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B9636

Sigma-Aldrich

S-Benzoylthiamine O-monophosphate

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Synonym(s):
Benfotiamine
Empirical Formula (Hill Notation):
C19H23N4O6PS
CAS Number:
Molecular Weight:
466.45
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.79

assay

≥98% (TLC)

Quality Level

form

powder or crystals

color

white to off-white

storage temp.

2-8°C

SMILES string

Cc1ncc(CN(C=O)\C(C)=C(/CCOP(O)(O)=O)SC(=O)c2ccccc2)c(N)n1

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+

InChI key

BTNNPSLJPBRMLZ-GHRIWEEISA-N

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This Item
SMB00294F6750T4625
S-Benzoylthiamine O-monophosphate

B9636

S-Benzoylthiamine O-monophosphate

-
Thiamine mononitrate ≥98% (HPLC)

SMB00294

Thiamine mononitrate

-
Thiamine hydrochloride reagent grade, ≥99% (HPLC)

T4625

Thiamine hydrochloride

Essential Grade
form

powder or crystals

form

powder

form

powder

form

powder

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

-

color

white to off-white

color

white to off-white

color

-

color

white

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

General description

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.

Application

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

Biochem/physiol Actions

S-Benzoylthiamine O-monophosphate (Benfotiamine) is a therapeutic agent. It helps in the prevention of diabetic complications such as, retinopathy, neuropathy and nephropathy. Benfotiamine inhibits the synthesis of glycation end products (AGEs) in diabetes. Benfotiamine is considered as a nutraceutical product for the prevention of diabetic neuropathy.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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Xiaoli Pan et al.
Neuroscience bulletin, 32(6), 591-596 (2016-10-04)
To date, we still lack disease-modifying therapies for Alzheimer's disease (AD). Here, we report that long-term administration of benfotiamine improved the cognitive ability of patients with AD. Five patients with mild to moderate AD received oral benfotiamine (300 mg daily) over
Pitchai Balakumar et al.
Pharmacological research, 61(6), 482-488 (2010-03-02)
Thiamine, known as vitamin B(1), plays an essential role in energy metabolism. Benfotiamine (S-benzoylthiamine O-monophoshate) is a synthetic S-acyl derivative of thiamine. Once absorbed, benfotiamine is dephosphorylated by ecto-alkaline phosphatase to lipid-soluble S-benzoylthiamine. Transketolase is an enzyme that directs the
Alaa Alkhalaf et al.
Diabetes care, 33(7), 1598-1601 (2010-04-24)
To investigate the effect of benfotiamine on urinary albumin excretion (UAE) and the tubular damage marker kidney injury molecule-1 (KIM-1) in patients with type 2 diabetes and nephropathy. Patients with type 2 diabetes and UAE equivalent to 15-300 mg/24 h
Rajesh Katare et al.
Journal of molecular and cellular cardiology, 49(4), 625-638 (2010-06-15)
Benfotiamine (BFT) is a transketolase activator that directs glucose to the pentose phosphate pathway. The present study investigated whether BFT improves the recovery after myocardial infarction (MI) and explored underlying mechanisms of protection. Non-diabetic and streptozotocin-induced type 1 diabetic mice
Umesh C S Yadav et al.
Free radical biology & medicine, 48(10), 1423-1434 (2010-03-12)
This study was designed to investigate the molecular mechanisms by which benfotiamine, a lipid-soluble analogue of vitamin B1, affects lipopolysaccharide (LPS)-induced inflammatory signals leading to cytotoxicity in the mouse macrophage cell line RAW264.7. Benfotiamine prevented LPS-induced apoptosis, expression of the

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