Dethiobiotin

Base Information

• Chemical Name: Dethiobiotin
• CAS No.: 533-48-2
• Deprecated CAS: 17866-65-8,29117-52-0
• Molecular Formula: C10H18 N2 O3
• Molecular Weight: 214.265
• Hs Code.: 2933990090
• European Community (EC) Number: 208-566-2
• UNII: 71U5JB52KS,I64P0B487B
• DSSTox Substance ID: DTXSID50876136
• Nikkaji Number: J9.406D
• Wikidata: Q27094671
• Metabolomics Workbench ID: 38369
• ChEMBL ID: CHEMBL1232381
• Mol file: 533-48-2.mol

Synonyms:desthiobiotin;desthiobiotin, (4R-cis)-isomer;desthiobiotin, (cis)-(+-)-isomer;dethiobiotin

Chemical Property of Dethiobiotin

Chemical Property:

• Vapor Pressure: 2.18E-10mmHg at 25°C
• Melting Point: 156-158°
• Refractive Index: 1.4550 (estimate)
• Boiling Point: 476.4°Cat760mmHg
• PKA: 4.77±0.10(Predicted)
• Flash Point: 241.9°C
• PSA: 78.43000
• Density: 1.095g/cm³
• LogP: 1.74900
• Storage Temp.: 2-8°C
• Solubility.: Aqueous Base (Slightly), DMSO (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 214.13174244
• Heavy Atom Count: 15
• Complexity: 243

Purity/Quality:

99%, ^*data from raw suppliers

D-Desthiobiotin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(NC(=O)N1)CCCCCC(=O)O
• Isomeric SMILES: C[C@H]1[C@H](NC(=O)N1)CCCCCC(=O)O
• Uses: D-Desthiobiotin is an analogue of Biotin (B389040) that binds less tightly to biotin-binding proteins such as Avidin and is easily displaced by Biotin.

Technology Process of Dethiobiotin

There total 40 articles about Dethiobiotin 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: 90.0%

dl-dethiobiotinol → dl-dethiobiotine (533-48-2,636-20-4,15720-25-9,34879-36-2,41625-34-7)

Guidance literature:

With oxygen; sodium hydrogencarbonate; platinum(IV) oxide; for 48h;

Reference yield:

6-(5-methyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-hexanoic acid (4793-80-0) → (+/-)-6-(5t-methyl-2-oxo-imidazolidin-4r-yl)-hexanoic acid (533-48-2,636-20-4,15720-25-9,34879-36-2,41625-34-7) + dl-dethiobiotine (533-48-2,636-20-4,15720-25-9,34879-36-2,41625-34-7)

Guidance literature:

With nickel; sodium carbonate; at 100 ℃; under 117681 Torr; Hydrogenation_.pH ca. 7.5;

DOI:10.1002/hlca.660280174 DOI:10.1002/hlca.19460290402 DOI:10.1021/ja01218a021 DOI:10.1021/ja01209a036

Reference yield:

6-(5-methyl-2-oxo-2,3-dihydro-1H-imidazol-4-yl)-hexanoic acid (4793-80-0) → (+/-)-6-(5t-methyl-2-oxo-imidazolidin-4r-yl)-hexanoic acid (533-48-2,636-20-4,15720-25-9,34879-36-2,41625-34-7) + dl-dethiobiotine (533-48-2,636-20-4,15720-25-9,34879-36-2,41625-34-7)

Guidance literature:

With nickel; sodium carbonate; at 100 ℃; under 117681 Torr; Hydrogenation_.pH ca. 7.5;

DOI:10.1002/hlca.660280174 DOI:10.1002/hlca.19460290402 DOI:10.1021/ja01218a021 DOI:10.1021/ja01209a036

upstream raw materials:

carbon dioxide

biotin

sodium hydrogencarbonate

phosgene

Downstream raw materials:

NHS-desthiobiotin

D-biotin

Refernces

• 1、 Melville. "-". . p. 1422. Retrieved 1944.
• 2、 Melville et al.. "-". . p. 497. Retrieved 1943.
• 3、 Guillerm et al.. "-". . p. 3776. Retrieved 1977.
• 4、 Dey, Sanghamitra,Lane, James M.,Lee, Richard E.,Rubin, Eric J.,Sacchettini, James C.. "Structural characterization of the mycobacterium tuberculosis biotin biosynthesis enzymes 7,8-diaminopelargonic acid synthase and dethiobiotin synthetase". . p. 6746 - 6760. Retrieved 2011/04/26.