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Saponification number
• gives some clue about the average size of fatty
  acids in a given sample of fat
• defined as the number of milligrams of KOH
  needed to neutralize the fatty acids in 1 g of fat
     • butter (large proportion of short chain FAs) sap. no. 220 –
       230
     • oleomargarine (long chain FAs) sap. No is 195 or less




 SELF RELIANCE FOR BETTER TOMORROW
Acetyl number
• some fatty acids have hydroxyl groups
                  OH                                    OH

 H3C        (CH2)21 CH COOH          H3C    (CH2)5      CH CH2 CH CH (CH2)7 COOH
       cerebronic acid                                  ricinoleic acid

  The acetyl number gives the proportion of these hydroxyl-containing
  fatty acids in a given sample of fat or oil
                  acetic anhydride
  fatty acid                               fatty acid                                fatty acid

       OH                                      O   C     CH3                              OH

                                                   O                                      +
                                           acetylated fatty acid                    H3C       COOH

                                                        titrate with standardized
                                                        KOH

               SELF RELIANCE FOR BETTER TOMORROW
Acetyl number
• the acetyl number is the number of
  milligrams of KOH needed to neutralize the
  acetic acid produced from 1 g of acetylated
  fat
  – examples:
    • castor oil             (146 –150)
    • cod liver oil          (1.1)
    • cottonseed oil         (21 – 25)
    • olive oil              (10.5)
    • peanut oil             (3.5)
   SELF RELIANCE FOR BETTER TOMORROW
Iodine number
                                            I   I
               H        H          I2
                                        H           H




• measures the degree of un-saturation in a given amount
  of fat or oil
• the iodine number is the number of grams of iodine
  absorbed by 100 g of fat
      • Cottonseed oil: 103 –111
      • Olive oil: 79 – 88
      • Linseed oil: 175 –202
• frequently used to determine adulteration of
  commercial lots of oils
    SELF RELIANCE FOR BETTER TOMORROW
Reichert–Meissl number
• measures the amount of volatile fatty acids
  (low MW and water soluble Fats)
• the R-M number is the number of milliliters
  of 0.1N alkali required to neutralize the
  soluble fatty acids distilled from 5 g of fat
• butter fat has a high R-M number

SELF RELIANCE FOR BETTER TOMORROW
Phospholipids
     • the major components of cell membranes
         – phosphoglycerides
                                     O



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


                                     O
                     phosphate


Phospholipids are generally composed of FAs, a nitrogenous base,
phosphoric acid and either glycerol, inositol or sphingosine



    SELF RELIANCE FOR BETTER TOMORROW
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

SELF RELIANCE FOR BETTER TOMORROW
Phosphatidyl inositol




       Commonly utilized in cellular signaling


SELF RELIANCE FOR BETTER TOMORROW
Sphingolipids
      Contain sphingosine instead of glycerol
                                                 OH


                                                              OH

                sphingosine                           NH2


                              R      long chain hydrocarbon
              HO


                       NH2        attach fatty acid here

                       OH         attach polar head group here




SELF RELIANCE FOR BETTER TOMORROW
1- phingomyelin (a ceramide)




It is a omnipresent component of animal cell membranes, where it is the
most abundant sphingolipid. It can comprise as much as 50% of the lipids in
certain tissues.It is usually lower in concentration than phosphatidylcholine



     SELF RELIANCE FOR BETTER TOMORROW
2-Ether glycerophospholipids
• Possess an ether linkage instead of an acyl
  group at the C-1 position of glycerol
  – platelet activating factor (PAF)
        – A potent mediator in inflammation, allergic response
          and shock, also responsible for asthma-like symptom
        – The ether linkage is stable in either acid or base
  – Plasmalogens: cis α, β-unsaturated ethers
     • The alpha/beta unsaturated ether can be
       hydrolyzed more easily

                 SELF RELIANCE FOR BETTER TOMORROW
3- Ether glycerophospholipids
                O                            CH3
                                                                             O                         CH3

      -O        P     O      CH2     CH2     N     CH3
                                                                    -O       P     O     CH2    CH2    N     CH3

                O                            CH3                             O                         CH3

H2C   CH        CH2                                           H2C   CH       CH2


 O    O                                                        O    O
                                                          H

                                                                    C    O
      C     O


      CH3                                                 H

                                                                                   A choline plasmalogen
                      platelet activating factor or PAF




                                   SELF RELIANCE FOR BETTER TOMORROW
4-Glycolipids
     HO                   R
                      O

                 NH         R'

                 O         SUGAR                          polar head is a sugar


                       beta linkage

There are different types of glycolipids: cerebrosides, gangliosides,
lactosylceramides



                          SELF RELIANCE FOR BETTER TOMORROW
GLYCOLIPIDS
• Cerebrosides
     • One sugar molecule
        – Galactocerebroside
        – Glucocerebrosides
• Sulfatides or sulfogalactocerebrosides
     • A sulfuric acid ester of galactocerebroside
• Globosides: ceramide oligosaccharides
     • Lactosylceramide
        – 2 sugars ( eg. lactose)
• Gangliosides
     • Have a more complex oligosaccharide attached
     • Biological functions: cell-cell recognition; receptors for
       hormones
                           SELF RELIANCE FOR BETTER TOMORROW
5- Cardiolipids
                          O                               O

     O          H2C   O   C      R1                  R4   C    O   CH2         O

R2   C      O    C    H   O               H               O    H   C     O     C    R3

                H2C   O   P      O    CH2 C    CH2 O      P    O   CH2

                          OH              OH              OH
                                                                             glycerol
 glycerol
                                          glycerol

 A polyglycerol phospholipid; makes up 15% of total lipid-phosphorus
 content of the myocardium – associated with the cell membrane




                              SELF RELIANCE FOR BETTER TOMORROW
6-Sulfolipids
• also called sulfatides or cerebroside sulfates
• contained in brain lipids
• sulfate esters of cerebrosides
• present in low levels in liver, lung, kidney,
  spleen, skeletal muscle and heart
• function is not established



             SELF RELIANCE FOR BETTER TOMORROW
STEROIDS
• Naturally occurring compounds having
  perhydrocyclopentanophenanthrene nucleus in their
  structure
• The ring contains 17 carbon atoms
• Generally contain CH3 at carbon 10 and 13
                                          18
                                  12             17
                      11
                    19             C 13          D         16
              1
        2                   9             14          15
                      10
              A             B 8
         3           5                7
              4             6


                  SELF RELIANCE FOR BETTER TOMORROW
Animal sterol-cholesterol
• It is the most abundant steroid
• Found in animal tissues and not in plants
• 140 g of cholesterol is present in normal
  human adult
• Structural formula is C27H45OH
• Considering asymmetric carbon atoms 512
  stereoisomers are possible
• The most abundant isomers are C3 (OH) and
  C5-10 fusion
                 SELF RELIANCE FOR BETTER
                        TOMORROW
Animal sterol-cholesterol
• Chemical structure


        CH3 at 10 and 13                                  Iso-octanyl at C17




                                   Un-saturation between C5 and C6
     OH at C3

                           SELF RELIANCE FOR BETTER TOMORROW
CHOLESTEROL FACTS
 • It is synthesized from acetyl CoA and eliminated as bile
 acids
 • It is a precursor of all other steroids in the body
 • It is a product of animal metabolism – found in foods of
 animal origin
 • It is an amphipathic lipid (hydrophobic and hydrophilic
 portions)
 • stored in the form ester in most of tissues.

                                                O
                                                ||
                                              R-C-O
hydrophilic
                                          Cholesterol ester (1st ring only)
                                          R = fatty acid hydrocarbon chain

         HO
                         SELF RELIANCE FOR BETTER TOMORROW
physical properties


 white crystalline solid, tasteless and odorless
 oxidized on exposure to air
 acts as insulator to nerves and brain tissue
 essential structural component of membranes
  transported in the circulation in lipoproteins



            SELF RELIANCE FOR BETTER TOMORROW
ROLES OF CHOLESTEROL
       AND BILE ACIDS AND ITS SALTS


The physiological roles of cholesterol include:

c) an important lipid component of biological membranes
d) precursor of steroid hormones and
e) source of bile acids


Bile acids are polar derivatives of cholesterol and aid in:

c) lipid digestion
d) lipid absorption
e) cholesterol excretion


                   SELF RELIANCE FOR BETTER TOMORROW
Cholestanone (ketones)




                                    Oxidation
         Carboxylic acids                                  Drastic oxidation
Cholesterol esters                 Cholesterol                         Mixture of
                                                                       ketones and
                        halogens




                                                     hydrogen
                                                                       hydroxy acids



               Cholesterol dihalides            Dihydrocholesterol




                            SELF RELIANCE FOR BETTER TOMORROW

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Phospholipids cholesterol

  • 1. Saponification number • gives some clue about the average size of fatty acids in a given sample of fat • defined as the number of milligrams of KOH needed to neutralize the fatty acids in 1 g of fat • butter (large proportion of short chain FAs) sap. no. 220 – 230 • oleomargarine (long chain FAs) sap. No is 195 or less SELF RELIANCE FOR BETTER TOMORROW
  • 2. Acetyl number • some fatty acids have hydroxyl groups OH OH H3C (CH2)21 CH COOH H3C (CH2)5 CH CH2 CH CH (CH2)7 COOH cerebronic acid ricinoleic acid The acetyl number gives the proportion of these hydroxyl-containing fatty acids in a given sample of fat or oil acetic anhydride fatty acid fatty acid fatty acid OH O C CH3 OH O + acetylated fatty acid H3C COOH titrate with standardized KOH SELF RELIANCE FOR BETTER TOMORROW
  • 3. Acetyl number • the acetyl number is the number of milligrams of KOH needed to neutralize the acetic acid produced from 1 g of acetylated fat – examples: • castor oil (146 –150) • cod liver oil (1.1) • cottonseed oil (21 – 25) • olive oil (10.5) • peanut oil (3.5) SELF RELIANCE FOR BETTER TOMORROW
  • 4. Iodine number I I H H I2 H H • measures the degree of un-saturation in a given amount of fat or oil • the iodine number is the number of grams of iodine absorbed by 100 g of fat • Cottonseed oil: 103 –111 • Olive oil: 79 – 88 • Linseed oil: 175 –202 • frequently used to determine adulteration of commercial lots of oils SELF RELIANCE FOR BETTER TOMORROW
  • 5. Reichert–Meissl number • measures the amount of volatile fatty acids (low MW and water soluble Fats) • the R-M number is the number of milliliters of 0.1N alkali required to neutralize the soluble fatty acids distilled from 5 g of fat • butter fat has a high R-M number SELF RELIANCE FOR BETTER TOMORROW
  • 6. Phospholipids • the major components of cell membranes – phosphoglycerides O O O R fatty acids (hydrophobic tail) glycerol O R' O- O O X P O phosphate Phospholipids are generally composed of FAs, a nitrogenous base, phosphoric acid and either glycerol, inositol or sphingosine SELF RELIANCE FOR BETTER TOMORROW
  • 7. 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 SELF RELIANCE FOR BETTER TOMORROW
  • 8. Phosphatidyl inositol Commonly utilized in cellular signaling SELF RELIANCE FOR BETTER TOMORROW
  • 9. Sphingolipids Contain sphingosine instead of glycerol OH OH sphingosine NH2 R long chain hydrocarbon HO NH2 attach fatty acid here OH attach polar head group here SELF RELIANCE FOR BETTER TOMORROW
  • 10. 1- phingomyelin (a ceramide) It is a omnipresent component of animal cell membranes, where it is the most abundant sphingolipid. It can comprise as much as 50% of the lipids in certain tissues.It is usually lower in concentration than phosphatidylcholine SELF RELIANCE FOR BETTER TOMORROW
  • 11. 2-Ether glycerophospholipids • Possess an ether linkage instead of an acyl group at the C-1 position of glycerol – platelet activating factor (PAF) – A potent mediator in inflammation, allergic response and shock, also responsible for asthma-like symptom – The ether linkage is stable in either acid or base – Plasmalogens: cis α, β-unsaturated ethers • The alpha/beta unsaturated ether can be hydrolyzed more easily SELF RELIANCE FOR BETTER TOMORROW
  • 12. 3- Ether glycerophospholipids O CH3 O CH3 -O P O CH2 CH2 N CH3 -O P O CH2 CH2 N CH3 O CH3 O CH3 H2C CH CH2 H2C CH CH2 O O O O H C O C O CH3 H A choline plasmalogen platelet activating factor or PAF SELF RELIANCE FOR BETTER TOMORROW
  • 13. 4-Glycolipids HO R O NH R' O SUGAR polar head is a sugar beta linkage There are different types of glycolipids: cerebrosides, gangliosides, lactosylceramides SELF RELIANCE FOR BETTER TOMORROW
  • 14. GLYCOLIPIDS • Cerebrosides • One sugar molecule – Galactocerebroside – Glucocerebrosides • Sulfatides or sulfogalactocerebrosides • A sulfuric acid ester of galactocerebroside • Globosides: ceramide oligosaccharides • Lactosylceramide – 2 sugars ( eg. lactose) • Gangliosides • Have a more complex oligosaccharide attached • Biological functions: cell-cell recognition; receptors for hormones SELF RELIANCE FOR BETTER TOMORROW
  • 15. 5- Cardiolipids O O O H2C O C R1 R4 C O CH2 O R2 C O C H O H O H C O C R3 H2C O P O CH2 C CH2 O P O CH2 OH OH OH glycerol glycerol glycerol A polyglycerol phospholipid; makes up 15% of total lipid-phosphorus content of the myocardium – associated with the cell membrane SELF RELIANCE FOR BETTER TOMORROW
  • 16. 6-Sulfolipids • also called sulfatides or cerebroside sulfates • contained in brain lipids • sulfate esters of cerebrosides • present in low levels in liver, lung, kidney, spleen, skeletal muscle and heart • function is not established SELF RELIANCE FOR BETTER TOMORROW
  • 17. STEROIDS • Naturally occurring compounds having perhydrocyclopentanophenanthrene nucleus in their structure • The ring contains 17 carbon atoms • Generally contain CH3 at carbon 10 and 13 18 12 17 11 19 C 13 D 16 1 2 9 14 15 10 A B 8 3 5 7 4 6 SELF RELIANCE FOR BETTER TOMORROW
  • 18. Animal sterol-cholesterol • It is the most abundant steroid • Found in animal tissues and not in plants • 140 g of cholesterol is present in normal human adult • Structural formula is C27H45OH • Considering asymmetric carbon atoms 512 stereoisomers are possible • The most abundant isomers are C3 (OH) and C5-10 fusion SELF RELIANCE FOR BETTER TOMORROW
  • 19. Animal sterol-cholesterol • Chemical structure CH3 at 10 and 13 Iso-octanyl at C17 Un-saturation between C5 and C6 OH at C3 SELF RELIANCE FOR BETTER TOMORROW
  • 20. CHOLESTEROL FACTS • It is synthesized from acetyl CoA and eliminated as bile acids • It is a precursor of all other steroids in the body • It is a product of animal metabolism – found in foods of animal origin • It is an amphipathic lipid (hydrophobic and hydrophilic portions) • stored in the form ester in most of tissues. O || R-C-O hydrophilic Cholesterol ester (1st ring only) R = fatty acid hydrocarbon chain HO SELF RELIANCE FOR BETTER TOMORROW
  • 21. physical properties white crystalline solid, tasteless and odorless oxidized on exposure to air acts as insulator to nerves and brain tissue essential structural component of membranes transported in the circulation in lipoproteins SELF RELIANCE FOR BETTER TOMORROW
  • 22. ROLES OF CHOLESTEROL AND BILE ACIDS AND ITS SALTS The physiological roles of cholesterol include: c) an important lipid component of biological membranes d) precursor of steroid hormones and e) source of bile acids Bile acids are polar derivatives of cholesterol and aid in: c) lipid digestion d) lipid absorption e) cholesterol excretion SELF RELIANCE FOR BETTER TOMORROW
  • 23. Cholestanone (ketones) Oxidation Carboxylic acids Drastic oxidation Cholesterol esters Cholesterol Mixture of ketones and halogens hydrogen hydroxy acids Cholesterol dihalides Dihydrocholesterol SELF RELIANCE FOR BETTER TOMORROW