" 8($(, >
AG. B+'* > !"$-$" -,i
NH4OH ,$-)$"8 i$ $($* $i+ C,SO4 > !"$-$"
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T.L 41 Q C T.D 12 Q C
K!($+,$" $($* $i+ > 1>12
L$+, $i) $($* !!+8 -i+i, 8 )('+'&'+* $" /(#!+i" 8 $($* -$+$&&i"
1>100
D$($* *i"#$) 1>2 $ F!C(3 9999 ,"/, i+, -i+. !+(!i 9999 i($"/
$ MILLON 9999 *!+$ ,"/,
$ AG. B+'* !+(!i > !"$-$" -,i
$ R!$)i I"!&!"'( 9999 i
K+i$( $) !+%$+"$
K"-S-S !"+#L
1. L$+,$" $($* $i+ $"i((i" 7H( i"/i" > M!+$
R'$
2. P$"$ > (!i ,$8 ii$*)$" !"$-$" *!+$ ,"/,
.
3. 9T#*'( H2SO4 -$"$)$"8 !"!+)$" !"/$" $i+ $+i"/ !!($ i"!+$()$"
!"/$" C$CO3 .
4. Fi(+$ > F!C(3 > i+,.
5. T!+!",) C$9T#*'( ,(&$ #$"/ "!+$(
6. 9T#*'( F'+*$(i" H2SO4 99999 M!+$
. 9DIAO > *!+$
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1. C$i+$"8 $, *i"#$) !"/)!
2. Ti$) ($+, $($* $i+8 ($+, $($* !$"'(8 /(i!+i"8 *i"#$) (!*$).
3. $ H2SO4 !"!+ 9999 *!+$ 8i($ i!"!+)$" 9999 ,"/, )!+,
4. $ F!C(3 9999 i
. B$, -!i&i) T.L 110 Q C
. $ F!C(3 9999 > i+, :i'(! $*-,+$"
9 O+' 9999 > ,"/,8 i+, )!+,
9 M!$ 9999 > ,"/, )!+,
9 P$+$ 9999 > i+, )!+,8 -,i
. $ $G.+'*>
FENOL 2016 19
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9 O+' 9999 > -,i
9 M!$ 9999 > -,i
9 P$+$ 9999 > $) $$ 8 ),"i"/
!. $ *$+G,i 9999 *!+$
&. $ $ -i)+$ 9999 09)!+'( 9999 K+i$( *!+!,)i8 !"$-$" ')!($
. M!+!,)i ($+,$" A/9$**'"i$)$( >
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$. B!+%$+"$C')!($ *,$ +'$
. R$$ !i)i -$i
. L$+,$" $($* $i+ !+!$)i $$* (!*$
. F!C(3 -i+ >i+'$
/. H2SO4 - >),"i"/ ')($
. HNO3 >*!+$ $+$
i. F+'! >*!+$ ,"/,
*!+$ ')!($
). N$OH >),"i"/ ')!($
P$"$)$" >),"i"/
ROU? >
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Biosintesis senyawa fenolik seagian esar ter!adi di sitoplasma $" i$%$(i
*!($(,i
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FENOL 2016 23
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FENOL 2016 24
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M!'! #$"/ i-$)$i ,",) *!"i"!i &!"'( !$+$ )'*!+i$(8 $$($
1. Hi+'(ii K('+'!";!"$ P+'! D'%
P+'! i"i )('+'!";!"$ i-$"$)$" $*-$i 350'C !)$"$" i"//i !"/$"
($+,$" "$+i,* i+')i$. R!$)i i"i $)$" *!"/$i()$" i'" &!"')i$ $" !!($
i$$*)$" $)$" *!"
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$"$('/ i"+$*'(!),(!+ *!"/$i()$" $$* 59!i+'),i"$ #$"/ *!*-,"#$i (i"/)$+
i)('!)$"$8 #$"/ )!*,i$" i,$ *!"
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A$* i"$*$8 $$( *,($ &!"i(-+'-$"'i8 i!",) !"/$" !$*i"$i
!";i*$i ($"/,"/ &!"i($($"i"8 $" $$* -9),*$+$ $-$ ii'i"!i $($* $+$
#$"/ !+,-$ $+i i+'i" $$, i+')i($i $$* i"$*$ -$$ -'ii -$+$. A$* -9
),*$+$
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$II. PEN8U9IAN DEN8AN KLT1. M!'! A"$(ii F!"'( !"/$" KLT
M!'! !+$i) ,",) -!*i$$" $" i!"i&i)$i !"#$%$ &!"'( !!+$"$
!"/$" KLT. S!"#$%$ !+!, ,*,*"#$ i!!)i !!($ i+'(ii $$* $$,
$$ $+i
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A$8 R. 1@0. A"$(ii Ki*i$ F$+*$i. L!*$/$ P!"!+i$" U"i:!+i$ H$$",i" >
M$)$$+.
Di+
H!+*$"8 J. R. 1@. A"$(ii F$+*$i. =$ M$)$$+.
A+$*8 )). 2015. M$)$($ Ki*i$ O+/$"i) B$$" A($*. U"i:!+i$ N!/!+i M$)$$+
F$),($ M$!*$i)$ $" I(*, P!"/!$,$" A($*.
->',*!".i-',*!"&!"i(9-+'-$"'i'.*(. Di$)! $"//$( 11 A-+i(
2016.
E+"i%$i. 2005. I'($i K,*$+i" D$+i D$," K$#, R$," Ri"$$", "$,,. T!i.
P+'i Ki*i$ P+'/+$* P$$$+ USU
R$$*,!8 T. J. 200. S,i! T'%$+ T! S#"!i '& N':!(8 C',*$+i"9$! HI91
P+'!$! I"ii'+. T!i. D!-$+*!" '& !*i+# R'! U"i:!+i#.
=+$$*'%".
R'#. 2011. M$)$($ F!"'(i). ->+'#-,+$)$-,$('//*$'#.('/-'.'*. Di$)!
-$$ $"//$( 12 M$+! 2015
Wi)i-!i$ $$* i"$*$ A"$+i)i*i$.2013 ASAM SINAMAT BAHAN UNTUK
PARFUM. ->%$%$$"i(*,)i*i$.%'+-+!.'*.
FENOL 2016 29
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->%%%.$$!*i$.!,22B$V2.VBi'i"!iVS!"#$%$VF!"'(i)VS$#,+$"VI"i/!"
',VI"'"!i$. Di$)! $"//$( 11 A-+i( 2014.
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