This document discusses phenols, including their medical and health uses, synthesis, and reactions. Phenols contain a hydroxyl group attached to an aromatic ring. They are used in medical procedures like muscle injections and ingrown toenail removal. Phenol is also used as a preservative in vaccines and throat sprays. It can be synthesized through processes like pyrolysis of sodium benzene sulfonate and air oxidation of cumene. While phenol has some health benefits as an antioxidant, exposure to high amounts can be toxic.
Phenol is the original antiseptic used by Joseph Lister who discovered antiseptics. It works well but is toxic. Phenol derivatives such as trichlorophenol are less toxic and widely used today as antiseptics. Antiseptics are chemical agents that slow or stop microbial growth on external surfaces and help prevent infections. They are commonly used for handwashing, pre-operative skin disinfection, and treating wounds.
Organophosphorus compounds are widely used as pesticides and some were developed as nerve agents. They work by inhibiting acetylcholinesterase, resulting in excess acetylcholine in synapses and stimulation of receptors. Acute poisoning causes cholinergic effects like bronchospasm, vomiting, and bradycardia. Without treatment, respiratory failure can be fatal. Pralidoxime and atropine are used as antidotes to regenerate acetylcholinesterase and block muscarinic effects, respectively. Chronic exposure may cause neuropathies or psychiatric issues.
This document summarizes information about phenols from a student group project. It discusses the structure of phenols, including examples like phenol, cresols, resorcinol, and naphthol. Methods of preparation and qualitative tests for phenols are described. Reactions of phenols through electrophilic aromatic substitution and rearrangements are summarized. Uses of specific phenols in applications like cleaners, medicines, and dyes are mentioned.
Indian Dental Academy: will be one of the most relevant and exciting training center with best faculty and flexible training programs for dental professionals who wish to advance in their dental practice,Offers certified courses in Dental implants,Orthodontics,Endodontics,Cosmetic Dentistry, Prosthetic Dentistry, Periodontics and General Dentistry.
This document provides an overview of intracanal medicaments used in endodontics. It discusses the history, rationale, objectives and classifications of intracanal medicaments. Various types of medicaments are described including essential oils, phenolic compounds, aldehydes, halogens, calcium hydroxide, and antibiotics. Calcium hydroxide is highlighted as a commonly used medicament due to its high pH and ability to disinfect root canals and promote tissue healing. The document also reviews the ideal properties, applications, and limitations of intracanal medicaments.
This document discusses phenol, including its introduction, nomenclature, preparation, reactions, safety measures, waste treatment, and removal from wastewater. Key points include:
- Phenol contains an -OH group directly attached to an aryl group and forms stronger hydrogen bonds than alcohols.
- Common phenols are named using either trivial names or IUPAC nomenclature specifying substituents.
- Phenol is prepared through hydrolysis of chlorobenzene, oxidation of isopropylbenzene, or diazotization of an arylamine.
- Phenols undergo oxidation to quinones or electrophilic aromatic substitution, and are used to make phenol
Phenol is the original antiseptic used by Joseph Lister who discovered antiseptics. It works well but is toxic. Phenol derivatives such as trichlorophenol are less toxic and widely used today as antiseptics. Antiseptics are chemical agents that slow or stop microbial growth on external surfaces and help prevent infections. They are commonly used for handwashing, pre-operative skin disinfection, and treating wounds.
Organophosphorus compounds are widely used as pesticides and some were developed as nerve agents. They work by inhibiting acetylcholinesterase, resulting in excess acetylcholine in synapses and stimulation of receptors. Acute poisoning causes cholinergic effects like bronchospasm, vomiting, and bradycardia. Without treatment, respiratory failure can be fatal. Pralidoxime and atropine are used as antidotes to regenerate acetylcholinesterase and block muscarinic effects, respectively. Chronic exposure may cause neuropathies or psychiatric issues.
This document summarizes information about phenols from a student group project. It discusses the structure of phenols, including examples like phenol, cresols, resorcinol, and naphthol. Methods of preparation and qualitative tests for phenols are described. Reactions of phenols through electrophilic aromatic substitution and rearrangements are summarized. Uses of specific phenols in applications like cleaners, medicines, and dyes are mentioned.
Indian Dental Academy: will be one of the most relevant and exciting training center with best faculty and flexible training programs for dental professionals who wish to advance in their dental practice,Offers certified courses in Dental implants,Orthodontics,Endodontics,Cosmetic Dentistry, Prosthetic Dentistry, Periodontics and General Dentistry.
This document provides an overview of intracanal medicaments used in endodontics. It discusses the history, rationale, objectives and classifications of intracanal medicaments. Various types of medicaments are described including essential oils, phenolic compounds, aldehydes, halogens, calcium hydroxide, and antibiotics. Calcium hydroxide is highlighted as a commonly used medicament due to its high pH and ability to disinfect root canals and promote tissue healing. The document also reviews the ideal properties, applications, and limitations of intracanal medicaments.
This document discusses phenol, including its introduction, nomenclature, preparation, reactions, safety measures, waste treatment, and removal from wastewater. Key points include:
- Phenol contains an -OH group directly attached to an aryl group and forms stronger hydrogen bonds than alcohols.
- Common phenols are named using either trivial names or IUPAC nomenclature specifying substituents.
- Phenol is prepared through hydrolysis of chlorobenzene, oxidation of isopropylbenzene, or diazotization of an arylamine.
- Phenols undergo oxidation to quinones or electrophilic aromatic substitution, and are used to make phenol
Chemical synthesis involves combining simpler compounds to form more complex ones. An example is the synthesis of the anticancer drug Taxol from the Pacific yew tree. The synthesis of flavonoids typically involves multiple steps including condensation reactions, rearrangements, and cyclizations to form the core flavone structure. Quercetin is a flavonoid with potential health benefits including reduced risk of heart disease and lung cancer. Ciprofloxacin is a broad-spectrum antibiotic synthesized through a multi-step process involving reactions such as condensation, cyclization, and rearrangements.
Chemical synthesis involves combining simpler compounds to form more complex ones. An example is the synthesis of the anticancer drug Taxol from the Pacific yew tree. The synthesis of flavonoids typically involves multiple steps including condensation reactions, rearrangements, and cyclizations to form the core flavone structure. Quercetin is a flavonoid with potential health benefits including reduced risk of heart disease and lung cancer. Ciprofloxacin is a broad-spectrum antibiotic synthesized through a multi-step process involving reactions such as condensation, cyclization, and amination.
Phenol is a toxic compound discovered in 1834 that has a variety of industrial and medical uses. It is absorbed through the skin, lungs, and gastrointestinal tract, distributing widely in the body before being metabolized and excreted in urine. Acute exposure can cause rapid nervous system effects like seizures and coma, while chronic exposure is associated with damage to the kidneys, liver, heart and skin. Phenol was also used by Nazis during World War II for individual executions by injection.
Plant phenolics are secondary metabolites that encompass several classes structurally diverse of natural products biogenetically arising from the shikimate-phenylpropanoids-flavonoids pathways. Plants need phenolic compounds for pigmentation, growth, reproduction, resistance to pathogens and for many other functions. Therefore, they represent adaptive characters that have been subjected to natural selection during evolution. Plants synthesize a greater array of secondary compounds than animals because they cannot rely on physical mobility to escape their predators and have therefore evolved a chemical defence against such predators. This article, after a short review of plant phenols and polyphenols as UV sunscreens, signal compounds, pigments, internal physiological regulators or chemical messengers, examines some findings in chemical ecology concerning the role of phenolics in the resistance mechanisms of plants against fungal pathogens and phytophagous insects.
Preparation of intranasal route drug delivery system by sneha gaurkarSneha Gaurkar
This document discusses intranasal drug delivery systems. It begins by describing the nasal route of administration and some advantages it provides over other routes. It then discusses various types of drugs, polymers, and excipients commonly used to formulate nasal sprays, gels, drops and other dosage forms. Specific examples are provided of formulations for a bronchodilator nasal spray and fentanyl nasal spray. Finally, emerging intranasal delivery approaches using nanoparticles and nanoemulsions are briefly summarized.
Phenol is an organic compound used widely in industry. It is produced at over 7 billion kg per year mainly through cumene synthesis from benzene, propene and oxygen. Its major uses are in producing plastics, resins, nylon and non-ionic detergents. Phenol is slightly acidic and is a precursor to many drugs, herbicides and pharmaceuticals. Exposure to phenol can cause skin and eye burns and internal organ damage. It is toxic in high doses and was even used for executions during WWII. Regulations control phenol levels in wastewater, drinking water and hazardous waste due to its toxicity.
A review of the history, research and clinical studies conducted with Propolair propolis vaporizers and diffusers. Manufactured by the Italian company, Kontak, it was invented by a beekeeper to aid those with respiratory ailments.
Clinical studies confirm its antibacterial effectiveness, as well as its capacity to clean the air of carcinogenic pollutants.
New research reveals it possesses the richest flavonoid content of important phenolic acids and compounds in this unique blend of Italian propolis. To date, these units are used in clinics, nurseries, hospitals, offices and homes around the world.
Phenol - Hazardous Substance Fact Sheet - Resources for Healthy Children www.scribd.com/doc/254613619 - For more information, Please see Organic Edible Schoolyards & Gardening with Children www.scribd.com/doc/254613963 - Gardening with Volcanic Rock Dust www.scribd.com/doc/254613846 - Double Food Production from your School Garden with Organic Tech www.scribd.com/doc/254613765 - Free School Gardening Art Posters www.scribd.com/doc/254613694 - Increase Food Production with Companion Planting in your School Garden www.scribd.com/doc/254609890 - Healthy Foods Dramatically Improves Student Academic Success www.scribd.com/doc/254613619 - City Chickens for your Organic School Garden www.scribd.com/doc/254613553 - Huerto Ecológico, Tecnologías Sostenibles, Agricultura Organica www.scribd.com/doc/254613494 - Simple Square Foot Gardening for Schools - Teacher Guide www.scribd.com/doc/254613410 - Free Organic Gardening Publications www.scribd.com/doc/254609890 ~ NJ Health
This document provides an overview of nasal drug delivery systems. It discusses the advantages of the nasal route for drug administration, including avoidance of first-pass metabolism and rapid drug absorption. Various therapeutic drug classes that can be delivered nasally are described, along with factors affecting nasal drug absorption. Common dosage forms like drops, sprays and gels are mentioned. Methods to enhance nasal drug delivery include structural modifications, formulation designs and absorption enhancers. Evaluation methods for nasal formulations involve in vivo studies in animal models like rats and rabbits. Applications include delivery of peptides, vaccines and diagnostic agents nasally.
This document discusses aromatic compounds and benzene chemistry. It begins by introducing aromatic hydrocarbons and noting they have different properties than aliphatic hydrocarbons. Benzene, the simplest aromatic hydrocarbon, is described as having posed problems for early chemists to determine its structure. Kekulé proposed benzene has alternating single and double bonds, but this did not explain its chemical behavior. The resonance structure of benzene is able to account for its reactivity. The document continues discussing nomenclature of aromatic compounds with different numbers of substituents on the benzene ring. Characteristic reactions of benzene like halogenation and nitration are also covered. Phenols are introduced as aromatic compounds containing an -OH group
Intranasal drug delivery system - Introduction, Nasal enzymes and nasal ph, cross sectional view of nose, factors affecting nasal absorption, general formulations of intranasal drugs, Intranasal dosage forms, nasal sprays, spray pump devices, nasal aerosols, compressed air nebulizers, nasal powder, nasal gels, applications of intranasal drug delivery system, delivery of intranasal vaccines, intranasal anaesthesia, Evaluation of intranasal formulation, ussing chamber, Advantages and disadvantages of intranasal drug delivery system
Introduction to Agrochemicals and PesticidesMD AHAD ALI
This document discusses various types of agrochemicals and pesticides. It begins by defining pests and pesticides, and provides classifications of pesticides including their target organisms and chemical structures. It then focuses on specific types of pesticides including organochlorinated pesticides such as DDT, organophosphorus pesticides such as parathion, and herbicides such as 2,4,5-Trichlorophenoxyacetic acid. For each pesticide, it discusses their preparation, uses, toxicity, and mechanisms or effects on organisms. The document provides information on how various pesticides work and their impacts on human health.
This document discusses phytosomes, which are novel drug delivery systems that involve complexing hydrophilic phytoconstituents from herbs with phospholipids. This improves the solubility, absorption, and bioavailability of poorly soluble active compounds from plants. Phytosomes are prepared by dissolving phospholipids and plant extracts or compounds in organic solvents. The solvent is then evaporated, forming a thin film. This film is hydrated to produce a suspension of phytosomes, which are complexes of the plant compounds surrounded and bound by phospholipids. Common phospholipids and solvents used in phytosome preparation are described.
What is anaesthesia?, stages of anaesthesia, classification of general anaesthetics, Structure activity relationship of general anaesthetics, mechanism of action and uses.
This document discusses various classes of antifungal drugs, including their mechanisms of action and toxicities. The main classes covered are polyenes, flucytosine, azoles, echinocandins, griseofulvin, terbinafine, and tolnaftate. Polyenes like amphotericin B and nystatin bind to ergosterol in the fungal cell membrane to create pores. Flucytosine is converted to 5-fluorouracil which inhibits fungal DNA and RNA synthesis. Azoles like ketoconazole and itraconazole inhibit ergosterol synthesis. Echinocandins are the newest class and inhibit beta-
Medicinal Chemistry and Pharmacology of Antifungal Agents and how to take care from fungal infections. Useful Course study material for the undergraduate , postgraduate and aspirants of Pharmacy , Pharmacology and Medicinal Chemistry.
This document provides information on proton pump inhibitors (PPIs), including their definition, mechanism of action, pharmacokinetics, indications, contraindications, adverse effects, drug interactions, nursing considerations, and patient teaching points. PPIs work by reducing stomach acid production and are commonly prescribed for conditions like dyspepsia, peptic ulcers, and gastroesophageal reflux disease. Adverse effects can include headaches, diarrhea and bone fractures with long term use. Nurses should monitor for side effects and educate patients on proper administration and signs of complications.
The technology uses reclaimed CO₂ as the dyeing medium in a closed loop process. When pressurized, CO₂ becomes supercritical (SC-CO₂). In this state CO₂ has a very high solvent power, allowing the dye to dissolve easily.
The cost of acquiring information by natural selectionCarl Bergstrom
This is a short talk that I gave at the Banff International Research Station workshop on Modeling and Theory in Population Biology. The idea is to try to understand how the burden of natural selection relates to the amount of information that selection puts into the genome.
It's based on the first part of this research paper:
The cost of information acquisition by natural selection
Ryan Seamus McGee, Olivia Kosterlitz, Artem Kaznatcheev, Benjamin Kerr, Carl T. Bergstrom
bioRxiv 2022.07.02.498577; doi: https://doi.org/10.1101/2022.07.02.498577
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Similar to organic chemistry lecture module - Phenols.pdf
Chemical synthesis involves combining simpler compounds to form more complex ones. An example is the synthesis of the anticancer drug Taxol from the Pacific yew tree. The synthesis of flavonoids typically involves multiple steps including condensation reactions, rearrangements, and cyclizations to form the core flavone structure. Quercetin is a flavonoid with potential health benefits including reduced risk of heart disease and lung cancer. Ciprofloxacin is a broad-spectrum antibiotic synthesized through a multi-step process involving reactions such as condensation, cyclization, and rearrangements.
Chemical synthesis involves combining simpler compounds to form more complex ones. An example is the synthesis of the anticancer drug Taxol from the Pacific yew tree. The synthesis of flavonoids typically involves multiple steps including condensation reactions, rearrangements, and cyclizations to form the core flavone structure. Quercetin is a flavonoid with potential health benefits including reduced risk of heart disease and lung cancer. Ciprofloxacin is a broad-spectrum antibiotic synthesized through a multi-step process involving reactions such as condensation, cyclization, and amination.
Phenol is a toxic compound discovered in 1834 that has a variety of industrial and medical uses. It is absorbed through the skin, lungs, and gastrointestinal tract, distributing widely in the body before being metabolized and excreted in urine. Acute exposure can cause rapid nervous system effects like seizures and coma, while chronic exposure is associated with damage to the kidneys, liver, heart and skin. Phenol was also used by Nazis during World War II for individual executions by injection.
Plant phenolics are secondary metabolites that encompass several classes structurally diverse of natural products biogenetically arising from the shikimate-phenylpropanoids-flavonoids pathways. Plants need phenolic compounds for pigmentation, growth, reproduction, resistance to pathogens and for many other functions. Therefore, they represent adaptive characters that have been subjected to natural selection during evolution. Plants synthesize a greater array of secondary compounds than animals because they cannot rely on physical mobility to escape their predators and have therefore evolved a chemical defence against such predators. This article, after a short review of plant phenols and polyphenols as UV sunscreens, signal compounds, pigments, internal physiological regulators or chemical messengers, examines some findings in chemical ecology concerning the role of phenolics in the resistance mechanisms of plants against fungal pathogens and phytophagous insects.
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This document discusses intranasal drug delivery systems. It begins by describing the nasal route of administration and some advantages it provides over other routes. It then discusses various types of drugs, polymers, and excipients commonly used to formulate nasal sprays, gels, drops and other dosage forms. Specific examples are provided of formulations for a bronchodilator nasal spray and fentanyl nasal spray. Finally, emerging intranasal delivery approaches using nanoparticles and nanoemulsions are briefly summarized.
Phenol is an organic compound used widely in industry. It is produced at over 7 billion kg per year mainly through cumene synthesis from benzene, propene and oxygen. Its major uses are in producing plastics, resins, nylon and non-ionic detergents. Phenol is slightly acidic and is a precursor to many drugs, herbicides and pharmaceuticals. Exposure to phenol can cause skin and eye burns and internal organ damage. It is toxic in high doses and was even used for executions during WWII. Regulations control phenol levels in wastewater, drinking water and hazardous waste due to its toxicity.
A review of the history, research and clinical studies conducted with Propolair propolis vaporizers and diffusers. Manufactured by the Italian company, Kontak, it was invented by a beekeeper to aid those with respiratory ailments.
Clinical studies confirm its antibacterial effectiveness, as well as its capacity to clean the air of carcinogenic pollutants.
New research reveals it possesses the richest flavonoid content of important phenolic acids and compounds in this unique blend of Italian propolis. To date, these units are used in clinics, nurseries, hospitals, offices and homes around the world.
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This document provides an overview of nasal drug delivery systems. It discusses the advantages of the nasal route for drug administration, including avoidance of first-pass metabolism and rapid drug absorption. Various therapeutic drug classes that can be delivered nasally are described, along with factors affecting nasal drug absorption. Common dosage forms like drops, sprays and gels are mentioned. Methods to enhance nasal drug delivery include structural modifications, formulation designs and absorption enhancers. Evaluation methods for nasal formulations involve in vivo studies in animal models like rats and rabbits. Applications include delivery of peptides, vaccines and diagnostic agents nasally.
This document discusses aromatic compounds and benzene chemistry. It begins by introducing aromatic hydrocarbons and noting they have different properties than aliphatic hydrocarbons. Benzene, the simplest aromatic hydrocarbon, is described as having posed problems for early chemists to determine its structure. Kekulé proposed benzene has alternating single and double bonds, but this did not explain its chemical behavior. The resonance structure of benzene is able to account for its reactivity. The document continues discussing nomenclature of aromatic compounds with different numbers of substituents on the benzene ring. Characteristic reactions of benzene like halogenation and nitration are also covered. Phenols are introduced as aromatic compounds containing an -OH group
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This document discusses various types of agrochemicals and pesticides. It begins by defining pests and pesticides, and provides classifications of pesticides including their target organisms and chemical structures. It then focuses on specific types of pesticides including organochlorinated pesticides such as DDT, organophosphorus pesticides such as parathion, and herbicides such as 2,4,5-Trichlorophenoxyacetic acid. For each pesticide, it discusses their preparation, uses, toxicity, and mechanisms or effects on organisms. The document provides information on how various pesticides work and their impacts on human health.
This document discusses phytosomes, which are novel drug delivery systems that involve complexing hydrophilic phytoconstituents from herbs with phospholipids. This improves the solubility, absorption, and bioavailability of poorly soluble active compounds from plants. Phytosomes are prepared by dissolving phospholipids and plant extracts or compounds in organic solvents. The solvent is then evaporated, forming a thin film. This film is hydrated to produce a suspension of phytosomes, which are complexes of the plant compounds surrounded and bound by phospholipids. Common phospholipids and solvents used in phytosome preparation are described.
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The technology uses reclaimed CO₂ as the dyeing medium in a closed loop process. When pressurized, CO₂ becomes supercritical (SC-CO₂). In this state CO₂ has a very high solvent power, allowing the dye to dissolve easily.
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This is a short talk that I gave at the Banff International Research Station workshop on Modeling and Theory in Population Biology. The idea is to try to understand how the burden of natural selection relates to the amount of information that selection puts into the genome.
It's based on the first part of this research paper:
The cost of information acquisition by natural selection
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bioRxiv 2022.07.02.498577; doi: https://doi.org/10.1101/2022.07.02.498577
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3. Phenols
v Phenols are molecules that have a hydroxyl
group attached to the carbon atom of an
aromatic ring.
v By definition, phenol is hydroxybenzene.
4. Nomenclature
• Phenol is a common name for the compound.
• Its IUPAC name would be benzenol, derived in the same
manner as the IUPAC names for aliphatic alcohols.
• When a phenol molecule is substituted with additional
groups, either the ortho, meta, para system or the
numbering system can be employed.
• In IUPAC nomenclature, the parent molecule is called
benzenol, and substituents are always numbered with
the OH group being given the understood first position.
• For the compounds below, the first name listed is the
common name and the second is the IUPAC name.
5. Medical & Health Uses of Phenol
v Pure phenol is used in certain medical
procedures and as an ingredient in numerous
treatments and laboratory applications.
v Phenol has numerous health benefits and can
be helpful to treat a few different conditions.
v But it can be dangerous and even deadly in high
amounts.
v Be careful in places that may contain high
levels of phenol, such as industrial
facilities.
v Don’t eat or drink anything that may have
been exposed to phenol or have
uncontrolled amounts of phenol in it.
6. Phenol Injection
Ø Phenol can be injected into your muscles to treat a
condition known as muscle spasticity.
Ø This happens when your brain doesn’t communicate
properly with your spinal cord and nerves.
Ø It causes your muscles to become tight.
Ø Muscle spasticity can even interrupt your ability to walk
or talk.
Ø It can be caused by conditions like Parkinson’s
disease, cerebral palsy, or brain trauma.
Ø A phenol injection helps limit the signals sent from your
nerves to your muscles that cause contractions.
Ø This allows you to move more easily and feel less
discomfort.
7. Chemical matrixectomy
q Phenol in the form of trichloroacetic acid is
commonly used in surgeries for in-grown
toenails, especially the more severe ingrown
toenails that don’t respond to other treatments.
q A small 2001 study of 172 people found that 98.8
percent of those who received a chemical
matrixectomy with phenol cauterization had
successful results.
q However, sodium hydroxide is gradually replacing
phenol matrixectomy as an ingrown toenail
treatment because it has fewer complications
{Journal of American Podiatric Medical Association ,
2014}.
8. Vaccine preservative
q Phenol is used as a preservative in at least
four vaccines.
q It helps keep bacteria from growing in and
contaminating the vaccine solutions.
q Pneumovax 23 for conditions like
pneumonia and meningitis
q Typhim Vi for typhoid fever
q ACAM2000 for smallpox
9. Sore throat spray
q Phenol is used in some throat sprays that can help
numb your throat and relieve symptoms caused
by a sore throat, or irritation in the mouth caused
by canker sores.
q The most common brand of phenol spray is
Chloraseptic which contains about 1.4% phenol.
q Phenol spray is safe to use at the recommend dose
for a short time.
q But using too much or giving it to children younger than 3-
years old can be unsafe.
q Read the ingredients label carefully to make sure you’re not
allergic to any other components of the spray.
10. Oral analgesics
v Many phenol-based products that help relieve
pain or irritation in or around your mouth
numb tissues in the mouth and lips.
v These products are used as a short-term
treatment for the symptoms of pharyngitis.
v This happens when your throat gets inflamed
from a bacterial or viral infection.
v Phenol-based products for mouth and throat
pain are widely available and safe to use in
small doses.
11. Phenol derivatives
v Phenol-derived compounds have a variety of
uses, including:
v Chemical Peels-Phenol in trichloroacetic acid is
used to penetrate through layers of skin to get
rid of old or damaged skin.
v Food and cosmetic preservatives. Phenol
derivative butylated hydroxytoluene (BHT) is a
common FDA-approved preservative used
in cosmetics and to keep food from going bad.
v It’s safe to consume in small amounts.
12. Phenol liquid
v Phenol liquid is often used in molecular biology with
trichloro-methane and chloroform to separate RNA,
DNA, or proteins, and isolate them in the pure form.
v This process is known as liquid-liquid extraction.
v It’s done by adding an equal amount of phenol and
chloroform to a solution of cells or tissues.
v The phenol-chloroform mixture separates molecules
based on how soluble the tissue sample is in that
solution.
v The pH level of phenol helps separate the DNA and
RNA.
13. Soap and antiseptic
v Soap containing phenol-based compounds is often called carbolic
soap.
v It’s been used as an antiseptic during surgery since 1867 or more.
v It’s remembered by millions in the United Kingdom for its distinct
smell and red streaks it left on bathroom sinks.
v Carbolic soap is still widely used throughout the world especially in
countries who receive foreign aid from organizations like the
Red Cross or Doctors Without Borders.
v It provides effective, low-cost hygiene to poverty-stricken
communities.
v Over time, pure phenol has been replaced by some of its
derivatives as an antiseptic.
v One derivative is n-hexylresorcinol, which can be found in cough
drops.
v The compound, butylated hydroxytoluene (BHT), has replaced
phenol as a food antioxidant.
14. Health benefits
Antioxidants
v Plant-based compounds containing phenol are
known to be antioxidants.
v Antioxidants can stop the reaction of free
radicals with other molecules in your body,
preventing damage to your DNA as well as
long-term health effects.
v Free radicals are molecules that have lost an
electron and become unstable.
v This makes them prone to react with and damage
molecules like DNA.
v Free radicals sometimes cause the molecules they
react with to create even more free radicals.
15. Health benefits cont’d
v Antioxidant molecules are like a barrier between
free radicals and healthy molecules:
antioxidants replace the missing electron and
render it harmless.
v Some notable phenolic antioxidants with proven
health effects include:
v Bioflavonoids, found in wines, teas, fruits, and
vegetables
v tocopherols including vitamin E, found in many
fruits, nuts & vegetables
v Resveratrol, found in fruits, nuts, and red wine
v Oregano oil composed of many beneficial
phenols like carvacrol, cymene, terpinine, and
thymol.
16. Cancer prevention
v Phenol-based compounds have been found to have
some cancer prevention properties.
v A 2010 animal review in Advances in Experimental
Medicine and Biology suggested that getting phenols
from a diet heavy in plants containing phenolic
compounds and foods fortified with phenols helped
strengthen the immune system and make cells more
resistant to cancer throughout their life cycle.
v Most of this research comes from animal models, but
human studies are also promising.
v According to a 2014 paper in Current Pharmaceutical
Biotechnology, the complex structures of phenolic
compounds can help make cancer cells more
receptive to chemotherapy treatments.
17. Risks
vPhenol may have its share of uses
and health benefits, but it can also
be toxic or cause long-term health
effects if you’re exposed to it in high
amounts.
18. vHow to avoid exposure:
v Be careful at work.
v Being exposed to phenol in industrial
facilities may increase your risk of heart
disease.
v This may be partly due to exposure to many other
industrial chemicals in addition to phenol.
v Don’t eat anything that might contain phenol.
v Consuming phenol in its pure form can damage
your esophagus, stomach, intestines, and other
digestive organs.
v It can be fatal if you have enough of it at one time.
19. vHow to avoid exposure cont’d:
v Don’t put it on your skin.
v Pure phenol can damage your skin if it makes
direct contact. This can include burns and
blisters.
v Don’t inhale it.
v Laboratory animals experienced breathing
difficulties and twitching of muscles when
they breathed in a lot of phenol for even a short
period of time. Phenol has also been shown to
cause systemic organ damage in laboratory
animals.
v Don’t drink it.
v Consuming water containing a lot of phenol can
make muscles spasm and affect your ability to
walk. Too much can be fatal.
20. Synthesis of Phenols
v Phenols are prepared in large quantities by
the pyrolysis of the sodium salt of
benzene sulfonic acid, by the Dow
process, and by the air oxidation of
cumene.
v You can also prepare small amounts of
phenol by the peroxide oxidation of
phenylboronic acid and the hydrolysis of
diazonium salts.
21. Pyrolysis of sodium benzene sulfonate
v In this process, benzene sulfonic acid is
reacted with aqueous sodium hydroxide.
v The resulting salt is mixed with solid sodium
hydroxide and fused at a high temperature.
v The product of this reaction is sodium
phenoxide, which is acidified with aqueous
acid to yield phenol.
22. Dow process
In the Dow process, chlorobenzene is reacted
with dilute sodium hydroxide at 300°C and 3000
psi pressure.
The following figure illustrates the Dow process.
23. Air oxidation of cumene
v The air oxidation of cumene (isopropyl
benzene) leads to the production of both
phenol and acetone.
v The mechanisms for the formation and
degradation of cumene hydroperoxide
require closer looks, which are provided
following the figure.
24. Cumene hydroperoxide formation
q The formation of the hydroperoxide
proceeds by a free radical chain reaction.
q A radical initiator abstracts a hydrogen free
‐
radical from the molecule, creating a
tertiary free radical.
q The creation of the tertiary free radical is the
initial step in the reaction.
25. v In the next step, the free radical is attracted to
an oxygen molecule.
v This attraction produces the hydroperoxide free
radical.
v Finally, the hydroperoxide free radical abstracts a
hydrogen free radical from a second molecule of
cumene to form cumene hydroperoxide and a new
tertiary free radical.
26. Cumene hydroperoxide
degradation.
v The degradation of the cumene
hydroperoxide proceeds via a carbocation
mechanism.
v In the first step, a pair of electrons on the
oxygen of the hydroperoxide's “hydroxyl
group” is attracted to a proton of the
H 3O + molecule, forming an oxonium ion.
27. v Next, the oxonium ion becomes stabilized when the
positively charged oxygen leaves in a water
molecule.
v This loss of a water molecule produces a new
oxonium ion.
v A phenide ion shift to the oxygen atom (which creates a
tertiary carbocation) stabilizes the positively charged
oxygen.
v (A phenide ion is a phenyl group with an electron bonding
pair available to form a new bond to the ring.)
28. The carbocation is stabilized by an acid base
‐
reaction with a water molecule, leading to the
formation of an oxonium ion.
The loss of a proton stabilizes the oxonium ion.
Next, a proton is picked up by the ether oxygen in
an acid base reaction, yielding a new oxonium ion.
‐
29. v The positively charged ether oxygen pulls the electrons in the
oxygen carbon bond toward itself, thus delocalizing the
‐
charge over both of the atoms.
v The partial positive charge on the carbon attracts the
nonbonding electron pair from the oxygen of the OH group,
allowing the electrons in the original oxygen carbon bond to
‐
be released back to the more electronegative oxygen atom.
v Finally, a proton is lost from the protonated acetone
molecule, leading to the formation of acetone.