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20-September-2008 09:29:04 - Biotin April 2007 Biotin Other names Vitamin B7; Vitamin H Identifiers CAS number 58-85-5 PubChem 171548 Properties Molecular formula C10H16N2O3S Molar mass 244.31 g/mol Solubility in water Soluble Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Vitamin H redirects here. In medical slang, Vitamin H may also refer to haloperidol. In gamer slang Vitamin H may also refer to the Halo series Biotin, also known as vitamin H or B7, has the chemical formula C10H16N2O3S Biotin; Coenzyme R, Biopeiderm, is a water-soluble B-complex vitamin which is composed of an ureido tetrahydroimidizalone 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 cofactor in the metabolism of fatty acids and leucine, and in gluconeogenesis. Contents 1 General overview 2 Sources 2.1 Dietary 3 Bioavailability 3.1 Factors that Affect Biotin Requirements 4 Uses 4.1 Hair Problems 4.2 Cradle cap seborrheic dermatitis 4.3 Diabetes 5 Deficiency 6 Toxicity 7 Biochemistry 8 Laboratory uses 9 Ruminant Nutrition 10 References 11 See also 12 External links General overview 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 not only assists in various metabolic reactions, but also helps to transfer carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequently, it is found in many cosmetic and health products for the hair and skin. Deficiency is extremely rare, as intestinal bacteria generally produce an excess of the body's daily requirement. For that reason, statutory agencies in many countries e.g., the Australian Department of Health and Aging do not prescribe a recommended daily intake. Sources Dietary Biotin is widely distributed in a variety of foods, but most often at low concentrations. Estimates are that the typical U.S. diet provides roughly 40 mcg/day. There are only a couple of foods which contain biotin in large amounts, including royal jelly and brewer's yeast. The most important natural sources of biotin in human nutrition are milk, liver, egg egg yolk, and some vegetables. The most important natural sources in feeding nonruminant animals are oilseed meals, alfalfa, and dried yeasts. It is important to note that the biotin content of food varies and can be influenced by factors such as plant variety, season, and yield endosperm-to-pericarp ratio.1 Recommended Adequate Intake for Biotin Age Biotin mcg/day Infants 0-6 months 5 7-12 months 6 Children 1-3 years 8 4-8 years 12 Males and Females 9-13 years 20 14-18 years 25 19-70 years 30 70+ years 30 Pregnant 18-50 30 Lactating 18-50 35 Adequate intake are determined for nutrients when there is insufficient scientific evidence to establish a Recommended Dietary Allowance RDA. These values are set as goals for individuals to support adequate nutritional status. NOTE: U.S. Food and supplement labels show 30 mcg of biotin as providing only 10% DV Daily Value because DVs are based on older and in some instances outdated RDAs for nutrients. Thus, the DV for biotin is 300 mcg even though there is now consensus that 30 mcg is adequate. There is no current Tolerable Upper Limit UL set for biotin as research has indicated that high levels of intake by humans has no detrimental effects.2 Bioavailability Studies on the bioavailability of biotin have been conducted in rats and in chicks. From these studies, it was concluded that biotin bioavailability may be low or variable depending on the type of food being consumed, but in general, approximately half of the biotin in most foods is considered to be biologically available. The biotin present in corn is readily available; however, most grain have about a 20-40% bioavailability of biotin 1. A possible explanation for the wide variability in biotin bioavailability is that it is due to ability of an organism to break various biotin-protein bonds from food. Whether an organism has an enzyme with the ability to break that bond will determine the bioavailability of biotin from the foodstuff 1. Factors that Affect Biotin Requirements The frequency of marginal biotin status is not known, but the incidence of low circulating biotin levels in alcoholics has been found to be much greater than in the general population. Also, relatively low levels of biotin have been reported in the urine or plasma of patients who have had partial gastrectomy or who have other causes of achlorhydria, burn patients, epileptics, elderly individuals, and athletes.1 Pregnancy and lactation may be associated with an increased demand for biotin. In pregnancy, this may be due to a possible acceleration of biotin catabolism, whereas in lactation, the higher demand has yet to be elucidated. Recent studies have shown that marginal biotin deficiency can be present in human gestation, as evidenced by increased urinary excretion of 3-hydroxyisovaleric acid, decreased urinary excretion of biotin and bisnorbiotin, and decreased plasma concentration of biotin. Additionally, smoking may further accelerate biotin catabolism in women.3 Uses Hair Problems Biotin supplements are often recommended as a natural product to counteract the problem of hair loss in both children and adults. There are, however, no studies that show any benefit in any case where the subject is not actually biotin deficient. The signs and symptoms of biotin deficiency include hair loss which progresses in severity to include loss of eye lashes and eye brows in severely deficient subjects. Some shampoos are available that contain biotin, but it is doubtful whether they would have any useful effect, as biotin is not absorbed well through the skin. Cradle cap seborrheic dermatitis Children with a rare inherited metabolic disorder called phenylketonuria PKU; in which one is unable to break down the amino acid phenylalanine often develop skin conditions such as eczema and seborrheic dermatitis in areas of the body other than the scalp. The scaly skin changes that occur in people with PKU may be related to poor ability to use biotin. Increasing dietary biotin has been known to improve seborrheic dermatitiscitation needed in these cases. Diabetes People with type 2 diabetes often have low levels of biotin. Biotin may be involved in the synthesis and release of insulin. Preliminary studies in both animals and people suggest that biotin may help improve blood glucose control in those with diabetes, particularly type 2 diabetes.4 Specifically, biotin doses in excess of nutritional requirements lower postprandial glucose and improve glucose tolerance.1 Deficiency Biotin deficiency is relatively rare and mild, and can be addressed with supplementation. Such deficiency can be caused by the excessive consumption of raw egg whites, which contain high levels of the protein avidin, which binds biotin strongly. Avidin is deactivated by cooking, while the biotin remains intact. Biotinidase deficiency is not due to inadequate biotin, but rather to a deficiency in the enzymes which process it. Signs of Biotin Deficiency: In general, appetite and growth are decreased. Dermatologic symptoms include dermatitis, alopecia, and achromotrichia absence or loss of pigment in the hair5. Perosis a shortening and thickening of bones is seen in the skeleton. FLKS fatty liver and kidney syndrome and hepatic steatosis also can occur.1 Toxicity Animal studies have indicated few, if any, effects due to toxic doses of biotin. This may provide evidence that both animals and humans may tolerate doses of at least an order of magnitude greater than each of their nutritional requirements. There are no reported cases of adverse effects from receiving high doses of the vitamin, particularly when used in the treatment of metabolic disorders causing sebhorrheic dermatitis in infants.6 Biochemistry Biotin is a cofactor responsible for carbon dioxide transfer in several carboxylase enzymes: Acetyl-CoA carboxylase alpha Acetyl-CoA carboxylase beta Methylcrotonyl-CoA carboxylase Propionyl-CoA carboxylase Pyruvate carboxylase The attachment of biotin to various chemical sites, called biotinylation, can be used as an important laboratory technique to study various processes including protein localization, protein interactions, DNA transcription and replication. Biotin itself is known to biotinylate histonescitation needed, but is not found naturally in chromatin. Holocarboxylase synthetase is involved in the binding of biotin. Biotin binds very tightly to the tetrameric protein avidin also streptavidin and neutravidin, with a dissociation constant Kd in the order of 10-15 mol/L Bonjour, 1977; Green 1975; and Roth, 1985. This is often used in different biotechnological applications. Until 2005, very harsh conditions were required to break the biotin-streptavidin bond.7 Laboratory uses In the biology laboratory, biotin is often chemically linked, or tagged, to a molecule or protein for biochemical assays. This process is called biotinylation. Since avidins bind preferentially to biotin, biotin-tagged molecules can be extracted from a sample by mixing them with beads with covalently-attached avidin, and washing away anything unbound to the beads. For example, biotin can be attached to a molecule of interest e.g. a protein, and this modified molecule will be mixed with a complex mixture of proteins. Avidin or streptavidin beads are added to the mixture, and the biotinylated molecule will bind to the beads. Any other proteins binding to the biotinylated molecule will also stay with the beads. All other unbound proteins can be washed away, and the scientist can use a variety of methods to determine which proteins have bound to the biotinylated molecule. Biotinylated antibodies are used to capture avidin or streptavidin in both the ELISPOT and ELISA techniques. Ruminant Nutrition Ruminal bacteria normally synthesize biotin. Biotin is not extensively metabolized in the rumen and increased intake of dietary biotin results in elevated concentrations of biotin in serum and milk.8 Unpublished epidemiologic data suggest a negative relationship between serum concentrations of biotin and the incidence of clinical lameness in dairy cattle. Feeding approximately 20 mg/day of supplemental biotin statistically improved measures of hoof health. Currently, insufficient data are available at this time to quantify the requirement for biotin of dairy cattle. References ^ a b c d e f Combs, Gerald F. Jr. 2008. The Vitamins: Fundamental Aspects in Nutrition and Health. San Diego: Elsevier, Inc. ISBN 9780121834937. ^ McGuire M, Beerman KA. Nutritional sciences: from fundamentals to food. California: Thomson Wadsworth, 2007. ^ Bowman, BA and Russell, RM., ed. 2006, Biotin, Present Knowledge in Nutrition, Ninth ion, Vol 1, Washington, DC: Internation Life Sciences Institute, ISBN 9781578811984 ^ Campbell, R. Keith Nov 2006. A Critical Review of Chromium Picolinate and Biotin. U.S. Pharmacist 31 11. ^ biology-online.org ^ Combs, Gerald F. Jr. 1998. The Vitamins: Fundamental Aspects in Nutrition and Health. Ithaca: Elsevier Academic Press. ISBN 0121834921. pg. 360 ^ Holmberg A, Blomstergren A, Nord O et al. 2005. The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis 26 3: 501-10. doi:10.1002/elps.200410070. PMID 15690449. ^ National Research Council 2001. Nutrient Requirements of Dairy Cattle. 7th rev. ed.. Natl. Acad. Sci., Washington, DC.. ISBN 0309069971. See also Biotinylation Avidin Streptavidin NeutrAvidin External links Jane Higdon, Biotin, Micronutrient Information Center, Linus Pauling Institute Biotin - Biocytin Brewer's YeastBiotin Complex Clercq, Pierre J. De 1997. Biotin: A Timeless Challenge for Total Synthesis. Chemical Review 97: 1755-1792. doi:10.1021/cr950073e. v d e Vitamins A11 Fat soluble A: Retinol - Beta-carotene - Tretinoin - Alpha-carotene D3: 7-Dehydrocholesterol → Previtamin D3 → Cholecalciferol D3 → Calcidiol → Calcitriol active form → Calcitroic acid D2: Ergosterol → Ergocalciferol D2 D analogues: Dihydrotachysterol - Calcipotriol - Tacalcitol E: Tocopherol - Tocotrienol K: Naphthoquinone - Phylloquinone/K1 - Menatetrenone/K2 Water soluble: B vitamins B1 Thiamine - B2 Riboflavin - B3 Niacin, Nicotinamide - B5 Pantothenic acid, Dexpanthenol, Pantethine - B6 Pyridoxine, Pyridoxal phosphate, Pyridoxamine - B7 Biotin - B9 Folic acid, Folinic acid - B12 Cyanocobalamin, Hydroxocobalamin, Methylcobalamin, Cobamamide Water soluble: other C Ascorbic acid - Choline see also enzyme cofactors v d e Enzyme cofactors Coenzymes vitamins: NAD+ B3 | NADP+ B3 | Coenzyme A B5 | THF / H4F B9, DHF, MTHF | Ascorbic acid C | Menaquinone K | Coenzyme F420 non-vitamins: ATP | CTP | SAM | PAPS | GSH | Coenzyme B | Coenzyme M | Coenzyme Q | Methanofuran | BH4 | H4MPT Organic prosthetic groups vitamins: TPP / ThDP B1 | FMN, FAD B2 | PLP / P5P B6 | Biotin B7 | Methylcobalamin, Cobamamide B12 non-vitamins: Haem / Heme | Lipoic acid | Molybdopterin | PQQ Metal prosthetic groups Ca2+ | Cu2+ | Fe2+, Fe3+ | Mg2+ | Mn2+ | Mo | Ni2+ | Se | Zn2+ Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Biotin Categories: Vitamins | Organosulfur compounds | CofactorsHidden categories: Articles needing additional references from April 2007 | All articles with statements | Articles with statements since March 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية Bosanski ÄŒesky Deutsch Eesti Español Euskara Français Galego í•œêµì–´ Hrvatski Italiano עברית Lëtzebuergesch Lietuvių Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português Română РуÑ?Ñ?кий SlovenÄ?ina СрпÑ?ки / Srpski Srpskohrvatski / СрпÑ?кохрватÑ?ки Basa Sunda Suomi Svenska Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 3 August 2008, at 07:48
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