Biotin hydrazide

Base Information

• Chemical Name: Biotin hydrazide
• CAS No.: 66640-86-6
• Molecular Formula: C10H18N4O2S
• Molecular Weight: 258.345
• Hs Code.: 29349990
• UNII: BD4VQ48JNV
• DSSTox Substance ID: DTXSID50985217
• Nikkaji Number: J851.206J
• Wikipedia: Biotin hydrazide
• Wikidata: Q25099619
• ChEMBL ID: CHEMBL4458159
• Mol file: 66640-86-6.mol

Synonyms:biotin hydrazide

Chemical Property of Biotin hydrazide

Chemical Property:

• Appearance/Colour: white or slightly yellow powder
• Vapor Pressure: 6.21E-16mmHg at 25°C
• Melting Point: 245-247 °C
• Refractive Index: 1.553
• Boiling Point: 633.1 °C at 760 mmHg
• PKA: 13.25±0.35(Predicted)
• Flash Point: 336.7 °C
• PSA: 121.55000
• Density: 1.243 g/cm³
• LogP: 1.45090
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ≤20 mg/mL
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 258.11504700
• Heavy Atom Count: 17
• Complexity: 313

Purity/Quality:

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

Biotin hydrazide ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C(C(S1)CCCCC(=O)NN)NC(=O)N2
• Isomeric SMILES: C1[C@H]2[C@@H]([C@@H](S1)CCCCC(=O)NN)NC(=O)N2
• Description: Biotin hydrazide is a biotinyl derivative used to label surface functional groups, antibodies, lectins, sugars, nucleic acids, or molecules with free carboxylic or keto groups. Biotin hydrazide is used as a probe for determining protein carbonylation, an irreversible posttranslational modification resulting from the actions of reactive oxygen species or lipid oxidation products. The reaction of this probe is direct and does not require catalysts or reducing agents.
• Uses: aldehyde reactive biotinylation reagent (+)-Biotin hydrazide has been used:the modification of alginatefor the labelling of mitochondrial proteins from non-muscle tissues as a component of glycoprotein staining solutionin periodic acid-biotin-hydrazide (PABH) assay for mucinsfor labeling surface functional groups, biologically active molecules such as antibodies, lectins, sugars, nucleic acids or molecules with free carboxylic or keto groups.for coupling to glycoproteins through the carbohydrate by hydrazone formation Biotin Hydrazide is a carbohydrate reactive biotinylation reagent used predominately for labeling monoclonal antibodies, unpaired cytosine residues in nucleic acids and glycoproteins.

Technology Process of Biotin hydrazide

There total 3 articles about Biotin hydrazide 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: 100.0%

biotin methyl ester (608-16-2) → biotin hydrazide (66640-86-6,1214641-84-5)

Guidance literature:

With hydrazine; In methanol; at 20 ℃;

DOI:10.1080/14756366.2021.2013832

Reference yield: 100.0%

biotin chloride (91853-90-6) → biotin hydrazide (66640-86-6,1214641-84-5)

Guidance literature:

With hydrazine;

DOI:10.1021/bc9005656

Reference yield:

biotin (58-85-5,22879-79-4) → biotin hydrazide (66640-86-6,1214641-84-5)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / methanol

2: hydrazine hydrate / Heating

With thionyl chloride; hydrazine hydrate; In methanol;

DOI:10.1016/j.bmcl.2014.08.030

upstream raw materials:

biotin methyl ester

biotin chloride

biotin

Downstream raw materials:

C₉₁H₁₀₃N₅O₂₅S₃

C₆₆H₈₅N₅O₁₉S₃

2,7-bis(hexahydro-2-oxo-1H-thieno<3,4-d>imidazole-4-pentanamido)-1,2,3,6,7,8-hexahydroisoindolo<5,6-f>isoindole-1,3,6,8-tetraone

Refernces

• 1、 Tian, Dan-mei,Qiao, Jia,Bao, Yu-zhou,Liu, Jie,Zhang, Xiao-kun,Sun, Xue-long,Zhang, You-wei,Yao, Xin-sheng,Tang, Jin-shan. "Design and synthesis of biotinylated cardiac glycosides for probing Nur77 protein inducting pathway". supporting information. p. 707 - 712. Retrieved 2019/01/22.
• 2、 Tieu, William,Jarrad, Angie M.,Paparella, Ashleigh S.,Keeling, Kelly A.,Soares Da Costa, Tatiana P.,Wallace, John C.,Booker, Grant W.,Polyak, Steven W.,Abell, Andrew D.. "Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase". supporting information. p. 4689 - 4693. Retrieved 2015/01/09.