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MilliporeSigma

F6625

Sigma-Aldrich

Flavin adenine dinucleotide disodium salt hydrate

≥95% (HPLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H31N9Na2O15P2 · xH2O
CAS Number:
84366-81-4
Molecular Weight:
829.51 (anhydrous basis)
Beilstein/REAXYS Number:
5326842
MDL number:
MFCD08277021
UNSPSC Code:
41106305
PubChem Substance ID:
24894909
NACRES:
NA.51

Key Documents

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biological source

microbial

Quality Level

200

assay

≥95% (HPLC)

form

powder

mol wt

829.51 g/mol

color

yellow to orange-brown

solubility

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

λmax

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

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

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

InChI key

GXTPHHZYFMAGLX-UJXBNFGUSA-L

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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.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCH0808
SLCH2518
SLCG2996
SLCD4326
SLCD6122

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João L Lagarto et al.
Sensors (Basel, Switzerland), 19(12) (2019-06-16)
Single Photon Avalanche Diode (SPAD) arrays are increasingly exploited and have demonstrated potential in biochemical and biomedical research, both for imaging and single-point spectroscopy applications. In this study, we explore the application of SPADs together with fiber-optic-based delivery and collection
Quan Liu et al.
Medical physics, 36(10), 4819-4829 (2009-11-26)
Hemoglobin concentration and oxygenation in tissue are important biomarkers that are useful in both research and clinical diagnostics of a wide variety of diseases such as cancer. The authors aim to develop simple ratiometric method based on the spectral filtering
Irina O Vvedenskaya et al.
Molecular cell, 70(3), 553-564 (2018-04-24)
Nucleoside-containing metabolites such as NAD+ can be incorporated as 5' caps on RNA by serving as non-canonical initiating nucleotides (NCINs) for transcription initiation by RNA polymerase (RNAP). Here, we report CapZyme-seq, a high-throughput-sequencing method that employs NCIN-decapping enzymes NudC and
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
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
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