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)

Nila Huda - Kimia ITS

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