Sintesis Hemiterpena Turunan 1-Bromo-3-Metil-2-Butena

Putri, Devi Anggraini (2015) Sintesis Hemiterpena Turunan 1-Bromo-3-Metil-2-Butena. Undergraduate thesis, Institut Teknologi Sepuluh Nopember.

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Abstract

Monoterpena dan seskuiterpena merupakan kelompok terpena yang paling banyak dimanfaatkan sebagai bahan pewangi. Hemiterpena sangat berpotensi sebagai senyawa pewangi, tetapi jarang dijumpai di alam. 3-Metil-2-butena-1-il asetat merupakan hemiterpena yang terdapat dalam minyak ylang-ylang (Cananga adorata), sedangkan 3-metil-2-butena-1-ol merupakan hemiterpena yang ditemukan dalam buah jeruk, anggur, dan raspberi. Penelitian yang dilakukan berhasil mensintesis tiga hemiterpena. Sintesis dilakukan dalam dua tahap, tahap pertama adalah reaksi asam karboksilat dengan natrium bikarbonat sehingga diperoleh garam natrium 3-fenil-2-propenoat. Reaksi substitusi nukleofilik 1-bromo-3-metil-2-butena pada tahap kedua dengan nukleofil ion karboksilat yang diperoleh pada tahap pertama diperoleh hemiterpena. Reaksi-reaksi yang melibatkan asam karboksilat berupa asam 3-fenil-2-propenoat, asam 2- metilbutanoat, dan asam 2-metilpropanoat masing-masing diperoleh hemiterpena 3-metil-2-butena-1-il-3-fenil-2-propenoat dengan rendemen 91%, 3-metil-2-butena-1-il-2-metilbutanoat dengan rendemen 83%, 3-metil-2-butena-1-il-2-metilpropanoat dengan rendemen 88%. 3-Metil-2-butena-1-il-3-fenil-2-propenoat dengan dengan struktur 3-fenil-2-propenoat menunjukkan panjang gelombang maksimum (λmaks) 300 nm yang merupakan daerah serapan UV-B sehingga berpotensi sebagai bahan tabir surya. =========================================================================================== Monoterpene and sesquiterpene are a group of terpene widely used as fragrance ingredient. Hemiterpene is potentially as fragrance compound, but rarely found in nature. 3-Methyl-1-yl acetate is hemiterpene on oil of ylang-ylang (Cananga adorata), while 3-methyl-2-butene-1-ol is hemiterpene found in fruits as citrus, grapes, and raspberry. This research aims to syntheses three hmiterpene. Synthesis approach with two steps, the first step was reacted between carboxylic acid 3-phenyl-2-propenoat with sodium bicarbonate obtained sodium salt of 3-phenyl-2- propenoat. The second steps nucleophilic substitution reaction of 1-bromo-3-methyl-2-butene with nucleophile of carboxylate ion obtained in the first steps was obtained hemiterpena. The reactions of carboxylic acids as 3-phenyl-2-propenoat acid, 2- metilbutanoat acid, and 2-methylpropanoat acid were obtained 3- methyl-2-butene-1-yl-3-phenyl-2-propenoat in 91% yield, 3- methyl-2-butene-1-yl-2-metilbutanoat in 83% yield, 3-methyl-2- butene-1-yl-2-metilpropanoat in 88% yield. 3-Methyl-2-butene-1- yl-3-phenyl-2-propenoat has 3-fenil-2-propenoat structure showed maximum wavelength (λmaks) 300 nm which is the area of UV-B has potentially as sunscreen ingredients.

Item Type: Thesis (Undergraduate)
Additional Information: RSKi 547.71 Put s
Uncontrolled Keywords: hemiterpena, pewangi, prenil bromida, hemiterpene, fragrance, prenyl bromide
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Mathematics and Science > Chemistry > (S1) Undergraduate Theses
Depositing User: Eny Widiastuti -
Date Deposited: 25 Apr 2018 08:15
Last Modified: 25 Apr 2018 08:15
URI: http://repository.its.ac.id/id/eprint/51808

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