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New Synthesis of 2-Hydroxyestrogen 2 …

26/11/2017 · New Synthesis of 2-Hydroxyestrogen 2-Monoglucuronides1) ..

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A method for the synthesis of 2-hydroxyestrone ..

It is now well understood that certain estrogens increase cell growth and proliferation more than others. With the advent of genetic test analysis it is now possible to identify inherited strengths and weaknesses of certain gene variants that are encoded in certain estrogen-specific biochemical pathways. This data can be used clinically for the purpose of constructing meaningful and evidence-based protocols, which aim to positively influence the pathways of estrogen metabolism. One section in the features estrogen metabolism genetics.

Synthesis of 2-hydroxyestradiol-17β - [PDF Document]
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A significant body of literature has identified a number or nutrients, botanicals and nutrient compounds which have varying effects on the estrogen-metabolizing and detoxifying pathways. Implementation of many of these compounds through an individualized process affords great potential for those affected by the potentially deleterious effects of aberrant estrogen metabolism.

Rmlrd in Nonhem lrrland SYNTHESIS OF 2-HYDROXYESTRADIOL-17fil P

New Synthesis of 2-Hydroxyestrogen 2-Monoglucuronides
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Lu LJ, Cree M, Josyula S, Nagamani M, Grady JJ, Anderson KE.
Increased urinary excretion of 2-hydroxyestrone but not 16alpha- hydroxyestrone in premenopausal women during a soya diet containing isoflavones.

Cancer Res 2000;
60: 1299-1305

New synthetic routes leading to catechol estrogen 2-monoglucuronides are described. Selective introduction of a glucuronyl residue into the C-2 hydroxyl group was undertaken by utilizing a steric interaction of the 3-hydroxyl group with a bulky substituent at C-4. For this purpose, 4-bromo-2-hydroxyestriol 16, 17-diacetate was used as a key intermediate. The Koenigs-Knorr reaction of this catechol with methyl α-acetobromoglucuronate in the presence of cadmium carbonate proceeded preferentially toward the C-2 hydroxyl group. Subsequent reductive dehalogenation followed by alkaline hydrolysis provided the desired 2-hydroxyestriol 2-glucuronide. In a similar fashion, 2-hydroxyestradiol and-2-hydroxyestrone 2-glucuronides were also prepared.

[A simple synthetic method of 2-hydroxyestrone-6,7 …

[A simple synthetic method of 2-hydroxyestrone-6,7-3H (author's transl)]
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Its important to address however, that genetics testing is not enough by itself to understand what the problems are. Ideally, one pairs a genetics test with a urinary sex hormone test. Urinary sex hormone testing is now the industry standard in our opinion, primarily because it is providing an evaluation of estrogen metabolites. On occasion, it is useful to measure the SHBG in serum (sex hormone binding globulin), which can reveal the level of bound versus unbound sex hormones. Elevations in the SHBG will reduce the availability of sex hormones to cells.

4 hydroxy estrone (4OHE1) and estradiol (4OHE2) are very reactive estrogens. They are highly prone to the formation of catechol estrogen-derived 3,4 semi-quinones, which are potent, electrophilic, free radical-generating molecules that have been shown to lead to DNA mutagenesis (10). Indeed, 4 hydroxy E1 and E2 are the most potent and potentially carcinogenic estrogens.

2-HYDROXYESTRONE-1,4,16,16-D4 CAS#: 81586-97-2
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  • In vitro synthesis of 16 alpha-hydroxyestrone by female ..

    Estrogen metabolite ratio: Is the 2-hydroxyestrone to 16α-hydroxyestrone ratio predictive for breast cancer

  • inactive metabolites 2-hydroxyestrone ..

    ESTRAMET 2-Hydroxyestrogen/16α-Hydroxyestrone ELISA Kit can be provided from Creative Diagnostics.

  • Estrogen Metabolism and Autoimmunity | Estradiol | …

    4-Hydroxyestrone-1,2,16,16-d4

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02/12/2011 · Estrogen metabolism and autoimmunity ..

N2 - A method for the synthesis of 2-hydroxyestrone/estradiol, 4-hydroxyestrone/estradiol, 3′-hydroxydiethylstilbestrol, 3′-hydroxyhexestrol, and 3′-hydroxydienestrol is reported, in which 2-iodoxybenzoic acid (IBX) and the corresponding phenolic estrogen are reacted. Treatment of the natural estrogens, estrone/estradiol, with stoichiometric amounts of IBX in dimethylformamide initially yielded a mixture of estrone/estradiol-2,3- and -3,4-quinones, which were reduced in situ to the corresponding catechols by treatment with a 1 M aqueous solution of ascorbic acid. Chromatographic separation of the reaction products afforded 2- and 4-hydroxyestrone/estradiol in good overall yields (79%). In the case of the synthetic estrogens containing two identical phenolic rings, protection of one ring is a prerequisite for the synthesis of the monocatechol. Thus, diethylstilbestrol and dienestrol were protected at one phenol ring as their methyl ethers. The resulting monophenols were treated with stoichiometric amounts of IBX for 1 h, followed by treatment with 1 M aqueous ascorbic acid to obtain the corresponding catechols in more than 70% yield. Furthermore, the catechol of diethylstilbestrol, protected at one ring, was reduced by catalytic hydrogenation at the C3-C4 double bond to obtain 3′-hydroxyhexestrol in 90% yield. Removal of the protected methoxy groups of the synthetic estrogen catechols was carried out by treatment with a 1 M solution of boron tribromide in dichloromethane. This method is highly efficient for the preparative scale synthesis of catechols of both natural and synthetic estrogens.

16α-Hydroxyestrone-[2,3,4-13C3] - …

AB - A method for the synthesis of 2-hydroxyestrone/estradiol, 4-hydroxyestrone/estradiol, 3′-hydroxydiethylstilbestrol, 3′-hydroxyhexestrol, and 3′-hydroxydienestrol is reported, in which 2-iodoxybenzoic acid (IBX) and the corresponding phenolic estrogen are reacted. Treatment of the natural estrogens, estrone/estradiol, with stoichiometric amounts of IBX in dimethylformamide initially yielded a mixture of estrone/estradiol-2,3- and -3,4-quinones, which were reduced in situ to the corresponding catechols by treatment with a 1 M aqueous solution of ascorbic acid. Chromatographic separation of the reaction products afforded 2- and 4-hydroxyestrone/estradiol in good overall yields (79%). In the case of the synthetic estrogens containing two identical phenolic rings, protection of one ring is a prerequisite for the synthesis of the monocatechol. Thus, diethylstilbestrol and dienestrol were protected at one phenol ring as their methyl ethers. The resulting monophenols were treated with stoichiometric amounts of IBX for 1 h, followed by treatment with 1 M aqueous ascorbic acid to obtain the corresponding catechols in more than 70% yield. Furthermore, the catechol of diethylstilbestrol, protected at one ring, was reduced by catalytic hydrogenation at the C3-C4 double bond to obtain 3′-hydroxyhexestrol in 90% yield. Removal of the protected methoxy groups of the synthetic estrogen catechols was carried out by treatment with a 1 M solution of boron tribromide in dichloromethane. This method is highly efficient for the preparative scale synthesis of catechols of both natural and synthetic estrogens.

catechols of natural and synthetic estrogens by ..

Clinically speaking, we find it very useful (and exciting) to pair the major genes of estrogen metabolism, side-by side with the actual molecular products of the enzymes.

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