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B4501

Sigma-Aldrich

Biotin

≥99% (HPLC), lyophilized powder

Synonym(s):

D-Biotin, Bios II, Coenzyme R, Vitamin B7, Vitamin H

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About This Item

Empirical Formula (Hill Notation):
C10H16N2O3S
CAS Number:
58-85-5
Molecular Weight:
244.31
Beilstein:
86838
EC Number:
200-399-3
MDL number:
MFCD00005541
UNSPSC Code:
12352201
eCl@ss:
34058011
PubChem Substance ID:
24891778
NACRES:
NA.21

biological source

synthetic (organic)

Quality Level

300

Assay

≥99% (HPLC)

form

lyophilized powder

technique(s)

HPLC: suitable

color

white to off-white

mp

231-233 °C (lit.)

solubility

ammonium hydroxide: 50 mg/mL (2 M)

storage temp.

2-8°C

SMILES string

[H][C@]12CS[C@@H](CCCCC(O)=O)[C@@]1([H])NC(=O)N2

InChI

1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1

InChI key

YBJHBAHKTGYVGT-ZKWXMUAHSA-N

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General description

Biotin is a water-soluble vitamin. Mammals depend on biotin via plant and microbial dietary sources. Biotin consists of two rings that are attached to valeric acid moiety as a side chain. One of the rings is attached to ureido group and the other ring is the tetrahydrothiophene group.

Application

Biotin may be used to elute proteins from avidin/streptavidin resins. Biotin has been used:
  • for culturing of oligodendrocytes.
  • as a vitamin supplement for the growth of Bacillus species.
  • for blocking endogenous biotin during immunohistology procedures.

Biochem/physiol Actions

Biotin is a small molecule and its presence with biologically active macromolecules does not affect the biological function of the macromolecule. The biotin-(strept)avidin system are is required for various applications. Biotin also works as a cofactor/coenzyme of carboxylating enzymes, such as pyruvate carboxylase, acetyl-CoA carboxylases 1 and 2, 3-methylcrotonyl-CoA carboxylase (MCC), and propionyl-CoA carboxylase (PCC). It catalyzes the formation of oxaloacetate from pyruvate and CO2. Biotin conjugation with avidin or streptavidin helps in linking the target molecule (antibody, nucleotide, protein A, etc.) with the labeling system (enzyme, fluorescent, chemiluminescent probes). This complex is used for many detection systems, such as immunoassays, DNA hybridization assays, immunohistochemistry, and flow cytometry. This approach is also applied for to the purification and characterization of various molecules of interest. Biotin is involved in the epigenetic regulation of genes, cell signaling, and the structure of chromatin.

Other Notes

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WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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The biotin-(strept)avidin system: principles and applications in biotechnology.
Diamandis EP and Christopoulos TK
Clinical Chemistry, 37, 625-625 (1991)
Isolation and culture of rat and mouse oligodendrocyte precursor cells.
Chen Y et al.
Nature Protocols, 2, 1044-1044 (2007)
Lone Frydelund-Larsen et al.
Experimental physiology, 92(1), 233-240 (2006-10-13)
Exercise induces a marked increase in interleukin-8 (IL-8) mRNA and protein expression within skeletal muscle fibres. Interleukin-8 belongs to a subfamily of CXC chemokines containing a Glu-Leu-Arg (ELR) motif. CXC chemokines with ELR motifs are potent angiogenic factors in vivo
Biotin: biochemical, physiological and clinical aspects
Said H M
Sub-Cellular Biochemistry, 56, 1-19 (2012)
Wei Wang et al.
The Journal of cell biology, 219(2) (2020-01-09)
Hemidesmosomes are specialized cell-matrix adhesion structures that are associated with the keratin cytoskeleton. Although the adhesion function of hemidesmosomes has been extensively studied, their role in mechanosignaling and transduction remains largely unexplored. Here, we show that keratinocytes lacking hemidesmosomal integrin
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Chromatograms

application for HPLC

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