Anisatin

Anisatin
Names
IUPAC name
4aβ,5,6a,7,8,9-Hexahydro-1α,5β,6aβ,7β-tetrahydroxy-5,9α-dimethylspiro[6H-4,9a-methanocyclopent[d]oxocin-6,3'-oxetane]-2,2'(1H)-dione
Identifiers
3DMet B05347
5230-87-5 
ChEMBL ChEMBL517697 
ChemSpider 103015 Yes
Jmol-3D images Image
KEGG C09294 
MeSH Anisatin
PubChem 12306850
Properties
Molecular formula
 C15H20O8
Molar mass 328.31 g·mol−1
log P -1.894
Acidity (pKa) 12.005
Basicity (pKb) 1.992
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Anisatin is an extremely toxic, insecticidally active component of the Shikimi plant.[1] It is used in folk remedies topically in Japan. Lethal dose = 1 mg/kg (i.p.) in mice. [2] Symptoms begin to appear about 1–6 hours after ingestion, beginning with gastrointestinal ailments, such as diarrhea, vomiting, and stomach pain, followed by nervous system excitation, seizures, loss of consciousness, and respiratory paralysis, which is the ultimate cause of death.[3]

See also

References

  1. ↑ Lane, John F.; Koch, Walter T.; Leeds, Norma S.; Gorin, George (1952). "The toxin of Illicium anisatum. I. The isolation and characterization of a convulsant principle: anisatin". Journal of the American Chemical Society 74 (13): 3211–2114. doi:10.1021/ja01133a002.
  2. ↑ Kouno, J Chem Soc Perkin Trans 1:1537 1988
  3. ↑ Naoru.com:シキミ(jpnese)