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15087-02-2

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15087-02-2 Usage

Uses

β-Estradiol 17-(β-D-glucuronide) sodium salt has been used as a standard to determine the quantity of β-Estradiol 17-(β-D-glucuronide) during UDP-glucuronosyltransferase assay. It has also been used as a constituent of modified synthetic oviduct fluid (m-SOF) for maturation of bovine cumulus oocyte complexes (COC).

Biological Activity

km: 75 μmestradiol 17-(β-d-glucuronide) is a substrate of the multidrug resistance protein 2 (mrp2).mrp2 is a member of the superfamily of atp-binding cassette (abc) transporters, which transport various molecules across extra- and intra-cellular membranes. mrp2 is a member of the mrp subfamily that is involved in multi-drug resistance. mrp2 is expressed in the apical side of the hepatocyte and functions in biliary transport.

Biochem/physiol Actions

Estradiol 17-(β-D-glucuronide) (E217G) is a naturally occurring conjugated estrogen. It is formed in the liver and later excreted in bile. Increased concentrations of E217G leads to the development of cholestasis during the later stages of pregnancy, a condition which occurs with high frequency in the Dubin-Johnson syndrome.

in vitro

estradiol 17-(β-d-glucuronide) was identified as an atp dependent, osmotically sensitive transport of the naturally occurring conjugated estrogen, and was found to be readily demonstrable in plasma membrane vesicles from populations of mrp-transfected hela cells. the involvement of mrp was confirmed by demonstrating that transport was completely inhibited by a monoclonal antibody specific for an intracellular conformational epitope of the protein [1].

in vivo

animal study found that estradiol 17-(β-d-glucuronide) could induce an immediate, profound and reversible inhibition of bile flow after its i.v. administration to the rat. moreover, the cholestasis degree was found to be dose-dependent in the range of 8.5 to 21 mumol/kg i.v. a dose of 11 mumol/kg i.v. was able to inhibit bile flow and bile acid secretory rate 65 to 70% within 15 to 30 min of its administration. in addition, the bile flow and bile acid secretion returned to near control levels within 3 hours [2].

references

[1] loe, d. w.,almquist, k.c.,cole, s.p., et al. atp-dependent 17β-estradiol 17-(β-d-glucuronide) transport by multidrug resistance protein (mrp). inhibition by cholestatic steroids. the journal of biological chemisty 271(16), 9683-9689 (1996).[2] meyers m, slikker w, pascoe g, vore m. characterization of cholestasis induced by estradiol-17 beta-d-glucuronide in the rat. j pharmacol exp ther. 1980 jul;214(1):87-93.

Check Digit Verification of cas no

The CAS Registry Mumber 15087-02-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,0,8 and 7 respectively; the second part has 2 digits, 0 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 15087-02:
(7*1)+(6*5)+(5*0)+(4*8)+(3*7)+(2*0)+(1*2)=92
92 % 10 = 2
So 15087-02-2 is a valid CAS Registry Number.
InChI:InChI=1/C24H32O8.Na/c1-24-9-8-14-13-5-3-12(25)10-11(13)2-4-15(14)16(24)6-7-17(24)31-23-20(28)18(26)19(27)21(32-23)22(29)30;/h3,5,10,14-21,23,25-28H,2,4,6-9H2,1H3,(H,29,30);

15087-02-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name sodium,3,4,5-trihydroxy-6-[(3-hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl)oxy]oxane-2-carboxylic acid

1.2 Other means of identification

Product number -
Other names -

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

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More Details:15087-02-2 SDS

15087-02-2Downstream Products

15087-02-2Relevant articles and documents

Novel and Efficient Synthesis of Estriol and its 16-Glucuronide via 2,4,16α-Tribromoestrone

Numazawa, Mitsuteru,Nagaoka, Masao,Tsuji, Masachika,Osawa, Yoshio

, p. 121 - 125 (2007/10/02)

A novel synthesis of estra-1,3,5(10)-triene-3,16α,17β-triol (5), sodium 3,17β-dihydroxyestra-1,3,5(10)-trien-16α-yl-β-D-glucopyranosuronate (12b) aand sodium 3-hydroxyestra-1,3,5(10)-trien-17β-yl-β-D-glucopyranosuronate (10b) is described. 2,4,16α-Tribromo-3-hydroxyestra-1,3,5(10)-trien-17-one (2a) was efficiently synthesized in one step with quantitative yield by bromination of 3-hydroxyestra-1,3,5(10)-trien-17-one (1) with cupric bromide.Treatment of (2a) with NaOH in aqueous pyridine under the controlled conditions gave the 16α-hydroxy-17-ketone (4a) without ketol rearrangement.The ketol (4a) was converted in quantitative yield into the triol (5) via a sodium borohydride reduction in the presence of palladium chloride.Reaction of (4a) with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucopyranosuronate using silver carbonate as a catalyst yielded the 16-monoglucuronide acetate methyl ester (11).The reductive removal of the bromines of (11) with sodium borohydride followed by NaOH hydrolysis gave the glucuronide (12b).A direct glucuronidation of 2,4-dibromoestra-1,3,5(10)-triene-3,17β-diol (8) and a subsequent hydrolysis of the 17-glucuronide (9) gave the glucuronide (10b).

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