4-Ipomeanol

4-Ipomeanol
4-Ipomeanol
Names
Preferred IUPAC name
1-(Furan-3-yl)-4-hydroxypentan-1-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C9H12O3/c1-7(10)2-3-9(11)8-4-5-12-6-8/h4-7,10H,2-3H2,1H3; Key: RJYQLMILDVERHH-UHFFFAOYSA-N
  • CC(CCC(=O)C1=COC=C1)O
Properties
C9H12O3
Molar mass 168.192 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

4-Ipomeanol (4-IPO) is a pulmonary pre-toxin isolated from sweet potatoes infected with the fungus Fusarium solani. One of the 4-IPO metabolites is toxic to the lungs, liver and kidney in humans and animals. This metabolite can covalently bind to proteins, thereby interfering with normal cell processes.

The toxic metabolite, an enedial, is mostly formed in the bronchiolar exocrine cells (club cells) in the lungs of rodents. Necrosis of bronchiolar cells is therefore the primary damaging effect of the toxin, due to this location of metabolism. The secondary pathological effects are edema, congestion and hemorrhage caused by the destruction of the bronchiolar exocrine cells. In humans the metabolite is mostly formed in the liver, and causes liver toxicity.

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