Specifications
- Purity
- ≥98% (HPLC)
- Appearance
- White to off white powder
- Identity
- 1H-NMR
Properties
- Solvents
- Slightly DMSO (1 mg/ml).
- Melting Point
- 165 °C (decom.)
- Density
- 1.444 g/cm3 (predicted)
Available from stock
S-Benzoylthiamine O-monophosphate
- SKU
- B0403
Category: Vitamins
- Synonyms
- Benfotiamine , Benzoylthiamine monophosphate
- 22457-89-2
- CAS-Number
- C19H23N4O6PS
- Molecular Formula
- 466.45
- Molecular Weight
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
- 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.
- Transportation
- Not dangerous goods
- Description
- Benfotiamine is a lipid-soluble form of vitamin B1 (thiamine). Benfotiamine 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 benfotiamine certainly makes it effective for the treatment of diabetic neuropathy, nephropathy and retinopathy. Benfotiamine appears to have a also cardioprotective role in potentiating angiogenesis and inhibiting apoptosis in diabetic complications. Benfotiamine also modulates pathways such as arachidonic acid (AA), nuclear transcription Factor κB (NF-κβ), 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. Benfotiamine 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.
- Smiles
- CC1=NC(N)=C(CN(/C(C)=C(CCOP(O)(O)=O)/SC(C2=CC=CC=C2)=O)C=O)C=N1
- InChi Key
- BTNNPSLJPBRMLZ-GHRIWEEISA-N
- References
- (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)
- InChi
- 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+
Benfotiamine is a lipid-soluble form of vitamin B1 (thiamine). Benfotiamine 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 benfotiamine certainly makes it effective for the treatment of diabetic neuropathy, nephropathy and retinopathy. Benfotiamine appears to have a also cardioprotective role in potentiating angiogenesis and inhibiting apoptosis in diabetic complications. Benfotiamine also modulates pathways such as arachidonic acid (AA), nuclear transcription Factor κB (NF-κβ), 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. Benfotiamine 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.
Additional information
| Synonyms | Benfotiamine, Benzoylthiamine monophosphate |
|---|---|
| Purity | ≥98% (HPLC) |
| Appearance | White to off white powder |
| CAS-Number | 22457-89-2 |
| Molecular Formula | C19H23N4O6PS |
| Molecular Weight | 466.45 |
| Identity | 1H-NMR |
| Solvents | Slightly DMSO (1 mg/ml). |
| Melting Point | 165 °C (decom.) |
| Density | 1.444 g/cm3 (predicted) |
| Smiles | CC1=NC(N)=C(CN(/C(C)=C(CCOP(O)(O)=O)/SC(C2=CC=CC=C2)=O)C=O)C=N1 |
| InChi Key | BTNNPSLJPBRMLZ-GHRIWEEISA-N |
| 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. |
| Transportation | Not dangerous goods |
| References | (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) |
| InChi | 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+ |
| Quantity | 1 g, 5 g, Bulk |
