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Anthraquinones Wiki2Web Clarity Challenge

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Study Guide: Anthraquinones: Chemistry, Applications, and Biological Significance

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Anthraquinones: Chemistry, Applications, and Biological Significance Study Guide

Fundamental Chemistry and History of Anthraquinones

Anthraquinones are a class of naturally occurring phenolic compounds based on the 9,10-anthraquinone skeleton, utilized in industrial applications.

Answer: True

Explanation: The definition provided states that anthraquinones are phenolic compounds based on the 9,10-anthraquinone skeleton, with both natural occurrence and industrial applications.

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The German chemists Carl Graebe and Carl Theodore Liebermann first used the name 'anthraquinone' in 1868 during their description of alizarin synthesis.

Answer: True

Explanation: Carl Graebe and Carl Theodore Liebermann are credited with first using the name 'anthraquinone' in 1868, specifically in the context of their work on alizarin synthesis from anthracene.

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The parent molecule for all anthraquinones is 2-Ethyl-9,10-anthraquinone.

Answer: False

Explanation: The parent molecule for anthraquinones is 9,10-anthraquinone, not 2-Ethyl-9,10-anthraquinone, which is a specific derivative used in industrial processes.

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The discovery of alizarin synthesis from anthracene by Graebe and Liebermann led to its industrial production and further research into anthraquinone chemistry.

Answer: True

Explanation: The synthesis of alizarin from anthracene by Graebe and Liebermann was a pivotal discovery that indeed spurred industrial production and advanced research in anthraquinone chemistry.

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According to the provided definition, what is the fundamental structural basis for anthraquinones?

Answer: The 9,10-anthraquinone skeleton

Explanation: The definition explicitly states that anthraquinones are based on the 9,10-anthraquinone skeleton.

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Who were the German chemists credited with first using the name 'anthraquinone' in 1868?

Answer: Carl Graebe and Carl Theodore Liebermann

Explanation: Carl Graebe and Carl Theodore Liebermann are identified as the German chemists who first used the name 'anthraquinone' in 1868.

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What significant discovery by Graebe and Liebermann led to the industrial production of alizarin and further research into anthraquinone chemistry?

Answer: The chemical synthesis of the red dye alizarin from anthracene

Explanation: The chemical synthesis of alizarin from anthracene by Graebe and Liebermann was the pivotal discovery that led to its industrial production and advanced anthraquinone research.

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Which of the following is the parent molecule for anthraquinones?

Answer: 9,10-anthraquinone

Explanation: The parent molecule for anthraquinones, forming their fundamental skeleton, is 9,10-anthraquinone.

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Natural Occurrence and Biosynthesis

Natural pigments derived from anthraquinone are exclusively found in fungi and lichens.

Answer: False

Explanation: Natural pigments derived from anthraquinone are found in a wide array of sources, including aloe latex, senna, rhubarb, cascara buckthorn, fungi, lichens, and certain insects, not exclusively fungi and lichens.

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The yellow color in lichens of the Teloschistaceae family is due to the presence of anthraquinones.

Answer: True

Explanation: Anthraquinones are indeed responsible for the yellow coloration observed in lichens belonging to the Teloschistaceae family.

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Anthraquinone biosynthesis in the bacterium *Photorhabdus luminescens* is carried out by a type I polyketide synthase.

Answer: False

Explanation: Anthraquinone biosynthesis in *Photorhabdus luminescens* is catalyzed by a type II polyketide synthase, not a type I.

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Chorismate serves as a precursor for anthraquinones in the plant *Morinda citrifolia*.

Answer: True

Explanation: Chorismate, formed via the shikimate pathway, is identified as a precursor for anthraquinones in *Morinda citrifolia*.

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Carmine is a blue pigment derived from plants, classified as an anthraquinone derivative.

Answer: False

Explanation: Carmine is a bright-red pigment derived from insects, not plants, and is an anthraquinone derivative, but not blue.

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Tests for anthraquinones in natural extracts have not yet been fully developed.

Answer: False

Explanation: Established analytical methods for detecting and quantifying anthraquinones in natural extracts have been developed.

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Senna glycosides are anthraquinone derivatives found in the *Frangula alnus* plant.

Answer: False

Explanation: Senna glycosides are derived from the senna plant, while frangulin is found in *Frangula alnus*.

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Natural pigments derived from anthraquinone are found in all of the following sources EXCEPT:

Answer: Petroleum crude oil

Explanation: The provided sources for natural anthraquinone pigments include aloe latex, senna, rhubarb, fungi, lichens, and insects, but not petroleum crude oil.

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What causes the yellow color in certain lichens, particularly in the Teloschistaceae family?

Answer: Anthraquinones

Explanation: The yellow color in lichens of the Teloschistaceae family is specifically attributed to the presence of anthraquinones.

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Which type of enzyme is responsible for anthraquinone biosynthesis in the bacterium *Photorhabdus luminescens*?

Answer: A type II polyketide synthase

Explanation: Anthraquinone biosynthesis in *Photorhabdus luminescens* is carried out by a type II polyketide synthase.

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What compound serves as a precursor for anthraquinones in the plant *Morinda citrifolia*?

Answer: Chorismate

Explanation: Chorismate is identified as the precursor for anthraquinones in the plant *Morinda citrifolia*.

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Which of the following is a bright-red pigment derived from insects and classified as an anthraquinone derivative?

Answer: Carmine

Explanation: Carmine is described as a bright-red pigment derived from insects and classified as an anthraquinone derivative.

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Which plant is the source of frangulin, an anthraquinone derivative?

Answer: *Frangula alnus*

Explanation: Frangulin is specifically mentioned as being found in the plant *Frangula alnus*.

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Industrial Applications

A major industrial application of anthraquinones is their use in the production of sulfuric acid.

Answer: False

Explanation: A major industrial application of anthraquinones is in the production of hydrogen peroxide, not sulfuric acid.

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The anthraquinone process is responsible for manufacturing millions of tons of hydrogen peroxide annually.

Answer: True

Explanation: The anthraquinone process is a large-scale industrial method, producing millions of tons of hydrogen peroxide each year.

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Sodium 2-anthraquinonesulfonate (AMS) was the first water-soluble anthraquinone derivative found to have a catalytic effect in alkaline pulping processes.

Answer: True

Explanation: Sodium 2-anthraquinonesulfonate (AMS) is recognized as the first water-soluble anthraquinone derivative to demonstrate catalytic activity in alkaline pulping processes.

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The 9,10-anthraquinone skeleton is a fundamental structural component found in many dyes, such as alizarin.

Answer: True

Explanation: The 9,10-anthraquinone skeleton is indeed a fundamental structural component in many dyes, including alizarin, contributing to their color properties.

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1-nitroanthraquinone and anthraquinone-1-sulfonic acid are examples of anthraquinone derivatives used as dyestuff precursors.

Answer: True

Explanation: 1-nitroanthraquinone and anthraquinone-1-sulfonic acid are explicitly mentioned as important derivatives of 9,10-anthraquinone that serve as dyestuff precursors.

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Soluble anthraquinones are used as reactants in redox flow batteries for electrical energy storage.

Answer: True

Explanation: Soluble anthraquinones, such as 9,10-anthraquinone-2,7-disulfonic acid, are indeed utilized as reactants in redox flow batteries for electrical energy storage.

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The industrial production of hydrogen peroxide primarily uses the parent 9,10-anthraquinone molecule.

Answer: False

Explanation: The industrial production of hydrogen peroxide primarily uses 2-Ethyl-9,10-anthraquinone or a related alkyl derivative, not the parent 9,10-anthraquinone molecule itself.

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C.I. Acid Blue 43 is an example of an anthraquinone dye used for cotton.

Answer: False

Explanation: C.I. Acid Blue 43 is an acid dye specifically used for wool, not cotton.

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What is a significant industrial application of anthraquinones related to hydrogen peroxide?

Answer: Their use in the production of hydrogen peroxide

Explanation: A significant industrial application of anthraquinones is their direct involvement in the production of hydrogen peroxide.

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Which specific anthraquinone derivative is typically used in the industrial production of hydrogen peroxide?

Answer: 2-Ethyl-9,10-anthraquinone or a related alkyl derivative

Explanation: The industrial production of hydrogen peroxide typically employs 2-Ethyl-9,10-anthraquinone or a related alkyl derivative, not the parent molecule or other derivatives.

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What is the name of the process that uses anthraquinones for the large-scale manufacturing of hydrogen peroxide?

Answer: The anthraquinone process

Explanation: The large-scale manufacturing of hydrogen peroxide using anthraquinones is known as the anthraquinone process.

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What is the approximate scale of hydrogen peroxide production using the anthraquinone process annually?

Answer: Millions of tons

Explanation: The anthraquinone process is responsible for producing millions of tons of hydrogen peroxide annually.

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Which anthraquinone derivative was the first water-soluble one found to have a catalytic effect in alkaline pulping processes?

Answer: Sodium 2-anthraquinonesulfonate (AMS)

Explanation: Sodium 2-anthraquinonesulfonate (AMS) was the first water-soluble anthraquinone derivative identified for its catalytic effect in alkaline pulping processes.

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The 9,10-anthraquinone skeleton is a fundamental structural component in many dyes, contributing to their:

Answer: Color properties

Explanation: The 9,10-anthraquinone skeleton is a fundamental structural component in many dyes, contributing directly to their color properties.

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Which of the following is NOT mentioned as an important derivative of 9,10-anthraquinone that serves as a dyestuff precursor?

Answer: 2-Ethyl-9,10-anthraquinone

Explanation: 1-nitroanthraquinone, anthraquinone-1-sulfonic acid, and dinitroanthraquinone are listed as dyestuff precursors. 2-Ethyl-9,10-anthraquinone is used in hydrogen peroxide production, not as a dyestuff precursor.

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How are soluble anthraquinones utilized in redox flow batteries?

Answer: As reactants for electrical energy storage

Explanation: Soluble anthraquinones are utilized as reactants in redox flow batteries for the purpose of electrical energy storage.

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What does the image titled 'Catalytic cycle for the anthraquinone process to produce hydrogen peroxide' depict?

Answer: The chemical method for industrial hydrogen peroxide production

Explanation: The image titled 'Catalytic cycle for the anthraquinone process to produce hydrogen peroxide' illustrates the chemical method used for the industrial production of hydrogen peroxide.

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What does C.I. Acid Blue 43 represent in the context of anthraquinone dyes?

Answer: An acid dye for wool

Explanation: C.I. Acid Blue 43 is identified as an acid dye used for wool within the selection of anthraquinone dyes.

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Medical and Toxicological Aspects

Anthracycline chemotherapy drugs are primarily derived from plant extracts.

Answer: False

Explanation: Anthracycline chemotherapy drugs are derived from the bacterium *Streptomyces peucetius*, not primarily from plant extracts.

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Daunorubicin, doxorubicin, and mitoxantrone are all examples of anthraquinone family drugs used in chemotherapy.

Answer: True

Explanation: Daunorubicin, doxorubicin, and mitoxantrone are indeed listed as drugs within the anthraquinone family that are employed in chemotherapy.

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Pixantrone is unique among anthracycline chemotherapy drugs for its severe cardiotoxic effects.

Answer: False

Explanation: Pixantrone is unique because it *does not* cause the severe cardiotoxic effects common to most other anthracycline chemotherapy drugs.

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Anthracenediones are exclusively used as chemotherapy drugs.

Answer: False

Explanation: Beyond chemotherapy, anthracenediones also include antimalarials and DNA dyes, indicating they are not exclusively used as chemotherapy drugs.

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Rhein, emodin, and aloe emodin are toxic anthraquinone derivatives extracted from *Cassia occidentalis*.

Answer: True

Explanation: Rhein, emodin, and aloe emodin are explicitly identified as toxic anthraquinone derivatives extracted from *Cassia occidentalis*.

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Toxic anthraquinone derivatives from *Cassia occidentalis* are known to cause a severe condition affecting the liver, muscles, and brain in adults.

Answer: False

Explanation: The severe condition, hepatomyoencephalopathy, caused by toxic anthraquinone derivatives from *Cassia occidentalis*, is known to affect children, not adults.

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Dantron, emodin, and some senna glycosides are anthraquinone derivatives known for their laxative effects.

Answer: True

Explanation: Dantron, emodin, and certain senna glycosides are indeed recognized anthraquinone derivatives with known laxative properties.

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Prolonged use of laxative anthraquinone derivatives can lead to melanosis coli, a condition of dark pigmentation in the stomach lining.

Answer: False

Explanation: Prolonged use of laxative anthraquinone derivatives can lead to melanosis coli, which is characterized by dark pigmentation of the *colon lining*, not the stomach lining.

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The bacterium *Streptomyces peucetius* is the natural source for anthracycline chemotherapy drugs.

Answer: True

Explanation: The bacterium *Streptomyces peucetius* is indeed identified as the natural source from which anthracycline chemotherapy drugs are derived.

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The images 'Aloe emodin', 'Daunorubicin', 'Mitoxantrone', and 'Pixantrone' represent various types of industrial solvents.

Answer: False

Explanation: The images represent chemical structures of anthraquinone derivatives, including chemotherapy drugs, not industrial solvents.

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From which natural source are anthracycline chemotherapy drugs derived?

Answer: The bacterium *Streptomyces peucetius*

Explanation: Anthracycline chemotherapy drugs are derived from the bacterium *Streptomyces peucetius*.

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Which of the following drugs belongs to the anthraquinone family and is used for chemotherapy?

Answer: Daunorubicin

Explanation: Daunorubicin is explicitly listed as an anthraquinone-family drug used in chemotherapy.

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What is a significant and common side effect of most anthracycline chemotherapy drugs, with the exception of pixantrone?

Answer: Irreversible cardiomyopathy

Explanation: Most anthracycline chemotherapy drugs, excluding pixantrone, are known to cause irreversible cardiomyopathy.

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Which anthracycline drug is noted for *not* causing the severe cardiotoxic effects common to others in its family?

Answer: Pixantrone

Explanation: Pixantrone is specifically highlighted as an anthracycline drug that does not cause the severe cardiotoxicity seen with most other drugs in its class.

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Beyond chemotherapy, anthracenediones include antimalarials like rufigallol and DNA dyes such as:

Answer: DRAQ5 and CyTRAK Orange

Explanation: Anthracenediones include antimalarials like rufigallol and DNA dyes such as DRAQ5 and CyTRAK Orange, used in flow cytometry and fluorescence microscopy.

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Which of the following anthraquinone derivatives extracted from *Cassia occidentalis* are known to be toxic?

Answer: Rhein and Emodin

Explanation: Rhein and Emodin are specifically listed among the toxic anthraquinone derivatives extracted from *Cassia occidentalis*.

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What severe health condition can be caused by toxic anthraquinone derivatives from *Cassia occidentalis* in children?

Answer: Hepatomyoencephalopathy

Explanation: Toxic anthraquinone derivatives from *Cassia occidentalis* are known to cause hepatomyoencephalopathy in children.

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Which of these anthraquinone derivatives is known for its laxative effects?

Answer: Dantron

Explanation: Dantron is explicitly mentioned as an anthraquinone derivative known for its laxative effects.

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Prolonged use and abuse of laxative anthraquinone derivatives can lead to what condition?

Answer: Melanosis coli

Explanation: Prolonged use and abuse of laxative anthraquinone derivatives can result in melanosis coli, a condition affecting the colon lining.

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Which of the following is a DNA dye or nuclear counterstain derived from anthracenediones, used in flow cytometry?

Answer: DRAQ5

Explanation: DRAQ5 is listed as a DNA dye or nuclear counterstain derived from anthracenediones, used in flow cytometry and fluorescence microscopy.

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Classification and Derivatives

Hypericin and fagopyrin are classified as naphthodianthrones, a type of anthraquinone derivative.

Answer: True

Explanation: Hypericin and fagopyrin are indeed classified as naphthodianthrones, which are a specific type of anthraquinone derivative.

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Alizarin and Dantron are classified as trihydroxyanthraquinones.

Answer: False

Explanation: Alizarin and Dantron are classified as dihydroxyanthraquinones, not trihydroxyanthraquinones.

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Parietin and Emodin are examples of trihydroxyanthraquinones.

Answer: True

Explanation: Parietin and Emodin are explicitly listed as examples of trihydroxyanthraquinones.

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Quinalizarin and rheoemodin are classified as tetrahydroxyanthraquinones.

Answer: True

Explanation: Quinalizarin and rheoemodin are indeed classified as tetrahydroxyanthraquinones.

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Carminic acid is a miscellaneous natural anthraquinone, encompassing Kermesic acid.

Answer: False

Explanation: Kermesic acid is a miscellaneous natural anthraquinone that encompasses Carminic acid, not the other way around.

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Hypericin and fagopyrin are classified as which type of anthraquinone derivative?

Answer: Naphthodianthrones

Explanation: Hypericin and fagopyrin are explicitly classified as naphthodianthrones, a type of anthraquinone derivative.

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Which of the following is an example of a dihydroxyanthraquinone?

Answer: Alizarin

Explanation: Alizarin is listed as an example of a dihydroxyanthraquinone.

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Which of these compounds is classified as a trihydroxyanthraquinone?

Answer: Parietin

Explanation: Parietin is explicitly listed as an example of a trihydroxyanthraquinone.

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Quinalizarin is an example of which type of anthraquinone based on hydroxyl groups?

Answer: Tetrahydroxyanthraquinone

Explanation: Quinalizarin is classified as a tetrahydroxyanthraquinone.

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Which of the following is considered a miscellaneous natural anthraquinone that encompasses Carminic acid?

Answer: Kermesic acid

Explanation: Kermesic acid is identified as a miscellaneous natural anthraquinone that encompasses Carminic acid.

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