Lecture No.2 Aldehyde, Ketone, and carboxylic acids - PowerPoint Presentation

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Lecture No.2

Aldehyde, Ketone, and carboxylic acids

Lecture No.2

Aldehyde, Ketone, and carboxylic acids

List of contents:Aldehyde, Ketone, and carboxylic acids.The carbonyl group.

Carbonyl Compounds. Aldehydes and Ketones.Biological Significance of Ketone Bodies.The presence of Aldehyde, Ketone, and carboxylic acids.Symptoms of diabetes.Types of Diabetes mellites.Ketogenesis.The function of ketone bodies.Glycogenolysis.

Gluconeogenesis.

Carboxylic acid.

Carboxylic acid in nature.

The pH of carboxylic acid solutions.What makes a carboxylic acid more acidic?Metabolic Acidosis.The Effect Of Metabolic Acidosis.

The Aim of Lecture:

To Know Aldehyde, Ketone, and carboxylic acids structures

as a type of

organic

Compounds, & their presence.

To Know the

carbonyl group and carbonyl

Compounds. To Know the Biological Significance of Ketone Bodies.To Know the Symptoms of DM, types of Diabetes mellites, & Ketogenesis.To Know the Glycogenolysis, & Gluconeogenesis.To Know the Effect Of Metabolic Acidosis

Aldehyde, Ketone, and carboxylic acids.Functional Groups Reactivity

Functional groups play a significant role in increasing organic compound reactivity, by controlling the direction of reactions; Alkyl chains (R₃ C - C R₃) are nonreactive, but when substituted gives unsaturated alkyl chains (R₂C=CR₂), the presence of functional group (> C = C <) allow for relative increase in both reactivity and specificity.The carbonyl group:

A

group

of organic molecules contains a carbon atom connected to an oxygen atom by a double bond,

This group is called a carbonyl group, and it has very different chemical properties than a double bond (> C = C <) in alkenes, because oxygen is more electronegative than carbon, and the bond is polar.

The local geometry around the carbonyl group is trigonal planar. The rest of the molecule doesn’t have to be planar. Figure (1). The trigonal planar carbon in the carbonyl group can attach to two other substituents leading to several subfamilies (aldehydes, ketones, carboxylic acids and esters).

Figure (1):

Carbonyl group, trigonal planar carbon in the carbonyl group can attach to two other substituents.

Carbonyl Compounds

Carbonyl Compounds are consist of carbon- oxygen double bounded (>C=O). Its polar or water soluble due to ability to form Hydrogen bonding, respectively as in, figure(2) bellow. Aldehyde, Ketone, and carboxylic acids are all containing of carbonyl group, so they called Carbonyl Compounds. Figure(2).

Figure(2): Carbonyl group.

The carbonyl group in Aldehydes and ketones are among the first examples of a class of compounds that possess (C = O )double bond that seen by oxidation of alcohols, primary alcohol oxidized to aldehyde, and

Carboxylic acid and its derivatives

, while secondary alcohol oxidized into ketone. Figure(3).

Figure(3): Aldehydes, ketones and

Carboxylic acid

are among the first examples a class of compounds that possess a (C = O )double bond, that seen by alcohols oxidation.

Aldehydes and KetonesBoth aldehydes and ketones contain a carbonyl group, a functional group with a carbon-oxygen double bond.The names for aldehyde and ketone compounds are derived using similar nomenclature rules as for alkanes and alcohols, and include the class-identifying suffixes 

-al and 

-one

, respectively. In an aldehyde, the carbonyl group is bonded to at least one hydrogen atom. In a ketone, the carbonyl group is bonded to two carbon atoms. An aldehyde group is represented as –CHO; a ketone is represented as

(>C=O)

or –CO–.

Figure(4) Figure(4): Aldehydes and Ketones. Aldehyde. Ketone.Biological Significance of Ketone Bodies: Aldehydes, and ketones are critical in human body, they present in organic compound as carbohydrates, fats, proteins, nucleic acids, hormones, vitamins in human body, and Drugs. One of the most important ketone is acetone (CH3)

2

C = O. Acetone is the most important ketone to health, and present in less than 1 mg/100 mL of blood. An excess of acetone in the bloodstream is a common symptom of diabetes mellites. Insulin is a hormone that allows glucose to enter cells from the bloodstream to reduce glucose level in circulation of blood. Diabetes mellites DM is a common disease present in two types Fig.5. The first is type one diabetes caused by inherditary disorder, while type two diabetes appear in older ages due to Insulin hormone resistance or defect in Insulin hormone production. Diabetic patient is a person with deficient in insulin, due to either lacking insulin or are resistant to insulin. Because there is no or low insulin hormone activity in the body, a diabetic is forced lipids to break down into fatty acids, and proteins for energy, which produces a large quantity of ketone bodies. This can be prevented by monitoring insulin levels within the body. However, if a diabetic's body is subjected to stress, such as an illness, disruption to insulin treatment, or surgery, a condition called diabetic ketoacidosis (DKA) can occur.

Symptoms of diabetes:

The main symptoms of Diabetes mellites are the followings:Always thirsty.Always tired. Always hungry.

Blurry vision.

Systemic weight loss.

Frequent urination.

Wounds that will not heal.

Types of Diabetes mellites:

There are two types of elevation or depressed blood sugar level these conditions are Hypoglycemia (low blood sugar) and hyperglycemia (high blood sugar) each have different warning signs and symptoms, but can lead to the same result—diabetic coma. “Warning signs are in danger because the blood sugar is dropping or is too low causing coma, some times this disease called the silent diabetes symptoms some one might miss(1). figure(5).

Fig.5: Type 1 and 2 in older ages diabettic patients

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Type 1 DM

Type 2 DM

When a diabetic's body is in a stressful situation, it produces hormones such as adrenaline, which increase the rate of converting fatty acids to energy. This causes ketone bodies to

accumulate. When so much acetone builds up in the blood, the body attempts to eliminate it all by causing excessive urination. Symptoms of diabetic ketoacidosis (DKA ) include:- Dehydration

- Deficiencies in salts such as potassium.

- Nausea

- Fatigue

- Confusion

- Abdominal cramping

- Excessive thirst- Decreased perspiration. DKA can be treated through undergoing insulin therapy, replenishing the body with the fluids and electrolytes, and diminishing stress. The most common way to test for an excess of ketones in the bloodstream is a urine test, also blood Glucose test will be more accurate . Although it is dependable way of determining ketone buildup, also ketone breathe excess is often associated with fruity smelling breath in diabetic patient. Figure (6).

(A) (B) (C) (D) Figure (6): A- Plasma concentration of Glucose, and Ketone Bodies at starvation. B-C :The Acetone-Urine test is a simple urine test to detect the level of acetones in the body. When the acetones in the blood go above a certain level. D- Estimation of blood Glucose concentration.Reference http://gooddayshealthcare.in/product/acetone-urin[Reference:

https://chem.libretexts.org/ and 5.3 Functions and Applications of Aldehydes and Ketones Difficulty Level: Basic | Created by: CK-12]https://www.google.com/url?sa=i&url=https%3A%2F%2Fwww.insider.com%2Fnormal-blood-sugar-levels&psig=AOvVaw0Eb-boIy8lq3uTTcEUI wQ&ust=1602575914116000&source=images&cd=vfe&ved=0CA0QjhxqFwoTCIDMht_KruwCFQAAAAAdAAAAABAhttps://www.google.com/url?sa=i&url=https%3A%2F%2Fblog.pregistry.com%2Fpositive-pregnancy-glucose%2F&psig=AOvVaw1Av_Qnxw_uHufzBPFdu8Uo&ust=1602575810820000&source=

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The presence of Aldehyde, Ketone, and carboxylic acids:

Aldehyde, Ketone, and carboxylic acids are present in different compounds of human body, here is some of them:-

①-Monosaccharide's: Monosaccharide's are carbohydrates which can not be hydrolyzed to small molecules, contain carbons with functional aldehyde, or keto group are present in nature. Aldohexose is glucose, Fructose is ketohexose respectively. Glucose is present in our blood, and gives rise to energy on oxidation.

②- Aldopentose Ribose is constituent of nucleic acids monomer or nucleotides of DNA & RNA shown in Figure ( 7).

Figure (7 ):

Nucleotid

of DNA & RNA containing Aldopentose Ribose. And its chemical structure://www.google.com/url?sa=i&url=http%3A%2F%2Fwww.phschool.com%2Fscience%2Fbiology_place%2Fbiocoach%2Fbioprop%2Fribose.html&psig=AOvVaw3cyk7mAoxGmOy6rNng8Mxv&ust=1602579481195000&source=images&cd=vfe&ved=0CA0QjhxqFwoTCOjM2v7XruwCFQAAAAAdAAAAABA

The presence of Aldehyde, Ketone, and carboxylic acids:

③ -Ketone Bodies: Ketone Bodies are: Acetoacetate, Beta-hydroxy butyrate,& Acetone. Ketone Bodies are water soluble fuels normally exported by the liver, but overproduction during fasting or diabetes mellitus DM

Figure (6): A , this figure show the level of Glucose, Fatty Acids, Ketone bodies in millimole / Liter of plasma are depressed through starvation. Glucose in millimole / Liter of plasma first 5.5 but after 7 days become 3.5 millimole / Liter & Fatty Acids 0.3 to be 1.19 millimole / Liter, and Ketone Bodies are formed

in times of fasting, even overnight while sleeping, the amount of ketone bodies in the blood increases.

Ketone Bodies are converted in the hepatic mitochondria to be used as fuel for human activities

Figure (8 ):

Figure (8 ): Ketone Bodies

structures.https://www.google.com/url?sa=i&url=https%3A%2F%2Fwww.nutritionadvance.com%2F ketogenesis-benefits-ketone bodies%2F&psig=AOvVaw3an2KBz5szdzbzBHoJLCAJ&ust=1602580185358000&source= images&cd=vfe&ved=0CAMQjB1qFwoTCPCUyM7aruwCFQAAAAAdAAAAABADKetogenesisKetogenesis is a metabolic pathway occurs primarily in the mitochondria of liver cells that produces ketone bodies,

which provide an alternative form of energy for the body. The body is constantly producing small amounts of ketone bodies that can make 22 ATP (Adenosine Tri Phosphate) each in normal circumstances, and it is regulated mainly by insulin. In a state of ketosis, ketone body production is increased when there are decreased carbohydrates or increased fatty acids. However, ketoacidosis can occur if too many ketone bodies accumulate, such as in cases of uncontrolled diabetes.2,3,4

The function of ketone bodies:GlycogenolysisIn healthy humans, the body is continually making a small amount of ketones to be used by the body for energy. But in case of fasting, even overnight while sleeping, the amount of ketone bodies in the blood increases by Ketogenesis

process.The normal pathways to create energy involve either stored carbohydrate or non-carbohydrate substances( Fatty acids or Proteins). When carbohydrate stores are available, the main pathway used is glycogenolysis. This involves the breakdown of glycogen stores in muscle and liver. Gluconeogenesis Gluconeogenesis, the production of glucose from non-carbohydrate sources such as lactate, is often utilized as well, especially in situations involving exercise. When carbohydrate stores are significantly decreased, or fatty acid concentration is increased, or

Diabetes mellites,

the ketogenesis metabolic pathway, and production of ketone bodies are increased. This can be seen in conditions such as type 1 diabetes, alcoholism, and starvation. Most organs and tissues can use ketone bodies as an alternative source of energy. The brain uses them as a major source of energy during periods where glucose is not readily available. This is because, unlike other organs in the body, the brain has an absolute minimum requirement of glucose. The heart typically uses fatty acids as its source of energy, but also can use ketones. The liver, although the primary site that produces ketone bodies, does not use ketone bodies because it lacks the necessary enzyme beta ketoacyl-CoA transferase.

2

Carboxylic acid.

Carboxylic acid is a class of organic carbonyl compounds have a carbonyl group( >C=O ), attached to a hydroxyl group ( -OH ) to generate a carboxyl group(

-COOH ). The carboxyl group consisting of a carbonyl (C=O) with a hydroxyl group (O–H) attached to the same carbon atom and is usually written as –COOH or CO2H. 

Carboxylic acids in nature:

Carboxylic acids are compounds occurring naturally in different stages of life cycles (living organism-Krebs cycle; fermentation processes, and geological processes) or can be produced in the laboratories or at large scale (synthesis) from oxidation reactions of aldehydes , and primary alcohols. The organic acids play significant roles in our society as evidenced by multiple applications in the field of medicine, agriculture, pharmaceuticals, food, and other industries. Carboxylic acids are used in the production of pharmaceutical drugs, also can be used as solvents, food additives, antimicrobials. The pH of carboxylic acid solutions

Organic acids are well-known as effective preservatives, and their antimicrobial action is due to the ability to change from undissociated to dissociated form, depending on the environmental pH, making them effective antimicrobial agents. An example, some organic salts (calcium and sodium propionate) prevent spoilage by inhibiting the growth of bacteria and fungi.

3

Carboxylic acid is a weak acid. For example Acetic acid meaning Vinegar, the other example in human body is a fatty acid. Using the definition of an acid as a "substance which donates protons (hydrogen ions) to other things", the carboxylic acids are acidic because of the hydrogen in the -COOH group. In solution of water, a hydrogen ion is transferred from the ( -COOH ) group to a water molecule, you get an acetate ion formed together with a hydroxonium ion, H

3

O

+, by the following equation: CH₃COOH + H₂O ↔ CH₃COO¯ + H3O+. Acetic acid. Acetate ion Hydroxonium ion.

What makes a carboxylic acid more acidic? Acidity of carboxylic acid is higher than alcohols. Carboxylate ion, is the conjugate base of carboxylic acid, also stabilized by two equivalent resonance structures in which the negative charge is effectively delocalized between two or more electronegative oxygen atoms. Figure (9 )

Fig.9: Carboxylic acid resonance structures showing increasing acidity, where R = CH₃.Metabolic AcidosisThe pH of blood is usually between 7.35 and 7.45. A pH of less than 7.0 is called acid and a pH greater than 7.0 is called basic (alkaline). So blood is slightly basic. At low pH the Arterial pH cause. Metabolic Acidosis, which refer to increase acid generation.

The Effect Of

Metabolic Acidosis:

1-

Ketoacidosis.2- Alcoholism.3- Renal tubular acidosis.

4- Ingestion Salicylates.1- Ketoacidosis, when you have diabetes and don't get enough insulin,& get dehydrated, body burns fat (leaving carbohydrates) as fuel, and that makes ketones accumulation in blood, so turn it acidic.

The Effect Of Metabolic Acidosis:

1- Ketoacidosis

, when some one have diabetes and don't get enough insulin,& get dehydrated, body burns fat (leaving carbohydrates) as fuel, and that makes ketones accumulation in blood, so turn it acidic.

2-

Alcoholism

, People who drink a lot of alcohol for a long time and don't eat enough also build up ketones.

3- Renal tubular acidosis. For healthy Kidneys, Kidney take acids out of blood and get rid of them in pee. Kidney diseases as well as some immune system and genetic disorders can damage kidney so they leave too much acid in blood.4- Ingestion Salicylates. is a medical emergency. Intentional ingestion or accidental overdose can cause Salicylate poisoning causes a variety of metabolic disorders making treatment difficult. In 2011 there were 30,000 cases of salicylate toxicity in the United States with 39 deaths. Affecting the oxidative phosphorylation in the mitochondria so the Lactate levels then increase due to the increase in anaerobic metabolism cause increase production of lactic acid along result in metabolic acidosis. Hyperventilation worsens in an attempt to compensate for the metabolic acidosis. Eventually, the patient fatigues, and metabolic acidosis become a powerful influence. This results in hemodynamic instability and end-organ damage

8

,9The clinical Features: The clinical Features evolved rapidly over 24 hours and early signs:

Cause nausea.-Vomiting. -Abdominal pain.The Carboxylic Acid Derivatives:

The group (RC=O) is called the acyl group, which is a part of the functional group of the carboxylic acid derivatives, these derivatives include, esters, and amides. Figure (10).

The Carboxylic Acid Derivatives

Carboxylic Acid Derivatives

Esters

amides

Examples in living systems

Acetyl coenzyme A

Paracetamol, Penicillin.

Figure (10: The Carboxylic Acid Derivatives.

Reference:1- ” says Gillian Goddard, MD, board certified in internal medicine and endocrinology, diabetes and metabolism, from Park Avenue Endocrinology & Nutrition. Learn about 

silent diabetes symptoms you might miss. On the other hand, you could notice high blood sugar leaving you fatigued, according to the Mayo Clinic.2.Green A, Bishop RE. Ketoacidosis - Where Do the Protons Come From? Trends Biochem

. Sci. 2019 Jun;44(6):484-489. [PubMed]

3.d'Avignon DA,

Puchalska

P, Ercal B, Chang Y, Martin SE, Graham MJ, Patti GJ, Han X, Crawford PA. Hepatic ketogenic insufficiency reprograms hepatic glycogen metabolism and the lipidome. JCI Insight. 2018 Jun 21;3(12) [PMC free article] [PubMed]4.Adeva-Andany MM,

Funcasta

-Calderón R, Fernández-Fernández C, Castro-Quintela E, Carneiro-Freire N. Metabolic effects of glucagon in humans. J Clin Transl Endocrinol. 2019 Mar;15:45-53. [PMC free article] [PubMed]2-Kiranjit K. Dhillon; Sonu Gupta.Author InformationLast Update: April 6, 2020.5-Biochemistry, Ketogenesis Kiranjit K. Dhillon; Sonu Gupta.Author

Information

Last Update: April 6, 2020.Introduction6- Introductory Chapter: Carboxylic Acids - Key Role in Life SciencesBy Georgiana Ileana Badea and Gabriel Lucian RaduSubmitted: March 12th 2018Reviewed: April 5th 2018Published: June 13th 2018DOI: 10.5772/intechopen.770217-Arterial Blood Gases | Michigan Medicinewww.uofmhealth.org › health-library

8- Patel SR. Toxicologic emergencies in the intensive care unit: management using reversal agents and antidotes. Crit Care Nurs Q. 2013 Oct-Dec;36(4):335-44. [PubMed]9- Salicylates Toxicity Tyler J. Runde; Thomas M. Nappe.

Author InformationLast

Update: July 13, 2020.

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