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F8384

Sigma-Aldrich

Flavin adenine dinucleotide disodium salt hydrate

suitable for cell culture, BioReagent

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C27H31N9Na2O15P2 · xH2O
CAS Number:
Molecular Weight:
829.51 (anhydrous basis)
Beilstein:
5326842
MDL number:
UNSPSC Code:
12352207
PubChem Substance ID:
NACRES:
NA.75
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biological source

bovine milk

product line

BioReagent

Assay

≥95%

form

powder

technique(s)

cell culture | mammalian: suitable

solubility

water: 50 mg/mL, clear

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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1 of 4

This Item
706418C112852376906
assay

97%

assay

97%

assay

98%

assay

98%

Quality Level

100

Quality Level

100

Quality Level

200

Quality Level

100

form

powder

form

powder

form

liquid

form

solid

mp

146-151 °C

mp

170-175 °C

mp

19 °C (lit.)

mp

122-124 °C (lit.)

functional group

carboxylic acid

functional group

carboxylic acid, hydroxyl, phenyl

functional group

-

functional group

carboxylic acid, hydroxyl, phenyl

General description

Flavin adenine dinucleotide (FAD) is a redox cofactor of flavoproteins, such as cytochrome-b5 reductase enzyme.[1] With the help of nicotinamide adenine dinucleotide phosphate (NADPH), FAD can be reduced to form FADH2.[2]

Application

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.
Flavin adenine dinucleotide disodium salt hydrate has been used as a component in the extraction buffer for plant tissue extraction.[3] It has also been used to study its effects on infarct areas of middle cerebral artery occlusion (MCAO) induced mice.[4]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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    Christiane Kiske et al.
    Journal of agricultural and food chemistry, 67(4), 1187-1196 (2019-01-04)
    The enantiomers of a homologous series (C6-C10) of 2-mercapto-4-alkanones were obtained by lipase-catalyzed kinetic resolution of the corresponding racemic 2-acetylthio-4-alkanones. Their configurations were assigned via vibrational circular dichroism and 1H NMR anisotropy based methods. Odor thresholds and odor qualities were
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    Chemical research in toxicology, 15(10), 1309-1317 (2002-10-22)
    Chemically reactive species formed from the metabolism of carboxylic acid-containing compounds have been proposed as mediators of their toxic side-effects. Two alternative metabolic pathways known to be involved in the generation of reactive acylating metabolites of carboxylic acids are acyl
    D Ahmad et al.
    Chirality, 6(5), 365-371 (1994-01-01)
    The significance of disturbances of lipid metabolism caused by xenobiotic acyl-CoAs as possible causes of peroxisomal proliferation has been studied with the enantiomers of 2-phenylpropionic acid (2-PPA), the (R)-enantiomer of which is converted to the acyl-CoA in rats while its
    A J Hutt et al.
    Chirality, 5(8), 596-601 (1993-01-01)
    The metabolism of (R,S)-ibuprofen has been investigated in 24 microbial cultures. Of these Cunninghamella elegans, Mucor hiemalis, and Verticillium lecanii catalyzed the oxidation of the drug to 2-[4-(2-hydroxy-2-methylpropyl)phenyl]propionic acid, a known mammalian metabolite. The extent of metabolism was greatest with
    D K Bhattacharyya et al.
    The Journal of biological chemistry, 271(4), 2179-2184 (1996-01-26)
    Examination of the crystal structure of the ovine prostaglandin endoperoxide synthase-1 (PGHS-1)/S- flurbiprofen complex (Picot, D., Loll, P.J., and Garavito, R.M. (1994) Nature 367, 243-2491) suggests (a) that the carboxyl group of arachidonic acid interacts with the arginino group of

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