pharchem ii postlabs
TRANSCRIPT
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POST-LABS
Pharmaceutical Organic Chemistry
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FUNCTIONAL GROUP
• ALIPHATIC • AROMATIC• ALCOHOL• CARBOXYLIC ACID• AMIDES• AMINES
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• ALDEHYDES• KETONE• ESTERS• ETHERS
FUNCTIONAL GROUP
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SALICYLIC ACID C7H6O3aka as____________
10 mL of Oil of wintergreen+
200 mL 25% NaOH Reflux distillation Cool and + HCl
Salicylic acid
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Salicylic acid
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Other method
• Sodium salicylate is by treated with sodium phenolate with carbon dioxide at high pressure (100 atm) and high temperature (390K) -a method known as the Kolbe-Schmitt reaction.
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Chemical Formula
• Salicylic acid C7H6O3• Me Salicylate C8H8O3• Sodium Hydroxide NaOH• Hydrochloric acid HCl
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Chemical Reactions
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Theoretical Yield
DENSITY Volume Mass MW2.13 g/ mL 200 mL =1.17 g/ mL 10 mL =
TY=( MW of the Product) ( Wgt Reactants) MW of the Reactants
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Solution for Theoretical Yield
TY=( MW of the Product) ( Wgt Reactants) MW of the Reactants
=
= _____?
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Percent Yield
Percent Yield= Actual Yield X 100 Theoretical Yield
Eg. Actual yield: 3 g
= = ___?
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Physical Properties
• Color = white• Odor = odorless• Appearance = crystalline powder• Melting Point = 158-161 C
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Chemical Properties
Reagents ResultBromine water white ppt (Tribromophenol-
bromide)
Ferric Chloride soln Violet solution
Methyl Alcohol Irritating/ pungent odor(forms and ester and water)
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Conclusion
• Salicylic acid can be done…..• It has it own physical and chemical
properties….
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Answers to Questions
1. What chemical group can you attribute the color change of salicylic acid with Ferric chloride soln?
Phenol group= monohydroxybenzoic acid
+ purple, blue, red or green color
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Structure of SA
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2. What are the pharmaceutical and medicinal uses of salicylic acid?
Anti-septic pain relieverKeratolytic Fever ReliefAnti-fungal
Answers to Questions
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Products with Salicylic acid
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Products with Salicylic acid
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3. What is the difference between natural and synthetic salicylic acid?
Natural SA (wintergreen leaves, sweet birch bark, willow bark)
Synthetic SA (synthesize in the lab)+ Natural SA does not have negative effects
Answers to Questions
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4. What are the major chemical classes of salicylates in medicine?
USESSalicylic acid = keratolytic/ antisepticSodium salicylate = analgesic/
antipyreticAcetyl SA = analgesic/ antipyreticMe Salicylate = liniment
Answers to Questions
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5. What pharmacologic category do drugs containing SA belong to?
Salicylates = NSAID
Answers to Questions
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METABOLISM of SA
• SA glucosyltransferase converts SA toIts metabolite SA glucoside.
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Synthesis of Acetylsalicylic acid 3 g of Salicylic acid + 6 mL acetic anhydride
+ 85% phosphoric acidHeat 10 mins in beaker
Distilled water+ 20 mL water then COOL
Scratch the walls of the flask, filter, washThe crystals, filter, then oven dry
WEIGH
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Preparations with ASA
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• Salicylic acid - C7H6O3• Acetic anhydride - C4H6O3• Phosphoric acid - H3PO4• Ferric Chloride - FeCl3• Sodium hydroxide - NaOH
Sulfuric acid - H2SO4• Acetic Acid• Acetylsalicylic acid
Chemical Formula
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Chemical reaction
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Theoretical Yield
DENSITY Volume Mass MWSA 1.443 g/cm3 3gAcetic 1.082 g cm3 6 mL
TY=( MW of the Product) ( Wgt Reactants) MW of the Reactants
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Solution for Theoretical Yield
TY=( MW of the Product) ( Wgt Reactants) MW of the Reactants
=
= _____?
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Percent Yield
Percent Yield= Actual Yield X 100 Theoretical Yield
Eg. Actual yield: 2.5 g
= = ___?
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Physical Properties
• Color = white• Odor = odorless• Appearance = crystal figures• Melting point = 135C
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Chemical Properties
Reagents ResultFerric Chloride Violet colored soln
Sodium hydroxide Yield water and Na salicylate
Ethanol, sulfuric acid Yield water andMe Salicylate
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Chemical reaction
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In conclusion:
• Acetylsalicylic acid can be done…..• It has it own physical and chemical
properties….
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Structure of ASA
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Answers to Questions
1. Give the products of Aspirin hydrolysis.
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2. Why is the salt form used in place of the original acetsalicylic acid in dosage from formulation?
- Salts of ASA are unstable in pharmaceutical dosage forms.
Answers to Questions
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3. Give the different therapeutic uses of acetylsalicylic acid?
- NSAID indicated for fever and pain (RA, Reiter’s syndrome, Osteoarthritis) and inflammation in the body.
- Prevents blood clots (stroke to occur, heart attacks)
Answers to Questions
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4. What are the side effects of acetylsalicylic acid?
- Gastrointestinal effects (stomach ulcerations, abdominal burning, pain, cramps, nausea, gastritis and bleeding)
- Tinnitus- Liver toxicity- Others: Rash, vertigo, dizziness, kidney
impairment.
Answers to Questions
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5. What are the conditions that lead to gastric mucosal irritation of acetylsalcylic acid?
- Alcohol intake- Corticosteroids- Pyrazolone derivatives (phenylbutazone)- Ibuprofen
Answers to Questions
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6. What is the storage requirement for salicylic acid?
Store at room temperatue.Away from moisture and lightDo not use if ASA has vinegar smell.
Answers to Questions
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Metabolism of Acetylsalicylic acid
• Glucuronidation• Active metabolite : Salicylate
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Synthesis of Methyl salicylate
60 mL methanol + 27.6 Salicylic acidH2SO4, swirlreflux 2 hrscool in iced bath
20% sodium carbonate(50 ml of hexane, 5 minutes)
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Drain off the aqueous layer from funnelWash hexane soln with
Water, drain soln containSodium salt of SA
Dry hexane soln with Mg sulfateThen, evaporate in fume hood
Synthesis of Methyl salicylate
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Chemical Formula
• Salicylic acid - C7H6O3 • Methanol - CH3OH • Hydrochloric acid - HCl• Hexane - C6H14• Magnesium SO4 - MgSO4• Sulfuric acid - H2SO4• Ferric Chloride - FeCl3• Me Salicylate -
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Chemical Reaction
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Chemical Reaction
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Theoretical Yield
DENSITY Volume Mass MWSA 1.44 g/cm³ 3gAcetic 1.08 g/cm³ 6mLASA 1.40 g/cm³
TY=( MW of the Product) ( Wgt Reactants) MW of the Reactants
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Solution for Theoretical Yield
TY=( MW of the Product) ( Wgt Reactants) MW of the Reactants
=
= _____?
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Percent Yield
Percent Yield= Actual Yield X 100 Theoretical Yield
Eg. Actual yield: 20 g
= = ___?
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Physical Properties
• Color = white• Odor = odorless• Appearance = crystalline powder• Melting Point = 135 C
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Chemical Properties
Reagents ResultFerric Chloride Violet colored soln
Sodium hydroxide Yields water andNa salicylate
Ethanol, H2SO4 Yields water and Me salicylate
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Structural of Methyl SA
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Answers to Questions:
1. What is the mechanism of methyl salicylate formation?
Carboxylic acid + alcohol = ester & water.
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2. What are the natural sources of methyl salicylate?
Pyrotaceae Family, Pyrola genus , Gaultheria genus
Wintergreen
Answers to Questions:
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3. What method is used in the extraction of methyl salicylate from plants?
Steam distillation to extract essential oilsWintergreen is purified thru application of
steam.Maceration is performed to isolate the
essential oil (Me Salicylate)
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4. What is the use of methyl salicylate? Give examples of its preparation available in the market?
Rubefacient in deep heating liniments.Flavoring agentsOdor masking agent
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Products with Me Salicylate
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6. Why is the internal use of methyl salicylate limited to small quantities only?
Can induce vomiting Severe fetal poisoning
Symptoms: tinnitus, NV, swelling, convulsion, kidney failure, dizziness, drowsiness and fever.
Answers to Questions: