17238-05-0 Usage
Description
Dihydrodaidzein is a hydroxyisoflavanone, an active and estrogenic metabolite derived from daidzein, an isoflavonoid phytoestrogenic compound found in various legumes such as soybeans, pea pods, clover, and kudzu. It is characterized by its light beige needle-like appearance and possesses vasodilatory properties, as well as the ability to stimulate the estrogen receptor-dependent growth of breast cancer MCF-7 cells at micromolar concentrations.
Uses
Used in Pharmaceutical Applications:
Dihydrodaidzein is used as a pharmaceutical agent for its estrogenic properties and vasodilatory action. It is particularly beneficial in the treatment and management of conditions related to estrogen deficiency and cardiovascular health.
Used in Cancer Research:
Dihydrodaidzein is used as a research compound for its potential role in the growth of breast cancer MCF-7 cells. Its ability to stimulate estrogen receptor-dependent growth makes it a valuable tool in understanding the underlying mechanisms of hormone-responsive cancers and the development of targeted therapies.
Used in Nutritional Supplements:
Dihydrodaidzein is used as an ingredient in nutritional supplements for its potential health benefits, including its estrogenic properties and cardiovascular effects. It may be particularly useful for individuals seeking to improve their overall health and well-being through the use of natural compounds.
Used in Functional Foods:
Dihydrodaidzein can be incorporated into functional foods for its potential health-promoting properties. Its presence in these products may contribute to the enhancement of their nutritional value and the promotion of specific health benefits, such as improved cardiovascular health and hormonal balance.
Used in Cosmetics:
Dihydrodaidzein may be used in the cosmetics industry for its estrogenic properties, which could potentially help in the development of products aimed at improving skin health and reducing the signs of aging.
Biological Activity
dihydrodaidzein, an active, estrogenic metabolite of daidzein in colonic bacteria, probably is further metabolized to various bioactive compounds including equol. as an estrogen receptor agonist, dihydrodaidzein, at micromolar concentrations, activates the estrogen receptor-dependent growth of breast cancer cells. daidzein, an isoflavonoid phytoestrogenic compound, is found in soybeans, clover, kudzu, and other legumes.
in vitro
prostatic fluid and plasma concentrations of dihydrodaidzein were sufficient to block the growth of benign human prostatic epithelial cells (prec). dihydrodaidzein showed a significant inhibitory effect on the growth of prostate cancer cell line lncap. additionally, dihydrodaidzein slightly triggered the apoptosis of prec. in addition to affecting apoptosis, dihydrodaidzein decreased proliferation, which was associated with the changes in cell cycle distribution and caspase 3 activation [1].
in vivo
male c57b1/6 wild type mice were administered orally with dihydrodaidzein at a dose of 25 mg/kg/day for 4 weeks. compared to the control groups, the neointima of mice treated with dihydrodaidzein was thickened. in dihydrodaidzein-treated mice, the intimal thickness in the non-injured right iliac artery was not altered. moreover, neointimal proliferation was selectively blocked by dihydrodaidzein via suppressing the migration and proliferation of vascular smooth muscle cell and dampening the endothelial apoptosis [2].
references
[1]. hedlund, t., bokhoven, a., johannes, w., nordeen, s., & ogden, l. prostatic fluid concentrations of isoflavonoids in soy consumers are sufficient to inhibit growth of benign and malignant prostatic epithelial cells in vitro. the prostate. 2006; 66(5): 557-566. [2]. shen, j., white, m., husband, a., hambly, b., & bao, s. phytoestrogen derivatives differentially inhibit arterial neointimal proliferation in a mouse model. european journal of pharmacology. 2006; 548(1-3): 123-128.
Check Digit Verification of cas no
The CAS Registry Mumber 17238-05-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,7,2,3 and 8 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 17238-05:
(7*1)+(6*7)+(5*2)+(4*3)+(3*8)+(2*0)+(1*5)=100
100 % 10 = 0
So 17238-05-0 is a valid CAS Registry Number.
InChI:InChI=1/C15H12O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-7,13,16-17H,8H2
17238-05-0Relevant articles and documents
Biotransformation of daidzein to equol by crude enzyme from Asaccharobacter celatus AHU1763 required an anaerobic environment
Thawornkuno, Charin,Tanaka, Michiko,Sone, Teruo,Asano, Kozo
, p. 1435 - 1438 (2009)
Asaccharobacter celatus AHU1763 is a Gram-positive, obligate anaerobic, non-spore forming, rod-shaped bacteria that was successfully isolated from rat cecal content. Daizein was converted to equol via dihydrodaidzein by this bacterium. A crude enzyme that converted daidzein to dihydrodaidzein was detected mainly in the culture supernatant. The ability of this enzyme dropped after the culture supernatant was exposed to a normal atmospheric environment for even 5 min. Furthermore, the enzyme responsible for changing dihydrodaidzein to equol was detected mainly in the cell debris, which required anaerobic conditions for its activity.
PRODUCTION METHOD OF OPTICALLY ACTIVE 3-SUBSTITUTED CHROMAN-4-OL COMPOUND
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Paragraph 0076-0078, (2017/01/02)
PROBLEM TO BE SOLVED: To provide a versatile and highly productive production method of an optically active 3-substituted chroman-4-ol compound. SOLUTION: A production method of an optically active 3-substituted chroman-4-ol compound includes performing a reduction reaction of a 3-substituted chroman-4-one compound in the presence of a metal complex represented by formula (I) (in formula (I), M represents a group 8 transition metal or the like, each of R1 and R2 independently represents a hydrogen atom, a 1-6C alkyl group or the like, R3 represents a 1-6C alkyl group or the like, R4 represents a 1-6C alkyl group or the like, Ar represents benzene bonded with M via a π bond or the like, and X represents a carbonyloxy group or the like). COPYRIGHT: (C)2015,JPOandINPIT
ISOFLAVONOID COMPOUNDS AND METHODS FOR THE TREATMENT OF CANCER
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Page/Page column 35; 37, (2012/05/20)
Provided herein is a pharmaceutical composition comprising at least one isoflavonoid. Also provided herein are methods of treating cancer, sensitizing cancer cells, and inducing apoptosis in cancer cells by administering such compositions.