Struktur & Klasifikasi Lipid
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Outline TP Lemak & Minyak
• Struktur dan Klasifikasi Lipid• Modifikasi Lemak Minyak• Peran dan Aplikasi Lemak Minyak dalam
Pengolahan Pangan
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STRUKTUR & KLASIFIKASI LIPID
Teknologi Lemak dan MinyakProgram Studi Ilmu dan Teknologi Pangan
Universitas Sebelas Maret Surakarta
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PENDAHULUAN
• Lipid didefinisikan sebagai komponen yang tidak larut air, tetapi larut dalam pelarut non-polar seperti petroleum ether, benzene, chloroform
• Fungsi lipid :Cadangan energiKomponen penyusun membran selPrekursor hormon (steroid dan prostaglandin)Dll
• Asam lemak merupakan komponen penting dalam lipid
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ASAM LEMAK
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• Asam lemak terdiri dari gugus karboksilat dan rantai karbon (R) yang terdiri dari atom H and C
1. Struktur Utama Asam Lemak
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• Nama trivial diberikan sebelum struktur kimia asam lemak diketahui dan biasanya menunjukkan sumber asal asam lemak
2. Tata Nama Asam Lemak
Asam Lemak Sumber
Asam Palmitat (Palmitic acid) Minyak sawit / Palm oil
Asam Arakhidat (Arachidic acid) Kacang tanah (Arachic hypogea)
Asam linoleat / linolenat(Linoleic / Linolenic acid)
Minyak linseed / Linseed oil
Risinoleat (Ricinoleic) Castor oil (Ricinus communis)
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• Nama sistematis / kimia : berdasarkan kesepkatan aturan dari ahli kimia dan biokimia
international tergantung pada struktur asam lemak
• Contoh: asam oleat adalah asam cis-9-oktadekenoat. Menunjukkan pada: Bentuk karboksilat (oat) 18 atom karbon (oktadek) Satu ikatan rangkap (en) Ikatan rangkap terletak pada atom 9 dan 10 (dihitung dari
ujung karboksil) Konfigurasi cis
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Asam lemak rantai panjang (Long Chain Fatty Acids) mempunyai ≥ 12 karbon
Asam lemak rantai sedang (Medium Chain Fatty Acids) mempunyai 6 – 10 karbon
Asam lemak rantai pendek (Short Chain Fatty Acids) mempunyai < 6 karbon
3. Klasifikasi Berdasarkan Panjang Rantai C
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Asam lemak jenuh (saturated fatty acids)
Asam lemak satu ikatan rangkap (monounsaturated fatty acids)
Asam lemak banyak ikatan rangkap (polyunsaturated fatty acids) PUFA
4. Klasifikasi Berdasarkan Struktur
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Asam lemak jenuh dan tidak jenuh
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a. Asam Lemak Jenuh• Tidak mempunyai ikatan rangkap• Pada suhu ruang berbentuk padat
b. Asam Lemak Satu Ikatan Rangkap• Satu ikatan rangkap• Pada suhu ruang berbentuk cair• Konfigurasi cis (Z)• Ikatan rangkap ada pada posisi tertentu :
• Δ9 = atom C ke-9 dari gugus karboksil pada asam oleat
• ω-9 atau n-9 = atom C ke-9 dari gugus metil pada asam oleat
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Struktur Asam Oleat
Gugus metil awal untuk penamaan omega (ω)
Gugus karboksil awal untuk penamaan Δ
ω-9
Δ9
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Nama umum asam cis monoena (satu ikatan rangkap)
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c. Asam Lemak Banyak Ikatan Rangkap (PUFA)• Mempunyai ikatan rangkap ≥ 2• Pada suhu ruang berbentuk cair• Konfigurasi ikatan rangkap cis(Z) • Terutama asam poliolefinat dengan pola interupsi
metilen yaitu ikatan rangkap dipisahkan oleh gugus metilen (CH2)
• Pola 1,4 merupakan karakteristik asam lemak alami
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Interupsi Metilen (methylene-interrupted)
Gugus metilen
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Methylene-interrupted polyene acids
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E – Z notation
• E-Z notation, or the E-Z convention, is the IUPAC preferred method of describing the stereochemistry of double bonds in organic chemistry. It is an extension of cis/trans notation that can be used to describe double bonds having three or four substituents.
• If the two groups of higher priority are on opposite sides of the double bond, the bond is assigned the configuration E (from entgegen, German: [ɛntˈɡeːɡən], the German word for "opposite").
• If the two groups of higher priority are on the same side of the double bond, the bond is assigned the configuration Z (from zusammen, German: [tsuˈzamən], the German word for "together").
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(E)-But-2-ene (Z)-But-2-ene
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Conjugated Fatty Acids
• Conjugated fatty acids are polyunsaturated fatty acids in which at least one pair of double bonds are separated by only one single bond, as in conjugated linoleic acid
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Struktur PUFA
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• Essential fatty acids, or EFAs, are fatty acids that humans and other animals must ingest because the body requires them for good health but cannot synthesize them.
• Alpha-linolenic acid (omega 3)Eighteen-carbon essential fatty acids that contain three double bonds 18:3 (9,12,15)
5. Essential Fatty Acids (EFAs)
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• Linoleic Acids (omega 6)Eighteen-carbon essential fatty acids that contain two double bonds 18:2 (9,12)
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KLASIFIKASI LIPID
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• Kelompok utama lipid :TrigliseridaFosfolipidSfingolipidLipoproteinSteroidLilin
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1. Trigiserida
• Trigliserida tiga asam lemak berikatan dengan sebuah molekul gliserol
• Nama lain : triasilgliserol• Trigliserida :
Minyak pada suhu ruang berbentuk cairLemak pada suhu ruang berbentuk padat
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Pembentukan Sebuah Trigliserida
• Glycerol + 3 FA’s Triglyceride + 3 H2O
H
H--C--OH
H--C--OH
H--C--OH
H
O
HO-C-R
O
HO-C-R
O
HO-C-R
+
H O
H--C--O--C--
O
H--C--O--C--
O
H--C--O--C--
H
R + H2O
R + H2O
R + H2O
(Ester bond)
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Struktur Trigliserida
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• C-1 and C-3 of the glycerol molecule become sn-1 and sn-3 respectively
• carbon 2 of triglycerides is frequently asymmetric since C-1 and C-3 may be substituted with different acyl groups
• by convention: the hydroxyl group at C-2 to the left and use the designation of sn-2 for that particular substituent
Stereospecific Numbering
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CH2OOC(CH2)16CH3
CH2OOC(CH2)12CH3
CH3(CH2)7CH=CH(CH2)7COOCH
• Asam stearat teresterifikasi pada posisi sn-1; asam oleat pada sn-2; dan asam miristat pada sn-3 (gambar di atas)
• Trigliserida tersebut dapat dinamakan : 1-stearoyl-2-oleoyl-3-miristoyl-sn-glyserol sn-glyserol-1-stearate-2-oleate-3-myristate sn-StOM sn-18:0-18:1-16:0
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• Fosfolipid : dua asam lemak dan sebuah gugus fosfat berikatan dengan sebuah molekul gliserol
• Merupakan komponen utama membran biologi
2. Fosfolipid
O R
O R'
OP
O
O
O
O-X
Ofatty acids (hydrophobic tail)
glycerol
phosphate
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Struktur Fosfolipid
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-OO-X
X = H (phosphatidic acid) - precursor to other phospholipids
X = CH2-CH2-N+(CH3)3 phosphatidyl choline
X = CH2-CH(COO-)NH3+ phosphatidyl serine
X = CH2-CH2-NH3+ phosphatidyl ethanolamine
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3. Sfingolipid
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Sfingosin
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Struktur Sfingolipid
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4. Steroid
• Merupakan kelompok lipid yang tidak tersaponifikasi• Mempunyai empat cincin• Paling banyak adalah sterol• Kolesterol merupakan sterol utama pada jaringan
hewani• Kolesterol dan ester turunannya merupakan
komponen utama lipoprotein plasma • Stigmasterol membran ditemukan pada membran sel
tanaman dan berbeda dengan kolesterol karena mempunyai ikatan rangkap pada posisi 22-23
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Struktur Dasar Steroid
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Steroid Numbering System
A B
C D1
2
34
56
7
8910
1112
13
14 15
16
1718
19
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Kolesterol
• A multi-ringed structure• Do not have a glycerol backbone• Waxy substance• Do not readily dissolve in water• Cholesterol is a sterol
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Functions of cholesterol
• serves as a component of membranes of cells (increases or moderates membrane fluidity)– Kolesterol berperan meningkatkan rigiditas membran
sel eukariot karena menpunyai stabilitas yang lebih tinggi dan mempengaruhi fluiditas
• precursor to steroid hormones and bile acids• storage and transport – cholesterol esters
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Testosterone(a steroid hormone)
Vitamin D3(cholecalciferol)
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5. Lipoprotein
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• Particles found in plasma that transport lipids including cholesterol
• Lipoprotein classes• chylomicrons: take lipids from small intestine
through lymph cells• very low density lipoproteins (VLDL)• intermediate density lipoproteins (IDL)• low density lipoproteins (LDL)• high density lipoproteins (HDL)
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Lipoprotein classes
• Chylomicrons B4885%
• VLDL B100/E 20% 55%
• IDLB100/E 35% 25%
• LDL B10060%
5%• HDL AI/II/E
20% 5%
protein choles.triglycerides
LDL is not measured but calculated:LDL-C = total cholesterol - (HDL-C + TG/5)
(Triglycerides must be <4.5 mmol/L or < 400 mg/dL)
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Struktur LDL
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6. Lilin (Wax)
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