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Transcript of Sintesis Turunan Vanilil Alkohol
SINTESIS EMPAT TURUNAN VANILIL ALKOHOL
Oleh : Nila Huda (1408100045)
Pembimbing : Prof. Dr. Mardi Santoso
Latar Belakang
Nila Huda - Kimia ITS
Vanilin (1)
Vanilla
planifolia
OH
O
O
O
O
O
O(1) (2)
Perasa &
Pewangi
Antioksidan
(380 ppm)
Anti bakteri
(Pengawet)
Latar Belakang
Nila Huda - Kimia ITS
oriental-ambery-
gourmand
2%
sweet chocolate
+ fresh minty
4%
Isobutavan® (2)
sweet &
creamy vanila
OH
O
O
O
O
O
OVanilin (1)
Latar Belakang
Nila Huda - Kimia ITS
(1)
OH
O
O
OH
O
NOH
O
O
NO
O
R
R
O
OH
O
NO
O
R
H2NOH
R(CO)Cl1 ekivalen
R(CO)Cl2 ekivalen
piridina
piridina
HClNaAsetat
(3) (4)
(5)
80-96%
88-92%
Dikusar et al., 2004, Chem Natural Compounds,
Vol. 40, No. 2, Hal. 180-183
Latar Belakang
Nila Huda - Kimia ITS
OH
O
O
OH
O
OH
1. NaBH4/NaOH
2. HCl/H2O
(1) (6)
Fowler, R.,1992, J. Chem. Educ., Vol. 69 (2), A43
68%
Hipotesis Penelitian
Nila Huda - Kimia ITS
OH
O
OH
O
O
O
O
R
O
R
(6) (7)
(a) R= CH2CH3
(b) R= (CH2)2CH3
(c) R= (CH2)3CH3
(d) R= (CH2)4CH3
OH
O
NOH
O
O
NO
O
R
R
O(3) (4)
Permasalahan Penelitian
Nila Huda - Kimia ITS
OH
O
OH
O
O
O
O
R
O
R
(6) (7)
(a) R= CH2CH3
(b) R= (CH2)2CH3
(c) R= (CH2)3CH3
(d) R= (CH2)4CH3
Tujuan Penelitian
Nila Huda - Kimia ITS
(a) R= CH2CH3
(b) R= (CH2)2CH3
(c) R= (CH2)3CH3
(d) R= (CH2)4CH3OH
O
OH
O
O
O
O
R
O
R
(6) (7)
Data Karakter Sensorinya
Sintesis 3-Metoksi 4-propanoiloksibenzil propanoat (7a)
Nila Huda - Kimia ITS
PROSEDUR
Nila Huda - Kimia ITS
OH
O
OH
O
O
O
O
O
(6)(7a)
Nila Huda - Kimia ITS
Keterangan :
1 = vanilil alkohol (6)
2 = hasil reaksi (7a)
Eluen = n-heksana : etil asetat (2:1)
Hasil Monitoring Sintesis Diester (7a) dengan
KLT
BACK
Nila Huda - Kimia ITS
Kromatogram Diester (7a) Hasil Sintesis
Nila Huda - Kimia ITS
Spektrum Massa Diester (7a)
Hasil Sintesis O
O
O
O
O (7a)
O
O
OH
O
·+
OH
O
OH
+·
OH
O
+O+
Mr = 266
Sintesis 4-(Butiriloksi)-3-metoksibenzil butirat (7b)
Nila Huda - Kimia ITS
PROSEDUR
Nila Huda - Kimia ITS
OH
O
OH
O
O
O
O
O
(6)(7b)
Nila Huda - Kimia ITS
Keterangan :
1 = vanilil alkohol (6)
2 = hasil reaksi (7b)
Eluen = n-heksana : etil asetat (2:1)
Hasil Monitoring Sintesis Diester (7b) dengan
KLT
BACK
Nila Huda - Kimia ITS
Kromatogram Diester (7b) Hasil Sintesis
Nila Huda - Kimia ITS
Spektrum Massa Diester (7b)
Hasil Sintesis O
O
O
O
O (7b)
OH
O
+
O
O
OH
O
+·
OH
O
OH
+·
O+
Mr = 294
Sintesis 3-Metoksi 4-pentanoiloksibenzil pentanoat (7c)
Nila Huda - Kimia ITS
PROSEDUR
Nila Huda - Kimia ITS
OH
O
OH
O
O
O
O
O
(6)(7c)
Nila Huda - Kimia ITS
Keterangan :
1 = vanilil alkohol (6)
2 = hasil reaksi (7c)
Eluen = n-heksana : etil asetat (2:1)
Hasil Monitoring Sintesis Diester (7c) dengan
KLT
BACK
Nila Huda - Kimia ITS
Kromatogram Diester (7c) Hasil Sintesis
Nila Huda - Kimia ITS
Spektrum Massa Diester (7c)
Hasil Sintesis O
O
O
O
O (7c)
OH
O
+
OH
O
OH
+·
O
O
OH
O
·+
+
O+
Mr = 322
Sintesis 4-(Heksanoiloksi)-3-metoksibenzil heksanoat (7d)
Nila Huda - Kimia ITS
PROSEDUR
Nila Huda - Kimia ITS
OH
O
OH
O
O
O
O
O
(6)(7d)
Nila Huda - Kimia ITS
Keterangan :
1 = vanilil alkohol (6)
2 = hasil reaksi (7d)
Eluen = n-heksana : etil asetat (2:1)
Hasil Monitoring Sintesis Diester (7d) dengan
KLT
BACK
Nila Huda - Kimia ITS
Kromatogram Diester (7d) Hasil Sintesis
Nila Huda - Kimia ITS
Spektrum Massa Diester (7d)
Hasil Sintesis O
O
O
O
O (7d)
OH
O
OH
+·
OH
O
+
O+
+
O
O
OH
O
·+
Mr = 350
Nila Huda - Kimia ITS
Perbandingan Data 1H-
NMR Diester Hasil Sintesis
Jenis Proton Pergeseran Kimia (ppm)
Diester (7a) Diester (7b) Diester (7c) Diester (7d)
-CH3 1,16 (t, 3H)
1,26 (t, 3H)
0,95 (t, 3H)
1,05 (t, 3H)
0,91 (t, 3H)
0,97 (t, 3H)
0,88 (t, 3H)
0,93 (t, 3H)
-CH2-
2,38 (m, 2H)
2,60 (m, 2H)
1,67 (m, 2H)
1,79 (m, 2H)
2,33 (t, 2H)
2,56 (t, 2H)
1,35 (m, 2H)
1,46 (m, 2H)
1,64 (m, 2H)
1,75 (m, 2H)
2,36 (t, 2H)
2,58 (t, 2H)
1,31 (m, 4H)
1,40 (m, 4H)
1,63 (m, 2H)
1,76 (m, 2H)
2,35 (t, 2H)
2,57 (t, 2H)
-OCH3 3,82 (s, 3H) 3,82 (s, 3H) 3,82 (s, 3H) 3,82 (s, 3H)
-OCH2- 5,08 (s, 2H) 5,08 (s, 2H) 5,07 (s, 2H) 5,07 (s, 2H)
ArH 6,92-7,01
(m, 3H)
6,92-7,01
(m, 3H)
6,92-7,00
(m, 3H)
6,92-7,00
(m, 3H)
O
O
O
O
R
R
O (7)
(a) R= CH2CH3
(b) R= (CH2)2CH3
(c) R= (CH2)3CH3
(d) R= (CH2)4CH3
Nila Huda - Kimia ITS
Perbandingan Data 13C-
NMR Diester Hasil Sintesis
Jenis Karbon Pergeseran Kimia (ppm)
Diester (7a) Diester (7b) Diester (7c) Diester (7d)
-CH3 9,20
9,28
13,72
13,81
13,85
13,87
14,05
14,11
-CH2-
27,47
27,72
18,57
18,69
36,01
36,33
22,33
22,39
27,16
27,21
33,89
34,18
22,45
22,48
24,77
24,85
31,35
31,44
34,13
34,42
O
O
O
O
R
R
O (7)
(a) R= CH2CH3
(b) R= (CH2)2CH3
(c) R= (CH2)3CH3
(d) R= (CH2)4CH3
Nila Huda - Kimia ITS
Perbandingan Data 13C-
NMR Diester Hasil Sintesis
Jenis Karbon Pergeseran Kimia (ppm)
Diester (7a) Diester (7b) Diester (7c) Diester (7d)
-OCH3 56,02 55,99 55,99 55,97
-OCH2- 65,88 65,87 65,88 65,91
ArCH
112,56
120,76
122,94
112,52
120,75
122,97
112,53
120,76
122,97
112,52
120,76
122,96
ArC
134,99
139,84
151,26
135,03
139,81
151,25
135,03
139,84
151,28
135,02
139,81
151,25
CO 172,63
174,35
171,84
173,62
171,98
173,78
172,01
173,82
O
O
O
O
R
R
O (7)
(a) R= CH2CH3
(b) R= (CH2)2CH3
(c) R= (CH2)3CH3
(d) R= (CH2)4CH3
Nila Huda - Kimia ITS
Profil Sensori Diester Hasil
Sintesis O
O
O
O
R
R
O (7)
(a) R= CH2CH3
(b) R= (CH2)2CH3
(c) R= (CH2)3CH3
(d) R= (CH2)4CH3
(7a) : fruity, citrus, vanilla, sweet
(7b) : berry, citrus
(7c) : chocolate, berry, citrus
(7d) : sweet, fruity, vanilla
Kesimpulan
Nila Huda - Kimia ITS
83%
O
O
O
O
O (7a)
OH
O
OH
(6)
O
O
O
O
O (7d)
O
O
O
O
O (7c)
82%
79%
65%
O
O
O
O
O (7b)
fruity,
citrus,
vanilla,
sweet
berry,
citrus
Chocolate,
berry,
citrus
sweet,
fruity,
vanilla
Nila Huda - Kimia ITS
1. Prof. Dr. Mardi Santoso
2. Direktorat Jenderal Pendidikan Tinggi,
Kementrian Pendidikan Nasional
3. Arif fadlan, M.Si.
4. Sofa Fajriah, S.Si.
5. Panelis PT. Gelora Djaja
6. Prof. Dr. Surya Rossa Putra & Drs. Agus
Wahyudi, MS.
7. Peserta Seminar
