Acids and Esters: Group 1

ACIDS AND ESTERS
GROUP 1
JUSTICE KARIKARI PH/PHA/20/0074
PHILIP AMOAHPH/PHA/20/0083
EMMANUEL AGYENIM BOATENG PH/PHA/20/0044
PRISCILLA OPPONG YEBOAH PH/PHA/20/0087
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TABLE OF CONTENT
 INTRODUCTION
 ACIDS
 MECHANISM OF ACTION
 BENZOIC ACID
 PERACETIC ACID
 USES
 ESTERS
 PARABENS
 MECHANISM OF ACTION
 REFERENCES
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INTRODUCTION
 AN ACID IS ANY HYDROGEN-CONTAINING SUBSTANCE THAT IS CAPABLE OF
DONATING A PROTON (HYDROGEN ION) TO ANOTHER SUBSTANCE.
 THERE ARE TWO FUNDAMENTAL TYPES OF ACIDS: WEAK AND STRONG ACIDS
 AN ESTER IS A CHEMICAL COMPOUND DERIVED FROM AN ACID IN WHICH AT

LEAST ONE –OH HYDROXYL GROUP HAS BEEN REPLACED BY AN –O- ALKYL
GROUP
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ACIDS
• ORGANIC ACIDS ARE THE ACIDS NORMALLY USED AS ANTIMICROBIAL AGENTS

• THESE ARE WEAK ACIDS AND WILL, THEREFORE, DISSOCIATE INCOMPLETELY
TO GIVE THE THREE ENTITIES HA, H + AND A - IN SOLUTION.
• AS THE UNDISSOCIATED FORM, HA, IS THE ACTIVE ANTIMICROBIAL AGENT,
THE IONIZATION CONSTANT KA IS VERY IMPORTANT AND THE PKA OF THE
ACID MUST BE CONSIDERED.
• EXAMPLES OF ACIDS COMMONLY USED INCLUDE BENZOIC ACID, SORBIC ACID,
ACETIC ACID.
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MECHANISM OF ACTION
 ACIDIC DISINFECTANTS FUNCTION BY DESTROYING THE BONDS OF NUCLEIC ACIDS

AND PRECIPITATING PROTEINS
 INCREASED ACIDITY OF THE CYTOPLASM CAN CAUSE THE FATTY ACIDS CHAINS OF THE
LIPIDS IN THE MEMBRANE TO BECOME PROTONATED. THIS PROTONATION CAN
INCREASE THE FLUIDITY OF THE MEMBRANE, CAUSING IT TO BECOME MORE
PERMEABLE.
 THIS CAN FURTHER AFFECT THE OH OF THE ENZYME ACTIVITY AND ALSO THE ACIDS
CAN BIND TO THE ACTIVE SITE OR ALLOSTERIC SITE OF THE THE ENZYME.
ACIDS ALSO CHANGE THE PH OF THE ENVIRONMENT MAKING IT DETRIMENTAL TO MANY
MICROORGANISMS
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BENZOIC ACID
 BENZOIC ACID(C7H6O2) IS A COMMONLY

USED ANTIMICROBIAL PRESERVATIVE
IN FOOD AND BEVERAGES, ESPECIALLY
IN CARBONATED BEVERAGES.
 ITS STRONGEST ANTIBACTERIAL
ACTIVITY IS AT PH 2.5-4.0.
 IT HAS INHIBITORY EFFECTS ON THE
PROLIFERATION OF BACTERIA AND
YEASTS, A MAJOR CAUSE OF FOOD
SPOILAGE.
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LIMITATIONS
• A LIMITATION ON ITS USE IS IMPOSED BY THE PH OF THE FINAL PRODUCT. IT

IS ADVISABLE TO LIMIT USE OF ACID TO PRESERVATION OF
PHARMACEUTICALS WITH THE MAXIMUM FINAL PH OF 5.0. IF POSSIBLE LESS
THAN 4.0.
• CONCENTRATION OF 0.05-0.1% ARE SUITABLE FOR ORAL PREPARATION.
• RESISTANT ORGANISMS ARE ABLE TO METABOLISE THE ACID RESULTING IN
COMPLETE LOSS OF ACTIVITY.
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PERACETIC ACID(C2H4O3)
 PERACETIC(C2H4O3) ACID IS PRODUCED BY A

REACTION BETWEEN HYDROGEN PEROXIDE AND
ACETIC ACID.
 IT OXIDIZES THE OUTER CELL MEMBRANE OF
MICROORGANISMS.
 THE OXIDATION CONSISTS OF ELECTRON
TRANSFER.
 WHEN A STRONGER OXIDANT IS USED, THE
ELECTRONS ARE TRANSFERRED TO THE
MICROORGANISM MUCH FASTER, CAUSING THE
MICROORGANISM TO BE DEACTIVATED RAPIDLY.
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USES OF PERACETIC ACID
IT IS USED MAINLY IN THE FOOD INDUSTRY AS A CLEANSER AND AS A

DISINFECTANT.
• IT IS ALSO APPLIED FOR THE DISINFECTION OF MEDICAL SUPPLIES AND TO
PREVENT BIOFILM FORMATION IN PULP INDUSTRIES.
• IT CAN BE APPLIED DURING WATER PURIFICATION AS A DISINFECTANT AND
FOR PLUMING DISINFECTION.
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ESTERS
 A SERIES OF ALKYL ESTERS OF P-HYDROXYBENZOIC ACID WAS

ORIGINALLY PREPARED TO OVERCOME THE MARKED PH DEPENDENCE
ON ACTIVITY OF THE ACIDS.
 PARABENS ARE ESTERS OF 4- HYDROXYBENZOIC ACID DIFFERING IN
THEIR ESTER GROUP WHICH COULD BE A METHYL, ETHYL,PROPYL,ETC.
 THESE PARABENS ARE LESS IONIZED , HAVING PKA VALUE IN THE
RANGE OF 8-8.5 AND EXHIBIT GOOD PRESERVATIVE ACTIVITY EVEN AT
PH LEVELS OF 7.8, ALTHOUGH OPTIMUM ACTIVITY IS AGAIN DISPLAYED
IN ACID SOLUTIONS.
 THEY ARE USED IN THE COSMETIC AND PHARMACEUTICAL INDUSTRIES
FOR PERSONAL LUBRICANTS, MOISTURIZERS, TOPICAL/PARENTERAL
PHARMACEUTICALS, ETC
 METHYL ESTER SULPHONATE IS A COMMONLY USED DETERGENT DUE
TO ITS HIGH DETERGENCY, WATER HARDNESS TOLERANCE AND
EXCELLENT BIODEGRADABILITY.
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ADVANTAGES
• THEY ARE EFFECTIVE AGAINST PROLIFERATION OF YEAST AND MOLDS AT LOWER

CONCENTRATIONS THAN WEAK ACIDS BUT LESS ACTIVE AGAINST BACTERIA (ESP. GRAM
NEGATIVE)EG. PSEUDOMONADS
• UNLIKE BENZOIC ACIDS FROM WHICH THEY ARE FORMED THEY RETAIN THEIR EFFICACY
AT PH LEVELS OF UP TO 8.0.
• THEY ARE CONSIDERED TO BE PH INDEPENDENT UNDER VALUES OF 8 WHERE THEY ARE
FULLY UNDISSOCIATED AND HAVE OPTIMUM ACTIVITY.
• COMBINATIONS OF METHYL AND PROPYLPARABENS ARE COMMONLY EMPLOYED TO
ACHIEVE BETTER ANTIMICROBIAL RESULTS
• COMBINATIONS OF ESTERS ARE ALSO USEFUL FOR 2 PHASE PRODUCTS (EMULSIONS)
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ADVANTAGES
• FOR THIS TYPE OF PRODUCT IN THAT THE MORE

WATER - SOLUBLE METHYL ESTER PROTECTS THE
AQUEOUS PHASE, WHEREAS THE PROPYL OR BUTYL
ESTERS GIVE PROTECTION TO THE OIL PHASE.
• SUCH COMBINATIONS ARE ALSO CONSIDERED TO
EXTEND THE RANGE OF ACTIVITY.
• AS INACTIVATION OF PARABENS OCCURS WITH NON -
IONIC SURFACTANTS DUE CARE SHOULD BE TAKEN
IN FORMULATION WITH BOTH MATERIALS.
• THEY ACT UPON THE CELL MEMBRANE (BY
INTERACTING WITH MEMBRANE PROTEINS AND
GENERATING DISORDERS IN MEMBRANE LIPIDS) AND
AFFECT THE FUNCTIONALITY OF ENZYMES
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MECHANISM OF ACTION
• ESTERS WORK BY INHIBITING THE ACTIVITY OF AN ENZYME CALLED

DIHYDROFOLATE REDUCTASE (DNA AND RNA) IN MICROBIAL CELLS. THIS
INHIBITION DISRUPTS THE GROWTH AND REPRODUCTION OF
MICROORGANISMS, ULTIMATELY LEADING TO THEIR DEATH.
13
SOME EXAMPLES OF ESTERS AND ACIDS WITH
MICROBIAL ACTIVITY
ACIDS
ORGANIC ACID ANTISEPTIC(ACIDS) PRESERVATIVES
DISINFECTANT
ACETIC ACID SALICYLIC ACID ASCORBIC ACID
CITRIC ACID SORBIC ACID PROPIONIC ACID
FORMIC ACID BENZOIC ACID ACETIC ACID
ESTERS
ESTERS ANTISEPTIC PRESERVATIVE
DISINFECTANT
ETHYL ACETATE BENZALKONIUM METHYL PARABEN
CHLORIDE 14
METHYL PARABEN BIGUANIDE ETHYL PARABEN

REFERENCE
• DENYER, P. S., HODGES, A. N., GORMAN, P. S. & GILMORE, F. B. (2011). HUGO

AND RUSSELL'S PHARMACEUTICAL MICROBIOLOGY. 8TH EDITION, WILEY-
BLACKWELL. ISBN: 978-1444330632
• KAR A. (2008). PHARMACEUTICAL MICROBIOLOGY. 1ST EDITION. NEW AGE
PUBLISHERS, 2008. ISB:N 978812242867-4
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ACIDS AND ESTERS

 AN ESTER IS A CHEMICAL COMPOUND DERIVED FROM AN ACID IN WHICH AT

• ORGANIC ACIDS ARE THE ACIDS NORMALLY USED AS ANTIMICROBIAL AGENTS

 ACIDIC DISINFECTANTS FUNCTION BY DESTROYING THE BONDS OF NUCLEIC ACIDS

 BENZOIC ACID(C7H6O2) IS A COMMONLY

• A LIMITATION ON ITS USE IS IMPOSED BY THE PH OF THE FINAL PRODUCT. IT

 PERACETIC(C2H4O3) ACID IS PRODUCED BY A

IT IS USED MAINLY IN THE FOOD INDUSTRY AS A CLEANSER AND AS A

 A SERIES OF ALKYL ESTERS OF P-HYDROXYBENZOIC ACID WAS

• THEY ARE EFFECTIVE AGAINST PROLIFERATION OF YEAST AND MOLDS AT LOWER

• FOR THIS TYPE OF PRODUCT IN THAT THE MORE

• ESTERS WORK BY INHIBITING THE ACTIVITY OF AN ENZYME CALLED

METHYL PARABEN BIGUANIDE ETHYL PARABEN

• DENYER, P. S., HODGES, A. N., GORMAN, P. S. & GILMORE, F. B. (2011). HUGO

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