D-PinitolCAS# 10284-63-6 |
- L-Quebrachitol
Catalog No.:BCN2727
CAS No.:642-38-6
Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 10284-63-6 | SDF | Download SDF |
| PubChem ID | 164619 | Appearance | Powder |
| Formula | C7H14O6 | M.Wt | 194.2 |
| Type of Compound | Miscellaneous | Storage | Desiccate at -20°C |
| Synonyms | 3-O-Methyl-D-Chiro-Inositol | ||
| Solubility | DMSO : 125 mg/mL (643.73 mM; Need ultrasonic) | ||
| Chemical Name | (1S,2S,4S,5R)-6-methoxycyclohexane-1,2,3,4,5-pentol | ||
| SMILES | COC1C(C(C(C(C1O)O)O)O)O | ||
| Standard InChIKey | DSCFFEYYQKSRSV-FEPQRWDDSA-N | ||
| Standard InChI | 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 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | D-Pinitol is a safe nutrient to reduce calorie consumption when supplementing with creatine. It exerts anti-inflammatory, insulin-like activities; and inhibits osteoclastogenesis from bone marrow stromal cells and macrophage cells, which in turn protect bone loss from ovariectomy. It inhibits the activation of p38, JNK, and NF-κB, the expression of p53, Bcl-2, Bax and NF-kB proteins, and reduces focal adhesion kinase (FAK) phosphorylation, c-Src kinase activity. |
| Targets | GLUT | Src | NF-kB | FAK | p53 | Bcl-2/Bax |
| In vitro | D-pinitol Inhibits Prostate Cancer Metastasis through Inhibition of αVβ3 Integrin by Modulating FAK, c-Src and NF-κB Pathways.[Pubmed: 23698767]Int J Mol Sci. 2013 May 8;14(5):9790-802.Prostate cancer is the most commonly diagnosed malignancy in men and shows a predilection for metastasis to the bone. D-Pinitol, a 3-methoxy analogue of d-chiro-inositol, was identified as an active principle in soy foods and legumes, and it has been proven to induce tumor apoptosis and metastasis of cancer cells.
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| In vivo | D-pinitol inhibits RANKL-induced osteoclastogenesis.[Pubmed: 22269833]Int Immunopharmacol. 2012 Mar;12(3):494-500.Numerous studies have indicated that inflammatory cytokines play a major role in osteoclastogenesis, leading to the bone resorption that is frequently associated with osteoporosis. D-Pinitol, a 3-methoxy analogue of D-chiroinositol, was identified as an active principle in soy foods and legumes.
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| Cell Research | D-pinitol promotes apoptosis in MCF-7 cells via induction of p53 and Bax and inhibition of Bcl-2 and NF-κB.[Pubmed: 24641404]Asian Pac J Cancer Prev. 2014;15(4):1757-62.Development of drugs from natural products has been undergoing a gradual evoluation. Many plant derived compounds have excellent therapeutic potential against various human ailments. They are important sources especially for anticancer agents. A number of promising new agents are in clinical development based on their selective molecular targets in the field of oncology.
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D-Pinitol Dilution Calculator
D-Pinitol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.1493 mL | 25.7467 mL | 51.4933 mL | 102.9866 mL | 128.7333 mL |
| 5 mM | 1.0299 mL | 5.1493 mL | 10.2987 mL | 20.5973 mL | 25.7467 mL |
| 10 mM | 0.5149 mL | 2.5747 mL | 5.1493 mL | 10.2987 mL | 12.8733 mL |
| 50 mM | 0.103 mL | 0.5149 mL | 1.0299 mL | 2.0597 mL | 2.5747 mL |
| 100 mM | 0.0515 mL | 0.2575 mL | 0.5149 mL | 1.0299 mL | 1.2873 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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D-pinitol inhibits RANKL-induced osteoclastogenesis.[Pubmed:22269833]
Int Immunopharmacol. 2012 Mar;12(3):494-500.
Numerous studies have indicated that inflammatory cytokines play a major role in osteoclastogenesis, leading to the bone resorption that is frequently associated with osteoporosis. D-Pinitol, a 3-methoxy analogue of D-chiroinositol, was identified as an active principle in soy foods and legumes. Here we found that D-Pinitol markedly inhibited the receptor activator of nuclear factor kappa B ligand (RANKL)-induced osteoclastic differentiation from bone marrow stromal cells and RAW264.7 macrophage cells. In addition, D-Pinitol also reduced RANKL-induced p38 and JNK phosphorylation. Furthermore, RANKL-mediated increase of IKK, IkappaBalpha, and p65 phosphorylation and NF-kappaB-luciferase activity was inhibited by D-Pinitol. However, D-Pinitol did not affect the proliferation and differentiation of osteoblasts. In addition, D-Pinitol also prevented the bone loss induced by ovariectomy in vivo. Our data suggest that D-Pinitol inhibits osteoclastogenesis from bone marrow stromal cells and macrophage cells via attenuated RANKL-induced p38, JNK, and NF-kappaB activation, which in turn protect bone loss from ovariectomy.
D-pinitol inhibits prostate cancer metastasis through inhibition of alphaVbeta3 integrin by modulating FAK, c-Src and NF-kappaB pathways.[Pubmed:23698767]
Int J Mol Sci. 2013 May 8;14(5):9790-802.
Prostate cancer is the most commonly diagnosed malignancy in men and shows a predilection for metastasis to the bone. D-Pinitol, a 3-methoxy analogue of d-chiro-inositol, was identified as an active principle in soy foods and legumes, and it has been proven to induce tumor apoptosis and metastasis of cancer cells. In this study, we investigated the anti-metastasis effects of D-Pinitol in human prostate cancer cells. We found that D-Pinitol reduced the migration and the invasion of prostate cancer cells (PC3 and DU145) at noncytotoxic concentrations. Integrins are the major adhesive molecules in mammalian cells and have been associated with the metastasis of cancer cells. Treatment of prostate cancer cells with D-Pinitol reduced mRNA and cell surface expression of alphavbeta3 integrin. In addition, D-Pinitol exerted its inhibitory effects by reducing focal adhesion kinase (FAK) phosphorylation, c-Src kinase activity and NF-kB activation. Thus, D-Pinitol may be a novel anti-metastasis agent for the treatment of prostate cancer metastasis.
D-pinitol promotes apoptosis in MCF-7 cells via induction of p53 and Bax and inhibition of Bcl-2 and NF-kappaB.[Pubmed:24641404]
Asian Pac J Cancer Prev. 2014;15(4):1757-62.
Development of drugs from natural products has been undergoing a gradual evoluation. Many plant derived compounds have excellent therapeutic potential against various human ailments. They are important sources especially for anticancer agents. A number of promising new agents are in clinical development based on their selective molecular targets in the field of oncology. D-Pinitol is a naturally occurring compound derived from soy which has significant pharmacological activitites. Therefore we selected D-Pinitol in order to evaluate apoptotic potential in the MCF-7 cell line. Human breast cancer cells were treated with different concentrations of D-Pinitol and cytotoxicity was measured by MTT and LDH assays. The mechanism of apoptosis was studied with reference to expression of p53, Bcl-2, Bax and NF-kB proteins. 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.
