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INTISARI

Sintesis analog kurkumin dari piperonal, veratraldehid dan pdimetilaminobenzaldehid serta perbandingan elusidasi struktur antara
eksperimen dan hasil kajian spektroskopi didasarkan metode DFTB3LYP/6-31G(d)
oleh
Mario Rowan Sohilait
11/322858/PPA/03588
Telah dilakukan sintesis beberapa senyawa analog kurkumin melalui
reaksi kondensasi aldol antara aseton dan beberapa derivat benzaldehid. Analisis
hasil sintesis dilakukan dengan HPLC, FT-IR, MS, 1H dan 13C-NMR. Reaksi
kondensasi aseton dengan derivat benzaldehid dari piperonal, veratraldehid, dan
para-dimetilaminobenzaldehid menghasilkan senyawa 1,5-bis(1,3-benzodioksol5il)penta-1,4-dien-3-on (padatan berwarna kuning pucat dengan rendemen
94,87%), senyawa 1,5-bis(3,4-dimetoksifenil)penta-1,4-dien-3-on (padatan
berwarna kuning dengan rendemen 83,38%) dan senyawa 1,5-bis[4(dimetilamino)fenil]penta-1,4-dien-3-on (padatan berwarna kuning keemasan
dengan rendemen 92,05%). Prediksi spektra ketiga senyawa analog kurkumin
tersebut dilakukan menggunakan perangkat lunak Gaussian09 dengan metode
DFT B3LYP himpunan basis 6-31G(d). Hasil spektra vibrasi IR dan pergeseran
kimia pada spektra 1H dan 13C-NMR mempunyai harga yang mendekati harga
yang diperoleh dari eksperimen.
Kata kunci : Analog kurkumin, piperonal, veratraldehid, DFT-B3LYP, paradimetilaminobenzaldehid.

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ABSTRACT

Synthesis of curcumin analogues from piperonal, veratraldehyde and pdimethylaminobenzaldehyde and comparison of structure elucidation
between the experiment and the result of spectroscopic studies using DFTB3LYP/6-31G(d) method
by
Mario Rowan Sohilait
11/322858/PPA/03588
Several curcumin analogues have been synthesized via condensation
reaction between acetone and several benzaldehyde derivatives. The products
were analyzed using HPLC, MS, FT-IR, 1H and 13C-NMR. The condensation of
acetone and benzaldehydes of piperonal, veratraldehyde and pdimethylaminobenzaldehyde gave 1,5-bis(1,3-benzodioxol-5yl)penta-1,4-dien-3one (pale yellow solid, 94.87% yield), 1,5-bis(3,4-dimethoxyphenyl)penta-1,4dien-3-one
(yellow
solid,
83.38%
yield)
and
1,5-bis[4(dimethylamino)phenyl]penta-1,4-dien-3-one (golden yellow, 92.05% yield),
respectively. The spectroscopic prediction of the curcumin analogues were
conducted using Gaussian09 software with the method of DFT using B3LYP/631G(d) basis set. It was showed that these methods gave similar IR vibration, 1H
and 13C-NMR spectra as those of experimental results.
Keywords:

Curcumin
analogues,
piperonal,
p-dimethylaminobenzaldehyde, DFT-B3LYP.

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veratraldehyde,