6706-15-6

Basic information

• Product Name: N1'-carboxybiotin
• Synonyms: N1'-carboxybiotin
• CAS NO: 6706-15-6
• Molecular Formula: C₁₁H₁₆N₂O₅S
• Molecular Weight: 288.32014
• Mol File: 6706-15-6.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.441g/cm³
• Refractive Index: 1.587
• CAS DataBase Reference: N1'-carboxybiotin(CAS DataBase Reference)
• NIST Chemistry Reference: N1'-carboxybiotin(6706-15-6)
• EPA Substance Registry System: N1'-carboxybiotin(6706-15-6)

Safety Data

• Hazardous Substances Data: 6706-15-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H16N2O5S/c14-8(15)4-2-1-3-7-9-6(5-19-7)13(11(17)18)10(16)12-9/h6-7,9H,1-5H2,(H,12,16)(H,14,15)(H,17,18)/t6-,7-,9-/m0/s1

Upstream product

• 144-55-8 sodium hydrogencarbonate 
• 58-85-5 biotin 

Downstream Products

• 58-85-5 biotin 

Relevant articles and documents

Mechanisms of Decarboxylation of Carboxybiotin

Carboxylation is decarboxylated by two different mechanisms at low pH, where the N 1' carboxyl is protonated (pK 4.25 at 2 deg C) and at high pH where it is ionized.The low-pH mechanism has a rate constant of 5.9 X 10-3min-1 at 2 deg C (activation energy 33 kcal/mol), while the high - pH one has a rate constant of 4.6 X 10-3min-1 at 25 deg C, with the two mechanisms showing equal rates at 25 deg C at pH 6.4.At pH 8 the D2O solvent isotope effect is 1.1 with a curved proton inventory, while at pH 3.4 the value is 1.6 with a linear proton inventory.The 13C isotope effect on decarboxylation is 1.023 at pH 8.2, but 1.012 for the lo w-pH reaction.The low-pH mechanism probably involves concerted protonation of N 1' and C - N bond cleavage, with an early transition state in which proton motion is ahead of C - N bond breaking.The high - pH mechanism has a moderately early transition state and gives the enolate as the product, with the small solvent isotope effect presumably arising from changes in the fractionation factors of protons in water hydrogen-bonded to the ureido oxygen.