Ascaridole

Source: Wikipedia, the free encyclopedia.
Ascaridole
Skeletal formula
Ball-and-stick model
Names
IUPAC name
1-Methyl-4-(1-methylethyl)-2,3-dioxabicyclo[2.2.2]oct-5-ene
Identifiers
3D model (
JSmol
)
121382
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.007.408 Edit this at Wikidata
EC Number
  • 208-147-4
KEGG
UNII
  • InChI=1S/C10H16O2/c1-8(2)10-6-4-9(3,5-7-10)11-12-10/h4,6,8H,5,7H2,1-3H3 checkY
    Key: MGYMHQJELJYRQS-UHFFFAOYSA-N checkY
  • O1OC2(\C=C/C1(C)CC2)C(C)C
Properties[1]
C10H16O2
Molar mass 168.23 g/mol
Appearance Colorless liquid
Density 1.010 g/cm3
Melting point 3.3 °C (37.9 °F; 276.4 K)
Boiling point 40 °C (104 °F; 313 K) at 0.2 mmHg
Hazards
GHS labelling:
GHS01: ExplosiveGHS07: Exclamation mark
Danger
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Ascaridole is a natural

Mexican tea (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 anthelmintic drug that expels parasitic worms
from plants, domestic animals and the human body.

History

α-Terpinene and ascaridole

Ascaridole was the first, and for a long time only, discovered naturally occurring

glycol, now known as ascaridole glycol, C10H18O3. 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/cm3. 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.[5] This structure was corrected by Otto Wallach in 1912.[6][7][8]

The first laboratory synthesis was demonstrated in 1944 by Günther Schenck and Karl Ziegler and might be regarded as mimicking the natural production of ascaridole. The process starts from α-terpinene which reacts with oxygen under the influence of chlorophyll and light. Under these conditions singlet oxygen is generated which reacts in a Diels–Alder reaction with the diene system in the terpinene.[8][9][10] 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.[11]

Properties

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

organic peroxides, 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.[1][6][12]
Ascaridole (organic peroxide) is forbidden to be shipped as listed in the
US Department of Transportation Hazardous Materials Table 49 CFR 172.101.[13]

Occurrence

Mexican Tea plant

The specific flavor of the Chilean tree

epazote (or Mexican tea, Dysphania ambrosioides, formerly Chenopodium ambrosioides)[14][15] where it typically constitutes between 16 and 70% of the plant's essential oil.[16][17] 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 through the year peaking around the time when the plant seeds become mature.[18]

Applications

Ascaridole is mainly used as an anthelmintic drug that expels parasitic worms (helminths) from the human body and plants. This property gave the name to the chemical, after Ascaris – 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 assay developed by Nelson in 1920. It was later substituted with modern gas chromatography and mass spectrometry methods.[19] The worms and their larvae were killed by immersion in a solution of ascaridole in water (about 0.015 vol%) for 18 hours at 50 °F (10 °C) or 12 hours at 60 °F (16 °C) or 6 hours at 65 to 70 °F (18 to 21 °C). Meanwhile, such immersion did not damage the roots and stems of plants such as Iris, Phlox, Sedum and others at 70 °F (21 °C) for 15 hours or longer.[12]

The wormseed plant itself (Mexican tea) is traditionally used in

folk medicine practiced in North and South America, China, and Turkey.[18][19]

Health issues

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

red blood cells and proteins in the urine, respectively) and jaundice (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.[17]

References

  1. ^
    ISBN 978-0-470-18024-2
    .
  2. ^ Hüthig (April 1908). "Commercial notes and scientific information on essential oils". Semi-annual Report of Schimmel & Co.: 12–120. 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 this video.
  3. ^ (Hüthig, April 1908), p. 116.
  4. S2CID 250895582
    .
  5. doi:10.1021/ja02221a016
    . See p. 1412.
  6. ^
    doi:10.1002/jlac.19123920104
    .
  7. doi:10.1021/ja02190a009
    .
  8. ^ a b Nelson, E. K. (1947). "Chapter 5: Oxides: Ascaridole". The Terpenes. Vol. 2. CUP Archive. pp. 446–452.
  9. S2CID 24081588
    .
  10. S2CID 8655604
    .
  11. ISBN 978-0-495-38857-9
    .
  12. ^ a b US Department of Agriculture (1972). "Technical Bulletin". Technical Bulletin. 1441: 65.
  13. OCLC 844215395.{{cite book}}: CS1 maint: others (link
    )
  14. ISBN 978-9968-31-235-6
    .
  15. ISBN 978-970-722-113-0
    .
  16. doi:10.1039/JR9380000829
    .
  17. ^
    ISBN 978-0-444-82590-2
    .
  18. ^
    ISBN 978-0-660-19073-0
    .
  19. ^ a b "Chenopodium ambrosioides". Medicinal Plants for Livestock. Ithaca, NY: Cornell University, Department of Animal Science. Archived from the original on 2006-02-21.
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