D-Biotin

Absorption

Systemic - approximately 50%

Toxicity

Prolonged skin contact may cause irritation.

Sources

Biotin is mainly derived from offal, eggs, fish, meat, seeds, nuts and certain vegetables (e.g. sweet potatoes), which are the foods with the highest biotin content. The specific amounts of biotin in different foods are shown in the table below:

Description

Biotin, a water-soluble B-complex vitamin, is integral to cell growth, fatty acid production, and metabolism. It plays a crucial role in the Kreb cycle, aiding in energy release from food and facilitating metabolic conversions and carbon dioxide transfer. Known for maintaining blood sugar levels and promoting hair and nail strength, biotin is prevalent in cosmetic and health products. Biotin deficiency, while rare, can lead to dry skin, seborrheic dermatitis, fungal infections, hair loss, neurological symptoms, and in infants, "cradle cap." In adults, it may result in anemia, depression, hair loss, high blood sugar, muscle pain, nausea, loss of appetite, and inflamed mucous membranes. Treatment typically involves biotin supplementation.

Chemical properties

White powder

Originator

Biotin,Solgar

The Uses of D-Biotin

Biotin is a B vitamin, an essential nutrient that occurs naturally in certain foods and is also used as a dietary supplement. This water-soluble vitamin is a cofactor for five carboxylases (propionyl-CoA carboxylase, pyruvate carboxylase, methylcrotonyl-CoA carboxylase [MCC], acetyl-CoA carboxylase 1, and acetyl-CoA carboxylase 2). Biotin also plays a key role in histone modification, gene regulation (by altering the activity of transcription factors), and cell signalling.

The Uses of D-Biotin

vitamin B complex

The Uses of D-Biotin

Growth factor present in minute amounts in every living cell. Plays an indispensable role in numerous naturally occurring carboxylation reactions. Occurs mainly bound to proteins or polypeptides. The richest sources are liver, kidney, pancreas, yeast, and milk. The biotin content of cancerous tumors is higher than that of normal tissue.

Indications

For nutritional supplementation, also for treating dietary shortage or imbalance.

What are the applications of Application

D-(+)-Biotin is an important ubiquitous metabolism coenzyme

Background

A water-soluble, enzyme co-factor present in minute amounts in every living cell. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk.

Definition

ChEBI: An organic heterobicyclic compound that consists of 2-oxohexahydro-1H-thieno[3,4-d]imidazole having a valeric acid substituent attached to the tetrahydrothiophene ring. The parent of the class of biotins.

Manufacturing Process

4-Carbomethoxy-2-(4,5-dihydrothiophen-3(2H)-one)valeric acid methyl ester was prepared from 4,5-dihydrothiophene as it was described in Baker et al., J. Org. Chem., 12, 167 (1947).
A solution of 60.0 g (0.182 mole) this ester in 550 ml absolute ethanol was treated with 91.6 g (1.45 moles) of ammonium formate. The reaction mixture refluxed for 5.0 hours. Then it was cooled, concentrated, and partitionated in a separatory funnel between 200 ml dichloromethane and 150 ml water. The aqueous phase was extracted three times with 50 ml portions of dichloromethane. The organic extracts were collected, dried over anhydrous sodium sulfate, and evaporated. 50 g (0.182 mole, 100%) 3-amino-4- carbomethoxy-2,5-dihydro-2-thiophenevaleric acid methyl ester was obtained as a colorless oil.
To a solution of 27.3 g (1 mole) of 3-amino-4-carbomethoxy-2,5-dihydro-2- thiophenevaleric acid methyl ester in 250 ml dry methanol was added 4.0 g (0.1 mole) of sodium hydroxide pellets. The reaction mixture was refluxed 4.0 hrs, cooled and concentrated to a volume of 50 ml. The residue was taken up in 80 ml dichloromethane and transfered to a separatory funnel. After the addition of 150 ml of 10% by weight aqueous sodium bicarbonate solution, the aqueous layer was extracted twice with 50 ml portions of dichloromethane. The organic phases were combined, dried over anhydrous sodium sulfate, and evaporated to yield 6.4 g (0.0234 mole) of recovered starting material. The aqueous phase was adjusted to pH 1 with 6 N hydrochloric acid and extracted three times with 75 ml portions of dichloromethane. The organic phases were pooled, dried over anhydrous sodium sulfate, and evaporated to yield 18.3 g (0.071 mole, 71%) of 3- amino-4-carbomethoxy-2,5-dihydro-2-thiophenevaleric acid as a tan solid, upon trituration with pet. ether.
The recovered starting material, 6.4 g (0.0234 mole) was dissolved in 70 ml dry methanol and treated with 1.0 g (0.025 mole) sodium hydroxide. The mixture was refluxed 5.0 hrs, cooled concentrated, and taken up in 80 ml dichloromethane. The organic phase was treated in a separatory funnel with 100 ml of 10% by weight aqueous sodium bicarbonate solution. The aqueous phase was extracted twice with 40 ml portions of dichloromethane. The aqueous phase was acidified to pH 1 with 6 N hydrochloric acid and extracted two times with 50 ml portions of dichloromethane. The organic phases were cooled, dried over anhydrous sodium sulfate, and evaporated to dryness to afford an additional 5.3 g (0.021 mole, 21%) of 3-amino-4-carbomethoxy- 2,5-dihydro-2-thiophenevaleric acid; m.p. 98°-102°C.

brand name

Bioepiderm (Sterling Winthrop).

Therapeutic Function

Vitamin

General Description

Pharmaceutical secondary standards for application in quality control, provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards.
Biotin is a water-soluble vitamin, essential for amino acids and carbohydrates metabolism. It is involved in de novo synthesis of purine nucleotides and plays a role in gene expression and DNA replication.

Biochem/physiol Actions

Biotin is a vital cofactor for carboxylase enzymes in several metabolic?pathways. It also functions as a coenzyme in the metabolism of fatty acids, isoleucine and valine. Biotin assists the transfer of carbon dioxide and also sustains a steady blood sugar level. Biotin is implicated in gluconeogenesis and citric acid cycle. It?is involved in?keratin?synthesis and hence?is used as?a supplement?for skin, hair and nail growth. Biotin is required for cell growth, production of fatty acids and the metabolism of fats and amino acids.

Safety Profile

An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx and SOx.

Purification Methods

D-(+)-Biotin crystallises from hot water in fine long needles with a solubility of 22 mg/100mL at 25o. Its solubility in 95% EtOH is 80 mg/100 mL at 25o. Its isoelectric point is at pH 3.5. Store solid and solutions under sterile conditions because it is susceptible to mould growth. [Confalone J Am Chem Soc 97 5936 1975, Wolf et al. J Am Chem Soc 67 2100 1945, Synthesis: Ohuri & Emoto Tetrahedron Lett 2765 1975, Harris et al. J Am Chem Soc 66 1756 1944.] The (+)-methyl ester has m 166-167o (from MeOH/Et2O), [] D 22 +57o (c 1, CHCl3) [du Vigneaud et al. J Biol Chem 140 643, 763 1941]; the (+)-S-oxide has m 200-203o, [] D 20 +130o (c 1.2, 0.1N NaOH) [Melville J Biol Chem 208 495 1954]; the SS-dioxide has m 274-275o(dec, 268-270o), and the SS-dioxide methyl ester has m 239-241o (from MeOH/Et2O) [Hofmann et al. J Biol Chem 141 207, 213 1941]. [Beilstein 27 III/IV 7979.]