Organic Chemistry: Anthraquinone Glycosides

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Questions and Answers

What is the primary aim of the extraction process described?

  • To isolate the anthraquinone glycosides (correct)
  • To synthesize new anthraquinone compounds
  • To analyze the anthraquinone glycosides
  • To dissolve the anthraquinone glycosides

Which piece of equipment is necessary for decanting liquids during the extraction process?

  • Large beaker
  • Separatory funnel (correct)
  • Centrifuge
  • Water bath

Which of the following is NOT listed as part of the equipment needed for the extraction?

  • Centrifuge tubes
  • Filter paper
  • Vacuum pump (correct)
  • Conical flasks

In addition to centrifuge tubes, what other type of glassware is mentioned for use in the extraction process?

<p>Beakers (B)</p> Signup and view all the answers

What is the function of the water bath in the extraction setup?

<p>To heat samples at a controlled temperature (A)</p> Signup and view all the answers

What is the primary purpose of Borntrager's test?

<p>Identify the aglycone part of anthraquinone glycosides. (C)</p> Signup and view all the answers

Which of the following reagents is NOT used in Borntrager's test?

<p>Acetic acid (B)</p> Signup and view all the answers

In what type of container is the Borntrager's test generally conducted?

<p>Test tube (D)</p> Signup and view all the answers

Which apparatus is necessary for the separation of compounds during Borntrager's test?

<p>Separatory funnel (D)</p> Signup and view all the answers

What is the role of dilute HCl in Borntrager's test?

<p>To hydrolyze the glycosidic bond. (B)</p> Signup and view all the answers

What is the purpose of adding Ferric Chloride solution during the procedure?

<p>To form a complex with glycosides (D)</p> Signup and view all the answers

What is the total volume of the solution after adding 3.5 ml of Ferric Chloride and 2 ml of Conc. HCl to 10 ml of the aqueous layer?

<p>13 ml (B)</p> Signup and view all the answers

How long should the solution be refluxed according to the instructions?

<p>20 minutes (C)</p> Signup and view all the answers

What components are specifically listed to be added after reflux?

<p>3.5 ml of Ferric Chloride and 2 ml of Conc. HCl (B)</p> Signup and view all the answers

Which reagent is used at a 60% w/v concentration during the procedure?

<p>Ferric Chloride (A)</p> Signup and view all the answers

What is the purpose of using chloroform in the extraction process described?

<p>To separate the aglycone part (D)</p> Signup and view all the answers

How many times is chloroform used for the extraction in the procedure?

<p>Twice (C)</p> Signup and view all the answers

What component is specifically referred to as the 'Aqueous layer' in the procedure?

<p>Glycone part (C)</p> Signup and view all the answers

What is the designation given to the chloroform layer in the extraction process?

<p>Fraction C (B)</p> Signup and view all the answers

Which part of the mixture does the term 'Aglycone part' refer to?

<p>The layer obtained from chloroform extraction (A)</p> Signup and view all the answers

What type of action do anthraquinone glycosides primarily have on the digestive system?

<p>Increase muscle tone and stimulate secretion (D)</p> Signup and view all the answers

Which of the following best describes the mechanism of action of anthraquinone glycosides?

<p>They stimulate the secretion of water and electrolytes (C)</p> Signup and view all the answers

What kind of glycosides are anthraquinone glycosides classified as?

<p>Stimulant cathartics (A)</p> Signup and view all the answers

In what part of the digestive system do anthraquinone glycosides primarily exert their effects?

<p>Large intestine (D)</p> Signup and view all the answers

The laxative effect of anthraquinone glycosides is mainly due to which of the following actions?

<p>Increasing the tone of smooth muscle (D)</p> Signup and view all the answers

What type of glycosides elicit a more drastic reaction?

<p>Anthranol glycosides (A)</p> Signup and view all the answers

Which drug is NOT mentioned as commonly used in the content provided?

<p>Rhodiola (C)</p> Signup and view all the answers

What type of action do anthranol glycosides cause?

<p>Discomforting and gripping action (C)</p> Signup and view all the answers

Among the following, which is a characteristic of anthraquinone glycosides compared to anthranol glycosides?

<p>They elicit a less drastic reaction. (C)</p> Signup and view all the answers

Which of the following is true about anthranol and anthrone glycosides?

<p>They elicit a more drastic reaction than anthraquinone glycosides. (D)</p> Signup and view all the answers

Aloe and Rhubarb are not recommended due to their irritating actions which increase the chance for ______ effect.

<p>gripping</p> Signup and view all the answers

The anthraquinone hydrolyzed to give ______ which are di, tri, or tetra - hydroxyanthraquinone.

<p>aglycone</p> Signup and view all the answers

Hydrolyzed anthraquinones can produce ______ hydroxyanthraquinones.

<p>di</p> Signup and view all the answers

The irritating actions of Aloe and Rhubarb increase the chance for gripping ______.

<p>effect</p> Signup and view all the answers

Anthraquinone is hydrolyzed to give aglycone which are di, ______, or tetra - hydroxyanthraquinone.

<p>tri</p> Signup and view all the answers

Extract with [10 ml of ________] two times.

<p>Chloroform</p> Signup and view all the answers

The ________ layer corresponds to the Glycone part.

<p>Aqueous</p> Signup and view all the answers

The Chloroform layer is referred to as the ________ part (monoanthrone).

<p>Aglycone</p> Signup and view all the answers

The Aglycone part can also be known as ________ part during the extraction.

<p>Fraction C</p> Signup and view all the answers

Place in a ________ funnel for the extraction procedure.

<p>separatory</p> Signup and view all the answers

The main reagent used in the procedure is ______ acid.

<p>Conc.HCl</p> Signup and view all the answers

The method of extraction described in the procedure is called ______.

<p>Decoction</p> Signup and view all the answers

One of the reagents mentioned in the procedure is ______.

<p>Chloroform</p> Signup and view all the answers

The ______ chloride solution is used at a 60% w/v concentration.

<p>Ferric</p> Signup and view all the answers

To perform the extraction, materials are placed in a ______ bottle.

<p>reagent</p> Signup and view all the answers

Fraction A contains the whole ______.

<p>glycosides</p> Signup and view all the answers

Fraction B contains the ______.

<p>aglycone</p> Signup and view all the answers

Fraction C contains the aglycone part known as ______.

<p>monoanthrone</p> Signup and view all the answers

The ______ action of anthraquinone glycosides primarily affects the digestive system.

<p>laxative</p> Signup and view all the answers

Anthraquinone glycosides are classified as ______ glycosides.

<p>anthranol</p> Signup and view all the answers

Shake the upper benzene layer with dilute ______ (10%) to check the intensity of the color.

<p>ammonia</p> Signup and view all the answers

A ______ color will be produced, which is very clear with monoanthrones than dianthrones.

<p>pink</p> Signup and view all the answers

The upper benzene layer is also referred to as the free ______.

<p>aglycone</p> Signup and view all the answers

The intensity of the color is checked to determine the presence of ______ in the sample.

<p>monoanthrones</p> Signup and view all the answers

A clear pink color indicates a positive reaction primarily with ______.

<p>monoanthrones</p> Signup and view all the answers

The mobile phase consists of n-propanol, ethyl acetate, and ______ in a ratio of 60:30:30.

<p>water</p> Signup and view all the answers

The standard compound used in the separation process is ______.

<p>Sennoside</p> Signup and view all the answers

The spray reagent utilized in the procedure is ______ 5% w/v.

<p>Alcoholic KOH</p> Signup and view all the answers

The mechanism of separation in this process is known as ______.

<p>adsorption</p> Signup and view all the answers

The developing technique applied in this method is referred to as ______.

<p>ascending</p> Signup and view all the answers

Flashcards

Anthraquinone Glycosides

Stimulant laxatives that increase colon muscle tone and stimulate water/electrolyte secretion.

Stimulant laxative

A type of laxative that increases bowel movements by stimulating the colon.

Colon muscle tone

The degree of contraction in the muscles of the large intestine.

Water and electrolyte secretion

Release of water and salts into the large intestine.

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Cathartic

A substance to induce bowel movements.

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Extraction aim

Isolate anthraquinone glycosides.

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Large Beaker Use

A large container often used for initial mixing.

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Centrifuge use

Separates substances by spinning at high speed.

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Separatory funnel use

Separates immiscible liquids by using different densities.

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Water bath use

Maintains a constant steady temperature.

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Anthranol glycosides reaction

Anthranol glycosides cause a stronger reaction compared to anthraquinone glycosides.

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Anthraquinone glycosides reaction

Anthraquinone glycosides cause a milder reaction compared to anthranol glycosides.

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Drugs causing discomfort

Some drugs derived from anthranols and anthroneselicit discomfort and strong gripping sensations.

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Common Anthranol-based drugs

Cascara, Frangula, Hypericum, and Senna are commonly used anthranol-based drugs.

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Anthraquinone vs Anthranol glycosides

Anthranol glycosides have a more intense reaction than anthraquinone glycosides.

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Chloroform Extraction

A technique used to separate the aglycone part (monoanthrone) from the glycone part of an anthraquinone glycoside. Chloroform, an organic solvent, preferentially dissolves the aglycone, while the glycone remains in the aqueous layer.

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Aglycone Part

The non-sugar portion of an anthraquinone glycoside. It is often hydrophobic (water-repelling) and soluble in organic solvents like chloroform.

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Glycone Part

The sugar portion of an anthraquinone glycoside. It is hydrophilic (water-loving) and remains in the aqueous layer during chloroform extraction.

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Fraction C

The chloroform layer containing the aglycone part (monoanthrone) after extraction. This fraction is isolated and further analyzed for specific anthraquinone glycosides.

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Separatory Funnel

A laboratory tool used to separate immiscible liquids (liquids that don't mix) based on their density.

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Borntrager's Test

A chemical test used to identify the aglycone part of anthraquinone glycosides.

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Aglycone

The non-sugar part of a glycoside, specifically the anthraquinone molecule in this case.

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Dilute Ammonia (10%)

A weak solution of ammonia in water, commonly used in Borntrager's test as a reagent.

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Whole Glycosides Fraction A

A portion of the glycosides extracted from a plant, often containing a mixture of different glycosides.

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Reflux (20 min)

A process of heating a mixture with continuous condensation and return of the vapors to the reaction vessel. This technique allows for prolonged heating without loss of volatile reactants.

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Ferric Chloride Solution (60% w/v)

A concentrated solution of iron chloride in water. This solution is typically used as a reagent to detect the presence of certain compounds.

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Concentrated HCl Acid

A highly acidic solution of hydrogen chloride in water. This acid is used to adjust the pH of the reaction mixture.

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Why are these reagents added during reflux?

Ferric chloride and hydrochloric acid are added during reflux to promote a chemical reaction. This process is likely used to modify the glycosides or induce a specific transformation.

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What is decoction?

A method of extraction where plant material is boiled in water to extract soluble compounds.

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Why is chloroform used?

Chloroform is used to extract the non-sugar part (aglycone) of anthraquinone glycosides, which is soluble in organic solvents.

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What is the purpose of Borntrager's test?

Borntrager's test identifies the presence of the aglycone part of anthraquinone glycosides.

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What is the role of reflux?

Reflux allows prolonged heating without losing volatile reactants by continuously condensing and returning vapors to the reaction vessel.

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What is Borntrager's Test used for?

Borntrager's Test is used to identify the presence of aglycones in a sample.

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Hydrolyzed Anthraquinone

When an anthraquinone glycoside is broken down, it releases the 'active' part, the aglycone.

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Why are Aloe and Rhubarb not recommended?

Because they can irritate the colon and cause strong gripping sensations due to their anthraquinone content.

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Monoanthrones vs. Dianthrones

Monoanthrones produce a clearer pink color in the Borntrager's test compared to dianthrones, indicating their presence or absence.

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Aglycone Fraction

The non-sugar portion (anthraquinone molecule) of anthraquinone glycosides obtained after chloroform extraction.

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What does the intensity of the pink color indicate?

The intensity of the pink color produced in Borntrager's test indicates the relative abundance of monoanthrones compared to dianthrones. A stronger pink color suggests a higher concentration of monoanthrones.

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Mobile Phase

The solvent mixture used in chromatography, moving the compounds through the stationary phase. It's a combination of n-propanol, ethyl acetate, and water (60:30:30) in this case.

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Standard Compound

A known substance used for reference during analysis, helping to identify and quantify the target compound (sennoside in this case).

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Spray Reagent

A chemical solution used to visualize the separated compounds on the chromatography plate. It's Alcoholic KOH 5%w/v in this case.

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Mechanism of Separation

The process by which compounds are separated based on their different affinities to the stationary phase. Here, it's 'adsorption' - compounds stick to the stationary phase differently.

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Developing (Ascending)

The process where the mobile phase carrying the compounds moves upwards on the stationary phase, leading to separation based on their interactions.

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Study Notes

Anthraquinone Glycosides

  • Anthraquinone glycosides are stimulant cathartics

  • Increase colon smooth muscle tone and stimulate water/electrolyte secretion

  • Hydrolyzed in the colon to pharmacologically active aglycones (8-12 hours after ingestion)

  • Used to treat constipation where milder drugs are ineffective

  • Used before procedures requiring bowel evacuation

  • Habit forming, long-term use can lead to dependence and loss of normal bowel function

  • Anthranols/anthrones cause a more drastic reaction than corresponding anthraquinones (discomforting, gripping action)

  • Common glycosides include cascara, frangula, hypericum, and senna

  • Aloe and rhubarb are less desirable due to irritating actions increasing the risk of gripping

  • Hydrolysis converts anthraquinones into aglycones (tri-, tetra-hydroxyanthraquinone, anthrones, dianthrones, oxanthrones)

Isolation and Identification

  • Aim: Isolate anthraquinone glycosides
  • Equipment: Large beakers, conical flasks, centrifuge, centrifuge tubes, separatory funnel, water bath, round bottom flask, filter paper, bottle
  • Reagents: Concentrated hydrochloric acid, chloroform, 60% ferric chloride solution
  • Method of extraction: Decoction
  • Plant used: Senna (C.acutifolia, C.angustifolia), family Leguminosae
  • Procedure details involve placing Senna leaves in water, boiling, cooling, filtering, separating the filtrate with chloroform (multiple shakes)

Chemical tests

  • General Reaction: Boil crude drug (e.g., Aloe) with water, add kieselguhr, filter, then react with solutions for tests.
  • Schoneten's Reaction (Borax test): To identify anthraquinone glycosides in general. Use borax and heat then add solution to test tube containing water. Results in green fluorescence, due to aloe-emodinanthranols released from barbaloin
  • Bromine Test: To identify Aloin. Add an equal volume of bromine solution. Results in a color change.
  • Borntrager test: Identify aglycones of anthraquinones, use separatory funnel, test tube, dilute HCl, and benzene.

Chromatography

  • Thin Layer Chromatography (TLC): Used to identify anthraquinone glycosides. Stationary phase is silica gel G, while mobile phase uses n-propanol, ethyl acetate, water (60:30:30). A spray reagent (alcoholic KOH) is used for visualizing spots (intensify by spray with nitric acid and heating.)

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