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ptaquiloside

ptaquiloside Structural

What is ptaquiloside?

Description

Ptaquiloside1 is a natural norsesquiterpene glucoside toxin present in bracken ferns2 (Pteridium aquilinum and other species). In 1983, it was isolated and characterized by Kiyoyuki Yamada and colleagues at Nagoya University (Japan), the University of Tokyo, and JEOL Ltd. (Tokyo).
Ptaquiloside is a carcinogen and the cause of hemorrhagic disease and bright blindness in cattle and other livestock. It can enter the milk and meat of affected animals and is known to cause esophageal and gastric cancer in humans. In 2019, Lars Holm Rasmussen and co-workers at the University of Copenhagen elucidated the biochemical fate of ptaquiloside in cattle.
Ptaquiloside has been well studied and reported, including in Chapter 13 of Color Atlas of Diseases and Disorders of Cattle (3rd ed., 2011) and in several publications cited by Science.gov in the 2000s and 2010s.
Although ptaquiloside is highly toxic, no safety data sheets for it are available.
1. SciFinder: Spiro[cyclopropane-1,5′-(5H)inden]-3′(2′H)-one, 7′a-(β-d-glucopyranosyloxy)-1′,3′a,4′,7′a-tetrahydro-4′-hydroxy-2′,4′,6′-trimethyl-, (2′R,3′aR,4′S,7′aR)-. 2. People who collect the edible ostrich fern (Matteuccia struthiopteris) must be careful to avoid bracken ferns that grow in the same temperate climates.

Properties of ptaquiloside

Melting point: 85-89 °C(Solv: hexane (110-54-3); acetone (67-64-1))
Boiling point: 620.7±55.0 °C(Predicted)
alpha  D22 -188° (c = 1 in methanol)
Density  1.43±0.1 g/cm3(Predicted)
solubility  highly soluble
pka 12.85±0.70(Predicted)
appearance white powder
IARC 3 (Vol. 40, Sup 7) 1987

Safety information for ptaquiloside

Computed Descriptors for ptaquiloside

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