Benfotiamine - ≥98% , CAS No.22457-89-2

CAS: 22457-89-2 Cat. No.: B125436 Molecular Weight: 466.45 EC Number: 245-013-4

GRADE & PURITY ≥98%

Synonyms

AB00052426_03 | benfotiamine | Spectrum5_001042 | {[(3E)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-[(E)-benzoylsulfanyl]pent-3-en-1-yl]oxy}phosphonic acid | A816214 | CAS-22457-89-2 | AKOS016339593 | SBI-0051900.P002 | s4798 | BCP13283 | I

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

S-Benzoylthiamine O-monophosphate (Benfotiamine) is an amphiphilic S-acyl thiamine derivative.It is a lipid-soluble vitamin. Benfotiamine contains a thiazole ring.Benfotiamine has a greater bioavailability than thiamine.

S-Benzoylthiamine O-monophosphate has been used to determine its effect on ischemia and reperfusion in skeletal muscles of rat.

Specifications

Synonyms

AB00052426_03 | benfotiamine | Spectrum5_001042 | {[(3E)-4-{N-[(4-amino-2-methylpyrimidin-5-yl)methyl]formamido}-3-[(E)-benzoylsulfanyl]pent-3-en-1-yl]oxy}phosphonic acid | A816214 | CAS-22457-89-2 | AKOS016339593 | SBI-0051900.P002 | s4798 | BCP13283 | I

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Benfotiamine, the lipid-soluble thiamine derivative used as a treatment for diabetic neuropathy, can inhibit three major pathways(the hexosamine pathway, the advanced glycation end product (AGE) formation pathway and the diacylglycerol (DAG)?protein kinas

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763405
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763405
• Canonical Smiles: CC1=NC=C(C(=N1)N)CN(C=O)C(=C(CCOP(=O)(O)O)SC(=O)C2=CC=CC=C2)C
• IUPAC Name: S-[(E)-2-[(4-amino-2-methylpyrimidin-5-yl)methyl-formylamino]-5-phosphonooxypent-2-en-3-yl] benzenecarbothioate
• InChIKey: BTNNPSLJPBRMLZ-GHRIWEEISA-N
• INCHI: 1S/C19H23N4O6PS/c1-13(23(12-24)11-16-10-21-14(2)22-18(16)20)17(8-9-29-30(26,27)28)31-19(25)15-6-4-3-5-7-15/h3-7,10,12H,8-9,11H2,1-2H3,(H2,20,21,22)(H2,26,27,28)/b17-13+
• Isomeric SMILES: CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(\CCOP(=O)(O)O)/SC(=O)C2=CC=CC=C2)/C
• Molecular Weight: 466.45
• Reaxy-Rn: 771326
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=771326&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzoic acids and derivatives
• Alternative Parents: Thiobenzoic acids and derivatives Benzoyl derivatives Aminopyrimidines and derivatives Monoalkyl phosphates Imidolactams Tertiary carboxylic acid amides Heteroaromatic compounds Thioesters Amino acids and derivatives Carbothioic S-esters Sulfenyl compounds Azacyclic compounds Carbonyl compounds Hydrocarbon derivatives Organic oxides Organopnictogen compounds Primary amines
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Benzoic acid or derivatives - Thiobenzoic acid or derivatives - Benzoyl - Aminopyrimidine - Monoalkyl phosphate - Organic phosphoric acid derivative - Phosphoric acid ester - Pyrimidine - Alkyl phosphate - Imidolactam - Heteroaromatic compound - Tertiary carboxylic acid amide - Thiocarboxylic acid ester - Amino acid or derivatives - Carbothioic s-ester - Carboxamide group - Sulfenyl compound - Azacycle - Thiocarboxylic acid or derivatives - Organoheterocyclic compound - Carboxylic acid derivative - Amine - Organooxygen compound - Organonitrogen compound - Organic oxide - Organosulfur compound - Hydrocarbon derivative - Carbonyl group - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Primary amine - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzoic acids and derivatives. These are organic compounds containing a carboxylic acid substituent attached to a benzene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

Discover Target: APEX1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LMNA Tbio Prelamin-A/C (36751 Activities)

Discover Target: LMNA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

Discover Target: PMP22

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO
• Sensitivity: heat sensitive
• Melt Point(°C): 192 °C
• Molecular Weight: 466.400 g/mol
• XLogP3: 0.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 10
• Exact Mass: 466.108 Da
• Monoisotopic Mass: 466.108 Da
• Topological Polar Surface Area: 181.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 697.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1