3DChem.com - Chemistry, Structures & 3D Molecules a visual and interactive website showcasing the beautiful world of chemistry

Ipriflavone (Molecule of the Month for June 2008)

isoflavone



Ipriflavone is a synthetic isoflavone which is used to maintain bone density and to prevent osteoporosis in postmenopausal women. It is not used to treat osteoporosis. It slows down the action of the osteoclasts (bone-eroding cells), allowing the osteoblasts (bone-building cells) to build up bone mass. Plants use isoflavones and their derivatives as phytoalexin compounds to ward off disease-causing pathogenic fungi and other microbes. In addition, soybean uses isoflavones to stimulate soil-microbe rhizobium to form nitrogen-fixing root nodules.

Isoflavones are a class of organic compounds and biomolecules related to the flavonoids. Many act as phytoestrogens in mammals. They are also very strong antioxidants.[citation needed] Several selected isoflavones and isoflavone-rich foods possess activity against cancer, including certain types of breast and prostate cancer. Isoflavone (3-phenyl-4H-1-benzopyr-4-one) differs from flavone in the following: in isoflavones, the position of the phenyl group on the 4H-1-benzopyr-4-one skeleton is in position 3 relative to the oxygen of the ring, whereas in flavones it is in position 2. Isoflavones are polyphenolic compounds produced almost exclusively by the members of the Fabaceae/Leguminosae (bean) family.

Most members of the Fabaceae family contain significant quantities of isoflavones. Analysis of levels in various species has found that the highest levels of genistein and daidzein were found in psoralea (Psoralea corylifolia). Various legumes including kudzu (Pueraria lobata), lupine (Lupinus spp), fava bean (Vicia faba), and soy (Glycine max) contained substantial amounts of isoflavones according to this analysis. Highly processed foods made from legumes, such as tofu, retained most of their isoflavone content, with the exception of fermented miso, which actually has increased levels. Other dietary sources of isoflavones include chick pea (biochanin A), alfalfa (formononetin and coumestrol), and peanut (genistein).

Formal Chemical Name (IUPAC)
3-phenyl-7-propan-2-yloxychromen-4-one

References

http://en.wikipedia.org/wiki/Ipriflavone

Picture of Ipriflavone

click on the picture above to interact
with the 3D model of the
Ipriflavone structure
(this will open a new browser window)

Picture of Ipriflavone

C18 H16 O3



Update by Karl Harrison
(Molecule of the Month for June 2008 )