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Lipids

-an organic compound found in living organisms that it insoluble in water but soluble in
nonpolar solvents.
-for long term energy storage (faots/oils)
-elements of biological structures (phospholipids, cell membranes, waxes)

Fatty Acids
-lipids contain FA [CH3(CH2)nCOOH]
-is a naturally occurring monocarboxylic acid

The fatty acids present in naturally occurring lipids almost always have the ff. 3 characteristics:
-an unbranched carbon chain
-an even number of carbon atoms in the carbon chain
-double bonds, when present in the carbon chain, in a cis configuration

Saturated & Unsaturated Fatty Acids


1. Saturated Fatty Acid (SFA)
-FA with a carbon chain in which all C-C bonds are single bonds
2. Unsaturated Fatty Acid (UFA)
-FA with a carbon chain in which all C-C bonds are double bonds (the DB has the cis
conformation)
* monounsaturated fatty acid (MUFA) – 1 double bond
* polyunsaturated fatty acid (PUFA) – 2 or more double bonds (rarely
conjugated/consecutive)

Omega ( ) Family of Fatty Acids


-Linolenic acid, in particular, is an example of an omega-3 fatty acid, which has been found to
lower blood triglyceride levels and reduce the risk of heart attack
-The name omega-3 means that there is a double bond three carbons in from the noncarboxyl
end of the chain
-An omega-3 fatty acid is an UFA with its endmost double bond 3 carbon atoms away from its
methyl end
-An omega-6 fatty acid is an UFA with its endmost double bond 6 carbon atoms away from its
methyl end

Biochemically important Omega-3 & Omega-6 FA


Omega-3 Acids Omega-6 Acids
Linolenic acid (18:3) ESSENTIAL Linoleic acid (18:2) ESSENTIAL
Eicosapentaenoic acid (20:5) Arachidonic acid (20:4)
Docosahexaenoic acid (20:6)
Name No. of Carbons Melting Point (Celsius)
Saturated
Lauric 12 43.2
Myristic 14 53.9
Palmitic 16 63.1
Stearic 18 68.8
Arachidic 20 76.5
Unsaturated
Palmitoleic 16 -0.1
Oleic 18 13.4
Linoleic 18 -12
Linolenic 18 -11
Arachidonic 20 -49.5
The MP of a FA depends on the length of the carbon chain and on the # of double bonds
present in thee carbon chain.

Lipid Functions
Based on biochemical function, lipids are divided into 5 categories:
1. Energy-storage lipids (TAG)
2. Membrane lipids (phospholipids, sphingoglycolipids, cholesterol)
3. Emulsification lipids (bile acids)
4. Messenger lipids (steroid hormones, eicosanoids)
5. Protective-coating lipids (biological waxes)
Molisch Test
-used to determine the presence of carbohydrates regardless of structure
-reagent: a-naphthol in alcohol
-conc. H2SO4 acts as the dehydrating reagent and serves as a catalyst for the hydrolysis of di- &
polysaccharides
-presence of purple ring at the interface between the carbohydrate solution & conc. H2SO4 is a
positive indication of carb structure
-monosaccharides react more quickly than di- and polysaccharides, which must slowly undergo
hydrolysis before they react w/ Molisch reagent.

Seliwanoff’s Test
-test for ketones
-differentiate between ketohexoses & aldohexoses
-uses conc. HCl for the dehydrating agent but the condensation agent is resorcinol
-ketohexoses are dehydrated to 5-hydroxymethylfurfural, which undergoes condensation with
resorcinol within 2 minutes to form a red-colored product
-the appearance of peach color is negative

Test for Reducing Property of Sugar


-A Reducing sugar is one that can be oxidized
-in order to be a reducing sugar, the molecule must contain a free anomeric carbon, since it is
the open0chain form of the aldehyde that is able to react (and be oxidized)

Osazone Test
-phenylhydrazine (C6H5NHNH2) reacts with C1 and C2 of reducing sugars to form derivatives
called osazones
-formation of these distinctive yellow crystalline derivatives is useful for comparing the
structures of sugars
-osazone crystals have a characteristic shape under the light microscope and help in the
identification of the sugar type
-osazones of monosaccharides (glucose & fructose) are formed on hot after about 15mins, and
have the same crystal shape needles under the microscope
-osazones of reducing disaccharides (maltose & lactose) are formed after a longer time (up to
30mins) and crystal appears slowly after cooling and can be distinguished under the microscope
as follows:
a. lactose = tuft needles b. maltose = broad needles

Iodine Test
-iodine form a blue, black, or gray complex w/ starch and is used as an experimental test for the
presence of starch
-the color of the complex formed depends on the structure of the polysaccharide and the
strength and age of the iodine solution
-iodine does not form a complex with simpler carbohydrates (mono & disaccharides)
-amylose (starch) is helically coiled in solution, and it is this helical structure that is necessary to
form the blue complex w/ iodine; mono & disaccharides are too small to be helically coiled
-amylopectin, cellulose, and glycogen form different colors with iodine – red,brown, purple

Bial’s Test
-test for the presence of pentoses
-Bial’s reagent include orcinol, HCl, and ferric chloride
-in the presence of a pentose, the pentose will be dehydrated to form furfural. The solution will
turn bluish and a ppt may form
-all other colors indicate a negative result for pentoses
-note that hexoses generally react to form green, red, brown products

Mucic Acid Test


-specific test for galactose and lactose
-reagent: concentrated nitric acid
-produces a mucic acid (C6H10O8) – broken glass/rhombic crystal

Principle involved: 1,6- oxidation of sugars whereby galactose- containing carbohydrates form a
meso compound which upon standing yields a crystal.
-oxidation of most monosaccharides by nitric acid yields soluble dicarboxylic acids (aldaric acid)
-however, oxidation of galactose yields an insoluble mucic acid
-lactose will also yield a mucic acid, due to hydrolysis of the gylcosidic linkage between its
glucose and galactose subunits

Test for Reducing Property of Sugar


-Sugars with free aldehyde groups can reduce either cupric ions in alkaline medium (fehling’s or
benedict’s rgts) or in an acid medium (barfoed’s rgts) to produce red or orange colored ppt of
cuprous ions

-they can also reduce the silver ions in alkaline medium (Tollen’s rgt) to produce a metallic
silver giving a siilverr mirror

-heating in a boiling water bath is necessary for these reactions

Fehling’s Test
-Fehling A (CuSO4 dissolved in dil. H2SO4) and Fehling B (sodium potassium tartarate dissolved
in dil. NaOH)
-one test for reducing sugars involves Fehling’s rgt , which contains Cu2+ ions in an aqueous
solution. If a reducing agent is present, the Cu2+ is reduced to Cu+ and forms a red precipitate
of Cu2O
-therefore, if Fehling’s solution is added to a solution containing a reducing sugar, a red ppt will
form.
-sometimes the rxn mixture must be heated in order for the ppt to form
- the color of ppt may vary from red to orange to green (green is mixture of orange & blue ppt)
Benedict’s Test
-in the reaction between the reducing sugar and Benedict’s reagent, copper (II) ion is required
to copper (I) by the aldehyde functional group
-the formation of red to orange ppt indicates the presence of reducing sugar

Tollen’s test
-Tollen’s reagent is ammoniacal silver nitrate solution
-the test involves a mild oxidizing agent. In the Tollen’s test, silver (I) ion is reduced to metallic
silver. The formation of a silver mirror on the inside of the test tube indicates the presence of a
reducing sugar.
-the Tollen’s reagent must be freshly prepared to produce the proper results.
-Appearance of silver mirror (+)

Picric Acid Test


-reagents: picric acid (2,4,6-trinitrophenol or TNP)
-principle: reduction of picric acid to picramic acid [C6H2OHNH2(NO2)2] by the reducing sugar
produces mahogany red color (dark brown –red)

Hydrolysis of Disaccharides
-Disaccharides and polysaccharides can be hydrolyzed in the presence of acid or specific
enzyme
-when a disaccharide is hydrolyzed, the products are the individual monosaccharides

Hydrolysis of Sucrose

Hydrolysis of Polysaccharide
-when polysaccharide is hydrolyzed, the products will depend on how long the mixture is
allowed to react, the conc. Of acid/enzyme, and other factors
-polysaccharides are very long and have many glycosidic bonds to hydrolyze
-they cannot all be hydrolyzed at the same time, so the product is a mixture of dextrins,
maltose, & glucose
- if a polysaccharide sample is hydrolyzed completely (which means that it must react for a
while), the product is glucose

Iodine turns blue-black if starch is present. When iodine no longer changes color, there is no
starch present