Raloxifene 6-Glucuronide

Base Information

• Chemical Name: Raloxifene 6-Glucuronide
• CAS No.: 174264-50-7
• Molecular Formula: C₃₄H₃₅NO₁₀S
• Molecular Weight: 649.719
• Hs Code.: 29389090
• UNII: 446O3AY2S7
• Nikkaji Number: J1.215.010E
• Wikidata: Q27258722
• ChEMBL ID: CHEMBL177798
• Mol file: 174264-50-7.mol

Synonyms:Raloxifene 6-Glucuronide;174264-50-7;UNII-446O3AY2S7;446O3AY2S7;beta-D-Glucopyranosiduronic acid, 2-(4-hydroxyphenyl)-3-(4-(2-(1-piperidinyl)ethoxy)benzoyl)benzo(b)thien-6-yl;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((2-(4-hydroxyphenyl)-3-(4-(2-(piperidin-1-yl)ethoxy)benzoyl)benzo[b]thiophen-6-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid;Raloxifene-6-Glucuronide;CHEMBL177798;Raloxifene (6-Glucuronidation);AKOS040736552;CS-O-05684;HY-135581;CS-0113548;Q27258722;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(2-(4-hydroxyphenyl)-3-(4-(2-(piperidin-1-yl)ethoxy)benzoyl)benzo[b]thiophen-6-yloxy)tetrahydro-2H-pyran-2-carboxylic acid;(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[[2-(4-hydroxyphenyl)-3-[4-(2-piperidin-1-ylethoxy)benzoyl]-1-benzothiophen-6-yl]oxy]oxane-2-carboxylic acid;.BETA.-D-GLUCOPYRANOSIDURONIC ACID, 2-(4-HYDROXYPHENYL)-3-(4-(2-(1-PIPERIDINYL)ETHOXY)BENZOYL)BENZO(B)THIEN-6-YL

Chemical Property of Raloxifene 6-Glucuronide

Chemical Property:

• Melting Point: 210-214°C (dec.)
• Refractive Index: 1.682
• PSA: 194.46000
• LogP: 3.57850
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 10
• Exact Mass: 649.19816749
• Heavy Atom Count: 46
• Complexity: 1010

Purity/Quality:

98%min ^*data from raw suppliers

Raloxifene 6-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)OC5C(C(C(C(O5)C(=O)O)O)O)O)C6=CC=C(C=C6)O
• Isomeric SMILES: C1CCN(CC1)CCOC2=CC=C(C=C2)C(=O)C3=C(SC4=C3C=CC(=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)C(=O)O)O)O)O)C6=CC=C(C=C6)O
• Uses: A metabolite of Raloxifene, a nonsteroidal estrogen receptor mixed agonist/antagonist Raloxifene 6'-glucuronide can be used as a labelled metabolite of Raloxifene, a nonsteroidal estrogen receptor mixed agonist/antagonist Raloxifene 6'-glucuronide can be intended for use as an internal standard for the quantification of Raloxifene by GC- or LC-mass spectrometry.

Technology Process of Raloxifene 6-Glucuronide

There total 3 articles about Raloxifene 6-Glucuronide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2S,3S,4S,5R,6S)-6-{2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid → 4-[6-Hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]benzothien-2-yl]phenyl-D-glucopyranosiduronicacid (174264-50-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Yield given;

DOI:10.1016/S0960-894X(97)00142-X

Reference yield:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester (174264-49-4) → 4-[6-Hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]benzothien-2-yl]phenyl-D-glucopyranosiduronicacid (174264-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH / dioxane / 60 °C

2: tetrabutylammonium fluoride / tetrahydrofuran

With lithium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1016/S0960-894X(97)00142-X

Reference yield:

Raloxifen (84449-90-1) + UDP-glucuronic acid (1245697-26-0,106864-00-0,14520-48-0,30329-32-9,3545-73-1,5918-40-1) → raloxifene-6-glucuronide (174264-50-7)

Guidance literature:

With human UDP-glucuronosyltransferase 1A₉; magnesium chloride; alamethicin; D-Glucaro-1,4-lacton; at 37 ℃; pH=7.4; Kinetics; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1007/s11095-012-0666-z

upstream raw materials:

(2S,3S,4S,5R,6S)-3,4,5-Triacetoxy-6-{2-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzoyl]-benzo[b]thiophen-6-yloxy}-tetrahydro-pyran-2-carboxylic acid methyl ester

Raloxifen

UDP-glucuronic acid