23111-00-4 Usage
Description
Nicotinamide riboside chloride, also known as NIAGEN, is a crystal form of Nicotinamide riboside (NR) chloride, which is a new form of pyridine-nucleoside of vitamin B3. It functions as a precursor to nicotinamide adenine dinucleotide (NAD+) and is generally recognized as safe (GRAS) for use in foods and dietary supplements. Nicotinamide riboside chloride increases NAD+ levels, activates SIRT1 and SIRT3, and enhances oxidative metabolism, providing protection against high-fat diet-induced metabolic abnormalities.
Uses
1. Used in Dietary Supplements:
Nicotinamide riboside chloride is used as a dietary supplement for enhancing oxidative metabolism and protection against high-fat diet-induced metabolic abnormalities. It acts as a source of vitamin B3 (niacin) and is involved in nicotinate and nicotinamide metabolism.
2. Used in Mitochondrial Function and Insulin Sensitivity Improvement:
Nicotinamide riboside chloride is used as a nutrient to improve mitochondrial function and insulin sensitivity. It is a naturally occurring vitamin B-3 present in the human diet and acts as an NAD+ precursor, which is suggested to enhance these functions.
3. Used in Oxidative Gene Expression and Metabolic Flexibility:
Nicotinamide riboside chloride is used as a supplement to increase NAD+-restoring capability and subsequent oxidative gene expression in skeletal muscle cells. In vivo mouse models have shown improvements in insulin sensitivity and oxidative energy metabolism, including enhanced metabolic flexibility, increased aerobic exercise capacity, and indications of improved mitochondrial biogenesis.
4. Used in Nicotinic Acid and Nicotinamide Metabolism:
Nicotinamide riboside is used as a nutrient in the metabolism of nicotinic acid and nicotinamide, playing a role in the overall metabolic processes of the body.
5. Used as a NAD(+) Precursor:
Nicotinamide riboside is used as a NAD(+) precursor, which is essential for cellular energy production and various other biological processes. It acts via activation of the NAD+-dependent sirtuin enzyme family, thereby regulating oxidative metabolism.
History
Nicotinamide riboside (NR) was first described in 1944 as a growth factor, termed Factor V, for Haemophilus influenza, a bacterium that lives in and depends on blood. Factor V, purified from blood, was shown to exist in three forms: NAD+, NMN and NR. NR was the compound that led to the most rapid growth of this bacterium.Notably, H. influenza cannot grow on nicotinic acid, nicotinamide, tryptophan or aspartic acid, which were the previously known precursors of NAD+.In 2000, yeast Sir2 was shown to be an NAD+-dependent protein lysine deacetylase, which led several research groups to probe yeast NAD+ metabolism for genes and enzymes that might regulate lifespan. Biosynthesis of NAD+ in yeast was thought to flow exclusively through NAMN (nicotinic acid mononucleotide).When NAD+ synthase (glutamine-hydrolysing) was deleted from yeast cells, NR permitted yeast cells to grow. Thus, these Dartmouth College investigators proceeded to clone yeast and human nicotinamide riboside kinases and demonstrate the conversion of NR to NMN by nicotinamide riboside kinases in vitro and in vivo. They also demonstrated that NR is a natural product found in cow’s milk.
Biological Functions
Nicotinamide riboside (NR) is a newly discovered form of vitamin B3 that is found naturally in trace amounts in milk. No one really thought much about NR until scientists discovered that our bodies can convert NR into something called nicotinamide adenine dinucleotide (NAD+). And NAD+—at least for healthy-aging researchers—is kind of a big deal.NAD+ is a coenzyme found in all living cells, and it plays a vital role in energy metabolism and maintaining proper cell functioning. Levels of NAD+ also happen to decline significantly as we get older, and these declining levels apparently drive the aging process.
Biological Activity
Nicotinamide Riboside is an NAD+ precursor. It is a substrate for nicotinamide riboside kinases (NRK1/2). Nicotinamide Riboside shows neuroprotective effects in a mouse model of type 2 diabetes and improves mitochondrial function in muscle stem cells in aged mice. The compound also corrects non-alchoholic fatty liver disease phenotype induced by NAD+ deficiency or high-fat diet in mice. Orally bioavailable.
in vitro
Nicotinamide Riboside supplementation increases NAD+ content and sirtuin activity in cultured mammalian cells.
in vivo
Nicotinamide Riboside, a precursor to nicotinamide adenine
dinucleotide(NAD), restores tissue NAD+ depletion induced by?acute
kidney injury (AKI)?to that of the sham group, increases autophagy and
sirtuin1 (Sirt1).
Check Digit Verification of cas no
The CAS Registry Mumber 23111-00-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,3,1,1 and 1 respectively; the second part has 2 digits, 0 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 23111-00:
(7*2)+(6*3)+(5*1)+(4*1)+(3*1)+(2*0)+(1*0)=44
44 % 10 = 4
So 23111-00-4 is a valid CAS Registry Number.
23111-00-4Relevant articles and documents
New crystalline salts of nicotinamide riboside as food additives
Haase, Robert,Hery-Barranco, Adrian,Pala, Laura,Parris, Jaclyn,Schabert, Günter,Spingler, Bernhard,Spitz, Urs
, (2021)
NR+ is a highly effective vitamin B3 type supplement due to its unique ability to replenish NAD+ levels. While NR+ chloride is already on the market as a nutritional supplement, its synthesis is challenging, expensive, and low yielding, making it cumbersome for large-scale industrial production. Here we report the novel crystalline NR+ salts, D/L/DL-hydrogen tartrate and D/L/DL-hydrogen malate. Their high-yielding, one-pot manufacture does not require specific equipment and is suitable for multi-ton scale production. These new NR+ salts seem ideal for nutritional applications due to their bio-equivalence compared to the approved NR+ chloride. In addition, the crystal structures of all stereoisomers of NR+ hydrogen tartrate and NR+ hydrogen malate and a comparison to the known NR+ halogenides are presented.
Synthesis method of beta-nicotinamide riboside chloride
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Paragraph 0017; 0024-0029, (2021/03/11)
The invention discloses a synthesis method of beta-nicotinamide riboside chloride. According to the method, TMSCl is used as a chlorination reagent, boron trifluoride diethyl ether is used as a catalyst, and a glycosylation reaction of tetraacetylribose and nicotinamide is catalyzed. The reaction conditions are mild, and the product yield is high; the used reagents are low in cost, easy to obtainand suitable for industrial production; the reaction conditions are relatively safe and environmentally friendly, the reaction process is simple, and ion exchange reaction is not needed; a reaction product is relatively easy to purify and separate, and high quality of the product can be ensured; and the reagents used in the reaction process are lower in cost, and the production cost can be reduced.
Synthesis method of beta-nicotinamide mononucleotide
-
, (2020/09/20)
The invention discloses a synthesis method of beta-nicotinamide mononucleotide, and relates to the technical field of drug synthesis. The synthesis method mainly comprises the following steps of S1, mixing and reacting nicotinamide, hexamethyldisilazane and a catalyst I in a reaction kettle to obtain silanization-protected nicotinamide; S2, adding tetraacetyl ribose, a solvent, a catalyst II and methanol for reaction so as to generate nicotinamide triacetyl riboside; S3, adding methanol and n-propylamine to generate nicotinamide riboside; S4, adding trimethyl phosphate and phosphorus oxychloride to generate beta-nicotinamide mononucleotide; and S5, separating and purifying the beta-nicotinamide mononucleoside acid. According to the invention, a plurality of continuous steps are controlledto be carried out in one reaction container, and the steps of separating and purifying an intermediate are avoided, so that the method has the advantages of high yield and high production efficiency.