D-Biotin/high quality CAS NO.58-85-5

Product Name: D-Biotin

Synonyms: Biotin for system suitability;D-Biotin High purity Vitamin H CAS:58-85-5 22879-79-4 CAS NO.58-85-5;)]-6a,7,8,10a-Tetrahydro-1-hydroxy-6,9-dimethyl-3-pentyl-6H-dibenzo[b,d]pyran-6-methanol;RONACARE(TM) BIOTIN PLUS;PHOTOPROBE(R) BIOTIN;VITAMIN B7;VITAMIN H;BIOTIN(V-H)

CAS: 58-85-5

MF: C10H16N2O3S

MW: 244.31

EINECS: 200-399-3

Product Categories: -;cyclic compounds;PHARMACEUTICALS;Miscellaneous Natural Products;Other Reagents;Biochemistry;Vitamins;API;Vitamin series;Inhibitor;Biotinylation Reagents;RONIACOL;Isolabel;biotinyl;Nutritional Supplements;Vitamins and derivatives;Biotin Derivatives;Intermediates & Fine Chemicals;Vitamin Ingredients;Inhibitors

Mol File: 58-85-5.mol

D-Biotin Structure

D-Biotin Chemical Properties

Melting point 231-233 °C(lit.)

alpha 89 º (c=1, 0.1N NaOH)

density 1.2693 (rough estimate)

refractive index 90.5 ° (C=2, 0.1mol/L NaOH)

storage temp. 2-8°C

solubility H2O: 0.2 mg/mL Solubility increases with addition of 1 N NaOH.

form powder

PH 4.5 (0.1g/l, H2O)

optical activity [α]20/D +91±2°, c = 1% in 0.1 M NaOH

Water Solubility Soluble in hot water, dimethyl sulfoxide, alcohol and benzene.

Sensitive Light Sensitive

Merck 14,1231

BRN 86838

Stability: Stable, but light sensitive. Incompatible with strong oxidizing agents, strong bases, strong acids, formaldehyde, chloramine-T, nitrous acid.

InChIKey YBJHBAHKTGYVGT-ZKWXMUAHSA-N

CAS DataBase Reference 58-85-5(CAS DataBase Reference)

NIST Chemistry Reference Biotin(58-85-5)

EPA Substance Registry System 1H-Thieno[3,4-d] imidazole-4-pentanoic acid, hexahydro-2-oxo-, (3aS,4S,6aR)-(58-85-5)

Safety Information

Hazard Codes Xn

Risk Statements 20/21/22-36/37/38

Safety Statements 24/25-36-26

WGK Germany 1

RTECS XJ9088200

F 8

TSCA Yes

HS Code 29362930

Hazardous Substances Data 58-85-5(Hazardous Substances Data)

Toxicity LD50 orally in Rabbit: > 2000 mg/kg

MSDS Information

Provider Language

Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic acid English

ACROS English

SigmaAldrich English

ALFA English

D-Biotin Usage And Synthesis

Description D-Biotin, also called Vitamin H, is a colorless, water-soluble member of the group of B-vitamins. Formerly it was known as vitamin H or coenzyme R. It has many benefits for the hair, skin, and nails. 

It is composed of a ureido ring fused with a tetrahydrothiophene ring. A valeric acid substituent is attached to one of the carbon atoms of the tetrahydrothiophene ring. Biotin is a coenzyme for carboxylase enzymes, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis.

Subclinical deficiency of Biotin can cause mild symptoms, such as hair thinning or skin rash typically on the face. Thus, This product is recommended for general food fortification and dietary supplement applications. 

Generally, D-Biotin can be used for baby food and dietetics, for solid and liquid pharmaceutical preparations, for cosmetic preparations, and for use in the fermentation industry.

Physicochemical property Biotin is widely distributed in animals and plants, and the natural presence of biotin is mainly in the form of binding with other molecules. The biochemical structure of biotin includes a shuttle chain containing five carbon atoms and two five-membered heterocycles. In vivo the shuttle of the side chain binds with lysine s residue of enzyme protein, playing a role of coenzyme. Biotin may have 8 different isomers, of which only D-biotin has biological activity. Under normal circumstances, biotin is quite stable, only in the strong acid, alkali, formaldehyde and UV treatment will be destroyed. Biotin is the carrier of carboxyl in the carboxylation reaction required large ATP. The carboxyl group is temporarily bound to a nitrogen atom on the bicyclic ring system of biotin, such as in the reaction of pyruvate carboxylase catalyzing the pyruvate carboxylation of oxaloacetate.

structural formula

Figure1: The structural formula of the biotin molecule

Physiological function Biotin is necessary for cell growth, the production of fatty acids, and the metabolism of fats and amino acids. It plays a role in the citric acid cycle, which is the process by which biochemical energy is generated during aerobic respiration. Biotin is a coenzyme for carboxylase enzymes, involved in the synthesis of fatty acids, isoleucine, and valine, and in gluconeogenesis. In addition, biotin is widely used throughout the biotechnology industry to conjugate proteins for biochemical assays.

We need biotin about 100 to 300 micrograms per day. There is an antibiotic protein that could combine with biotin in the egg white egg. After combining, it cannot be absorbed by the digestive tract; resulting in animal biotin deficiency, at the same time loss of appetite, glossitis, dermatitis dermatitis, hair removal and so on. However, there is no case of biotin deficiency on human, probably because in addition to food sources, intestinal bacteria can also synthesize biotin. Biotin is a coenzyme of a lot of enzymes in the human body. It participates in the metabolism of aliphatic acid, carbohydrate, vitamin B12, folic acid and pantothenic acid; promoting synthesis of protein and urea, and also promoting excretion.

Help fat, glycogen and amino acids for normal synthesis and metabolism in the human body;

Promote the normal operation and growth of sweat glands, nerve tissue, bone marrow, male gonads, skin and hair, and reduce eczema, dermatitis symptoms;

Prevent white hair and hair loss, contribute to the treatment of baldness;

Relieve muscle pain;

Promote synthesis and excretion of urea, purine synthesis and oleic acid biosynthesis;

For the treatment of atherosclerosis, stroke, dyslipidemia, hypertension, coronary heart disease and blood circulation disorders.

Biotin and fat metabolism As a coenzyme of phthalocyanine coenzyme A, Biotin is involved in the synthesis of fatty acids, catalyzing the formation of glycine CoA. The reaction is the first step in the synthesis of fatty acids, and then through the cytoplasmic multi-enzyme complex and fatty acid synthase synthesize palmitic acid from the phthalocyanine-CoA. In the prolongation of carbon chain in the fatty acid, the propanedio phthalide-ACP is involved in the reaction as a donor of the dicarbon unit, and the dipropyl phthalide-ACP is derived from the phthalide-CoA. It can be seen that biotin is necessary for the synthesis of fatty acids and the extension of carbon chains in fatty acid. Biotin deficiency can lead to abnormal lipid metabolism, resulting in changes of fatty acid composition in the body. In addition, synthesis of saturated fatty acid decreased, synthesis of triglyeeride increased, and fat in the liver and kidney increased by 2 to 5 times. Biotin-deficient diets increase the rate of desiccation of palmitic acid in liver tissue by five folds. Palmitic acid increased, at the same time stearic acid reduced. Biotin is also a necessary material for synthesis of long-chain unsaturated fatty acid and fatty acid metabolism. Biotin is also associated with the synthesis of acetylcholine and the metabolism of cholesterol. The lack of biotin reduces the ability of animals to synthesize arachidonic acid from linoleic acid, leading to the accumulation of linoleic acid in the body.

Biotin deficiency Biotin deficiency appears to be rare, but some groups may be more susceptible.Biotin supplements are widely available but rarely necessary.

A deficiency can lead to:

Hair loss

A scaly red rash around the eyes, nose, mouth, and genitals

Cracks in the corner of the mouth

Sore tongue that may be magenta in color

Dry eyes

Loss of appetite

 

Other symptoms may include:

Depression

Lethargy and fatigue

Hallucinations

Insomnia

Numbness and tingling in the hands and feet

Impaired immune function and increased susceptibility to infections

Pregnant women appear to break down biotin more quickly, and this may lead to a marginal deficiency. Symptoms have not been observed, but such a deficiency could lead to developmental problems for the fetus.

Food source

Liver

Peanuts

Yeast

Whole-wheat bread

Cheddar cheese

Pork

Salmon

Sardines

Avocado

Raspberries

Bananas

Mushrooms

Cauliflower

Egg yolk

Henan CoreyChem Co., Ltd, based on the original Zhengzhou Cote Chemical Research Institute, be brave in absorbing highly educated talents & overseas returnees; actively responded to Zhengzhou City High-tech Zone Government’s Special Care Policy, reorganized and founded in National University of Science and Technology Park, which is a high-tech, stock enterprise of high-end chemical Custom synthesis;The park was created by the People's Government of Henan Province, and proved by Ministry of Education and the National Science & Technology, taking the construction mode of "many college a park, and common development", mainly depends on Zhengzhou University and Henan University’s scientific research and talent advantage to set up Universities, scientific research institute and enterprise scientific research achievements transformation platform, to make high-tech enterprises incubate,  is the new high-tech talent gathering base, high and new technology industry enterprise radiation base, colleges and universities technological innovation base.

 

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Our R&D center building area is 811 square meters, with 3 contributing proffesor of technical advisor, 4 Dr., 10 masters, and 28 research staff. Our level of chemical synthesis is known to the industry. So we have accumulated rich experience in synthetic methods design and exploring the synthesis of new technology. Not only we are good in heterocyclic chemistry, chiral chemistry (asymmetric synthesis and enzyme reactions), metal organic synthesis, high throughput chemistry, also specializes in bioorganic chemistry, including nucleosides, nucleotides, sugar chemistry, peptide chemistry. R & D center has many sets of 10 liters, 20 liters, 50 liters, 100L multifunction high and low pressure reaction still, rotary evaporator, anhydrous anaerobic reaction devices, hydrogenation equipment, cryogenic process (-120 degrees) equipment, to complete mg level custom synthesis and kg level process development experiments. The Existing 600M NMR, LCMS, Fourier Infrared Spectrometer, liquid chromatography, differentialscanning calorimetry, and other advanced detection equipment areto ensure quality and efficient completion of R&D projects. So far our completed custom synthesis products is more than 5300 species, where dozens of them are non-CAS declaration products, almost including all types of organic reactions.

 

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