Flavin adenine dinucleotide disodium salt Chemical Properties

Melting point:

>203°C (dec.)

storage temp. 

2-8°C

solubility 

Methanol (Slightly, Heated), Water (Slightly)

form 

Powder

color 

yellow to orange-brown

Water Solubility 

5 g/L

Merck 

14,4091

BRN 

5326842

Stability:

Hygroscopic

InChI

InChI=1/C27H33N9O15P2.Na.H/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);;/t14-,15+,16+,19-,20+,21+,26+;;/s3

InChIKey

PGEPWKYNISSNIQ-JQOOTDDSNA-N

SMILES

C(N1C2=CC(C)=C(C)C=C2N=C2C(NC(=O)N=C12)=O)[C@H](O)[C@H](O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@@H]1[C@H]([C@@H](O)[C@H](N2C=NC3=C(N=CN=C23)N)O1)O.[NaH] |&1:19,21,23,36,37,38,40,r|

CAS DataBase Reference

84366-81-4(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25-22

WGK Germany 

3

RTECS 

AU7470000

F 

8-10-21

HS Code 

29339900

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

Flavin adenine dinucleotide disodium salt Usage And Synthesis

Description

Flavin Adenine Dinucleotide Disodium Salt hydrate is an adenine-containing enzymatic redox cofactor. Also known as flavin cofactors and is critical electron transporter in living systems. FAD has been used as a predominant fluorophore to study unstained eosinophils, which exhibit autofluorescence compared to other leucocytes.

Chemical Properties

yellow-orange powder

Uses

The prosthetic group of certain flavoproteins including D-amino acid oxidase, glucose oxidase, glycine oxidase, fumaric hydrogenase, histaminase, and xanthine oxidase. Riboflavin kinase tumor necrosis factor receptor 1 NADPH oxidase.

Uses

Used as a redox cofactor (electron carrier) for flavoproteins including succinate dehydrogenase (complex), alpha-ketoglutarate dehydrogenase, apoptosis-inducing factor 2 (AIF-M2) , AMID), folate/FAD-dependent tRNA methyltransferase, and N-hydroxylated flavoprotein monooxygenase.

Definition

ChEBI: Flavin adenine dinucleotide disodium is a flavin nucleotide.

Application

Flavin adenine dinucleotide disodium salt is the sodium salt form of Flavin adenine dinucleotide (FAD). FAD is used by flavoproteins as redox cofactors (electron carriers), including succinate dehydrogenase (complex), α-ketoglutarate dehydrogenase, apoptosis inducing factor 2 (AIF-M2, AMID), folate/FAD-dependent tRNA methyltransferase, and N-hydroxylated flavoprotein monooxygenase. FAD is a component of the pyruvate dehydrogenase complex. Flavin adenine dinucleotide disodium salt hydrate has been used as a component of plant tissue extraction buffers.

Biological Activity

Flavin adenine dinucleotide (FAD) disodium salt is a redox cofactor, a prosthetic group of proteins, involved in several important enzymatic reactions during metabolism.

in vitro

Poly(Flavin adenine dinucleotide, FAD) characterized by an additional polymer-type redox reaction is a highly effective electrocatalyst for NADH oxidation: operating at the lowest potentials reported for NADH transducers (0.00 V, pH 7.4), poly(FAD) is characterized by the electrochemical rate constant of 1.8 ± 0.6×10 -3 cm/s, which is at the level of the NADH mass-transfer constant. Poly(FAD)-modified electrodes are characterized by the dramatically improved stability and, is the most advantageous NADH transducers for analytical chemistry.

in vivo

With Flavin adenine dinucleotide (2 mg/kg), the chlorpromazine (CPZ)-induced decrease in ventricular fibrillation threshold (VFT) is significantly cancelled. Flavin adenine dinucleotide cancels the effect of CPZ on canine heart mitochondria. After injection of Flavin adenine dinucleotide, the dogs show a transient hypotension within 10 min, then their blood pressures recover to the initial level. Flavin adenine dinucleotide also prevents mitochondrial dysfunction induced by chlorpromazine.

Purification Methods

Small quantities of FAD are purified by paper chromatography using tert-butyl alcohol/water, cutting out the main spot and eluting with water. Larger amounts can be precipitated from water as the uranyl complex by adding a slight excess of uranyl acetate to a solution at pH 6.0, dropwise and with gentle stirring. The solution is set aside overnight in the cold, and the precipitate is centrifuged off, washed with small portions of cold EtOH, then with cold peroxide-free diethyl ether. It is dried in the dark under vacuum over P2O5 at 50-60o. The uranyl complex is suspended in water, and, after adding sufficient 0.01M NaOH to adjust the pH to 7, the precipitate of uranyl hydroxide is removed by centrifugation [Huennekens & Felton Methods Enzymol 3 954 1957]. It can also be crystallised from water. It should be kept in the dark. More recently it was purified by elution from a DEAE-cellulose (Whatman DE 23) column with 0.1M phosphate buffer pH 7, and the purity was checked by TLC. [Holt & Cotton, J Am Chem Soc 109 1841 1987, Beilstein 26 III/IV 3632.]

Flavin adenine dinucleotide disodium salt(84366-81-4)Related Product Information

• Adenosine
• Ethylenediaminetetraacetic acid disodium salt
• Adenine
• Disodium nucleotide
• NAD+
• Pamidronate disodium salt
• Riboflavin 5'-Monophosphate Sodium Salt
• Clodronate disodium
• Riboflavin
• Sodium Monofluorophosphate
• 2-fa
• RIBITYL-3,4-XYLIDINE*
• LUMIFLAVINE
• FLAVIN ADENINE DINUCLEOTIDE 2NA (FAD)
• Flavoxate hydrochloride
• Purine
• Diphosphate
• 1-deaza-FAD