Anisatin

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
CAS Number	5230-87-5
3DMet	B05347
ChEMBL	ChEMBL517697
ChemSpider	103015
Jmol interactive 3D	Image
KEGG	C09294
MeSH	Anisatin
PubChem	12306850
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	328.32 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).
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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

• Japanese star anise

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)