Anisatin information

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
CAS Number	5230-87-5 ;
3D model (JSmol)	Interactive image;
3DMet	B05560;
ChEBI	CHEBI:182764;
ChEMBL	ChEMBL517697 ;
ChemSpider	103015 ;
ECHA InfoCard	100.208.646
KEGG	C09294 ;
MeSH	Anisatin
PubChem CID	12306850;
UNII	W9K8802FZL ;
CompTox Dashboard (EPA)	DTXSID6058396 ;
	InChI 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 Key: GEVWHIDSUOMVRI-QWNPAUMXSA-N ;
	SMILES 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
Chemical formula	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). verify (what is ?) Infobox references

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]

^ "Anisatin". PubChem, National Library of Medicine, US National Institutes of Health. 11 May 2019. Retrieved 17 May 2019.
^ 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.
^ 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.
^ "Naoru.com:シキミ(Japanese)". Archived from the original on 2018-09-09. Retrieved 2009-03-11.

[PubChem-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.

Anisatin information

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Anisatin

Illicium verum

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