STRUKTUR dan KLASIFIKASI LIPID

LIPID

 Merupakan kelompok heterogen dari senyawa

yang mempunyai sifat umum :
– Relatif tidak larut air
– Larut dalam pelarut organik non polar (eter,
kloroform, benzen dsb)

http://www.wiley.com/college/te
st/0471787159/biology_basics/a
nimations/lipids.swf
KLASIFIKASI
KLASIFIKASI (Bloor)
 LIPID SEDERHANA : ester asam lemak dengan
alkohol
– LEMAK (Gliserida) : ester asam lemak dengan gliserol
– Lilin (wax) : ester asam lemak dengan alkohol
monovalen rantai panjang
 LIPID KOMPLEKS
– FOSFOLIPID - SFINGOLLIPID
– GLIKOLIPID - LIPOPROTEIN
 STEROL
ASAM LEMAK
 Merupakan derivat asam karboksilat rantai
panjang
 Rumus umum :

CH3 (CH 2)n COOH n = 0 : CH 3COOH n = 1 : propionic acid

n is almost always even

ASAM LEMAK :
 ASAM LEMAK JENUH
 ASAM LEMAK TAK JENUH :
– Tunggal ( monounsaturated fatty acid / MUFA )
– Ganda (poliunsaturated fatty acid/PUFA )
 Asam lemak jenuh
Nama umum Nama kimia Rumus kimia Sumber
Asam butirat Butanoic acid CH3(CH2)2COOH Butter
Asam kaproat Hexanoic acid CH3(CH2)4COOH Butter, minyak kelapa
dan sawit
Asam kaprilat Octanoic acid CH3(CH2)6COOH Butter, minyak kelapa
dan sawit
Asam kaprat Dekanoic acid CH3(CH2)8COOH minyak kelapa dan sawit,
butter
Asam laurat Dodecanoic acid CH3(CH2)10COOH minyak kelapa dan sawit,
butter
Asam miristat Tetradecanoic acid CH3(CH2)12COOH minyak kelapa dan sawit,
lemak hewan
Asam palmitat Heksadekanoic acid CH3(CH2)14COOH Lemak hewani dan
minyak nabati
Asam stearat Oktadekanoic acid CH3(CH2)16COOH Banyak pd lemak hewani,
sedikit pd minyak nabati
Asam arakidat Eikosanoic acid acid CH3(CH2)18COOH Kacang tanah
 Asam lemak tak jenuh
Nama umum Nama kimia Rumus kimia Sumber
Monoenoat
Asam oleat Cis 9-octadecenoic C17H33COOH plant and animal fats
Asam elaidat Trans 9-Octadecenoic C17H33COOH animal fats
Dienoat
Asam linoleat 9,12-Octadecadienoic C17H31COOH peanut, linseed, and
cottonseed oils
Trietenoat
Asam linolenat 9,12,15-Octadecatrienoic C17H29COOH linseed and other seed
oils
Eleostearic 9,11,13-Octadecatrienoic C17H29COOH peanut seed fats
Tetraenoat
Moroctic 4,8,12,15- C17H27COOH fish oils
Octadecatetraenoic
Pentaenoat
Arachidonic 5,8,11,14- C19H31COOH races in animal fats
Eicosatetraenoic
Hexaetenoat
Titik cair dan kelarutan Asam Lemak dalam Air

Melting Point

Solubility in H O 2

Chain Length
 Asam lemak
tak jenuh

Asam
lemak jenuh
 ASAM LEMAK JENUH Vs.
ASAM LEMAK TAK JENUH
Polar head group

Saturated Fatty Acid Monounsaturated

Fatty Acid
No double bonds
1 double bond

Stearic Acid C-18 Oleic Acid C-18

Modified from Nelson & Cox, Lehninger Principles of Biochemistry, 4th Edition, Fig. 10-1.
Efek Ikatan Rangkap terhadap Suhu Cair
F. A. M. P. (0C)

16:0 60
16:1 1
18:0 63
18:1 16
18:2 -5
18:3 -11
20:0 75
20:4 -50
Efek Ikatan Rangkap terhadap Titik Cair

M.P.

# Double bonds
ASAM LEMAK TAK JENUH TUNGGAL

 Monoenoic acid (monounsaturated)

H3C Ikatan rangkap pada

asam lemak alami pada
posisi cis

HOOC
ASAM LEMAK TAK JENUH GANDA
 Dienoic acid: linoleic acid

CH3 (CH 2)4 CH=CH CH 2 CH=CH (CH 2)7 COOH

cis
linoleic acid
ASAM LEMAK TAK JENUH GANDA
 Polyenoic acid (polyunsaturated)

COOH

CH3
ASAM LEMAK TAK JENUH
 Penamaan didasarkan pada letak ikatan rangkap

18 9 1
H
H3C (CH 2)7 C CH(CH 2)7COOH

10

18:1,9 or 9 18:1

 2 3 4 5 6 7 8 9 10 18
H3C CH 2CH 2CH2CH 2CH 2CH 2CH2CH CH(CH 2)7COOH

n 17 10 9 1

9, C18:1 or n-9, 18:1

B. Essential Fatty Acids
 The body can synthesize all of the fatty acids it
needs from carbohydrates, fat or protein except for
two:
1. Linoleic acid
2. Linolenic acid
– PUFAs
– Found in plant & fish oils
Flax flower – flax Rape flower –
seed rape seed borage flower –
borage seed

Saff flower – saff

seed
http://www.wiley.com/college/test/
0471787159/biology_basics/animat
ions/lipids.swf
 Lemak ( GLISERIDA )

 Adalah suatu ester asam lemak dengan gliserol.

 Gliserol ialah suatu trihidroksi alkohol terdiri dari 3
atom C.
 Satu molekul gliserol dapat mengikat :
1 molekul asam lemak : monogliserida
2 molekul asam lemak : digliserida
3 molekul asam lemak : trigliserida
 Struktur umum gliserida :
 R : asil asam lemak
http://www.educationscotland.gov.uk/hi
ghersciences/chemistry/animations/oilsf
ats.asp
http://telstar.ote.cmu.edu/biology/Mem
branePage/index2.html
http://www.wiley.com/college/test/0471
787159/biology_basics/animations/lipid
s.swf
Lemak

O O O
CH2OH
O
O R O R O R
H C OH
OH OH R O
CH2OH
OH O R O R
glycerol
O O

MONOGLYCERIDE DIGLYCERIDE TRIGLYCERIDE

 GLYCERIDA

H2 C OH O
H2 C O C (CH 2 )16 CH 3
HC OH O
HC OH O
H2 C O C (CH2 )16 CH3
H2 C O C (CH 2 )16 CH 3
Monoglyceride (a - monostearin) Diglyceride (a, a' - distearin)
O
H2 C O C (CH 2 )16 CH3 ( C18 )
O
HC O C (CH 2 )14 CH3 (C16 )
O
H2 C O C (CH 2 )16 CH3 (C18 )

Triglyceride (b - palmityl distearin)

Metode Analisa
untuk pemeriksaan lemak
 Angka penyabunan
 Angka Iodin
 free fatty acids
 Angka acetyl
 Bilangan Reichert-Meissl
 Angka peroksida
Lilin (Waxes)
 Lilin (wax) ialah ester asam lemak dengan
monohidroksi alkohol yang mempunyai rantai
karbon panjang, 14- 34 atom C.
 Struktur umum lilin :
O

H3C (CH 2)14 C O CH 2 (CH 2)28-CH 3

fatty acid
long chain alcohol
Lilin (Waxes)

H3C (CH 2)14 CH2-OH cetyl alcohol

H3C (CH 2)24 CH2-OH hexacosanol

H3C (CH 2)28 CH2-OH triacontanol (myricyl alcohol)

Examples of long chain monohydric alcohols found in waxes

 ☺Contoh : setilalkohol, mirisilalkohol
☺Sumber lilin : lebah madu, ikan paus atau lumba-lumba

Spermaceti source Carnauba wax source

Bee’s wax
 Fosfolipid

 Fosfolipid atau fosfatidat ialah suatu gliserida yang

mengandung fosfor dalam bentuk ester asam fosfat.
 Gugus yang diikat oleh asam fosfatidat ialah kolin
(fosfatidilkolin), etanolamin (fosfatidiletanolamin), serin
(fosfatidilserin) dan inositol (fosfatidilinositol).

O H2C O C R2

R1 C O CH O
Formation of an ester:
H2C O P O
O O
R'OH + HO-C-R" R'-O-C-R'' + H2O O
phosphatidate
FOSFOLIPID
 STRUKTUR UMUM :
 O

O O R
fatty acids (hydrophobic tail)
glycerol O R'
O-
O O X
P

O
phosphate

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

 O

O H2C O C R2

R1 C O CH O O

O H2C O C R2
H2C O P O
R1 C O CH O CH3
O H
+
OH H2C O P O CH2 CH2 N CH3
OH
OH
H O CH3
OH H
phosphatidyl- H H phosphatidylcholine
inositol H OH
Sphingolipids

Sphingolipids adalah derivat lipid sphingosine, mempunyai

ekor hidrokarbon rantai panjang dengan ujung gugus polar
berupa gugus amine
OH

OH

sphingosine NH2

R long chain hydrocarbon

HO

NH2 attach fatty acid here

OH attach polar head group here

Sphingomyelin
HO R
O

NH R' usually palmitic acid

O-
O O
P N(CH3)+

O
phosphatidyl choline (also can be ethanolamine)

Sphingomyelin terdapat pada jaringan syaraf dan otak

 Ceramide

 Ceramide adalah derivat sfingosin yang mengandung asil

dari asam lemak
 Terdapat dalam jumlah kecil pada jaringan tumbuhan
maupun hewan
OH OH
H
H2C C CH

NH CH

O C HC

R (CH2 )12

ceramide CH3
 GLIKOLIPID

HO R
O

NH R'

O SUGAR polar head is a sugar

beta linkage
There are different types of glycolipids: cerebrosides, gangliosides,
lactosylceramides
STEROID

 Struktur dasar : siklopentanoperhidrofenantrene

18
12 17
11
19 C 13 D 16
1
2 9 14 15
10 8
A B
3 5 7
4 6
Cholesterol dan cholesterol ester
H3C
CH3

CH3 H
hydrophobic
O
H H

OH drawn this way R

usually palmitate

hydrophillic
 V. Cholesterol – a Sterol

 Hanya dihasilkan oleh hewan

 Berfungsi sebagai: :
– Structure membran sel
– Sintesis empedu, hormon, vitamin D
LIPOPROTEIN
 Gabungan antara lipid dan protein
 Terdapat pada plasma darah
 Bagian lipid terdiri dari trigliserida, fosfolipid dan ester
kolesterol (kolesterol yang berikatan dengan asam lemak)
dan kolesterol bebas
 Klasifikasi lipoprotein :
• chylomicrons:
• very low density lipoproteins (VLDL)
• intermediate density lipoproteins (IDL)
• low density lipoproteins (LDL)
• high density lipoproteins (HDL)
Struktur Lipoprotein :
MOLEKUL LIPOPROTEIN

 Contoh : LDL
LIPOPROTEIN
 HDL
 IDL
 LDL
 VLDL
 CHYLOMIKRON
Lipoprotein Density Diameter (nm) Protein % of Phospholip Triacylglycerol %
class (g/mL) dry wt id % of dry wt

HDL 1.063-1.21 5 – 15 33 29 8

LDL 1.019 – 1.063 18 – 28 25 21 4

IDL 1.006-1.019 25 - 50 18 22 31

VLDL 0.95 – 1.006 30 - 80 10 18 50

chylomicrons < 0.95 100 - 500 1-2 7 84

Komposisi dan susunan lipoprotein pada manusia

(most proteins have densities of about 1.3 – 1.4 g/mL and lipid aggregates
usually have densities of about 0.8 g/mL)
 LIPIDS

Copyright © 2009 Pearson Education, Inc.

 3.8 Fats are lipids that are mostly energy-storage
molecules
 Lipids are water insoluble (hydrophobic, or water
fearing) compounds that are important in energy
storage
– They contain twice as much energy as a polysaccharide
 Fats are lipids made from glycerol and fatty acids

Copyright © 2009 Pearson Education, Inc.

 3.8 Fats are lipids that are mostly energy-storage
molecules
 Fatty acids link to glycerol by a dehydration reaction
– A fat contains one glycerol linked to three fatty acids
– Fats are often called triglycerides because of their structure

Animation: Fats

Copyright © 2009 Pearson Education, Inc.

Glycerol

Fatty acid
 3.8 Fats are lipids that are mostly energy-storage
molecules
 Some fatty acids contain double bonds
– This causes kinks or bends in the carbon chain because the
maximum number of hydrogen atoms cannot bond to the
carbons at the double bond
– These compounds are called unsaturated fats because they
have fewer than the maximum number of hydrogens
– Fats with the maximum number of hydrogens are called
saturated fats

Copyright © 2009 Pearson Education, Inc.

 3.9 Phospholipids and steroids are important
lipids with a variety of functions
 Phospholipids are structurally similar to fats and are
an important component of all cells
– For example, they are a major part of cell membranes, in
which they cluster into a bilayer of phospholipids
– The hydrophilic heads are in contact with the water of the
environment and the internal part of the cell
– The hydrophobic tails band in the center of the bilayer

Copyright © 2009 Pearson Education, Inc.

Hydrophilic Water
heads

Hydrophobic
tails

Water
 3.9 Phospholipids and steroids are important
lipids with a variety of functions
 Steroids are lipids composed of fused ring structures
– Cholesterol is an example of a steroid that plays a
significant role in the structure of the cell membrane
– In addition, cholesterol is the compound from which we
synthesize sex hormones

Copyright © 2009 Pearson Education, Inc.

 3.10 CONNECTION: Anabolic steroids pose
health risks
 Anabolic steroids are synthetic variants of testosterone
that can cause a buildup of muscle and bone mass
– They can be sold as prescription drugs and used to treat
certain diseases
– They may also be abused with serious consequences, such as
liver damage that can lead to cancer

Copyright © 2009 Pearson Education, Inc.

 Omega - 6 versus Omega - 3

Omega – 6
 Linoleic
Omega – 3
 Linolenic
 Cold water fish
 Help dissolve blood clots
 Lower blood pressure
 Dilate the arteries
METABOLISME