| Identification | Back Directory | [Name]
D-DESTHIOBIOTIN | [CAS]
533-48-2 | [Synonyms]
CAS_533-48-2
Dethiobiotin
DESTHIOBIOTIN
D-DESTHIOBIOTIN
DL-DESTHIOBIOTIN
Desulfurized biotin
D-DESTHIOBIOTIN USP/EP/BP
d-Desthiobiotin >=98% (TLC)
5-METHYL-2-OXO-4-IMIDAZOLINE-CAPROIC ACID
5-Methyl-2-oxo-4-imidazolidinehexanoic acid
6-(5-methyl-2-oxo-imidazolidin-4-yl)hexanoic acid
(4R)-2-Oxo-5α-methylimidazolidine-4α-hexanoic acid
(4R-cis)-5-methyl-2-oxoimidazolidine-4-hexanoic acid
4-Imidazolidinehexanoic acid, 5-methyl-2-oxo-, (4R,5S)-
[4R,5S,(+)]-5-Methyl-2-oxo-4-imidazolidinehexanoic acid
6-((4R,5S)-5-Methyl-2-oxoiMidazolidin-4-yl)hexanoic acid | [EINECS(EC#)]
208-566-2 | [Molecular Formula]
C10H18N2O3 | [MDL Number]
MFCD00213804 | [MOL File]
533-48-2.mol | [Molecular Weight]
214.26 |
| Chemical Properties | Back Directory | [Melting point ]
156-158° | [alpha ]
D21 +10.7° (c = 2) | [Boiling point ]
354.4°C (rough estimate) | [density ]
1.1404 (rough estimate) | [refractive index ]
1.4550 (estimate) | [storage temp. ]
2-8°C
| [solubility ]
Aqueous Base (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
4.77±0.10(Predicted) | [color ]
White to Off-White | [InChI]
InChI=1S/C10H18N2O3/c1-7-8(12-10(15)11-7)5-3-2-4-6-9(13)14/h7-8H,2-6H2,1H3,(H,13,14)(H2,11,12,15)/t7-,8+/m0/s1 | [InChIKey]
AUTOLBMXDDTRRT-UHFFFAOYSA-N | [SMILES]
C1(=O)N[C@@H](C)[C@@H](CCCCCC(O)=O)N1 |
| Hazard Information | Back Directory | [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. | [Definition]
ChEBI: (4R,5S)-dethiobiotin is the (4R,5S)-isomer of dethiobiotin. It is a conjugate acid of a (4R,5S)-dethiobiotin(1-). It is an enantiomer of a (4S,5R)-dethiobiotin. | [Biological Activity]
Desthiobiotin is a non-sulfur containing biotin derivative th at binds less strongly to biotin-binding proteins and is easily dislocated by biotin. | [IC 50]
Microbial Metabolite; Human Endogenous Metabolite | [storage]
Store at 2-8°C | [Purification Methods]
Dissolve desthiobiotin in 0.5% Na2CO3, filter, acidify with HCl to Congo Red, concentrate to a small volume (2-3 mL) to give fine needles, filter it off and recrystallise it twice from H2O, m 157-158o. It also crystallises from 95% EtOH. The methyl ester crystallises from MeOH and sublimes at 100o/high vacuum, m 69-70o, [] D +2.6o (c 2, CHCl3). [Melville et al. Science 98 497 1943, J Am Chem Soc 66 1422 1944, Beilstein 25 III/IV 1543.] |
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