17238-05-0

Usage

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.

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

Upstream product

• 112182-89-5 7,4'-diethoxymethoxyisoflavanone 
• 486-66-8 daidzein 
• 17720-60-4 2,4,4'-trihydroxy deoxybenzoin 
• 487-49-0 1-(2,4-dihydroxyphenyl)-2-(4-methoxyphenyl)ethanone 
• 81267-11-0 4',7-diacetoxyisoflavan-4-one 
• 108-46-3 recorcinol 
• 156-38-7 4-hydroxyphenylacetate 
• 112182-88-4 4,4'-diethoxymethoxy-α-hydroxymethyl-2-hydroxydesoxybenzoin 
• 141330-21-4 3-<2,4-Bis<(2-methoxyethoxy)methoxy>phenyl>-7-<(2-methoxyethoxy)methoxy>-4H-1-benzopyran-4-on 
• 113250-45-6 3-<2,4-Bis(methoxymethoxy)phenyl>-7-(methoxymethoxy)-4H-1-benzopyran-4-on 
• 141330-20-3 7-(Methoxymethoxy)-3-<4-(methoxymethoxy)phenyl>-4H-1-benzopyran-4-on 
• 141330-30-5 (+/-)-2,3-Dihydro-7-(methoxymethoxy)-3-<4-(methoxymethoxy)phenyl>-4H-1-benzopyran-4-on 

Downstream Products

• 124093-19-2 trans-2,3-dihydro-7-hydroxy-3-(4-hydroxyphenyl)-4H-benzopyran-4-ol 
• 531-95-3 equol 
• 531-95-3 equol 
• 1264702-88-6 C₁₉H₂₁NO₄ 
• 1264703-19-6 C₁₈H₁₉NO₄ 
• 1264702-89-7 C₁₉H₂₃NO₄ 
• 1264834-67-4 C₁₉H₂₁NO₃ 
• 1264702-68-2 C₂₀H₂₁NO₃ 
• 1394853-04-3 C₁₉H₁₉NO₃ 
• 1394853-05-4 C₂₀H₂₁NO₃ 
• 1394853-06-5 C₂₃H₂₇NO₃ 

Related news

Enhanced biosynthesis of Dihydrodaidzein (cas 17238-05-0) and dihydrogenistein by a newly isolated bovine rumen anaerobic bacterium08/24/2019

A rod-shaped and Gram-positive anaerobic bacterium, named Niu-O16, which was isolated from bovine rumen contents, was found to be capable of anaerobically converting isoflavones daidzein and genistein to dihydrodaidzein (DHD) and dihydrogenistein (DHG), respectively. The metabolites DHD and DHG ...detailed

Relevant academic research and scientific papers

Biotransformation of daidzein to equol by crude enzyme from Asaccharobacter celatus AHU1763 required an anaerobic environment

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.

Structure–activity relationship of phytoestrogen analogs as ERα/β agonists with neuroprotective activities

A set of isoflavononid and flavonoid analogs was prepared and evaluated for estrogen receptor α (ERα) and ERβ transactivation and anti-neuroinflammatory activities. Structure–activity relationship (SAR) study of naturally occurring phytoestrogens, their metabolites, and related isoflavone analogs revealed the importance of the C-ring of isoflavonoids for ER activity and selectivity. Docking study suggested putative binding modes of daidzein 2 and dehydroequol 8 in the active site of ERα and ERβ, and provided an understanding of the promising activity and selectivity of dehydroequol 8. Among the tested compounds, equol 7 and dehydroequol 8 were the most potent ERα/β agonists with ERβ selectivity and neuroprotective activity. This study provides knowledge on the SAR of isoflavonoids for further development of potent and selective ER agonists with neuroprotective potential.

PRODUCTION METHOD OF OPTICALLY ACTIVE 3-SUBSTITUTED CHROMAN-4-OL COMPOUND

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

Synthesis and anti-tumor activities of novel oxazinyl isoflavonoids

The design, synthesis and biological evaluation of a novel series of oxazinyl isoflavonoids is described. Several analogs were shown to exhibit growth inhibitory effects against SKOV-3, DU-145 and HL-60 human colon cancer cell lines with IC50 values in the micromolar range. The cellular potency of compounds 7e and 12h were found to have greater in vitro inhibitory activities than phenoxodiol, the parental compound currently in late-stage clinical trials for the treatment of cancer. The results shown are suitable for further lead optimization.

ISOFLAVONOID COMPOUNDS AND METHODS FOR THE TREATMENT OF CANCER

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.

Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities

Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.

Production of isoflavone derivatives

Methods for the hydrogenation of isoflavones are described which provide access to workable quantities of isoflavan-4-ols, isoflav-3-enes, and isoflavans. The isoflavone derivatives can be obtained in high purity and in near quantitative yields whilst employing pharmaceutically acceptable reagents and solvents.

Experimental and DFT 1H NMR study of conformational equilibria in trans-4′,7-dihydroxyisoflavan-4-ol and trans-isoflavan-4-ol

The solution-state conformational equilibria of trans-4′ ,7-dihydroxyisoflavan-4-ol (1) and transisoflavan-4-ol (2) were assessed based on the temperature dependence of their vicinal coupling constants J H-2α,H-3 and JH-3,H-4 in comp

The Synthesis, Structure, and Anticancer Activity of cis- and trans-4',7-Dihydroxyisoflavan-4-ols

cis-4',7-Dihydroxyisoflavan-4-ol (4) and trans-4',7-dihydroxyisoflafan-4-ol (5), two proposed metabolites of daidzein (4',7-dihydroxyisoflavone), have been synthesized and fully characterized for the first time.The vicinal coupling constants of the pyran