Ascaridol

Structural formula
	Structural formula without stereochemistry
General
Surname	Ascaridol
other names	1-isopropyl-4-methyl-2,3-dioxabicyclo [2.2.2] oct-5-en ( IUPAC ) ; 1,4-epidioxy-p-menth-2-en;
Molecular formula	C 10 H 16 O 2
Brief description	pale greenish yellow liquid
External identifiers / databases
EC number	208-147-4
ECHA InfoCard	100.007.408
PubChem	10545
ChemSpider	10105
Wikidata	Q419442
properties
Molar mass	168.23 g · mol -1
Physical state	liquid
density	1.01 g cm −3
Melting point	3 ° C
boiling point	113–114 ° C (2.6 k Pa ), explosive decomposition> 130 ° C
solubility	hardly soluble in water
Refractive index	1.4769 (20 ° C)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Ascaridol is a chemical compound and a natural plant substance. This is a monocyclic monoterpene - peroxide with not clearly enlightened absolute configuration . In 1943 it could be produced synthetically for the first time by Günther Otto Schenck and Karl Ziegler . It is synthesized from pinene and oxygen in the presence of chlorophyll . It used to be used as an anthelmintic .

Occurrence

Mexican goosefoot ( Dysphania ambrosioides )

Ascaridol is found in the so-called fragrant goosefoot ( worm herb ) and in the oil of the Boldo leaves . Ascaridol is unstable due to the peroxide group.

Historical

Ascaridol was the first naturally occurring organic peroxide to be discovered . It was isolated from plants of the genus goosefoot ( Chenopodium ). Hüthig recognized the explosive character of ascaridol as early as 1908 and determined the molecular formula with C ₁₀ H ₁₆ O ₂ . In the reaction of Ascaridol with sulfuric acid or in the reduction with zinc powder / acetic acid to form p -Cymol. These results were confirmed by EK Nelson in 1911. Nelson clearly showed that ascaridol contains neither a hydroxy nor a carbonyl group . An almost correct structural proposal by Nelson was corrected in 1912 by Otto Wallach .

The first laboratory synthesis was achieved in 1944 by Günther Otto Schenck and Karl Ziegler . The educt α- terpinene reacts with oxygen in the presence of chlorophyll and light. Under these reaction conditions, singlet oxygen is first generated photochemically , which reacts in a hetero- Diels-Alder reaction with the diene system in terpinene. As early as 1945 this reaction was industrially developed in Germany into a technical process for the production of large quantities of ascaridol. Ascaridol was used as an inexpensive drug against worms.

Physiological effect

Ascaridol is allergenic. As a degradation product of monoterpenes u. a. In tea tree oil , it is responsible for the allergenicity of some essential oils.

Web links

Ascaridol at chemistryworld.de

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on Ascaridol. In: Römpp Online . Georg Thieme Verlag, accessed on June 8, 2014.
↑ David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-29.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
^ Günther, O. Schenck, K. Ziegler: The synthesis of Ascaridols. In: The natural sciences. 32, 1944, pp. 157-157, doi : 10.1007 / BF01467891 .
↑ Schimmel's Report April 1908, p. 108.
↑ Yu. A. Arbuzov: The Diels-Alder Reaction with Molecular Oxygen as Dienophile . In: Russian Chemical Reviews . 34, No. 8, 1965, p. 558. doi : 10.1070 / RC1965v034n08ABEH001512 .
^ EK Nelson: A Chemical Investigation of the Oil of Chenopodium . In: Journal of the American Chemical Society . 33, No. 8, 1911, pp. 1404-1412. doi : 10.1021 / ja02221a016 .
^ Wallach, O .: in Justus Liebig's Annalen der Chemie 392 (1912) 61.
^ Wallach, O .: in Chemisches Zentralblatt 83 (1912) 921.
^ EK Nelson: A Chemical Investigation of the Oil of Chenopodium. II . In: Journal of the American Chemical Society . 35, 1913, pp. 84-90. doi : 10.1021 / ja02190a009 .
↑ ^a ^b CUP Archives: The Terpenes. CUP Archive, pp. 446–452 ( limited preview in Google Book search).
^ Pape, M .: Industrial Applications of Photochemistry . (pdf) In: Pure and Applied Chemistry . 41, No. 4, 1975, pp. 535-558.
↑ Schenck, GO; Ziegler, K .: The Synthesis of Ascaridol . In: Natural Sciences . 32, No. 14-26, p. 157. doi : 10.1007 / BF01467891 .
^ William Brown: Organic Chemistry. Cengage Learning, 2008, ISBN 978-0-495-38857-9 , p. 967 ( limited preview in Google Book Search).
↑ BM Hausen et al .: Degradation products of monoterpenes are the sensitizing agents in tea tree oil. Am J Contact Dermat. 10/2/1999. Pp. 68-77; PMID 10357714 .

[Römpp-1] Entry on Ascaridol. In: Römpp Online . Georg Thieme Verlag, accessed on June 8, 2014.

[CRC-2] David R. Lide (Ed.): CRC Handbook of Chemistry and Physics . 90th edition. (Internet version: 2010), CRC Press / Taylor and Francis, Boca Raton, FL, Physical Constants of Organic Compounds, pp. 3-29.

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Günther, O. Schenck, K. Ziegler: The synthesis of Ascaridols. In: The natural sciences. 32, 1944, pp. 157-157, doi : 10.1007 / BF01467891 .

[5] Schimmel's Report April 1908, p. 108.

[6] Yu. A. Arbuzov: The Diels-Alder Reaction with Molecular Oxygen as Dienophile . In: Russian Chemical Reviews . 34, No. 8, 1965, p. 558. doi : 10.1070 / RC1965v034n08ABEH001512 .

[7] EK Nelson: A Chemical Investigation of the Oil of Chenopodium . In: Journal of the American Chemical Society . 33, No. 8, 1911, pp. 1404-1412. doi : 10.1021 / ja02221a016 .

[Wal1-8] Wallach, O .: in Justus Liebig's Annalen der Chemie 392 (1912) 61.

[Wal2-9] Wallach, O .: in Chemisches Zentralblatt 83 (1912) 921.

[10] EK Nelson: A Chemical Investigation of the Oil of Chenopodium. II . In: Journal of the American Chemical Society . 35, 1913, pp. 84-90. doi : 10.1021 / ja02190a009 .

[b1-11] CUP Archives: The Terpenes. CUP Archive, pp. 446–452 ( limited preview in Google Book search).

[12] Pape, M .: Industrial Applications of Photochemistry . (pdf) In: Pure and Applied Chemistry . 41, No. 4, 1975, pp. 535-558.

[13] Schenck, GO; Ziegler, K .: The Synthesis of Ascaridol . In: Natural Sciences . 32, No. 14-26, p. 157. doi : 10.1007 / BF01467891 .

[14] William Brown: Organic Chemistry. Cengage Learning, 2008, ISBN 978-0-495-38857-9 , p. 967 ( limited preview in Google Book Search).

[15] BM Hausen et al .: Degradation products of monoterpenes are the sensitizing agents in tea tree oil. Am J Contact Dermat. 10/2/1999. Pp. 68-77; PMID 10357714 .