Synonym
D-Pinitol; (+)-Pinitol; D-(+)-Pinitol; Methylinositol; D-(+)-Pinitol;
IUPAC/Chemical Name
3-O-methyl-D-chiro-inositol
InChi Key
DSCFFEYYQKSRSV-KLJZZCKASA-N
InChi Code
InChI=1S/C7H14O6/c1-13-7-5(11)3(9)2(8)4(10)6(7)12/h2-12H,1H3/t2-,3-,4-,5-,6+,7+/m0/s1
SMILES Code
O[C@@H]1[C@@H]([C@H]([C@@H]([C@H]([C@H]1O)O)O)OC)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
D-pinitol exerts hypoglycemic activity and protective effects in the cardiovascular system. D-pinitol has antiviral and larvicidal activities.
In vitro activity:
The results revealed that D-pinitol significantly inhibited the proliferation of MCF-7 cells in a concentration-dependent manner, while upregulating the expression of p53, Bax and down regulating Bcl-2 and NF-kB. Thus the results obtained in this study clearly vindicated that D-pinitol induces apotosis in MCF-7 cells through regulation of proteins of pro- and anti-apoptotic cascades.
Reference: Asian Pac J Cancer Prev. 2014;15(4):1757-62. https://pubmed.ncbi.nlm.nih.gov/24641404/
In vivo activity:
D-pinitol increased the concentration of nitrite, which was inhibited by L-NAME and calmidazolium (10 μM). D-pinitol increased the phosphorylation level of eNOS activation site at Ser1177 and reduced the phosphorylation level of its inactivation site at Thr495. In normotensive mice, the intraperitoneal administration of D-pinitol (10 mg/kg) induced a significant reduction of the SBP after 30 min. The present results led this study to conclude that D-pinitol has an endothelium- and NO-dependent vasodilator effect in mouse mesenteric artery through a mechanism dependent on the activation of eNOS by the calcium-calmodulin complex, which can explain its hypotensive effect in mice.
Reference: Front Pharmacol. 2018 May 22;9:528. https://pubmed.ncbi.nlm.nih.gov/29872397/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
5.0 |
1.03 |
| DMSO |
57.7 |
296.97 |
| PBS (pH 7.2) |
5.0 |
1.03 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
194.18
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Rengarajan T, Nandakumar N, Rajendran P, Haribabu L, Nishigaki I, Balasubramanian MP. D-pinitol promotes apoptosis in MCF-7 cells via induction of p53 and Bax and inhibition of Bcl-2 and NF-κB. Asian Pac J Cancer Prev. 2014;15(4):1757-62. doi: 10.7314/apjcp.2014.15.4.1757. PMID: 24641404.
2. Sethi G, Ahn KS, Sung B, Aggarwal BB. Pinitol targets nuclear factor-kappaB activation pathway leading to inhibition of gene products associated with proliferation, apoptosis, invasion, and angiogenesis. Mol Cancer Ther. 2008 Jun;7(6):1604-14. doi: 10.1158/1535-7163.MCT-07-2424. PMID: 18566231.
3. Moreira LN, Silva JF, Silva GC, Lemos VS, Cortes SF. Activation of eNOS by D-pinitol Induces an Endothelium-Dependent Vasodilatation in Mouse Mesenteric Artery. Front Pharmacol. 2018 May 22;9:528. doi: 10.3389/fphar.2018.00528. PMID: 29872397; PMCID: PMC5972298.
4. Koh ES, Kim S, Kim M, Hong YA, Shin SJ, Park CW, Chang YS, Chung S, Kim HS. D‑Pinitol alleviates cyclosporine A‑induced renal tubulointerstitial fibrosis via activating Sirt1 and Nrf2 antioxidant pathways. Int J Mol Med. 2018 Apr;41(4):1826-1834. doi: 10.3892/ijmm.2018.3408. Epub 2018 Jan 19. PMID: 29393366; PMCID: PMC5810208.
In vitro protocol:
1. Rengarajan T, Nandakumar N, Rajendran P, Haribabu L, Nishigaki I, Balasubramanian MP. D-pinitol promotes apoptosis in MCF-7 cells via induction of p53 and Bax and inhibition of Bcl-2 and NF-κB. Asian Pac J Cancer Prev. 2014;15(4):1757-62. doi: 10.7314/apjcp.2014.15.4.1757. PMID: 24641404.
2. Sethi G, Ahn KS, Sung B, Aggarwal BB. Pinitol targets nuclear factor-kappaB activation pathway leading to inhibition of gene products associated with proliferation, apoptosis, invasion, and angiogenesis. Mol Cancer Ther. 2008 Jun;7(6):1604-14. doi: 10.1158/1535-7163.MCT-07-2424. PMID: 18566231.
In vivo protocol:
1. Moreira LN, Silva JF, Silva GC, Lemos VS, Cortes SF. Activation of eNOS by D-pinitol Induces an Endothelium-Dependent Vasodilatation in Mouse Mesenteric Artery. Front Pharmacol. 2018 May 22;9:528. doi: 10.3389/fphar.2018.00528. PMID: 29872397; PMCID: PMC5972298.
2. Koh ES, Kim S, Kim M, Hong YA, Shin SJ, Park CW, Chang YS, Chung S, Kim HS. D‑Pinitol alleviates cyclosporine A‑induced renal tubulointerstitial fibrosis via activating Sirt1 and Nrf2 antioxidant pathways. Int J Mol Med. 2018 Apr;41(4):1826-1834. doi: 10.3892/ijmm.2018.3408. Epub 2018 Jan 19. PMID: 29393366; PMCID: PMC5810208.
1. Rengarajan, T., Nandakumar, N., Rajendran, P., et al. D-pinitol promotes apoptosis in MCF-7 cells via induction of p53 and bax and inhibition of Bcl-2 and NF-κB Asian Pac. J. Cancer Prev. 15(4) , 1757-1762 (2014).
2. Moreira, L.N., Silva, J.F., Silva, G.C., et al. Activation of eNOS by D-pinitol induces an endothelium-dependent vasodilatation in mouse mesenteric artery Front. Pharmacol. 9:528, (2018).
3. Koh, E.S., Kim, S., Kim, M., et al. D‑Pinitol alleviates cyclosporine A‑induced renal tubulointerstitial fibrosis via activating Sirt1 and Nrf2 antioxidant pathways Int. J. Mol. Med. 41(4) , 1826-1834 (2018).
4. Bates, S.H., Jones, R.B., and Bailey, C.J. Insulin-like effect of pinitol Br. J. Pharmacol. 130(8) , 1944-1948 (2000).
