sintesis turunan vanilil alkohol
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SINTESIS EMPAT TURUNAN VANILIL ALKOHOLOleh : Nila Huda (1408100045) Pembimbing : Prof. Dr. Mardi Santoso
Latar BelakangO O
Vanilla planifoliaO
O OH O O
Vanilin (1)
(1)
(2)
Perasa & Pewangi Antioksidan (380 ppm) Anti bakteri (Pengawet)Nila Huda - Kimia ITS
2%
Latar BelakangO O
O OH O O
O
oriental-amberygourmand
Vanilin (1)
Isobutavan (2) sweet & creamy vanila
4%sweet chocolate + fresh mintyNila Huda - Kimia ITS
Latar BelakangO O N N OH
H2NOHO OH
R(CO)Cl 2 ekivalen piridina
O
R
HCl NaAsetatOH
O
O R O O O N O
80-96% (4)
(3)
(1)R(CO)Cl 1 ekivalen piridina
R
O
88-92% (5)
Dikusar et al., 2004, Chem Natural Compounds, Vol. 40, No. 2, Hal. 180-183Nila Huda - Kimia ITS
OH
Latar BelakangO OH
1. NaBH4/NaOH 2. HCl/H2OO OH OH O
(1)
68% (6)
Fowler, R.,1992, J. Chem. Educ., Vol. 69 (2), A43
Nila Huda - Kimia ITS
Hipotesis PenelitianO N N OH O R
O OH R O
O
(3)O
(4)
OH
O O O
R
O OH
RO
O
(a) R= CH2CH3 (b) R= (CH2)2CH3 (c) R= (CH2)3CH3 (d) R= (CH2)4CH3
(6)
(7)
Nila Huda - Kimia ITS
Permasalahan PenelitianOH O O O
R
O OH
RO
O
(a) R= CH2CH3 (b) R= (CH2)2CH3 (c) R= (CH2)3CH3 (d) R= (CH2)4CH3
(6)
(7)
Nila Huda - Kimia ITS
Tujuan PenelitianOH O O O
R
O OH
RO
O
(a) R= CH2CH3 (b) R= (CH2)2CH3 (c) R= (CH2)3CH3 (d) R= (CH2)4CH3
(6)
(7)
Data Karakter SensorinyaNila Huda - Kimia ITS
Sintesis 3-Metoksi 4-propanoiloksibenzil propanoat (7a)
Nila Huda - Kimia ITS
PROSEDUR
OH
O O O O
O OH
(6)O
(7a)
Nila Huda - Kimia ITS
Hasil Monitoring Sintesis Diester (7a) dengan KLT
Keterangan : 1 = vanilil alkohol (6) 2 = hasil reaksi (7a) Eluen = n-heksana : etil asetat (2:1)Nila Huda - Kimia ITS
BACK
Kromatogram Diester (7a) Hasil Sintesis
Nila Huda - Kimia ITS
Mr = 266
O O
Spektrum Massa Diester (7a) Hasil SintesisO+
O O
(7a)
OH
OH
+O
+
+
OO OH
O O O
OH
Nila Huda - Kimia ITS
Sintesis 4-(Butiriloksi)-3-metoksibenzil butirat (7b)
Nila Huda - Kimia ITS
PROSEDUR
OH
O O O O
O OH
(6)O
(7b)
Nila Huda - Kimia ITS
Hasil Monitoring Sintesis Diester (7b) dengan KLT
Keterangan : 1 = vanilil alkohol (6) 2 = hasil reaksi (7b)
Eluen = n-heksana : etil asetat (2:1)
BACKNila Huda - Kimia ITS
Kromatogram Diester (7b) Hasil Sintesis
Nila Huda - Kimia ITS
Mr = 294
O O
Spektrum Massa Diester (7b) Hasil SintesisO
O O
(7b)
+
OH
+
OHO OH
+
O OHO O O
+O
Nila Huda - Kimia ITS
Sintesis 3-Metoksi 4-pentanoiloksibenzil pentanoat (7c)
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PROSEDUR
OH
O O O O
O OH
(6)O
(7c)
Nila Huda - Kimia ITS
Hasil Monitoring Sintesis Diester (7c) dengan KLT
Keterangan : 1 = vanilil alkohol (6) 2 = hasil reaksi (7c)
Eluen = n-heksana : etil asetat (2:1)
BACKNila Huda - Kimia ITS
Kromatogram Diester (7c) Hasil Sintesis
Nila Huda - Kimia ITS
Mr = 322
O O
Spektrum Massa Diester (7c) Hasil SintesisO
O O
(7c)
+
OH
+
OH
+
+OH
O
O OHO O
O
+O
Nila Huda - Kimia ITS
Sintesis 4-(Heksanoiloksi)-3-metoksibenzil heksanoat (7d)
Nila Huda - Kimia ITS
PROSEDUR
OH
O O O O
O OH
(6)O
(7d)
Nila Huda - Kimia ITS
Hasil Monitoring Sintesis Diester (7d) dengan KLT
Keterangan : 1 = vanilil alkohol (6) 2 = hasil reaksi (7d) Eluen = n-heksana : etil asetat (2:1)Nila Huda - Kimia ITS
BACK
Kromatogram Diester (7d) Hasil Sintesis
Nila Huda - Kimia ITS
Mr = 350
O O
Spektrum Massa Diester (7d) Hasil SintesisO
O O
(7d)
+
OH
+
OH
+
O OH
O OHO O
O
+O
+
Nila Huda - Kimia ITS
O
R O O
Perbandingan Data 1HNMR Diester Hasil SintesisJenis Proton -CH3
R O
O
(a) R= CH2CH3 (b) R= (CH2)2CH3 (c) R= (CH2)3CH3 (d) R= (CH2)4CH3
(7)
Diester (7a) 1,16 (t, 3H) 1,26 (t, 3H) 2,38 (m, 2H) 2,60 (m, 2H)
Pergeseran Kimia (ppm) Diester (7b) Diester (7c) 0,95 (t, 3H) 0,91 (t, 3H) 1,05 (t, 3H) 1,67 (m, 2H) 1,79 (m, 2H) 2,33 (t, 2H) 2,56 (t, 2H) 0,97 (t, 3H) 1,35 (m, 2H) 1,46 (m, 2H) 1,64 (m, 2H) 1,75 (m, 2H) 2,36 (t, 2H) 2,58 (t, 2H) 3,82 (s, 3H) 5,07 (s, 2H) 6,92-7,00 (m, 3H)
Diester (7d) 0,88 (t, 3H) 0,93 (t, 3H) 1,31 (m, 4H) 1,40 (m, 4H) 1,63 (m, 2H) 1,76 (m, 2H) 2,35 (t, 2H) 2,57 (t, 2H) 3,82 (s, 3H) 5,07 (s, 2H) 6,92-7,00 (m, 3H)
-CH2-
-OCH3 -OCH2ArH
3,82 (s, 3H) 5,08 (s, 2H) 6,92-7,01 (m, 3H)
3,82 (s, 3H) 5,08 (s, 2H) 6,92-7,01 (m, 3H)Nila Huda - Kimia ITS
O
R O O
Perbandingan Data 13CNMR Diester Hasil Sintesis
R O
O
(a) R= CH2CH3 (b) R= (CH2)2CH3 (c) R= (CH2)3CH3 (d) R= (CH2)4CH3
(7)
Jenis Karbon -CH3
Diester (7a) 9,20 9,28 27,47 27,72
Pergeseran Kimia (ppm) Diester (7b) Diester (7c) 13,72 13,85 13,81 18,57 18,69 36,01 36,33 13,87 22,33 22,39 27,16 27,21 33,89 34,18
Diester (7d) 14,05 14,11 22,45 22,48 24,77 24,85 31,35 31,44 34,13 34,42
-CH2-
Nila Huda - Kimia ITS
O
R O O
Perbandingan Data NMR Diester Hasil Sintesis
13C-
R O
O
(a) R= CH2CH3 (b) R= (CH2)2CH3 (c) R= (CH2)3CH3 (d) R= (CH2)4CH3
(7)
Jenis Karbon -OCH3 -OCH2ArCH
Diester (7a) 56,02 65,88 112,56 120,76
Pergeseran Kimia (ppm) Diester (7b) Diester (7c) 55,99 55,99 65,87 65,88 112,52 112,53 120,75 120,76
Diester (7d) 55,97 65,91 112,52 120,76
122,94 134,99ArC 139,84 151,26 172,63 174,35
122,97 135,03139,81 151,25 171,84 173,62Nila Huda - Kimia ITS
122,97 135,03139,84 151,28 171,98 173,78
122,96 135,02139,81 151,25 172,01 173,82
CO
O
R O O
Profil Sensori Diester Hasil SintesisR O O
(a) R= CH2CH3 (b) R= (CH2)2CH3 (c) R= (CH2)3CH3 (d) R= (CH2)4CH3
(7)
(7a) : fruity, citrus, vanilla, sweet (7b) : berry, citrus (7c) : chocolate, berry, citrusNila Huda - Kimia ITS
(7d) : sweet, fruity, vanilla
Kesimpulan79%fruity, citrus, vanilla, sweet
O O O O O
83%berry, citrus
O O O
OH
O O
(7a)
(7b)
82%Chocolate, berry, citrus
O
O OHO O
65%sweet, fruity, vanilla
O O O O
(6)
O O
(7c)Nila Huda - Kimia ITS
O
(7d)
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
Nila Huda - Kimia ITS