Anisatin

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Anisatin
Stereo skeletal formula of anisatin
Names
IUPAC name
(1'S,2'R,3S,4'R,5'R,7'R,8'R,11'R)-4',5',7',11'-tetrahydroxy-2',7'-dimethyl-9'-oxaspiro[oxetane-3,6'-tricyclo[6.3.1.0¹,⁵]dodecane]-2,10'-dione
Identifiers
5230-87-5 N
3DMet B05347
ChEMBL ChEMBL517697 N
ChemSpider 103015 YesY
Jmol 3D model Interactive image
KEGG C09294 N
MeSH Anisatin
PubChem 12306850
Properties
C15H20O8
Molar mass 328.32 g·mol−1
log P -1.894
Acidity (pKa) 12.005
Basicity (pKb) 1.992
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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)