MARY KIMBERLY L.

ESPALDON

CHEM LAB EXAM

CARBOHYDRATES
saccharides
Most abundant organic molecule
First molecule in the energy cycle
MONOSACCHARIDES
Building blocks of carbohydrates
Two types:
1. Aldose polyhydroxy aldehyde
2. Ketose polyhydroxy ketone

Derivatives of monosaccharides
1. Sugar acids
2. Sugar alcohol
3. Deoxysugars
4. Amino sugars
5. Sugar phosphates
DISACCHARIDES
-d-glucose
Lactose
-d-galactose
-d-glucose
Sucrose
-d-fructose
-d-glucose
Cellobiose
-d-glucose
-d-glucose
Maltose
-d-glucose
POLYSACCHARIDES

Isomers molecules with the same

molecular formula but have a different
arrangement of atoms in space
Compounds do
CONSTITUTIONAL not have the same
connectivity
Different
FUNCTIONAL
functional groups
Mirror images;
ENANTIOMERS
nonsuperimposable
Not mirror images
DIASTREOMERS
of one another
Stereoisomers
ANOMERS
that differ in at the
anomeric carbon
Only different at
EPIMERS
one stereogenic
center
ALDOPENTOSES
Ribose
Xylose
Arabinose
Lyxose
ALDOHEXOSES
Glucose
Mannose
Galactose
Talose
Altrose
Idose
KETOPENTOSES
Ribulose
Xylulose
KETOHEXOSES
Fructose
Tagatose

Linear homoglycans

Branched
homoglycans
Heteroglycans
Glycuronans
Glycosaminoglycans

Glucans
amylose,
cellulose, chitin
Galactans
agar,
carrageenan
Glucans
glycogen,
amylopectin
Glucomannans,
galactomannans
Contains uronic acids
Mucopolysaccharides

Starch
Reserve carbohydrates for plants
Found in plant seeds and tubers
Form in which glucose is stored for
later use by plants
Composed of two polysaccharides:
1. Amylose water soluble
(20%)
2. Amylopectin water
insoluble (80%)
Hydrolysis of starch would give only
glucose
Amylose
Linear polymer
4000 monomers of glucose joined by
-1,4-glycoside bonds
Amylopectin
Highly branched polymer
24-30 units of glucose joined by 1,4-glycoside bonds and branch at
points -1,6-glycoside bonds
Glycogen
Reserve carbohydrate for animals

MARY KIMBERLY L. ESPALDON

Non-linear, branched polymer

Lower molecular weight; higher
branching than amylopectin
Branching every 12-18 units
Cellulose
Most abundant organic compound
on Earth
Linear polymer
3000 glucose monomers joined by
-1,4-glycoside bonds
ISOLATION OF CARBOHYDRATES
Glycogen from chicken liver
o Energy storage polysaccharide in
animals
o Branched chain
o Linear chain of glucose units
o Connected by -1,4-glycosidic
bonds and branched every 1-10
units linked by -1,6-glycosidic
bonds
o Isolation:
Homogenization disrupts
the membrane
0.1% acetic acid removes
protein via precipitation
Glycogen is insoluble in
ethanol
Method:
Protein denaturation
Solubility of glycogen
Starch from potatoes
o Energy storage of polysaccharide in
plants
o Mixture of amylose and amylopectin
o Isolation:
Starch is slightly soluble in
H2O
Method: selective dissolution
HYDROLYSIS OF CARBOHYDRATES
Acid hydrolysis
o 2N HCl
o Complete hydrolysis
o Efficient method to obtain
monosaccharides
o Starch/glycogen glucose
Enzymatic hydrolysis
o Salivary amylase -amylase
o Very specific
o Yield a mixture of glucose, maltose,
dextrin and other hydrolysates
THIN LAYER CHROMATOGRAPHY
Based on adsorption
Stationary phase: silica G-250
Mobile phase: butanol: acetic acid:
ether: H2O (9:6:3:1)
Visualizing agent: p-anisaldehyde

Appear as dark green spots

LIPIDS
Insoluble in water
Soluble in organic nonpolar solvents
Hydrophobic nature due to the
predominance of hydrocarbons chains
Functions:
o Storage and transport of metabolic
fuel
o Structural component of cell
membrane
o Carriers of lipid-soluble vitamins
Vitamins A, D, E, K
Hypervitaminosis excess
vitamins
o Provide supply of essential fatty
acids
o Body insulation
Saponification basic hydrolysis of lipids,
produces soap
FATTY ACIDS
Synthesis occurs in the liver
Naturally occurring fatty acids even
number of carbon atoms
Two types:
o Saturated no carbon-carbon
double bond present
o Unsaturated carbon-carbon double
bond present
Two essential fatty acids:
o Linoleic acid
o Linolenic acid
PROSTAGLANDINS (PGS)
Synthesized from linoleic acid forms
eicosanoids
Cyclopentane ring with 2 side chains
(carboxyl group in one chain)
Development of inflammatory responses
Pain chemicals
Wound-healing process
FATTY ACID ESTERS
Acylglycerols esters formed between a
fatty acid and glycerol
Triglycerides
o From plants oils liquid at room
temperature
o From animals fats solid at room
temperature
PHOSPHOLIPIDS
Zwitterionic compounds of an alcohol that is
attached by a phosphodiester bridge to
either:
o Diacylglycerol
o Sphingosine

MARY KIMBERLY L. ESPALDON

Phosphoglycerides, glycerophosphates or
phosphoglycerol phospholipids that
contain glycerol
Lecithin
o Alcohol-soluble
o Acetone-insoluble
o Emulsifier in the food industry
Cephalin
o Alcohol-insoluble
o Acetone-insoluble
o Abundant in the brain nervous tissue
o Mixture of phosphatidyl
ethanolamine and phosphatidyl
serine
STEROIDS
Derivative of
perhydrocyclopentanophenanthrene
True terpenes
Synthesized from isoprene via squalene
Fused ring system essentially planar
structure
o Cis-fused ring bent structures
o Trans-fused ring flat structures;
cholesterol and testosterone
Sterols
o Steroids containing one or more
hydroxyl groups
o Cholesterol secondary alcohol
o Very hydrophobic, non-saponifiable,
unsaturated
o Component of all cell membranes,
precursor of bile acids, steroid
hormones and vitamin D
Sex hormones
o Testosterone
o Estrogens
o Progesterone
Adrenocorticoid hormones
o Stress hormone
o Synthesize and secrete cortisol
o Functions:
Increased glucogenesis
Anti-inflammatory action
Protein breakdown
Aldosterone
o Secretion of aldosterone from the
adrenal cortex
o Functions stimulates renal
reabsorption of Na+ and excretion of
K+ in the kidney tubules
Vitamin D
o Lipid soluble vitamins
o Derived from isoprenoids or
terpenoids
o Vitamin D2 found in plants
o Vitamin D3 found in animals

o Stored in adipose and liver tissue

Bile acids
o Contains lechitin and bile salts
o Pka = 6 not fully ionized in
physiologic pH
o Hydroxyl groups are in alpha
(above) orientation
o Methyl groups are in beta (below)
orientation
o Cholic acid
TERPENOIDS OR ISOPRENOIDS
Multiples of isoprene units
Most of plants pleasant odors come from
terpenoids
Vitamin A
o Collective term for:
Retinol
Retinoic acid
Retinal
-carotene
o Functions:
essential for vision
Rhodopsin visual pigment
Vitamin E
o vegetables oils, eggs
o naturally occurring tocopherols
o natural antioxidant
o least toxic fat-souble vitamin
Vitamin K
o Found in cabbage, cauliflower,
spinach, egg yolk
o Required in the hepatic synthesis of
prothrombin and clotting factors
o Hemolytic anemia and jaundice
SPHINGOLIPIDS
Isolated from the brain
Backbone compound: ceramide contains
sphingosine or 4 sphingenine
Complete hydrolysis releases:
o 1 mole of fatty acid
o 1 mole of sphingosine
o 1 mole of phosphoric acid
o 1 mole of choline
Glycolipids
o Does not contain phosphorus
o Primary hydroxyl group is
glycosylated substituted with a
carbohydrate
EXTRACTION OF LIPID
Chicken egg yolk
o Rich in lipids such as phospholipids,
triglycerides, triacylglycerols an
cholesterol
Phospholipid: lecithin
Fatty acids in acylated form
in triglyceride

MARY KIMBERLY L. ESPALDON

Unsaturated
linoleic, palmitoleic,
linoleic
Saturated
o Yellow color Is due to: carotenoid
alcohol zeaxanthin
Extraction by percolation at room
temperature
o Sample is allowed to stand with the
extracting solvent for a certain
period of time
o Solvent fractionation depends on
the differential solubility of lipids in
organic solvents
o Extracting solvents are introduced in
increasing polarity step gradient
1. Hexane least polar
2. Acetone
3. Hot ethanol most polar
o Hexane solvent
Lipids interact by induced
dipole induced dipole
interaction with hexane
Hexane extract contains the
least polar dipole
o Acetone solvent
Lipids interact by dipole
induced dipole and induced
dipole induced dipole
Intermolecular H-bonding
Extract contains sterol
o Hot ethanol solvent
Lipids interact by ion-dipole
interaction, hydrogen
bonding and dipole-induced
dipole interactions
Contains the most polar
lipids
Zwitterionic lipids
Amphiphatic lipids
COLUMN CHROMATOGRAPHY
Normal phase
Preparative procedure
Descending
Adsorption
Stationary phase solid silica gel

Mobile phase solvent system

Lipids are eluted in order of increasing
polarity
o Hexane
1. Sterol ester
2. Fatty acid methyl ester
3. Triglyceride
4. Phosphoglyceride or
glycophosphatide
5. Lecithin
6. Cephalin
o Acetone
Sterol
o Hot ethanol: sphingolipids
1. Sphingoglycolipids
2. Sphingomyelin
Solvent system in the mobile phase are
interacting one by one in increasing polarity
step gradient
1. Petroleum ether: ethyl ether (9:1)
2. 5% methane in dichloromethane
3. Dichloromethane: methanol: water
(1:3:1)
THIN LAYER CHROMATOGRAPHY
Normal phase
Analytical and preparative procedure
Ascending
Adsorption
Stationary phase: solid silica gel
Mobile phase: solvent system
2-dimensional: 2 developments
Used two solvent systems:
1. Petroleum ether: methanol: water
more polar
2. Petroleum ether: methanol: NH4OH
less polar
Visualizing agents:
1. I2
Yellowish brown spot against
a blue background
Oxidized the lipid and is
reduced to I-1 (yellow)
Prolonged exposure makes
the spots turn violet
2. Ninhydrin reagent
Blue to violet spots for lipids

MARY KIMBERLY L. ESPALDON

QUALITATIVE TESTS

TEST
Molisch
Carbohydrates

Iodine
Starch and Glycogen

Anthrone
Carbohydrates

Benedicts
Reducing sugars

Barfoeds
Reducing monosaccharides and
disaccharides

Bials Orcinol
Pentoses

Seliwanoffs
Ketohexoses

Mucic Acid
Galactose

Osazone
Reducing factor

CARBOHYDRATES
REAGENTS
(+) RESULT
Conc. H2SO4
Violet ring at interphase
-napthol
Blue-black starch
Iodine solution
Red glycogen

REACTION
Redox, ANE, furfural
formation
Furfural formation
complexation
Redox, ANE, furfural
formation

Conc. H2SO4, anthrone

Blue-green sln

CuSO4, NaC6H5O2,
NaCO3

Brick red ppt

Oxidation in less basic

CuAc2, acetic acid

Brick red ppt

Oxidation in aciding

Orcinol, HCl, FeCl3

Blue-green sln

Furfural formation

Resorcinol, HCl

Cherry red sln

Furfural formation

Conc. HNO3,

Broken glass crystals

Oxidation

2-DNPhenylhydrazine
reagent

Orange crystals

Osazone formation