| Revision as of 14:00, 28 October 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,081 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'CASNo').← Previous edit |
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{{chembox |
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| verifiedrevid = 443400642 |
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| verifiedrevid = 457819543 |
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| Name = Ascaridole |
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| Name = Ascaridole |
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| ImageFileL1 = Ascaridol.svg |
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| appearance = Colorless liquid |
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| ImageSizeL1 = 75px |
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| ImageFile = Ascaridol2.png |
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| ImageAltL1 = Skeletal formula |
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| ImageSize = 160px |
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| ImageName = Ascaridole |
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| ImageFileR1 = Ascaridole-3D-balls.png |
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| ImageAltR1 = Ball-and-stick model |
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| IUPACName = 1-methyl- 4-(1-methylethyl)- 2,3-dioxabicyclooct- 5-ene |
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| IUPACName = 1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclooct-5-ene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo = <!-- blanked - oldvalue: 512-85-6 --> |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| ChEMBL = 467614 |
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| CASNo = 512-85-6 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 1718D0GEVJ |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 467614 |
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| PubChem = 10545 |
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| PubChem = 10545 |
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| Beilstein = 121382 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| KEGG = C09836 |
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| EC_number = 208-147-4 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10105 |
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| ChemSpiderID = 10105 |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 2866 |
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| ChEBI = 2866 |
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| SMILES = O1OC2(\C=C/C1(C)CC2)C(C)C |
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| SMILES = O1OC2(\C=C/C1(C)CC2)C(C)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3 |
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| StdInChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = MGYMHQJELJYRQS-UHFFFAOYSA-N |
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| StdInChIKey = MGYMHQJELJYRQS-UHFFFAOYSA-N |
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| Section2 = {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula = C<sub>10</sub>H<sub>16</sub>O<sub>2</sub> |
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| Formula = C<sub>10</sub>H<sub>16</sub>O<sub>2</sub> |
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| MolarMass = 168.23 g/mol |
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| MolarMass = 168.23 g/mol |
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| Appearance = Colorless liquid |
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| Density = 1.010 g/cm<sup>3</sup> |
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| Density = 1.010 g/cm<sup>3</sup> |
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| MeltingPt = 3.3 °C |
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| MeltingPtC = 3.3 |
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| BoilingPt = 40 °C at 0.2 mmHg |
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| BoilingPtC = 40 |
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| BoilingPt_notes = at 0.2 mmHg |
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| Reference = <ref name=b2>Richard J. Lewis, Richard J. Lewis (Sr.) , Wiley-Interscience, 2008, ISBN 0470180242 p. 114</ref> |
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| Properties_ref= <ref name=b2>{{cite book | last1= Lewis|first1= R. J.|last2= Lewis|first2= R. J. Sr | url = https://books.google.com/books?id=LkIWiNg4FGEC&pg=PA114 | title = Hazardous Chemicals Desk Reference | publisher = Wiley-Interscience | year = 2008 | isbn = 978-0-470-18024-2 | page = 114 }}</ref> |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS01}}{{GHS07}} |
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| GHSSignalWord = Danger |
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| HPhrases = {{H-phrases|}} |
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| PPhrases = {{P-phrases|}} |
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'''Ascaridole''' is a natural ] classified as a bicyclic ] that has an unusual bridging ] functional group. It is a colorless liquid with a pungent smell and taste that is soluble in most organic solvents. Like other low molecular weight ]s, it is unstable and prone to explosion when heated or treated with organic acids. Ascaridole determines the specific flavor of the Chilean tree ] and is a major constituent of the oil of ] (wormseed). It is a component of natural medicine, tonic drinks and food flavoring in Latin American cuisine. As part of the oil, ascaridole is used as an ] drug that expels ]s from plants, domestic animals and the human body. |
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'''Ascaridole''' is a natural ] classified as a bicyclic monoterpenoid that has an unusual bridging ] functional group. It is a colorless liquid with a pungent smell and taste that is soluble in most organic solvents. Like other low molecular weight ]s, it is unstable and prone to rapid decomposition when heated or treated with organic acids. Ascaridole determines the specific flavor of the Chilean tree ] and is a major constituent of the oil of ] (wormseed). It is a component of natural medicine, tonic drinks and food flavoring in Latin American cuisine. As part of the oil, ascaridole is used as an ] drug that expels ]s from plants, domestic animals and the human body. |
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==History== |
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==History== |
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{{multiple image |
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{{double image|left|Alpha terpinene.png|53|Ascaridol.svg|60|α-Terpinene and ascaridole}} |
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Ascaridole was the first, and for a long time only, discovered naturally occurring ]. It was isolated from ] oil and named by Hüthig in 1908 who described its explosive character and determined its chemical formula as C<sub>10</sub>H<sub>16</sub>O<sub>2</sub>. Hüthig also noted the indifference of ascaridole to aldehydes, ketones or phenols that characterized it as non-alcohol. When reacted with sulfuric acid, or reduced |
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| image1 = Alpha terpinene.png |
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with zinc powder and ], ascaridole formed ].<ref>Schimmel's Report, 1908, April, p. 108</ref><ref>{{cite journal|last1=Arbuzov|first1=Yu A|title=THE DIELS–ALDER REACTION WITH MOLECULAR OXYGEN AS DIENOPHILE|journal=Russian Chemical Reviews|volume=34|pages=558|year=1965|doi=10.1070/RC1965v034n08ABEH001512|issue=8}}</ref> These results were confirmed in a detailed study by E. K. Nelson in 1911, in particular that ascaridole explodes upon heating, reacting with sulfuric, hydrochloric, nitric or ]s. Nelson showed that the new substance contained neither hydroxyl nor carbonyl group and that upon oxidation with ] it forms a ], now known as '''ascaridole glycol''' C<sub>10</sub>H<sub>18</sub>O<sub>3</sub>. The glycol is more stable than ascaridole and has a higher melting point of about 64 °C, boiling point of 272 °C, and density of 1.098 g/cm<sup>3</sup>. Nelson also predicted the chemical structure of ascaridole which was almost correct, but had the peroxide bridge not along the molecular axis, but between the other, off-axis carbon atoms.<ref>{{cite journal|last1=Nelson|first1=E. K.|journal=Journal of the American Chemical Society|volume=33|pages=1404|year=1911|doi=10.1021/ja02221a016|issue=8}}</ref> This structure was corrected by ] in 1912.<ref name=Wal /><ref>{{cite journal|last1=Nelson|first1=E. K.|journal=Journal of the American Chemical Society|volume=35|pages=84|year=1913|doi=10.1021/ja02190a009}}</ref><ref name=b1>E. K. Nelson , CUP Archive pp. 446–452</ref> |
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| image2 = Ascaridol.svg |
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| footer = α-Terpinene and ascaridole |
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Ascaridole was the first, and for a long time only, discovered naturally occurring ]. It was isolated from '']'' oil and named by Hüthig in 1908. He found that when heated to between 130° and 150 °C "there occurs, with sudden boiling in which the temperature momentarily rises to about 250°, a decomposition of an explosive character, occasionally accompanied by ignition. At the same time a very disagreeable skatol-like odour, difficult to define, is observed. In the course of the examination it was found that during the decomposition a gas is split off." He determined its chemical formula as C<sub>10</sub>H<sub>16</sub>O<sub>2</sub>.<ref>{{cite journal |last1=Hüthig |title=Commercial notes and scientific information on essential oils |journal=Semi-annual Report of Schimmel & Co. |date=April 1908 |pages=12–120 |url=https://babel.hathitrust.org/cgi/pt?id=mdp.39015065358650&view=1up&seq=109}} Ascaridole is discussed in the section titled "Wormseed oil, American", pp. 109–119. Ascaridole is named on p. 111; its empirical formula is stated on p. 114; the "explosive character" of the decomposition on heating is mentioned on p. 115. Some of the text can be seen about nine minutes into .</ref> Hüthig also noted the indifference of ascaridole to ]s, ]s or ]s that characterized it as non-]. When reacted with ], or reduced with ] powder and ], ascaridole formed ].<ref>(Hüthig, April 1908), p. 116.</ref><ref>{{cite journal | last1 = Arbuzov | first1 = Yu. A. | title = The Diels–Alder Reaction with Molecular Oxygen as Dienophile | journal = Russ. Chem. Rev. | volume = 34 | page = 558 | year = 1965 | doi = 10.1070/RC1965v034n08ABEH001512 | issue = 8 | bibcode = 1965RuCRv..34..558A | s2cid = 250895582 }}</ref> A detailed study was done by E. K. Nelson in 1911. He described the decomposition as apparently a molecular rearrangement, and found that it reacts with sulfuric, ], ], or ]s. Nelson showed that the new substance contained neither a ] nor a ] group and that upon reduction with ] it formed a ], now known as '''ascaridole glycol''', C<sub>10</sub>H<sub>18</sub>O<sub>3</sub>. The glycol is more stable than ascaridole and has a higher ] of about 64 °C, ] of 272 °C, and ] of 1.098 g/cm<sup>3</sup>. Nelson also predicted the chemical structure of ascaridole which was almost correct, but had the peroxide bridge not along the molecular axis, but between the other, off-axis carbon atoms.<ref>{{cite journal | last1 = Nelson | first1 = E. K. | journal = ] | volume = 33 | issue = 8 | pages = 1404–1412 | title = A Chemical Investigation of the Oil of ''Chenopodium'' | year = 1911 | doi = 10.1021/ja02221a016 | bibcode = 1911JAChS..33.1404N | url = https://zenodo.org/record/1429020 }} See p. 1412.</ref> This structure was corrected by ] in 1912.<ref name=Wal/><ref>{{cite journal | last1 = Nelson | first1 = E. K. | journal = ] | title = A Chemical Investigation of the Oil of ''Chenopodium''. II | volume = 35 | pages = 84–90 | year = 1913 | issue = 1 | doi = 10.1021/ja02190a009 | bibcode = 1913JAChS..35...84N | url = https://zenodo.org/record/1428997 }}</ref><ref name=b1>{{cite book | author = Nelson, E. K. | chapter-url = https://books.google.com/books?id=IxE9AAAAIAAJ&pg=PA446 | title = The Terpenes | volume = 2 | chapter = Chapter 5: Oxides: Ascaridole |year = 1947| publisher = CUP Archive | pages = 446–452 }}</ref> |
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The first laboratory synthesis was demonstrated in 1944 by Günter Schenck and ] and might be regarded as mimicking the natural production of ascaridole. The process starts from α-] which reacts with oxygen under the influence of ] and light. Under these conditions ] is generated which reacts in a ] with the diene system in the terpinene.<ref name=b1/><ref>{{cite journal|title=Industrial applications of photochemistry|author=Pape, M.|url=http://www.iupac.org/publications/pac/pdf/1975/pdf/4104x0535.pdf|page=535|year=1975|journal=Pure and Applied Chemistry |volume=41|issue=4}}</ref><ref>{{cite journal|title = Die Synthese des Ascaridols|author = Günther, O. Schenck and K. Ziegler |journal = Naturwissenschaften|volume = 32|issue = 14–26|year = 1944|pages = 157|doi = 10.1007/BF01467891}}</ref> Since 1945, this reaction has been adopted into the industry for large-scale production of ascaridole in Germany. It was then used as an inexpensive drug against intestinal worms.<ref>William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn , Cengage Learning, 2009, ISBN 0495388572 p. 967</ref> |
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The first laboratory synthesis was demonstrated in 1944 by Günther Schenck and ] and might be regarded as mimicking the natural production of ascaridole. The process starts from α-] which reacts with oxygen under the influence of ] and light. Under these conditions ] is generated which reacts in a ] with the diene system in the terpinene.<ref name=b1/><ref>{{cite journal | title = Industrial Applications of Photochemistry | last = Pape | first = M. | url = http://www.iupac.org/publications/pac/pdf/1975/pdf/4104x0535.pdf | pages = 535–558 | year = 1975 | journal = Pure Appl. Chem. | volume = 41 | issue = 4 | doi=10.1351/pac197541040535| s2cid = 24081588 }}</ref><ref>{{cite journal | title = Die Synthese des Ascaridols | trans-title = The Synthesis of Ascaridoles | last1 = Schenck | first1 = G. O. | author2-link = Karl Ziegler | last2 = Ziegler | first2 = K. | journal = Naturwissenschaften | language = German | volume = 32 | issue = 14–26 |date=April–June 1944 | page = 157 | doi = 10.1007/BF01467891 | bibcode = 1944NW.....32..157G | s2cid = 8655604 | issn = 0028-1042 }}</ref> Since 1945, this reaction has been adopted into the industry for large-scale production of ascaridole in Germany. It was then used as an inexpensive drug against intestinal worms.<ref>{{cite book | last1 = Brown | first1 = W. H. | last2 = Foote | first2 = C. S. | last3 = Iverson | first3 = B. L. | last4 = Anslyn | first4 = E. V. | url = https://books.google.com/books?id=mTHQB7MkUFsC&pg=PA967 | title = Organic Chemistry | publisher = Cengage Learning | year = 2009 | isbn = 978-0-495-38857-9 | page = 967 }}</ref> |
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==Properties== |
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==Properties== |
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Ascaridole is a colorless liquid that is soluble in most organic solvents. It is toxic and has a pungent, unpleasant smell and taste. Like other pure, low molecular weight ]s, it is unstable and prone to explosion when heated to a temperature above 130 °C or treated with organic acids. When heated, it emits fumes which are poisonous and possibly carcinogenic.<ref name=Wal>{{cite journal|title = Zur Kenntnis der Terpene und der ätherischen Öle|author = O. Wallach|journal = Justus Liebig's Annalen der Chemie|volume = 392|issue = 1|year = 1912|pages = 49–75|doi = 10.1002/jlac.19123920104}}</ref><ref name=b2/><ref name=b3>, United States. Dept. of Agriculture, 1972, p. 65</ref> |
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Ascaridole is a colorless liquid that is soluble in most organic solvents. It is toxic and has a pungent, unpleasant smell and taste. Like other pure, low molecular weight ]s, it is unstable and prone to violent decomposition when heated to a temperature above 130 °C or treated with organic acids. When heated, it emits fumes which are poisonous and possibly carcinogenic.<ref name=b2/><ref name=Wal>{{cite journal | title = Zur Kenntnis der Terpene und der Ätherischen Öle | trans-title = Regarding Terpenes and Essential Oils | language = German | last = Wallach | first = O. | journal = ] | volume = 392 | issue = 1 | year = 1912 | pages = 49–75| doi = 10.1002/jlac.19123920104 | url = https://zenodo.org/record/1427599 }}</ref><ref name=b3>{{cite journal | url = https://books.google.com/books?id=FbN6dFVyoM0C&pg=PA65 | title = Technical Bulletin | volume = 1441 | journal = Technical Bulletin | author = US Department of Agriculture | year = 1972 | page = 65 }}</ref> |
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Ascaridole (organic peroxide) is forbidden to be shipped as listed in the ] Hazardous Materials Table 49 CFR 172.101.<ref>{{Cite book |title=Hazardous materials compliance pocketbook. |date=2011 |publisher=J.J. Keller & Associates |others=J.J. Keller & Associates |isbn=978-1-60287-954-6 |location=Neenah, Wis. |oclc=844215395}}</ref> |
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==Occurrence== |
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==Occurrence== |
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The specific flavor of the Chilean tree ] (''Peumus boldus'') primarily originates from ascaridole. Ascaridole is also a major component of ] (or Mexican Tea, '']'' formerly ''Chenopodium ambrosioides'')<ref>, EUNED, ISBN 9968312355, p. 245</ref><ref>Ana Luisa Anaya Lang , Plaza y Valdes, 2003, ISBN 9707221135 p. 323</ref> where it typically constitutes between 16 and 70% of the plant's ].<ref name=asc>{{cite journal|title = Chenopodium oil. Part III. Ascaridole|author = Humphrey Paget|journal = J. Chem. Soc.|volume = 392|issue = 1|year = 1938|pages = 829–833|doi = 10.1039/JR9380000829}}</ref><ref name=b5>Ellene Tratras Contis , Elsevier, 1998, ISBN 0444825908 pp. 408–409</ref> The content of ascaridole in the plant depends on cultivation and is maximal when the nitrogen to phosphorus ratio in the soil is about 1:4. It also changes though the year peaking around the time when the plant seeds become mature.<ref> Ernest Small, National Research Council Canada , NRC Research Press, 2006, ISBN 0660190737, pp. 295–296</ref> |
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The specific flavor of the Chilean tree ] (''Peumus boldus'') primarily originates from ascaridole. Ascaridole is also a major component of ] (or Mexican tea, '']'', formerly ''Chenopodium ambrosioides'')<ref>{{cite book | url = https://books.google.com/books?id=2QreGuGsG3EC&pg=PA245 | last = Garro Alfaro | first = J. E. | title = Plantas Competidoras: un componente más de los agroecosistemas | publisher = EUNED | isbn = 978-9968-31-235-6 | page = 245 }}</ref><ref>{{cite book | last = Lang | first = A. L. A. | url = https://books.google.com/books?id=H6j8zaDYSYEC&pg=PA323 | title = Ecología Química | publisher = Plaza y Valdés | year = 2003 | isbn = 978-970-722-113-0 | page = 323 }}</ref> where it typically constitutes between 16 and 70% of the plant's ].<ref name=asc>{{cite journal | title = ''Chenopodium'' Oil. Part III. Ascaridole | last = Paget | first = H. | journal = J. Chem. Soc. | volume = 392 | issue = 1 | year = 1938 | pages = 829–833 | doi = 10.1039/JR9380000829 }}</ref><ref name=b5>{{cite book | last = Contis | first = E. T. | chapter-url = https://books.google.com/books?id=N631xMSk-RIC&pg=PA408 | title = Food Flavors: Formation, Analysis, and Packaging Influences | chapter = Some Toxic Culinary Herbs in North America | editor1-last = Tucker | editor1-first = A. O. | editor2-last = Maciarella | editor2-first = M. J. | publisher = Elsevier | year = 1998 | isbn = 978-0-444-82590-2 | pages = 408–409 }}</ref> The content of ascaridole in the plant depends on cultivation and is maximal when the ] to ] ratio in the ] is about 1:4. It also changes through the year peaking around the time when the plant seeds become mature.<ref name=small>{{cite book | last = Small |first = E. | url = https://books.google.com/books?id=UL9lpNrx0kwC&pg=PA295 | title = Culinary Herbs | publisher = NRC Research Press | year = 2006 | isbn = 978-0-660-19073-0 | pages = 295–296 }}</ref> |
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==Applications== |
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==Applications== |
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Ascaridole is mainly used as an ] drug that expels ]s (helminths) from body and plants. This property gave the name to this chemical, after '']'' – a genus of the large intestinal roundworms. In the early 1900s, it was a major remedy against intestinal parasites in humans, cats, dogs, goats, sheep, chickens, horses and pigs, and it is still used in livestock, particularly in the Central American countries. The dosage was specified by the ascaridole content in the oil, which was traditionally determined with an ] developed by Nelson in 1920. It was later substituted with modern ] and ] methods.<ref name=cornell>, Cornell University, Department of Animal Science</ref> The worms and their larvae were killed by immersion in a solution of ascaridole in water (about 0.015 vol%) for 18 hours at {{convert|50|F}} or 12 hours at {{convert|60|F}} or 6 hours at {{convert|65|to|70|F|C}}. Meanwhile, such immersion did not damage the roots and stems of plants such as '']'', '']'', '']'' and others at {{convert|70|F}} for 15 hours or longer.<ref name=b3/> |
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Ascaridole is mainly used as an ] drug that expels ]s (helminths) from the human body and plants. This property gave the name to the chemical, after '']'' – a genus of the large intestinal roundworm. In the early 1900s, it was a major remedy against intestinal parasites in humans, cats, dogs, goats, sheep, chickens, horses, and pigs, and it is still used in livestock, particularly in the Central American countries. The dosage was specified by the ascaridole content in the oil, which was traditionally determined with an ] developed by Nelson in 1920. It was later substituted with modern ] and ] methods.<ref name=cornell>{{cite web|url=http://www.abc.cornell.edu/plants/medicinal/epazote.html |title=''Chenopodium ambrosioides'' |work=Medicinal Plants for Livestock |publisher=Cornell University, Department of Animal Science |location=Ithaca, NY |archive-url=https://web.archive.org/web/20060221023614/http://www.abc.cornell.edu/plants/medicinal/epazote.html |archive-date=2006-02-21 }}</ref> The worms and their larvae were killed by immersion in a solution of ascaridole in water (about 0.015 vol%) for 18 hours at {{convert|50|°F|°C}} or 12 hours at {{convert|60|°F|°C}} or 6 hours at {{convert|65|to|70|F|C}}. Meanwhile, such immersion did not damage the roots and stems of plants such as '']'', '']'', '']'' and others at {{convert|70|°F|°C}} for 15 hours or longer.<ref name=b3/> |
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The wormseed oil itself (Mexican Tea) is traditionally used in Mexican cuisine for flavoring dishes and preventing ] from bean-containing food.<ref name=b5/> It is also part of tonic drinks and infusions to expel ]s and treat asthma, arthritis, dysentery, stomach ache, malaria and nervous diseases in folk medicine practiced in North and South Americas, China and Turkey.<ref name=cornell/><ref>Ernest Small, National Research Council Canada , NRC Research Press, 2006, ISBN 0660190737 p. 296</ref> |
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The wormseed plant itself (Mexican tea) is traditionally used in ] for flavoring dishes and preventing ] from ]-containing food.<ref name=b5/> It is also part of ]s and infusions to expel ]s and treat ], ], ], ], ], and ]s in ] practiced in North and South America, China, and Turkey.<ref name=small/><ref name=cornell/> |
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==Health issues== |
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== Health issues == |
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The usage of wormseed oil on humans is limited by the toxicity of ascaridole and has therefore been discouraged. In high doses, wormseed oil causes irritation of skin and mucous membrane, nausea, vomiting, constipation, headache, ], ], temporal deafness and blindness. Prolonged action induces depression of the ] and delirium which transits into convulsions and coma. Long-term effects include ] (] in the ]s), ] and ] (presence of ] and proteins in the ], respectively) and ] (yellowish pigmentation of the skin). Fatal doses of wormseed oil were reported as one teaspoon for a 14 month old baby (at once) and daily administration of 1 mL over three weeks to a 2 year-old child. Ascaridole is also carcinogenic in rats.<ref name=b5/> |
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The usage of wormseed oil on humans is limited by the toxicity of ascaridole and has therefore been discouraged. In high doses, wormseed oil causes ] of skin and ], ], ], ], ], ], ], temporary ] and ]. Prolonged action induces depression of the ] and ] which transits into ]s and ]. Long-term effects include ] (] in the ]s), ], and ] (presence of ] and proteins in the ], respectively) and ] (yellowish pigmentation of the skin). Fatal doses of wormseed oil were reported as one teaspoon for a 14-month-old baby (at once) and daily administration of 1 mL over three weeks to a 2-year-old child. Ascaridole is also carcinogenic in rats.<ref name=b5/> |
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==References== |
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== References == |
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