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Merck

F6625

Flavin adenine dinucleotide disodium salt hydrate

≥95% (HPLC), powder

Sinónimos:

FAD, FAD-Na2, Riboflavin 5′-adenosine diphosphate disodium salt, FAD-Na2

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Fórmula empírica (notación de Hill):
C27H31N9Na2O15P2 · xH2O
Número CAS:
84366-81-4
Peso molecular:
829.51 (anhydrous basis)
UNSPSC Code:
41106305
NACRES:
NA.51
PubChem Substance ID:
24894909
MDL number:
MFCD08277021
Beilstein/REAXYS Number:
5326842

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Nombre del producto

Flavin adenine dinucleotide disodium salt hydrate, ≥95% (HPLC), powder

InChI

1S/C27H33N9O15P2.2Na.H2O/c1-10-3-12-13(4-11(10)2)35(24-18(32-12)25(42)34-27(43)33-24)5-14(37)19(39)15(38)6-48-52(44,45)51-53(46,47)49-7-16-20(40)21(41)26(50-16)36-9-31-17-22(28)29-8-30-23(17)36;;;/h3-4,8-9,14-16,19-21,26,37-41H,5-7H2,1-2H3,(H,44,45)(H,46,47)(H2,28,29,30)(H,34,42,43);;;1H2/q;2*+1;/p-2/t14-,15+,16+,19-,20+,21+,26+;;;/m0.../s1

SMILES string

[Na+].[Na+].[H]O[H].Cc1cc2N=C3C(=O)NC(=O)N=C3N(C[C@H](O)[C@H](O)[C@H](O)COP([O-])(=O)OP([O-])(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6c(N)ncnc56)c2cc1C

InChI key

GXTPHHZYFMAGLX-UJXBNFGUSA-L

biological source

microbial

assay

≥95% (HPLC)

form

powder

Quality Level

200

mol wt

829.51 g/mol

color

yellow to orange-brown

solubility

H2O: soluble-50 mg/mL, clear, slightly orang to deep orange

λmax

375-377 nm
448-450 nm

fluorescence

(EmM Anhydrous 10.5 - 11.8 pH 7.0, Lambda Max 448 to 450 nm
EmM Anhydrous 8.5 - 9.5 pH 7.0, Lambda Max 375 to 377 nm)

storage temp.

−20°C

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Application

FAD is used to remove reactive oxygen species (ROS) from mammalian cells. The fluorescence mechanism of FAD is used to study energy-dependent intramitochondrial redox potential. FAD is used as a predominant fluorophore to study unstained eosinophils, which exhibit autofluorescence compared to other leucocytes.
Flavin adenine dinucleotide (FAD) is used as a redox cofactor (electron carrier) by flavoproteins including succinate dehydrogenase (complex), α-ketoglutarate dehydrogenase, apoptosis-inducing factor 2 (AIF-M2, AMID), folate/FAD-dependent tRNA methyltransferases, and N-hydroxylating flavoprotein monooxygenases. FAD is a component of the pyruvate dehydrogenase complex.

General description

Flavin adenine dinucleotide disodium salt hydrate (FAD-Na2) is an adenine-containing enzymatic redox cofactor. Also known as flavin cofactors, FAD is critical electron transporter in living systems. They catalyze several 1-2 electron redox reactions. e.g., β-oxidation of fatty acids occurs in the presence of FAD as a cofactor. FAD is one of the two active coenzymes of vitamin B12(riboflavin). FAD displays a significantly shorter excited state lifetime in aqueous solutions than its analog, flavin mononucleotide.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000526477
0000526477
0000524432
0000524432
0000521727

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Ruofan Cao et al.
Journal of biomedical optics, 25(1), 1-16 (2020-01-11)
Two-photon fluorescence lifetime imaging microscopy (FLIM) is widely used to capture autofluorescence signals from cellular components to investigate dynamic physiological changes in live cells and tissues. Among these intrinsic fluorophores, nicotinamide adenine dinucleotide (phosphate) (NAD(P)H) and flavin adenine dinucleotide (FAD)-essential
J Rösner et al.
Journal of microscopy, 264(2), 215-223 (2016-07-02)
Dynamic alterations in flavin adenine dinucleotide (FAD) fluorescence permit insight into energy metabolism-dependent changes of intramitochondrial redox potential. Monitoring FAD fluorescence in living tissue is impeded by photobleaching, restricting the length of microfluorimetric recordings. In addition, photodecomposition of these essential
Van Long Nguyen et al.
Analytical biochemistry, 594, 113616-113616 (2020-02-10)
Flavin adenine dinucleotide (FAD) is an active coenzyme of vitamin B2 involved in oxidation and reduction reactions. In this study we have developed a fully automated method for the analysis of FAD by fluorescence detection. FAD is extracted from whole
Martina Kieninger et al.
Biomolecules, 10(4) (2020-04-15)
Flavin cofactors, like flavin adenine dinucleotide (FAD), are important electron shuttles in living systems. They catalyze a wide range of one- or two-electron redox reactions. Experimental investigations include UV-vis as well as infrared spectroscopy. FAD in aqueous solution exhibits a
A N Mayeno et al.
Journal of leukocyte biology, 51(2), 172-175 (1992-02-01)
Unstained human eosinophils exhibit marked autofluorescence in comparison to other leukocytes due to a granule-associated fluorescent substance. Fluorescence spectroscopy of granule extracts reveals excitation maxima at approximately 380 and approximately 450 nm with a single emission at approximately 520, characteristic
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