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

    What is the primary purpose of Borntrager's test?

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

    What kind of glycosides are anthraquinone glycosides classified as?

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

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

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

    What type of glycosides elicit a more drastic reaction?

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

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

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

    What type of action do anthranol glycosides cause?

    <p>Discomforting and gripping action</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.</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.</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

    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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    Lab Anthraquinones PDF

    Description

    This quiz focuses on the properties and uses of anthraquinone glycosides, including their role as stimulant cathartics and their effects on bowel function. It also discusses the hydrolysis process that converts anthraquinones into active aglycones and the various types of glycosides. Test your knowledge on isolation and identification techniques in organic chemistry.

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