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Name |
Tacalcitol |
EINECS | N/A |
CAS No. | 57333-96-7 | Density | 1.06 g/cm3 |
PSA | 60.69000 | LogP | 5.56060 |
Solubility | N/A | Melting Point |
N/A |
Formula | C27H44O3 | Boiling Point | 565 °C at 760 mmHg |
Molecular Weight | 416.645 | Flash Point | 238.4 °C |
Transport Information | N/A | Appearance | N/A |
Safety | Risk Codes | R50/53; R33; R26/27/28 | |
Molecular Structure | Hazard Symbols | N,T+ | |
Synonyms |
1a,24R-Dihydroxyvitamin D3;Bonalfa;Curatoderm;PRI 2191;TV 02;9,10-Secocholesta-5,7,10(19)-triene-1,3,24-triol,(1a,3b,5Z,7E,24R)- (9CI);1a,24(R)-Dihydroxycholecalciferol; |
Article Data | 9 |
tacalcitol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; Darkness; | 98% |
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 40h; Darkness; | 98% |
tacalcitol
Conditions | Yield |
---|---|
With hydrogen fluoride In water; acetonitrile at 20℃; for 24h; | 76% |
With methanol; AG 50W-X4 resin at 20℃; methanolysis; | 33 mg |
tacalcitol
Conditions | Yield |
---|---|
Stage #1: C41H74O4Si2 With potassium carbonate In methanol at 20℃; for 5h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux; | 75% |
tacalcitol
Conditions | Yield |
---|---|
Stage #1: C46H76O4Si2 With potassium carbonate In methanol at 20℃; for 5h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Reflux; | 75% |
tacalcitol
Conditions | Yield |
---|---|
With (1S)-10-camphorsulfonic acid In methanol; chloroform at 20℃; for 2.5h; | 65% |
Stage #1: C39H72O3Si2 With tetrabutyl ammonium fluoride In tetrahydrofuran at 50 - 55℃; for 2h; Stage #2: With maleic anhydride In ethyl acetate at 30 - 35℃; for 24h; | 300 mg |
1α,3β,24(R)-trihydroxycholesta-5,7-diene
tacalcitol
Conditions | Yield |
---|---|
In diethyl ether Irradiation; |
(S)-2-((3R,3aR,7S,7aR)-octahydro-7-hydroxy-3a-methyl-1H-inden-3-yl)propyl 4-methylbenzenesulfonate
tacalcitol
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C 2.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C 3.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 3.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C 4.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C 5.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 6.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 7.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 8.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 8.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 9.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 10.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 11.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 12.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 13.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme |
(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol
tacalcitol
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1.1: 93 percent / pyridine / 12 h / 0 °C 2.1: 91 percent / dimethylsulfoxide / 2 h / 90 °C 3.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C 4.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 4.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C 5.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C 6.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 7.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 8.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 9.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 9.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 10.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 11.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 12.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 13.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 14.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme | |
Multi-step reaction with 11 steps 1: 1H-imidazole; dmap / N,N-dimethyl-formamide / 96 h / 20 °C 2: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 20 °C 3: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 5: lithium hexamethyldisilazane / tetrahydrofuran / 15 h / -78 - 20 °C 6: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 65 °C 7: hydrogen; palladium 10% on activated carbon / methanol / 15 h 8: dipyridinium dichromate / dichloromethane / 20 °C 9: n-butyllithium / tetrahydrofuran / 18 h / -78 °C 10: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness 11: hydrogen fluoride / acetonitrile; water / 24 h / 20 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: 1H-imidazole / N,N-dimethyl-formamide / 50 - 55 °C 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / -5 - 5 °C 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide; sodium hypochlorite; sodium hydrogencarbonate / dichloromethane; water / 0.17 h / -5 - 5 °C 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 - -60 °C 4.2: -70 - 20 °C 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 55 - 60 °C 6.1: pyridinium chlorochromate / dichloromethane / 20 °C 7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr 8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C 9.1: n-butyllithium / tetrahydrofuran / 1 h / -70 - -60 °C 9.2: 1.5 h / -65 - -10 °C 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Darkness View Scheme | |
Multi-step reaction with 10 steps 1.1: 1H-imidazole; ammonium chloride / N,N-dimethyl-formamide / 50 - 55 °C / Inert atmosphere 2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere 3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane / 4 h / 20 °C / Inert atmosphere 4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -70 °C / Inert atmosphere 4.2: -70 - 20 °C / Inert atmosphere 5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 60 °C / Inert atmosphere 6.1: dipyridinium dichromate / dichloromethane / 20 °C 7.1: palladium 10% on activated carbon; hydrogen / tetrahydrofuran; methanol / 24 h / 2280.15 - 2660.18 Torr 8.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere 9.1: n-butyllithium / tetrahydrofuran / 1 h / -65 °C / Inert atmosphere 9.2: 1.5 h / -65 - -10 °C / Inert atmosphere 10.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 40 h / 20 °C / Darkness View Scheme |
<1R-<1β(R*),3aα,4β,7aβ>>-octahydro-4-hydroxy-β,7a-dimethyl-1H-indene-1-propanenitrile
tacalcitol
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: 98 percent / imidazole / dimethylformamide / 12 h / 80 °C 2.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1 h / -78 - 0 °C 2.2: 91 percent / hexamethylphosphoramide / tetrahydrofuran; hexane / 7 h / -60 - 20 °C 3.1: 94 percent / tert-butanol; potassium; hexamethylphosphoramide / diethyl ether / 13 h / 0 - 20 °C 4.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 5.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 6.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 7.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 7.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 8.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 9.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 10.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 11.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 12.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme |
De-A,B-(24R)-8β-[(tert-butyldimethylsilyl)oxy]-cholestan-24-ol
tacalcitol
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 93 percent / N,N-diisopropylethylamine / CH2Cl2 / 0 - 20 °C 2.1: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / Heating 3.1: 96 percent / pyridinium dichromate; pyridinium p-toluenesulfonate / CH2Cl2 / 40 h / 0 °C 4.1: lithium diisopropylamide / hexane; tetrahydrofuran / 2 h / -78 - 20 °C 4.2: 76 percent / tetrahydrofuran; hexane / -78 - 20 °C 5.1: 92 percent / Et3N / bis-triphenylphosphine palladium dichloride / dimethylformamide / 2 h / 70 °C 6.1: 83 percent / hydrogen; quinoline / Lindlar catalyst / hexane / 0.5 h 7.1: 94 percent / 2,2,4-trimethyl-pentane / 4 h / Heating 8.1: tetrabutylammonium fluoride / tetrahydrofuran / 20 h / 20 °C 9.1: 33 mg / AG 50W-X4 resin; methanol / 20 °C View Scheme |
1. Introduction of Tacalcitol
Tacalcitol, with the IUPAC Name of (1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(2R,5S)-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, is one kind of powder. And it belongs to the Product categories which include Vitamin D3 analogs.
2. Properties of Tacalcitol
Tacalcitol has the following properties: (1)Density: 1.06 g/cm3; (2)Flash Point: 238.4 °C; (3)Index of Refraction: 1.545; (4)Boiling Point: 565 °C at 760 mmHg; (5)Vapour Pressure: 4.05E-15 mmHg at 25°C; (6)Appearance: White solid; (7)Index of Refraction: 1.545; (8)Molar Refractivity: 124.3 cm3; (9)Molar Volume: 392.7 cm3.
3. Structure Descriptors of Tacalcitol
You could convert the following datas into the molecular structure:
(1).Canonical SMILES: CC(C)C(CCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C)O
(2).Isomeric SMILES: C[C@H](CC[C@@H](C(C)C)O)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](C
[C@@H](C3=C)O)O)C
(3).InChI: 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
(4).InChIKey: BJYLYJCXYAMOFT-SEZLTJOTSA-N
4. Toxicity of Tacalcitol
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
dog | LD50 | subcutaneous | 10ug/kg (0.01mg/kg) | BEHAVIORAL: FOOD INTAKE (ANIMAL) BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)" | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. |
mouse | LD50 | intravenous | 559ug/kg (0.559mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. |
mouse | LD50 | oral | 3050ug/kg (3.05mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. |
mouse | LD50 | subcutaneous | 419ug/kg (0.419mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. |
rat | LD50 | intravenous | 556ug/kg (0.556mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. |
rat | LD50 | oral | 3279ug/kg (3.279mg/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. |
rat | LD50 | subcutaneous | 100ug/kg (0.1mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. | |
rat | LD50 | subcutaneous | 100ug/kg (0.1mg/kg) | SKIN AND APPENDAGES (SKIN): HAIR: OTHER | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 17, Pg. 4615, 1989. |