5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid

• ChemBase ID: 8
• Molecular Formular: C10H16N2O3S
• Molecular Mass: 244.31064
• Monoisotopic Mass: 244.08816338
• SMILES: S1[C@H]([C@H]2NC(=O)N[C@H]2C1)CCCCC(=O)O
• Canonical SMILES: OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2
• InChI: InChI=1S/C10H16N2O3S/c13-8(14)4-2-1-3-7-9-6(5-16-7)11-10(15)12-9/h6-7,9H,1-5H2,(H,13,14)(H2,11,12,15)/t6-,7-,9-/m0/s1
• InChIKey: YBJHBAHKTGYVGT-ZKWXMUAHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid
• IUPAC Traditional name: 5-[(3aS,4S,6aR)-2-oxo-hexahydro-1H-thieno[3,4-d]imidazolidin-4-yl]pentanoic acid; biotin
• Brand Name: Biodermatin; Bioepiderm; Bios II; Factor S; Lutavit H2; Meribin; Rovimix H2; Biotin Forte
• Synonyms: (3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic Acid; Lutavit H2; Meribin; NSC 63865; Rovimix H2; Bios II; D-BIOTIN; Vitamin B 7; D(+)-Biotin; (+)-Biotin; (+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acid; cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acid; Vitamin H; Vitamin B7; D(+)-Biotin; D-Biotin; Coenzyme R; Biotin; Biotinum; Biotin; D-Biotin; Biotin; Vitamin B₇; Biopeiderm; 5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid; Bioepiderm; Factor S; D-BIOTIN, USP GRADE; 吡哆素; 生物素; D-生物素; Biotin 生物素; 维生素 B7; 维生素 H; 辅酶 R; 生物素

Database IDs

• CAS Number: 58-85-5
• EC Number: 200-399-3
• MDL Number: MFCD00005541
• Beilstein Number: 86838
• PubChem SID: 160963471; 24891512; 24851733; 24871542; 24891795; 46508694; 24891716; 24891778
• PubChem CID: 171548
• CHEBI ID: 15956
• ATC CODE: A11HA05
• CHEMBL: 857
• Chemspider ID: 149962
• DrugBank ID: DB00121
• KEGG ID: D00029
• Unique Ingredient Identifier: 6SO6U10H04
• Wikipedia Title: Biotin

CALCULATED PROPERTIES

JChem

• Acid pKa: 4.4043164
• H Acceptors: 3
• H Donor: 3
• LogD (pH = 5.5): -0.8081781
• LogD (pH = 7.4): -2.5652478
• Log P: 0.31942365
• Molar Refractivity: 60.0509 cm^3
• Polarizability: 23.706692 Å^3
• Polar Surface Area: 78.43 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.17
• LOG S: -2.3
• Solubility (Water): 1.22e+00 g/l

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble10 mg/mL at 25 °C, clear, colorless; 0.22 mg/mL at 25 oC [MERCK INDEX (1996)]; 22 mg/100 mL in water; H2O: soluble0.2 mg/mL (Solubility increases with addition of 1 N NaOH.); Water
• Apperance: lyophilized powder; powder; White crystalline needles; White Solid
• Melting Point: 229-234 °C; 231-233 °C(lit.); 232-233; 232-233 °C; 232-233°C
• Optical Rotation: [α]20/D +91±2°, c = 1% in 0.1 M NaOH
• Hydrophobicity(logP): 0.5

Safety Information

• Storage Condition: 2-8°C; Refrigerator
• Storage Warning: IRRITANT
• RTECS: XJ9088200
• German water hazard class: 1
• TSCA Listed: false
• NFPA704:
  

  1

  1

  0
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Cofactor responsible for carbon dioxide transfer

Product Information

• Purity: ≥98.0%; ≥99%; ≥99% (TLC); ≥99.0% (T); 95+%
• Grade: analytical standard; certified reference material; Ph Eur; SAJ special grade; TraceCERT®; USP
• Packaging: ampule of 100 mg
• Suitability: meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for insect cell culture; suitable for plant cell culture
• Ignition Residue: ≤0.1% (as SO4)
• Cation Traces: Ca: ≤50 mg/kg; Cd: ≤5 mg/kg; Co: ≤5 mg/kg; Cr: ≤5 mg/kg; Cu: ≤5 mg/kg; Fe: ≤10 mg/kg; K: ≤50 mg/kg; Mg: ≤5 mg/kg; Mn: ≤5 mg/kg; Na: ≤500 mg/kg; Ni: ≤5 mg/kg; Pb: ≤5 mg/kg; Zn: ≤5 mg/kg
• Biological Source: Occurs in yeast, eggs and liver. Also prod. by various other microorganisms and isol. from various higher plant sources, e.g. maize seedlings, leaves of Raphanus sativus
• Shelf Life: (limited shelf life, expiry date on the label)
• Loss on Drying: ≤0.5% loss on drying
• Application(s): Additive for cosmetic and feedstuffs; Bacterial growth factor for ""egg white injury""
• Quality Level: PREMIUM
• Feature: standard type water soluble vitamin
• Pharmacopeia: testing & handling conforms to Pharmacopeia
• Empirical Formula (Hill Notation): C10H16N2O3S

DETAILS

MP Biomedicals - 02101023

Crystalline

MP Biomedicals - 02199537

Solid

MP Biomedicals - 02194634

Cell Culture Reagent
Crystalline

DrugBank - DB00121

• Drug Groups: approved; nutraceutical
• Description: 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. [PubChem]
• Indication: For nutritional supplementation, also for treating dietary shortage or imbalance.
• Pharmacology: 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; changes in mental status, generalized muscular pains (myalgias), hyperesthesias and paresthesias. The treatment for biotin deficiency is to simply start taking some biotin supplements. A lack of biotin in infants will lead to a condition called seborrheic dermatitis or "cradle cap". Biotin deficiencies are extremely rare in adults but if it does occur, it will lead to anemia, depression, hair loss, high blood sugar levels, muscle pain, nausea, loss of appetite and inflamed mucous membranes.
• Toxicity: Prolonged skin contact may cause irritation.
• Affected Organisms: Humans and other mammals
• Absorption: Systemic - approximately 50%
• References: Holmberg A, Blomstergren A, Nord O, Lukacs M, Lundeberg J, Uhlen M: The biotin-streptavidin interaction can be reversibly broken using water at elevated temperatures. Electrophoresis. 2005 Feb;26(3):501-10. [Pubmed]
• External Links: Wikipedia; PDRhealth; Drugs.com

Sigma Aldrich - B4639

Biochem/physiol Actions
对于氨基酸、能量代谢和脂肪酸合成有重要作用的必要维生素。它是四种哺乳类动物羧化酶中的辅基，促进二氧化碳的结合与输送。

Sigma Aldrich - 91827

General description
Certified content by quantitative NMR incl. uncertainty and expiry are given in the certificate.Download your certificate at: http://www.sigma-aldrich.com.
Legal Information
TraceCERT is a registered trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - 14400

Other Notes
Reviews1,2; Avidin-Biotin technology;

Sigma Aldrich - B0301

Biochem/physiol Actions
对于氨基酸、能量代谢和脂肪酸合成有重要作用的必要维生素。它是四种哺乳类动物羧化酶中的辅基，促进二氧化碳的结合与输送。

Sigma Aldrich - B4501

Application
可用于从抗生物素蛋白/链霉抗生物素蛋白树脂上洗脱蛋白质。
包装
1, 5, 10, 25 g in poly bottle
100, 500 mg in poly bottle

Sigma Aldrich - 47868

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.

Toronto Research Chemicals - B389040

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

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