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isoflavone

3-phenyl-4H-1-benzopyran-4-one. C15 H10 O2, melting point 148 C UV(max) 245 nm (log e 4.41), 307 nm (log e 3.82) One of the 3 classes of phytoestrogens. Enriched in soy, chickpeas, red clover & coffee. The 2 major forms of isoflavones genistein & daidzein are formed from precursors genistin & daidzin. Uses: - treatment of menopausal symptoms [6] Contraindications: - avoid high doses in women with breast cancer Adverse effects: - high doses > 150 mg/day for 5 year may result in endometrial hyperplasia [4] Mechanism of action: 1) diminishes LDL cholesterol 2) reduces menopausal symptoms [5] 3) no improvement in plasma lipids in postmenopausal women [3] 4) small improvement in bone mineral density in postmenopausal women [3]

Interactions

drug adverse effects of estrogens

Related

phytoestrogen soy bean (Tofu, Tempe)

Specific

daidzein equol fisetin genistein isoflavonoid

General

flavone ketone

Properties

SIZE: MW = 222.2 G/MOL

Database Correlations

PUBCHEM cid=72304

References

  1. Journal Watch 22(9):70-71, 2002 Hann LL et al, Obstet Gynecol, 99 389, 2002
  2. Merck Index, I2th ed, Merck & Co, Rahway NJ, 1996 # 5189
  3. Journal Watch 24(16):130, 2004 Kreijkamp-Kaspers S, Kok L, Grobbee DE, de Haan EH, Aleman A, Lampe JW, van der Schouw YT. Effect of soy protein containing isoflavones on cognitive function, bone mineral density, and plasma lipids in postmenopausal women: a randomized controlled trial. JAMA. 2004 Jul 7;292(1):65-74. PMID: 15238592
  4. Prescriber's Letter 11(9): 2004 Soy for Preventing Aging Effects in Older Women Detail-Document#: 200914 (subscription needed) http://www.prescribersletter.com
  5. Bolanos R, Del Castillo A, Francia J. Soy isoflavones versus placebo in the treatment of climacteric vasomotor symptoms: systematic review and meta-analysis. Menopause. 2010 May-Jun;17(3):660-6. Review. PMID: 20464785
  6. Medical Knowledge Self Assessment Program (MKSAP) 18, American College of Physicians, Philadelphia 2018

Component-of

Avlimil Trifolium pratense, red clover (Promensil)