化合物信息

ID:8

C₁₀H₁₆N₂O₃S

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

YBJHBAHKTGYVGT-ZKWXMUAHSA-N

OC(=O)CCCC[C@@H]1SC[C@H]2[C@@H]1NC(=O)N2

S1[C@H]([C@H]2NC(=O)N[C@H]2C1)CCCCC(=O)O

LogD (pH = 7.4)

-2.57

LogD (pH = 5.5)

-0.81

Log P

0.32

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

4.40

极化表面积

78.43

极化性

24.69

摩尔折射率

60.05

LOG S

-1.88

Vitamin HD-BIOTINBios II5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acidD-BiotinD(+)-BiotinBiotinVitamin B7Coenzyme RBiotin 生物素辅酶 R(+)-Biotin(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acidBiotin生物素维生素 H维生素 B7cis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acidD(+)-BiotinD-BIOTIN, USP GRADEBioepidermFactor SBiopeidermVitamin B₇Biotinum吡哆素BiotinD-Biotin生物素D-生物素Rovimix H2Meribin(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanoic AcidLutavit H2NSC 63865Vitamin B 7Vitamin Hcis-Tetrahydro-2-oxothieno(3,4-d)imidazoline-4-valeric acidbiotincis-(+)-Tetrahydro-2-oxothieno[3,4]imidazoline-4-valeric acidCoenzyme R(+)-cis-Hexahydro-2-oxo-1H-thieno[3,4]imidazole-4-valeric acidD-(+)-biotincis-Hexahydro-2-oxo-1H-thieno(3,4)imidazole-4-valeric acidvitamin B7(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-valeric acid5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acidD-BiotinBIOTIN

Factor SBios IILutavit H2Rovimix H2BiodermatinBioepidermMeribinBiotin Forte

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

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

国际非专利药品(INN)

biotinabiotinbiotinebiotinum

美国药典/FDA物质标识码

MetaboLights数据库

BRENDA Ligand数据库

Drug Central Database

Cofactor responsible for carbon dioxide transfer

• 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

• Knappe, J., Annu. Review, Biochem., 39: 757-76, (1970)

• Bayer, E. and Uilchek, M., Methods Enzymol., 34: 265-7, (1974).

• Bayer, E. and Uilchek, M., Methods Enzymol. , 34 : 265-7, (1974).

• Knappe, J., Annu. Review, Biochem. , 39 : 757-76, (1970)

• Traub, et al.: Nature, 178, 649 (1942)

• du Vigneaud, et al.: J. Biol. Chem., 146, 475 (1942)

• Hugues, M., et al.: Biochemistry, 31, 12 (1942)

• Siegel, H., et al.: Experienta, 37, 789 (1942)

• Vesely, D.L., Science, 216, 1329 (1942)

• Vasilevskis, J. et al., J.A.C.S., 1978, 100, 7423, (synth, bibl)

• Baggiolini, E.G. et al., J.A.C.S., 1982, 104, 6460, (synth)

• Whitney, R.A., Can. J. Chem., 1983, 61, 1158, (synth)

• Senuma, M. et al., Chem. Pharm. Bull., 1990, 38, 882, (rev, synth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1037

• De Titta, G.T. et al., J.A.C.S., 1994, 116, 6485, (cryst struct, nmr)

• De Clercq, P.J. et al., Chem. Rev., 1997, 97, 1755-1792, (rev, synth)

• Marx, M. et al., J.A.C.S., 1977, 99, 6754, (synth, bibl)

• Uskokovic, M.R., Kirk-Othmer Encycl. Chem. Technol., 3rd edn., Wiley, 1978, 24, 41, (rev)

• Lee, H.L. et al., Tetrahedron, 1987, 43, 4887, (synth)

• Alczar, V. et al., Tetrahedron, 1990, 46, 1057, (synth)

• Moolenaar, M.J. et al., Angew. Chem., Int. Ed., 1995, 34, 2391, (synth)

• Chavan, S.P. et al., J.O.C., 2001, 66, 6197-6201, (synth)

• De Titta, G.T. et al., J.A.C.S., 1976, 98, 1920, (cryst struct)

• Ohrui, H. et al., Agric. Biol. Chem., 1978, 42, 865, (synth)

• Bentley, R., Trends Biochem. Sci., 1985, 10, 51, (rev, abs config)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1715

• Deroose, F.D. et al., J.O.C., 1995, 60, 321, (synth, bibl)

• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 285, (bibl, synth)

• Chen, F.-E. et al., Synthesis, 2000, 2004-2008, (synth, ir, pmr, ms)

• Seki, M. et al., Tet. Lett., 2002, 43, 3269-3272, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VSU100

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1317C, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 809C, (ir)

• Harris, S.A. et al., J.A.C.S., 1944, 66, 1756, (synth, resoln)

• Jansen, A.B.A. et al., J.C.S., 1962, 4909; 1964, 1530, (-Biotin)

• Corey, E.J. et al., Tet. Lett., 1988, 29, 57, (synth)

• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, BGD100

• Trotter, J. et al., Biochemistry, 1966, 5, 713, (cryst struct, abs config)

• Green, N.M. et al., J.C.S.(C), 1970, 1330, (cd, ord)

• Bonjour, J.-P., Handbook of Vitamins, (ed. Machlin, L.J.), M. Dekker, New York, 1984, 403, (rev)

• Dakshinamurti, K. et al., Ann. N.Y. Acad. Sci., (Eds.), 1985, 447, (book)

• Bihovsky, R. et al., Tetrahedron, 1990, 46, 7667, (synth)

名称和标识

别名

商标名

Factor SBios IILutavit H2Rovimix H2BiodermatinBioepidermMeribinBiotin Forte

IUPAC标准名

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

IUPAC传统名

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

API名称

Biotin

国际非专利药品(INN)

biotinabiotinbiotinebiotinum

参考文献

PubChem文献

数据源提供

• Knappe, J., Annu. Review, Biochem., 39: 757-76, (1970)

• Bayer, E. and Uilchek, M., Methods Enzymol., 34: 265-7, (1974).

• Bayer, E. and Uilchek, M., Methods Enzymol. , 34 : 265-7, (1974).

• Knappe, J., Annu. Review, Biochem. , 39 : 757-76, (1970)

• Traub, et al.: Nature, 178, 649 (1942)

• du Vigneaud, et al.: J. Biol. Chem., 146, 475 (1942)

• Hugues, M., et al.: Biochemistry, 31, 12 (1942)

• Siegel, H., et al.: Experienta, 37, 789 (1942)

• Vesely, D.L., Science, 216, 1329 (1942)

• Vasilevskis, J. et al., J.A.C.S., 1978, 100, 7423, (synth, bibl)

• Baggiolini, E.G. et al., J.A.C.S., 1982, 104, 6460, (synth)

• Whitney, R.A., Can. J. Chem., 1983, 61, 1158, (synth)

• Senuma, M. et al., Chem. Pharm. Bull., 1990, 38, 882, (rev, synth)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1037

• De Titta, G.T. et al., J.A.C.S., 1994, 116, 6485, (cryst struct, nmr)

• De Clercq, P.J. et al., Chem. Rev., 1997, 97, 1755-1792, (rev, synth)

• Marx, M. et al., J.A.C.S., 1977, 99, 6754, (synth, bibl)

• Uskokovic, M.R., Kirk-Othmer Encycl. Chem. Technol., 3rd edn., Wiley, 1978, 24, 41, (rev)

• Lee, H.L. et al., Tetrahedron, 1987, 43, 4887, (synth)

• Alczar, V. et al., Tetrahedron, 1990, 46, 1057, (synth)

• Moolenaar, M.J. et al., Angew. Chem., Int. Ed., 1995, 34, 2391, (synth)

• Chavan, S.P. et al., J.O.C., 2001, 66, 6197-6201, (synth)

• De Titta, G.T. et al., J.A.C.S., 1976, 98, 1920, (cryst struct)

• Ohrui, H. et al., Agric. Biol. Chem., 1978, 42, 865, (synth)

• Bentley, R., Trends Biochem. Sci., 1985, 10, 51, (rev, abs config)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 1715

• Deroose, F.D. et al., J.O.C., 1995, 60, 321, (synth, bibl)

• Nicolaou, K.C. et al., Classics in Total Synthesis, Targets, Strategies, Methods, VCH, 1996, 285, (bibl, synth)

• Chen, F.-E. et al., Synthesis, 2000, 2004-2008, (synth, ir, pmr, ms)

• Seki, M. et al., Tet. Lett., 2002, 43, 3269-3272, (synth)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VSU100

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 1, 1317C, (nmr)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 1, 809C, (ir)

• Harris, S.A. et al., J.A.C.S., 1944, 66, 1756, (synth, resoln)

• Jansen, A.B.A. et al., J.C.S., 1962, 4909; 1964, 1530, (-Biotin)

• Corey, E.J. et al., Tet. Lett., 1988, 29, 57, (synth)

• Lewis, R.J., Food Additives Handbook, Van Nostrand Reinhold International, New York, 1989, BGD100

• Trotter, J. et al., Biochemistry, 1966, 5, 713, (cryst struct, abs config)

• Green, N.M. et al., J.C.S.(C), 1970, 1330, (cd, ord)

• Bonjour, J.-P., Handbook of Vitamins, (ed. Machlin, L.J.), M. Dekker, New York, 1984, 403, (rev)

• Dakshinamurti, K. et al., Ann. N.Y. Acad. Sci., (Eds.), 1985, 447, (book)

• Bihovsky, R. et al., Tetrahedron, 1990, 46, 7667, (synth)

生物活性

PubChem BioAssay

产品质量级别

PREMIUM

适用性

meets USP testing specifications

plant cell culture tested

suitable for plant cell culture

suitable for cell culture

suitable for insect cell culture

Empirical Formula (Hill Notation)

C10H16N2O3S

有效期

(limited shelf life, expiry date on the label)

干燥失重

≤0.5% loss on drying

燃烧残渣

≤0.1% (as SO4)

药典

testing & handling conforms to Pharmacopeia

特征

standard type water soluble vitamin

包装

ampule of 100 mg

应用领域

Additive for cosmetic and feedstuffs

Bacterial growth factor for ""egg white injury""

生物来源

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

保存注意事项

IRRITANT

TSCA收录

false

RTECS编号

XJ9088200

保存条件

2-8°C

Refrigerator

NFPA704

个人保护装置

Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

保存温度

2-8°C

德国WGK号

描述信息

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

External Links

• [Wikipedia]

• [PDRhealth]

• [Drugs.com]

MP Biomedicals

02101023

Crystalline

02194634

Cell Culture Reagent
Crystalline

02199537

Solid

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

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。

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。

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.
法律信息
TraceCERT 注册商标 Sigma-Aldrich Co. LLC

14400

Other Notes
综述1,2；亲和素-生物素技术；

47868

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

Wikipedia

Biotin

TRC

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

ChEBI

CHEBI:15956

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.