![Tacalcitol [1,24(R)-Dihydroxyvitamin D3] 57333-96-7](/picture/img/Tacalcitol [1,24(R)-Dihydroxyvitamin D3] Chemical Structure.png)
Tacalcitol [1,24(R)-Dihydroxyvitamin D3; 1.alpha.,24R-Dihydroxyvitamin D3] is a vitamin D3 analog (isomer of Vitamin D3) that promotes normal bone development by regulating calcium. acalcitol also stimulates the synthesis of nerve growth factor in epidermal keratinocytes and regulates immunological and inflammatory processes.
Physicochemical Properties
| Molecular Formula | C27H44O3 |
| Molecular Weight | 416.646 |
| Exact Mass | 416.329 |
| Elemental Analysis | C, 77.84; H, 10.65; O, 11.52 |
| CAS # | 57333-96-7 |
| Related CAS # | Tacalcitol monohydrate;93129-94-3 |
| PubChem CID | 5283734 |
| Appearance | White to off-white solid powder |
| Density | 1.1±0.1 g/cm3 |
| Boiling Point | 565.0±50.0 °C at 760 mmHg |
| Flash Point | 238.4±24.7 °C |
| Vapour Pressure | 0.0±3.5 mmHg at 25°C |
| Index of Refraction | 1.546 |
| LogP | 6.12 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 6 |
| Heavy Atom Count | 30 |
| Complexity | 676 |
| Defined Atom Stereocenter Count | 7 |
| SMILES | C=C1[C@H](C[C@@H](C/C1=C/C=C2[C@]3([C@@](C)([C@H](CC3)[C@@H](CC[C@H](C(C)C)O)C)CCC/2)[H])O)O |
| InChi Key | BJYLYJCXYAMOFT-RSFVBTMBSA-N |
| InChi Code | InChI=1S/C27H44O3/c1-17(2)25(29)13-8-18(3)23-11-12-24-20(7-6-14-27(23,24)5)9-10-21-15-22(28)16-26(30)19(21)4/h9-10,17-18,22-26,28-30H,4,6-8,11-16H2,1-3,5H3/b20-9+,21-10-/t18-,22-,23-,24+,25-,26+,27-/m1/s1 |
| Chemical Name | (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5R)-5-hydroxy-6-methylheptan-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol |
| Synonyms | PRI2191; TV 02; PRI-2191; TV-02; 1,24(R)-Dihydroxyvitamin D3; 1.alpha.,24R-Dihydroxyvitamin D3; Bonalfa; Curatoderm; PRI 2191; TV02; |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.(3). This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| References |
[1]. Synthesis of active forms of vitamin D. Part IX. Synthesis of 1α,24-dihydroxycholecalciferol. J. Chem. Soc., Perkin Trans. 1, 1975, 1421-1424. [2]. Synthetic studies of vitamin D3 analogues from bile acids. Part 3. Syntheses of 1α,25-, 1α,24R-, and 1α,24S-dihydroxycholecalciferols from lithocholic acid and their biological activities. J. Chem. [3]. Vitamin D derivatives: calcitriol and tacalcitol inhibits interleukin-6 and interleukin-8 expression in human nasal polyp fibroblasts. Adv.Med.Sci. (2010) 55 86. [4]. Freckling Promoted by Topical Tacalcitol in a Japanese Boy with Left Eyelid Vitiligo.Pediatr Dermatol. 2011 Oct 20. [5]. 1 alpha,24R-dihydroxyvitamin D3 has an ability comparable to that of 1 alpha,25-dihydroxyvitamin D3 to induce keratinocyte differentiation.J Dermatol. 1990 Nov;17(11):707-9. [6]. Effect of 1,24R-dihydroxyvitamin D3 on the growth of human keratinocytes.J Dermatol. 1990 Feb;17(2):97-103. |
| Additional Infomation | Tacalcitol is a hydroxy seco-steroid that is calciol which carries hydroxy groups at positions 1S and 24R. It is a vitamin D3 analog which is used for the treatment of psoriasis vulgaris in adults, especially on the scalp. It has a role as an antipsoriatic, a vitamin D receptor agonist and an antineoplastic agent. It is a member of D3 vitamins, a hydroxy seco-steroid, a secondary alcohol and a seco-cholestane. It is functionally related to a calciol. |
Solubility Data
| Solubility (In Vitro) | DMSO: ≥ 100 mg/mL (~240.0 mM) |
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.75 mg/mL (6.60 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.75 mg/mL (6.60 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.75 mg/mL (6.60 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 27.5 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4001 mL | 12.0005 mL | 24.0010 mL | |
| 5 mM | 0.4800 mL | 2.4001 mL | 4.8002 mL | |
| 10 mM | 0.2400 mL | 1.2000 mL | 2.4001 mL |