(3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol

Base Information

• Chemical Name: (3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol
• CAS No.: 1246302-80-6
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 409.605
• DSSTox Substance ID: DTXSID70390607
• Wikidata: Q82187495
• Mol file: 1246302-80-6.mol

Synonyms:1246302-80-6;cholest-5-en-3beta,4beta-diol(d7);4|A-Hydroxy Cholesterol-d7;(3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol;4-Hydroxy Cholesterol-d7;AC1MMZCW;4beta-hydroxy-cholesterol(d7);cis-5-Cholestene-3,4-diol-d7;d7-4beta-hydroxycholesterol;4?-Hydroxy Cholesterol-d7;4-?-Hydroxy Cholesterol-D7;4beta-Hydroxy Cholesterol-d7;4 beta -Hydroxy Cholesterol-d7;DTXSID70390607;LMST01010003;CS-T-55875;HY-124265S;PD086685;CS-0202330;J-010889

Chemical Property of (3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol

Chemical Property:

• Melting Point: 154-159°C
• PSA: 40.46000
• LogP: 6.35950
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Heated)
• XLogP3: 7.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 409.393717927
• Heavy Atom Count: 29
• Complexity: 624

Purity/Quality:

98%,99%, ^*data from raw suppliers

4β-Hydroxy Cholesterol-d7 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4O)O)C)C
• Isomeric SMILES: [2H]C([2H])([2H])C([2H])(CCC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H]([C@@H]4O)O)C)C)C([2H])([2H])[2H]
• Uses: 4β-Hydroxy Cholesterol-d7 is a labelled metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential and also a new endogenous CYP3A marker. 4β-Hydroxy Cholesterol-d7 is a labelled metabolite of Cholesterol. It is formed from Cholesterol by the drug-metabolizing enzyme cytochrome P 450 3A4. A potential ligand for the nuclear receptor LXR and also a new endogenous CYP3A marker. 4β-hydroxycholesterol-d7 has been used: as an internal standard to spike plasma samples ultra-high-pressure liquid,chromatography–tandem mass spectrometry (UHPLC-MS/MS) analysisto spike serum samples for mass spectrometry measurementsas an internal standard for the quantification of human colon biopsies samples using HPLC-MS

Technology Process of (3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol

There total 2 articles about (3S,4R,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6,7,7,7-tetradeuterio-6-(trideuteriomethyl)heptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,4-diol 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:

C29H41(2)H7O3 (1363529-54-7) → C27H39(2)H7O2 (1246302-80-6)

Guidance literature:

With methanol; potassium hydroxide; at 20 ℃; for 2.5h;

DOI:10.1002/jlcr.1952

Reference yield:

(25,26,26,26,27,27,27-2H7)-cholesterol (83199-47-7) → C27H39(2)H7O2 (1246302-80-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: bromine / chloroform / 0.5 h / -10 °C / Inert atmosphere; Darkness

1.2: 17 h / -10 - 20 °C / Inert atmosphere; Darkness

2.1: methanol; potassium hydroxide / 2.5 h / 20 °C

With methanol; bromine; potassium hydroxide; In chloroform;

DOI:10.1002/jlcr.1952

upstream raw materials:

C₂₉H₄₁⁽²⁾H₇O₃

(25,26,26,26,27,27,27-²H₇)-cholesterol

Refernces