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biotin
5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid

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Name:5-[(3aR,6S,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoic acid
CAS Number: 58-85-5Picture of molecule3D/inchi
Other(deleted CASRN):15720-24-8
ECHA EINECS - REACH Pre-Reg:200-399-3
FDA UNII: 6SO6U10H04
Nikkaji Web:J94.599D
Beilstein Number:86838
MDL:MFCD00005541
XlogP3-AA:0.30 (est)
Molecular Weight:244.31412000
Formula:C10 H16 N2 O3 S
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:nutrient supplements
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Patents:Search
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Pubchem Patents:Search
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NCBI:Search
 FDA/DG SANTE Petitions, Reviews, Notices:
182.8159 Biotin View - review
FDA Mainterm (SATF):58-85-5 ; BIOTIN
FDA Regulation:
FDA PART 101 -- FOOD LABELING
Subpart A--General Provisions
Sec. 101.9 Nutrition labeling of food.


FDA PART 107 -- INFANT FORMULA
Subpart D--Nutrient Requirements
Sec. 107.100 Nutrient specifications.


FDA PART 182 -- SUBSTANCES GENERALLY RECOGNIZED AS SAFE
Subpart I--Nutrients
Sec. 182.8159 Biotin.
 
Physical Properties:
Appearance:white to off-white crystalline powder (est)
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Melting Point: 232.00 °C. @ 760.00 mm Hg
Boiling Point: 573.58 °C. @ 760.00 mm Hg (est)
Flash Point: 573.00 °F. TCC ( 300.70 °C. ) (est)
logP (o/w): 0.861 (est)
Soluble in:
 water, 220 mg/L @ 25 °C (exp)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: antiseborrhoeic agents
hair conditioning
skin conditioning
 
Suppliers:
A.M.G.L.T.
Biotin
AIDP
Biotin 1% Vitamin H 1%
AIDP
Biotin USP Vitamin H 97%-100.5%
American International Chemical, LLC.
BIOTIN 10% (On Mannitol)
American International Chemical, LLC.
Biotin
Atlantic Chemicals
Biotine (Vitamin H)
AuNutra® Industries
Biotin 1%
AuNutra® Industries
D-Biotin 1% on DCP
BBFY Industrial
Biotin
BOC Sciences
For experimental / research use only.
Biotin >98%
Odor: characteristic
Use: Biotin, also known as vitamin H or coenzyme R, is a water-soluble B-vitamin (vitamin B7).
Charkit Chemical
BIOTIN, D- PURE
Dow Chemical
D-Biotin USP/EP
ECSA Chemicals
D-BIOTIN PH.EUR.
ECSA TRADE THE MOST UPDATED FINANCIAL PUBLICATION ON THE WORLD OF CHEMISTRY
Farbest-Tallman Foods
ZMC d-Biotin 1% on Maltodextrin
Flavor: bland
It is an essential nutrient used in food, beverage and dietary supplement applications including nutrient enhanced foods and beverages.
Farbest-Tallman Foods
ZMC d-Biotin 100% USP
Flavor: bland
It is an essential nutrient used in food, beverage and dietary supplement applications including nutrient enhanced foods and beverages.
Foodchem International
D-Biotin
George Uhe Company
D-Biotin (Pure And Feed Grade)
Glentham Life Sciences
D-(+)-Biotin, 98%
Glentham Life Sciences
D-(+)-Biotin, EP, USP grade
Graham Chemical
Vitamin H (
Indis NV
For experimental / research use only.
Biotin 2%
Jiangyin Healthway
Vitamin H (D-Biotin)
New functional food ingredients
Maypro Industries
Biotin min. 99% FCC
OQEMA
Biotin 2%
OQEMA
Biotin Pure
Penta International
D-BIOTIN FCC (VITAMIN H)
Penta International
D-BIOTIN USP (VITAMIN H)
Prinova
Biotin
Sigma-Aldrich
For experimental / research use only.
Biotin European Pharmacopoeia (EP) Reference Standard
Silver Fern Chemical
Vitamin H (D-Biotin) 2%
Zanos
D-Biotin Pure
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
nutrient supplements
Recommendation for biotin usage levels up to:
 not for fragrance use.
 
Recommendation for biotin flavor usage levels up to:
 not for flavor use.
 
Safety References:
European Food Safety Authority (EFSA) reference(s):

Scientific Opinion on the substantiation of a health claim related to a combination of thiamin, riboflavin, niacin, pantothenic acid, pyridoxine, D-biotin and pumpkin seed oil and maintenance of normal hair pursuant to Article 13(5) of Regulation (EC) No 1924/2006
View page or View pdf

Scientific Opinion on the safety and efficacy of D-(+)-biotin as a feed additive for all animal species based on a dossier submitted by EUROPE-ASIA Import Export GmbH
View page or View pdf

Scientific Opinion on the safety and efficacy of biotin as a feed additive for all animal species based on a dossier submitted by VITAC EEIG
View page or View pdf

Scientific Opinion on Dietary Reference Values for biotin
View page or View pdf

Outcome of public consultations on the draft Scientific Opinions of the EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA) on Dietary Reference Values for biotin and pantothenic acid
View page or View pdf

Biotin and contribution to normal energy-yielding metabolism: evaluation of a health claim pursuant to Article 14 of Regulation (EC) No 1924/2006
View page or View pdf

EPI System: View
ClinicalTrials.gov:search
Daily Med:search
Chemical Carcinogenesis Research Information System:Search
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):58-85-5
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :171548
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:1
5-[(3aR,6S,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoic acid
Chemidplus:0000058855
RTECS:XJ9088200 for cas# 58-85-5
 
References:
 5-[(3aR,6S,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoic acid
NIST Chemistry WebBook:Search Inchi
Canada Domestic Sub. List:58-85-5
Pubchem (cid):171548
Pubchem (sid):134971956
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
FDA Substances Added to Food (formerly EAFUS):View
CHEBI:View
CHEMBL:View
Golm Metabolome Database:Search
Metabolomics Database:Search
KEGG (GenomeNet):C00120
HMDB (The Human Metabolome Database):HMDB00030
FooDB:FDB014510
YMDB (Yeast Metabolome Database):YMDB00282
Export Tariff Code:2936.29.5030
FDA Listing of Food Additive Status:View
MedlinePlusSupp:View
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
 biological additives
 
Occurrence (nature, food, other):note
 apple plant
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 avocado fruit
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 banana fruit
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 barley seed
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 bean black bean root
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 bean fava bean seed
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 bean field bean root
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 cacao sprout
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 cauliflower
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 corn cob
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 cotton seed
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 egg
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 elder black elder fruit
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 fenugreek sprout
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 garlic bulb
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 grape fruit
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 lentil seed
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 mackerel
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 oat seed
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 pea seed
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 peanut seed
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 salmon
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 sardine
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 sesame seed
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 soybean seed
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 tomato fruit
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 walnut english walnut nut
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 watercress plant
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 wheat seed
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 yeast
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Synonyms:
 biodermatin
(+)-biotin
D-biotin
D-(+)-biotin
delta-biotin
D-biotin (pure and feed grade)
 biotin (vitamin H) USP30
 biotin 1%
ZMC D-biotin 1% on maltodextrin
 biotin 1% trituration
 biotin 1% Vitamin H 1%
 biotin 10% (on mannitol)
ZMC D-biotin 100% USP
 biotin 2%
D-biotin FCC (vitamin H)
 biotin Pure
 biotin USP
D-biotin USP (vitamin H)
 biotin USP vitamin H 97%-100.5%
 biotine
 biotine (Vitamin H)
5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid
 hexahydro-2-oxo-[3as-(3a,4β,6a)]-1H-Thieno[3,4-d]imidazole-4-pentanoic acid
 hexahydro-2-oxo-[3aS-(3aa,4b,6aa)]-1H-Thieno[3,4-d]imidazole-4-pentanoic acid
cis-hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acid
(3aS,4S,6aR)-hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid
5-[(3aR,6S,6aS)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-6-yl]pentanoic acid
 injacom H
 lutavit H2
 rovimix H2
cis-tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acid
1H-thieno[3,4-d]imidazole-4-pentanoic acid, hexahydro-2-oxo-, (3aS,4S,6aR)-
 vitamin B7
 vitamin H
 
 
Notes:
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. 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. Present in many foods; particularly rich sources include yeast, eggs, liver, certain fish (e.g. mackerel, salmon, sardines), soybeans, cauliflower and cow peas. Dietary supplement. Isol. from various higher plant sources, e.g. sweet corn seedlings and radish leaves Biotin D(+) is a cofactor responsible for carbon dioxide transfer in several carboxylase enzymes:; 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 which is one of the strongest known protein-ligand interactions, approaching the covalent bond in strength. This is often used in different biotechnological applications. Until 2005, very harsh conditions were required to break the biotin-streptavidin bond.; Biotin is a water-soluble B-complex vitamin which is composed of an 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 used in cell growth, the production of fatty acids, metabolism of fats, and amino acids. It plays a role in the Kreb cycle, which is the process in which energy is released from food. Biotin not only assists in various metabolic chemical conversions, but also helps with the transfer of carbon dioxide. Biotin is also helpful in maintaining a steady blood sugar level. Biotin is often recommended for strengthening hair and nails. Consequenty, it is found in many cosmetic and health products for the hair and skin. Biotin deficiency is a rare nutritional disorder caused by a deficiency of biotin. Initial symptoms of biotin deficiency include: Dry skin, Seborrheic dermatitis, Fungal infections, rashes including erythematous periorofacial macular rash, fine and brittle hair, and hair loss or total alopecia. If left untreated, neurological symptoms can develop, including mild depression, which may progress to profound lassitude and, eventually, to somnolence; Biotin is an enzyme co-factor present in minute amounts in every living cell. Biotin is also known as vitamin H or B7 or coenzyme R. It occurs mainly bound to proteins or polypeptides and is abundant in liver, kidney, pancreas, yeast, and milk. Biotin has been recognized as an essential nutrient. Our biotin requirement is fulfilled in part through diet, through endogenous reutilization of biotin and perhaps through capture of biotin generated in the intestinal flora. The utilization of biotin for covalent attachment to carboxylases and its reutilization through the release of carboxylase biotin after proteolytic degradation constitutes the 'biotin cycle'. Biotin deficiency is associated with neurological manifestations, skin rash, hair loss and metabolic disturbances that are thought to relate to the various carboxylase deficiencies (metabolic ketoacidosis with lactic acidosis). It has also been suggested that biotin deficiency is associated with protein malnutrition, and that marginal biotin deficiency in pregnant women may be teratogenic. Biotin acts as a carboxyl carrier in carboxylation reactions. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lysine residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. There are four biotin-dependent carboxylases in mammals: those of propionyl-CoA (PCC), 3-methylcrotonyl-CoA (MCC), pyruvate (PC) and acetyl-CoA carboxylases (isoforms ACC-1 and ACC-2). All but ACC-2 are mitochondrial enzymes. The biotin moiety is covalently bound to the epsilon amino group of a Lys residue in each of these carboxylases in a domain 60-80 amino acids long. The domain is structurally similar among carboxylases from bacteria to mammals. Evidence is emerging that biotin participates in processes other than classical carboxylation reactions. Specifically, novel roles for biotin in cell signaling, gene expression, and chromatin structure have been identified in recent years. Human cells accumulate biotin by using both the sodium-dependent multivitamin transporter and monocarboxylate transporter 1. These transporters and other biotin-binding proteins partition biotin to compartments involved in biotin signaling: cytoplasm, mitochondria, and nuclei. The activity of cell signals such as biotinyl-AMP, Sp1 and Sp3, nuclear factor (NF)-kappaB, and receptor tyrosine kinases depends on biotin supply. Consistent with a role for biotin and its catabolites in modulating these cell signals, greater than 2000 biotin-dependent genes have been identified in various human tissues. Many biotin-dependent gene products play roles in signal transduction and localize to the cell nucleus, consistent with a role for biotin in cell signaling. Posttranscriptional events related to ribosomal activity and protein folding may further contribute to effects of biotin on gene expression. Finally, research has shown that biotinidase and holocarboxylase synthetase mediate covalent binding of biotin to histones (DNA-binding proteins), affecting chromatin structure; Biotin, also known as vitamin H or B7, 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 it plays a role in gluconeogenesis.; Signs of Biotin Deficiency: In general, appetite and growth are decreased. Dermatologic symptoms include dermatitis, alopecia (hair loss) and achromotrichia (absence or loss of pigment in the hair.) Perosis (a shortening and thickening of bones) is seen in the skeleton. Fatty Liver and Kidney Syndrome (FLKS) and hepatic steatosis also can occur. Genetic defect could also cause biotin deficiency. Holocarboxylase synthetase deficiency is a genetic mutation. It is a severe metabolic disorder. Biochemical and clinical manifestation includes: ketolactic acidosis, organic aciduria, hyperammonemia, skin rash, feeding problems, hypotonie, seizures, development delay, alopecia, and coma. This disease is lethal, however, mentioned manifestation can be reversed by pharmacologic doses of biotin (10-100 mg per day).[citation needed]; at least seven biotinylation sites have been identified in human histones. Biotinylation of histones appears to play a role in cell proliferation, gene silencing, and the cellular response to DNA repair. Roles for biotin in cell signaling and chromatin structure are consistent with the notion that biotin has a unique significance in cell biology. (PMID: 15992684, 16011464)
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