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Page 1: Sintesis Turunan Vanilil Alkohol

SINTESIS EMPAT TURUNAN VANILIL ALKOHOL

Oleh : Nila Huda (1408100045)

Pembimbing : Prof. Dr. Mardi Santoso

Page 2: Sintesis Turunan Vanilil Alkohol

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)

Page 3: Sintesis Turunan Vanilil Alkohol

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)

Page 4: Sintesis Turunan Vanilil Alkohol

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

Page 5: Sintesis Turunan Vanilil Alkohol

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%

Page 6: Sintesis Turunan Vanilil Alkohol

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)

Page 7: Sintesis Turunan Vanilil Alkohol

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

Page 8: Sintesis Turunan Vanilil Alkohol

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

Page 9: Sintesis Turunan Vanilil Alkohol

Sintesis 3-Metoksi 4-propanoiloksibenzil propanoat (7a)

Nila Huda - Kimia ITS

Page 10: Sintesis Turunan Vanilil Alkohol

PROSEDUR

Nila Huda - Kimia ITS

OH

O

OH

O

O

O

O

O

(6)(7a)

Page 11: Sintesis Turunan Vanilil Alkohol

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

Page 12: Sintesis Turunan Vanilil Alkohol

Nila Huda - Kimia ITS

Kromatogram Diester (7a) Hasil Sintesis

Page 13: Sintesis Turunan Vanilil Alkohol

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

Page 14: Sintesis Turunan Vanilil Alkohol

Sintesis 4-(Butiriloksi)-3-metoksibenzil butirat (7b)

Nila Huda - Kimia ITS

Page 15: Sintesis Turunan Vanilil Alkohol

PROSEDUR

Nila Huda - Kimia ITS

OH

O

OH

O

O

O

O

O

(6)(7b)

Page 16: Sintesis Turunan Vanilil Alkohol

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

Page 17: Sintesis Turunan Vanilil Alkohol

Nila Huda - Kimia ITS

Kromatogram Diester (7b) Hasil Sintesis

Page 18: Sintesis Turunan Vanilil Alkohol

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

Page 19: Sintesis Turunan Vanilil Alkohol

Sintesis 3-Metoksi 4-pentanoiloksibenzil pentanoat (7c)

Nila Huda - Kimia ITS

Page 20: Sintesis Turunan Vanilil Alkohol

PROSEDUR

Nila Huda - Kimia ITS

OH

O

OH

O

O

O

O

O

(6)(7c)

Page 21: Sintesis Turunan Vanilil Alkohol

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

Page 22: Sintesis Turunan Vanilil Alkohol

Nila Huda - Kimia ITS

Kromatogram Diester (7c) Hasil Sintesis

Page 23: Sintesis Turunan Vanilil Alkohol

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

Page 24: Sintesis Turunan Vanilil Alkohol

Sintesis 4-(Heksanoiloksi)-3-metoksibenzil heksanoat (7d)

Nila Huda - Kimia ITS

Page 25: Sintesis Turunan Vanilil Alkohol

PROSEDUR

Nila Huda - Kimia ITS

OH

O

OH

O

O

O

O

O

(6)(7d)

Page 26: Sintesis Turunan Vanilil Alkohol

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

Page 27: Sintesis Turunan Vanilil Alkohol

Nila Huda - Kimia ITS

Kromatogram Diester (7d) Hasil Sintesis

Page 28: Sintesis Turunan Vanilil Alkohol

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

Page 29: Sintesis Turunan Vanilil Alkohol

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

Page 30: Sintesis Turunan Vanilil Alkohol

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

Page 31: Sintesis Turunan Vanilil Alkohol

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

Page 32: Sintesis Turunan Vanilil Alkohol

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

Page 33: Sintesis Turunan Vanilil Alkohol

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

Page 34: Sintesis Turunan Vanilil Alkohol

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