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Chemodex
S-Benzoylthiamine O-monophosphate
Product Details | |
---|---|
Synonyms | Benfotiamine; Benzoylthiamine monophosphate |
Product Type | Chemical |
Properties | |
Formula |
C19H23N4O6PS |
MW | 466.45 |
CAS | 22457-89-2 |
Purity Chemicals | ≥98% (HPLC) |
Appearance | White to off-white powder. |
Solubility | Slightly soluble in DMSO (1mg/ml). |
Identity | Determined by 1H-NMR. |
Declaration | Manufactured by Chemodex. |
Other Product Data |
Click here for Original Manufacturer Product Datasheet |
InChi Key | BTNNPSLJPBRMLZ-GHRIWEEISA-N |
Smiles | CC1=NC(N)=C(CN(/C(C)=C(CCOP(O)(O)=O)/SC(C2=CC=CC=C2)=O)C=O)C=N1 |
Shipping and Handling | |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | +4°C |
Handling Advice | Protect from light and moisture. |
Use/Stability | Stable for at least 2 years after receipt when stored at +4°C. |
Documents | |
MSDS | Inquire |
Product Specification Sheet | |
Datasheet | Download PDF |
S-Benzoylthiamine O-monophosphate is a lipid-soluble form of vitamin B1 (thiamine). S-Benzoylthiamine O-monophosphate facilitates the action of thiamine diphosphate, a cofactor for the enzyme transketolase. The activation of transketolase enzyme accelerates the precursors of advanced glycation end products (AGEs) towards the pentose phosphate pathway thereby reducing the production of AGEs. The reduction in AGEs subsequently decreases metabolic stress which benefits vascular complications seen in diabetes. The anti-AGE property of S-Benzoylthiamine O-monophosphate certainly makes it effective for the treatment of diabetic neuropathy, nephropathy and retinopathy. S-Benzoylthiamine O-monophosphate appears to have a also cardioprotective role in potentiating angiogenesis and inhibiting apoptosis in diabetic complications. S-Benzoylthiamine O-monophosphate also modulates pathways such as arachidonic acid (AA), nuclear transcription Factor κB (NF-κB), protein kinase B, mitogen-activated protein kinases (MAPK) and vascular endothelial growth factor receptor 2 (VEGFR2) signaling pathways, which are also responsible for it's anti-inflammatory and anti-tumor properties. S-Benzoylthiamine O-monophosphate has been shown to be a dual inhibitory action on COX-2 and LOX-5, supressing PKC and NF-κB activation, preventing the downregulation of PKB/Akt during diabetic complications and enhancing cell survival, regulating GSK-3 activity through Akt (rendering it's anti-AD activity) and inducing cell death through paraptosis.
(1) E. Beltramo, et al.; Acta Diabetol. 45, 131 (2008) | (2) P. Balakumar, et al.; Pharmacol. Res. 61, 482 (2010) | (3) V. Raj, et al.; Eur. Rev. Med. Pharmacol. Sci. 22, 3261 (2018) (Review)