6beta-Hydroxydexamethasone

Base Information

• Chemical Name: 6beta-Hydroxydexamethasone
• CAS No.: 55879-47-5
• Molecular Formula: C₂₂H₂₉FO₆
• Molecular Weight: 408.467
• UNII: 017VSH97RJ
• DSSTox Substance ID: DTXSID10204471
• Nikkaji Number: J819.900K
• Mol file: 55879-47-5.mol

Synonyms:6 beta-hydroxydexamethasone;6-BHDM;6-hydroxydexamethasone

Chemical Property of 6beta-Hydroxydexamethasone

Chemical Property:

• Vapor Pressure: 1.34E-17mmHg at 25°C
• Melting Point: 259-262°C
• Boiling Point: 613.2°C at 760 mmHg
• PKA: 12.06±0.70(Predicted)
• Flash Point: 324.6°C
• PSA: 115.06000
• Density: 1.38g/cm³
• LogP: 0.86650
• Storage Temp.: -20°C Freezer
• Solubility.: Dioxane (Very Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 408.19481680
• Heavy Atom Count: 29
• Complexity: 837

Purity/Quality:

97% ^*data from raw suppliers

6β-HydroxyDexamethasone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)CO)O)C)O)F)C)O
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3C[C@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)O
• Description: 6β-hydroxy Dexamethasone is a metabolite of dexamethasone (Item Nos. 11015 | 20340) that is more hydrophilic than the parent compound. Dexamethasone is metabolized by CYP3A4; therefore, quantification of the dexamethasone metabolites, 6α- and 6β-hydroxy dexamethasone, can be used to determine CYP3A4 enzyme activity in humans. The formation of 6-hydroxy dexamethasone metabolites is species-specific, with hamsters producing the highest amount. In rats, dexamethasone hydroxylation is sex-specific, with male rats producing metabolites in similar ratios to humans and female rats producing fewer hydroxylated metabolites than male rats.
• Uses: The hydrophilic metabolite of Dexamethasone (D298800).

Technology Process of 6beta-Hydroxydexamethasone

There total 2 articles about 6beta-Hydroxydexamethasone 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: 37.0%

dexamethasone (50-02-2) → 11-Dehydrodexamethasone + C22H29FO6 + C22H27FO6 + 6alpha-Hydroxydexamethasone (24703-12-6,55879-47-5)

Guidance literature:

With Bacillus megaterium DSM₃₁₉ CYP₁₀₆A₁; In aq. phosphate buffer; for 24h; pH=7.4; Enzymatic reaction;

DOI:10.1016/j.febslet.2015.07.011

Reference yield:

betamethasone dipropionate (5593-20-4) → betamethasone (378-44-9) + Betamethasone propionate (5534-13-4) + 6β-hydroxybetamethasone (24703-00-2,24703-12-6,55879-47-5) + 6β-hydroxybetamethasone 17-propionate (78144-00-0,91677-33-7)

Guidance literature:

With phosphate buffer; air; plasma of 20 d pregnant Sprague-Dawley rat; at 37 ℃; for 1h; Product distribution; metabolism with tissues (plasma, liver, brain, placenta) from mothers and fetuses of Sprague-Dawley rats sacrificed on day 20 of pregnancy and mice on day 17 of pregnancy, further in vivo;

DOI:10.1016/S0039-128X(81)90348-2

upstream raw materials:

betamethasone dipropionate

dexamethasone

Refernces

• 1、 Nakano, Masayuki,Nishiuchi, Masanori,Takeuchi, Masaharu,Yamada, Hideo. "CORRELATION BETWEEN METABOLISM OF BETAMETHASONE 17,21-DIPROPIONATE AND ADRENAL HYPERTROPHY IN RAT FETUSES". . p. 511 - 526. Retrieved 2007/10/02.