Anisatin

Anisatin
Stereo skeletal formula of anisatin
Names
Preferred IUPAC name
(1R,4S,5R,6S,6aR,7R,9R,9aS)-1,5,6a,7-Tetrahydroxy-5,9-dimethylhexahydrospiro[[4,9a]methanocyclopenta[d]oxocine-6,3′-oxetane]-2,2′(1H)-dione
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.208.646 Edit this at Wikidata
KEGG
MeSH Anisatin
UNII
  • InChI=1S/C15H20O8/c1-6-3-7(16)15(21)13(6)4-8(23-10(18)9(13)17)12(2,20)14(15)5-22-11(14)19/h6-9,16-17,20-21H,3-5H2,1-2H3/t6-,7-,8-,9+,12+,13+,14+,15-/m1/s1 ☒N
    Key: GEVWHIDSUOMVRI-QWNPAUMXSA-N checkY
  • O=C1OC[C@]14[C@@]2(O)[C@H](O)C[C@H]([C@]23C[C@@H](OC(=O)[C@@H]3O)[C@@]4(O)C)C
Properties
C15H20O8
Molar mass 328.317 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).
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Anisatin is an extremely toxic, insecticidally active component of the shikimi plant.[1][2] The lethal dose is 1 mg/kg (i.p.) in mice.[3] 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.[4]

  1. ^ "Anisatin". PubChem, National Library of Medicine, US National Institutes of Health. 11 May 2019. Retrieved 17 May 2019.
  2. ^ Lane JF, Koch WT, Leeds NS, Gorin G (1952). "The toxin of Illicium anisatum. I. The isolation and characterization of a convulsant principle: anisatin". Journal of the American Chemical Society. 74 (13): 3211–3215. doi:10.1021/ja01133a002.
  3. ^ Kouno I, Kawano N, Yang CS (1988). "New pseudoanisatin-like sesquiterpene lactones from the bark of Illicium dunnianum". Journal of the Chemical Society, Perkin Transactions 1 (6): 1537. doi:10.1039/P19880001537.
  4. ^ "Naoru.com:シキミ(Japanese)". Archived from the original on 2018-09-09. Retrieved 2009-03-11.