β-Nicotinamide Adenine Dinucleotide CAS 53-84-9 is a fundamental biological coenzyme found in all living cells. It is a dinucleotide consisting of two nucleotides joined through their phosphate groups: one nucleotide contains an adenine base (adenosine monophosphate, AMP), and the other contains a nicotinamide base (nicotinamide mononucleotide, NMN). The "β" denotes the stereospecific configuration of the glycosidic bond in the nicotinamide riboside moiety, which is essential for biological activity. NAD+ exists in two interconvertible redox states: the oxidized form (NAD+) and the reduced form (NADH).β-Nicotinamide Adenine Dinucleotide is the universal and indispensable redox coenzyme central to cellular metabolism and signaling. It is not merely a supplement but the active, endpoint molecule itself, serving as the direct co-substrate for hundreds of enzymes that govern energy production, genomic repair, and epigenetic regulation.
Nome :
β-Nicotinamide adenine dinucleotideNº CAS. :
53-84-9MF :
C₂₁H₂₇N₇O₁₄P₂MW :
663.43Pureza :
98%Aparência :
White to light yellow, hygroscopic powder.Condição de armazenamento :
Store at -20°C or below, desiccated, and protected from light.Chemical Properties
IUPAC Name: 1-[(2R,3R,4S,5R)-5-[({({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxyphosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-3-carbamoylpyridin-1-ium
Common Names: NAD; Coenzyme I; Diphosphopyridine nucleotide (DPN, obsolete)
Chemical Formula: C₂₁H₂₇N₇O₁₄P₂
Molecular Weight: 663.43 g/mol
Structure: Adenine-ribose-phosphate-phosphate-ribose-nicotinamide. The key functional group is the pyridinium ring on the nicotinamide, which accepts a hydride ion (H⁻) during reduction to form NADH.
Appearance: White to light yellow, hygroscopic powder.
Solubility: Freely soluble in water. Practically insoluble in most organic solvents like acetone or ethanol.
Stability: Highly unstable in solution. Degraded by heat, light, and extremes of pH. In neutral aqueous solutions, it undergoes gradual hydrolysis, especially at higher temperatures. The solid form is more stable but remains hygroscopic and sensitive to long-term storage.
Absorption Maxima:
NAD+: 259 nm (characteristic of adenine)
NADH: 259 nm and 340 nm (the 340 nm peak is used to spectrophotometrically monitor reduction reactions).
Redox Potential: The NAD⁺/NADH redox couple has a standard reduction potential (E°') of -0.32 V, making it a strong biological reducing agent.
Biological Activities
NAD+ is not merely a molecule but a central redox currency and signaling substrate for the cell.
Primary Role: Redox Cofactor
Catabolism: Serves as an essential hydride (H⁻) acceptor in catabolic pathways (e.g., glycolysis, TCA cycle, fatty acid β-oxidation), becoming reduced to NADH. This NADH then donates electrons to the electron transport chain to drive ATP synthesis.
Anabolism: Acts as a hydride donor in reductive biosyntheses (e.g., fatty acid and steroid synthesis).
Signaling Substrate for NAD+-Consuming Enzymes:
Sirtuins (SIRT1-7): NAD+ is an obligatory co-substrate for these deacetylase/deacylase enzymes. Sirtuins regulate gene silencing, DNA repair, metabolic control, and aging. Their activity is directly coupled to cellular NAD+ availability.
Poly(ADP-ribose) Polymerases (PARPs): Consume NAD+ to synthesize poly(ADP-ribose) (PAR) chains on target proteins, primarily involved in the detection and repair of DNA damage.
CD38/CD157: Major NAD+-consuming ectoenzymes that generate second messengers like cyclic ADP-ribose (cADPR), regulating calcium signaling and immune function. Their activity increases with age, contributing to NAD+ decline.
Role in Aging: Cellular NAD+ levels decline significantly with age across multiple tissues. This decline is believed to contribute to age-related pathologies by impairing mitochondrial function, DNA repair, and stress resistance. Restoring NAD+ levels is a major focus of aging research.
Biosynthesis
Cells maintain NAD+ pools through several de novoand salvage biosynthesis pathways:
1.De Novo Pathway (from Tryptophan): The longest pathway, starting with the amino acid tryptophan (Vitamin B3-independent).
2.Preiss-Handler Pathway (from Nicotinic Acid, NA): NA → NaMN → NaAD → NAD+.
3.Salvage Pathways (Primary in Mammals):
From Nicotinamide (NAM): NAM is recycled via the rate-limiting enzyme NAMPT to produce NMN, which is then converted to NAD+ by NMNAT.
From Nicotinamide Riboside (NR): NR is phosphorylated by NR kinases to NMN, then to NAD+.
From Nicotinic Acid Riboside (NAR): A less common salvage route.
Applications
Key Advantages & Benefits
1. Direct and Immediate Cofactor for Critical Enzymatic Assays
Benefit: Provides the definitive, unmodified substrate required for in vitroactivity of dehydrogenases, reductases, sirtuins, and PARPs. Its use guarantees assay validity and reproducibility, as it is the molecule natively recognized by these enzymes.
Application Scenario: In drug discovery for oncology, researchers screen compound libraries against purified PARP-1 enzyme. High-purity NAD+ is essential for the assay to identify inhibitors that block PARP's activity by competing for the NAD+ binding site, a mechanism used by PARP inhibitor cancer drugs like olaparib.
2. The Definitive Biochemical Standard for Metabolic Research
Benefit: Serves as the absolute reference compound for quantifying metabolic flux. Measuring the NAD+/NADH ratio is a critical indicator of cellular redox state and mitochondrial health.
Application Scenario: A research team studying mitochondrial dysfunction in neurodegenerative disease uses precise enzymatic cycling assays with NAD+ as the core reagent. They measure the NAD+/NADH ratio in neuronal cell lines treated with experimental compounds to determine if the therapy can restore a more youthful, energetically favorable redox balance.
3. Unmatched Purity for Signaling Studies
Benefit: High-purity, enzymatically verified NAD+ is required to study its non-redox, signaling functions without artifacts from contaminants that could activate or inhibit sensitive enzymes like sirtuins and CD38.
Application Scenario: In a study on caloric restriction and longevity, scientists use ultra-pure NAD+ to demonstrate direct activation of SIRT1 deacetylase activity in cell culture. Contaminant-free NAD+ is critical to conclusively prove that increased NAD+ levels are the mechanistic link between nutrient sensing and gene expression changes.
4. Gold Standard for In-Vitro Diagnostic (IVD) Kits
Benefit: Its well-defined reaction kinetics with specific dehydrogenases makes it the reliable core component in clinical diagnostic kits (e.g., for measuring lactate, ethanol, or glycerol).
Application Scenario: In a hospital clinical lab, an automated analyzer runs a lactate dehydrogenase (LDH) test on a patient's serum to assess tissue damage. The test relies on a stable, formulated NAD+ reagent to catalyze the conversion of lactate to pyruvate, generating a measurable signal proportional to LDH concentration.
β-Nicotinamide Adenine Dinucleotide (NAD+, CAS 53-84-9) is the non-negotiable, active biochemical currency of the cell. Its principal advantage is not as a direct dietary supplement but as the irreplaceable core reagent for science and diagnostics. For researchers, it is the gold-standard tool for probing metabolism and enzymology. For diagnostic manufacturers, it is the critical, validated component of clinical assays. While NAD+ precursors like NMN and NR are superior for in vivosupplementation due to bioavailability, NAD+ itself remains the ultimate reference molecule and the direct effector of cellular function. Its value lies in its definitive biological activity and its role as the essential standard against which all precursors are measured.
FAQs
Q1: Why is the "β-" form specified, and does it matter?
A: Absolutely. The "β-" refers to the specific three-dimensional orientation of the bond connecting the nicotinamide to the ribose sugar. This is the only stereochemical form recognized and utilized by human enzymes. The alpha (α-) anomer is biologically inactive. High-quality NAD+ must be verified as the pure β-form for reliable research or product efficacy.
Q2: Can I take oral NAD+ supplements to boost my cellular levels?
A: Direct oral NAD+ supplementation is considered highly inefficient. NAD+ is a large, charged molecule that is rapidly degraded in the digestive system by enzymes and gut bacteria before it can be absorbed intact. The established strategy is to supplement with precursors like NMN (Nicotinamide Mononucleotide) or NR (Nicotinamide Riboside), which are smaller, more stable, and efficiently converted into NAD+ inside cells.
Q3: What are the critical storage and handling requirements?
A: NAD+ is notoriously unstable. For the solid:
Store at -20°C or below, desiccated, and protected from light.
For solutions: Always prepare fresh in cold, neutral-pH buffer (e.g., 50-100 mM Tris or phosphate buffer, pH ~7.5). Do not freeze-thaw solutions. Use immediately or store at 0-4°C for a few hours only.
Never autoclave or heat solutions.
Q4: How do I verify the purity and activity of NAD+?
A: Request a Certificate of Analysis (CoA) from the supplier. Key quality indicators:
HPLC Purity: ≥95% for research, ≥98% for critical applications.
Enzymatic Activity Assay: The gold standard. Purity is confirmed by its ability to serve as a cofactor in a standardized dehydrogenase reaction (e.g., with alcohol dehydrogenase), measured by the specific increase in absorbance at 340 nm upon reduction to NADH.
Water Content (Karl Fischer): Should be low (<2%) due to hygroscopicity.
Q5: What's the difference between NAD+ and NADH supplements?
A: They represent different redox states and have different proposed mechanisms.
NAD+: The oxidized form. In supplements (typically sublingual/IV), it's proposed to provide the raw signaling substrate for sirtuins and PARPs.
NADH: The reduced form. Marketed for rapid cellular "energy" support, as it is the direct electron donor for ATP synthesis. It is extremely unstable in gastric acid.
Neither is efficiently absorbed orally compared to precursors like NMN/NR.
Q6: Is NAD+ used in IV therapy, and is there evidence?
A: Yes, it is a component of some IV "wellness" or "anti-aging" drips. Proponents claim direct delivery to the bloodstream bypasses gut degradation, potentially raising plasma NAD+ levels. While plausible mechanistically, robust, peer-reviewed clinical trials demonstrating significant and sustained tissue-level benefits from IV NAD+ are currently lacking. It remains an area of anecdotal reporting and ongoing research.
Q7: What is the main commercial source of NAD+?
A: Most commercial NAD+ is produced via fermentation using specially engineered yeast or bacterial strains. This biological production ensures the correct stereochemistry (β-form). Chemical synthesis is possible but more complex and costly for large-scale production of the correct isomer.
Cloridrato de Procaína CAS 51-05-8 é o sal cloridrato de procaína solúvel em água. É a formulação específica usada na medicina clínica, comercializada sob a famosa marca Procaína.NovocaínaEmbora seu uso na prática clínica tenha diminuído, continua sendo um medicamento historicamente fundamental e ainda é empregado em contextos médicos e terapêuticos específicos.
Detalhes
L(+)-Choline bitartrate CAS 87-67-2 is an organic salt compound formed from one molecule of choline (a quaternary ammonium cation and essential nutrient) and one molecule of L(+)-tartaric acid (a natural dicarboxylic acid). It is a specific, enantiomerically pure form of choline salt where the counterion is derived from natural tartaric acid.It is a high-purity, stable, and highly bioavailable source of essential choline, combining the vital nutrient with a natural, food-grade organic acid. It offers a superior balance of safety, solubility, and cost-effectiveness for dietary supplementation and food fortification.
Detalhes
L-Carnitine CAS 541-15-1 is a naturally occurring, quaternary ammonium compound biosynthesized from the amino acids lysine and methionine. It is a chiral molecule, with the L-enantiomer being the biologically active form. Structurally, it functions as a carrier molecule for long-chain fatty acids. L-Carnitine is the essential biological shuttle required for transporting long-chain fatty acids into the mitochondria for energy production. It is a conditionally essential nutrient that optimizes cellular energy metabolism, making it fundamental for muscular, cardiovascular, and metabolic health.
Detalhes
L-Carnitine-L-tartrate CAS 36687-82-8 is a well-defined, crystalline salt formed through the ionic bonding of one molecule of L-carnitine (the biologically active enantiomer) and one molecule of L-tartaric acid (the naturally occurring enantiomer). It is specifically engineered as a superior solid form of carnitine for dietary supplements and functional foods. L-Carnitine-L-tartrate is a non-hygroscopic, highly stable salt form of L-carnitine, specifically engineered for superior manufacturing and performance. It delivers the essential metabolic benefits of L-carnitine with added advantages for physical recovery, excelling in solid-dose and powdered supplement formulations where stability and clinical validation are paramount.
Detalhes
Trimethylamine hydrochloride (TMA·HCl) CAS 593-81-7 is the hydrochloride salt of trimethylamine (TMA), a simple tertiary alkylamine. It is a solid, crystalline form of the normally gaseous and foul-smelling trimethylamine, which makes it much more convenient to handle, store, and weigh precisely.Trimethylamine Hydrochloride is the safe, stable, and precisely weighable solid equivalent of gaseous trimethylamine (TMA). It transforms a hazardous, malodorous gas into a controllable reagent, eliminating the major handling and safety challenges while enabling exact stoichiometry in critical synthetic steps.
Detalhes
(S)-4-Chloro-3-hydroxybutyronitrile CAS 127913-44-4 is a chiral, bifunctional organic molecule serving as a versatile building block in asymmetric synthesis. It features a nitrile group, a secondary alcohol with defined (S)-stereochemistry, and a terminal chloro substituent, allowing for multiple divergent chemical transformations from a single, enantiomerically pure scaffold.(S)-4-Chloro-3-hydroxybutyronitrile is a privileged, enantiomerically pure chiral building block that provides a compact, multifunctional scaffold with three differentiable reaction sites. Its core value lies in enabling the efficient, stereocontrolled synthesis of complex chiral molecules, particularly pharmacologically active intermediates, with high atom economy and strategic flexibility.
Detalhes
Ethyl (S)-4-chloro-3-hydroxybutyrate CAS 86728-85-0 is a chiral, bifunctional ester and a highly valuable building block in asymmetric synthesis. It features a terminal chloro group, a secondary alcohol with defined (S)-stereochemistry, and an ethyl ester, providing three distinct reactive handles for chemical transformation from a single enantiomerically pure scaffold. This compound is a chirally pure, trifunctional building block that integrates a reactive ethyl ester, a stereodefined secondary alcohol, and a terminal chloride into a compact C4 skeleton. It is the preferred industrial precursor for synthesizing the chiral side chain of blockbuster statin drugs due to its optimal balance of reactivity, stability, and efficient biocatalytic production.
Detalhes
Ethyl (R)-4-cyano-3-hydroxybutyrate CAS 141942-85-0 is a chiral, bifunctional building block of significant importance in asymmetric synthesis. It contains a stereogenic center with (R)-configuration, an ethyl ester group, and a terminal nitrile group, making it a versatile precursor for constructing complex chiral molecules, particularly in pharmaceutical applications. This compound is a stereodefined, multifunctional chiral building block where the (R)-configured alcohol and versatile cyano group provide unique synthetic leverage. It serves as a privileged precursor for high-value pharmaceutical intermediates, particularly statin side chains, by offering superior and orthogonal reactivity compared to its chloro analog.
Detalhes
CONTATE-NOS
1st Floor, No. 477, Huancheng West Road, Nanqiao Town, Fengxian District, Shanghai,China
sales@qxscientific.com
+86 -13701740203
IPv6 SUPORTADO POR REDE
|
Mapa do site
|
XML |
Blogue |
política de Privacidade
Deixe um recado
Scan to Wechat/Whatsapp :
Português
English
Español
Português
