Tremetone

Tremetone
Names
	IUPAC name (R)-1-(2-(prop-1-en-2-yl)-2,3-dihydrobenzofuran-5-yl)ethanone
Identifiers
CAS Number	4976-25-4;
3D model (JSmol)	Interactive image;
ChemSpider	71024;
PubChem CID	78673;
CompTox Dashboard (EPA)	DTXSID501031865 ;
	InChI InChI=1S/C13H14O2/c1-8(2)13-7-11-6-10(9(3)14)4-5-12(11)15-13/h4-6,13H,1,7H2,2-3H3/t13-/m1/s1 Key: UVYUUQGGBNKRFU-CYBMUJFWSA-N;
	SMILES O=C(C1=CC=C(O[C@@H](C(C)=C)C2)C2=C1)C;
Properties
Chemical formula	C13H14O2
Molar mass	202.253 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Tremetone is a chemical compound found in tremetol, a toxin mixture from snakeroot (Ageratina altissima) that causes milk sickness in humans and trembles in livestock.^[1]^[2]^[3]^[4] Tremetone is the main constituent of at least 11 chemically related substances in tremetol.^[4] Tremetone is toxic to fish, but not to chicken, and is therefore not the major toxic compound in tremetol.^[2] Tremetol can be found in a number of different species of the Asteraceae family, including snakeroot and rayless goldenrod (Isocoma pluriflora).^[5]

References

^ Bonner, W. A. (1962). "Ketones from "white snakeroot" Eupatorium urticaefolium". Tetrahedron. 18 (11): 1295–1309. doi:10.1016/0040-4020(62)80010-6.
^ ^a ^b Bowen, Douglas M (1963). "The Synthesis and Pharmacological Action of Tremetone". J. Med. Chem. 6 (3): 315–319. doi:10.1021/jm00339a023. PMID 14185993.
^ Bonner, W. A. (1964). "The absolute configurations of tremetone and toxol". Tetrahedron. 20 (6): 1419–1425. doi:10.1016/S0040-4020(01)99135-5.
^ ^a ^b Lee, S. T. (2010). "Tremetone and structurally related compounds in white snakeroot (Ageratina altissima): a plant associated with trembles and milk sickness". J. Agric. Food Chem. 58 (15): 8560–8565. doi:10.1021/jf1012456. PMID 20681643.
^ "Metabolite Information: Tremetone".

[Bonner_1962-1] Bonner, W. A. (1962). "Ketones from "white snakeroot" Eupatorium urticaefolium". Tetrahedron. 18 (11): 1295–1309. doi:10.1016/0040-4020(62)80010-6.

[Bowen_1963-2] Bowen, Douglas M (1963). "The Synthesis and Pharmacological Action of Tremetone". J. Med. Chem. 6 (3): 315–319. doi:10.1021/jm00339a023. PMID 14185993.

[Bonner_1964-3] Bonner, W. A. (1964). "The absolute configurations of tremetone and toxol". Tetrahedron. 20 (6): 1419–1425. doi:10.1016/S0040-4020(01)99135-5.

[Lee_2010-4] Lee, S. T. (2010). "Tremetone and structurally related compounds in white snakeroot (Ageratina altissima): a plant associated with trembles and milk sickness". J. Agric. Food Chem. 58 (15): 8560–8565. doi:10.1021/jf1012456. PMID 20681643.

[5] "Metabolite Information: Tremetone".

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[2]

[3]

[4]

[5]

See also

References