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CAS No.: | 32222-06-3 |
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Name: | Calcitriol |
Article Data: | 55 |
Cas Database | |
Molecular Structure: | |
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Formula: | C27H44O3 |
Molecular Weight: | 416.645 |
Synonyms: | U 49562;Calcitriol (JAN/USAN);(1S,3R,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol;Calcitriol [USAN:BAN:INN:JAN];Ro 215535;9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol, (1.alpha.,3.beta,.5Z,7E)-;9,10-Secocholesta-5,7,10(19)-triene-1,3,25-triol,(1R,3a,5Z,7E)-;Calcitriolum [INN-Latin];(1alpha,3beta,5Z,7E)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol;Soltriol;Calcijex;Dihydroxyvitamin D3;Topitriol;1,25-(OH)2D3;1-alpha,25-Dihydroxyvitamin D3;1alpha,25-Dihydroxycholecalciferol; |
EINECS: | 250-963-8 |
Density: | 1.06 g/cm3 |
Melting Point: | 119-121 °C |
Boiling Point: | 565 °C at 760 mmHg |
Flash Point: | 238.4 °C |
Appearance: | white crystalline powder |
Hazard Symbols: |
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Risk Codes: | 26/27/28-63-36/37/38-20/21/22 |
Safety: | 36/37/39-45-36-26 |
Transport Information: | UN 2811 6.1/PG 1 |
PSA: | 60.69000 |
LogP: | 5.70470 |
[2H]-Pre-1,25-D3
calcitriol
Conditions | Yield |
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at 80℃; | 100% |
In acetone at 80.3℃; for 3h; | 26 mg |
at 70℃; for 2h; | |
In hexane; ethyl acetate at 65℃; | 182 mg |
In acetone at 80.3℃; Rate constant; Equilibrium constant; Thermodynamic data; var. temp.; kinetics, E(a), ΔG(excit.), ΔH(excit.), ΔS(excit.); |
calcitriol
Conditions | Yield |
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With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere; | 100% |
(1R,3aS,7aR)-1-((R)-5-Methoxymethoxy-1,5-dimethyl-hexyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene
calcitriol
Conditions | Yield |
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With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h; | 95% |
C
calcitriol
Conditions | Yield |
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With AG 50W-X4 resin In methanol; benzene at 20℃; for 19h; | A 95% B n/a C n/a |
calcitriol
Conditions | Yield |
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With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 24h; | 81% |
calcitriol
Conditions | Yield |
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Stage #1: 1α-[(triethylsilyl)oxy]-24-(tert-butoxycarbonyl)-25,26,27-trisnorvitamin D3 triethylsilyl ether With methyllithium In diethyl ether at 0℃; for 0.5h; Stage #2: With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.75h; Darkness; | 81% |
Conditions | Yield |
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In diethyl ether at -78℃; for 0.333333h; | 80% |
(1S),3(R)-9,10-secocholesta-5(E),7(E),10(19)-triene-1,3,25-triol
calcitriol
Conditions | Yield |
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With 9-acetylanthracene In ethanol Inert atmosphere; UV-irradiation; Cooling with ice; | 78% |
With 9-acetylanthracene In methanol at 0℃; for 2h; Irradiation; | 66% |
(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol
calcitriol
Conditions | Yield |
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With n-BuNF In tetrahydrofuran at 45℃; for 4h; | 71% |
With tetrabutyl ammonium fluoride In tetrahydrofuran for 24h; Ambient temperature; in the dark; Yield given; | |
With camphor-10-sulfonic acid In methanol at 20℃; for 12h; desilylation; |
calcitriol
Conditions | Yield |
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In acetone at 80℃; for 4h; | 70% |
1. Introduction of Calcitriol
Calcitriol is one kind of white or off-white crystalline powder. The IUPAC Name of it is (1R,5Z)-5-[(2E)-2-[(1R,7aR)-1-(6-hydroxy-6-methylheptan-2-yl)-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol. Calcitriol belongs to Miscellaneous Biochemicals;Vitamin D3 analogs;API;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals. The Classification Code of it is Bone Density Conservation Agents; Calcium channel agonists; Cardiovascular Agents; Drug / Therapeutic Agent; Growth Substances; Membrane Transport Modulators; Micronutrients; Mutation data; Regulator [calcium]; Reproductive Effect; Vasoconstrictor Agents; Vitamins.
2. Properties of Calcitriol
Physical properties about Calcitriol are:
(1)Empirical Formula: C27H44O3; (2)H bond acceptors: 3; (3)H bond donors: 3; (4)Freely Rotating Bonds: 9; (5)Polar Surface Area: 27.69 Å2; (6)Index of Refraction: 1.547; (7)Molar Refractivity: 124.35 cm3; (8)Molar Volume: 391.8 cm3; (9)Surface Tension: 44 dyne/cm; (10)Density: 1.06 g/cm3; (11)Flash Point: 238.4 °C; (12)Enthalpy of Vaporization: 97.51 kJ/mol; (13)Boiling Point: 565 °C at 760 mmHg; (14)Vapour Pressure: 4.05E-15 mmHg at 25°C; (15)CAS Registry Number: 32222-06-3; (16)Melting point: 119-121°C; (17)Storage temp: 2-8°C.
3. Structure Descriptors of Calcitriol
(1)InChI: InChI=1S/C27H44O3/c1-18(8-6-14-26(3,4)30)23-12-13-24-20(9-7-15-27(23,24)5)10-11-21-16-22(28)17-25(29)19(21)2/h10-11,18,22-25,28-30H,2,6-9,12-17H2,1,3-5H3/b20-10+,21-11-/t18?,22-,23-,24?,25?,27-/m1/s1
(2)InChIKey: InChIKey=GMRQFYUYWCNGIN-QKIYYVKWSA-N
(3)Smiles: CC(CCCC(C)(C)O)[C@H]1CCC\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CC(C3=C)O)O)C
4. Toxicity of Calcitriol
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
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mouse | LD50 | intraperitoneal | 1900ug/kg (1.9mg/kg) | SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE BEHAVIORAL: ATAXIA | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 4175, 1983. |
mouse | LD50 | oral | 1350ug/kg (1.35mg/kg) | BEHAVIORAL: ATAXIA SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 4175, 1983. |
mouse | LD50 | subcutaneous | 145ug/kg (.145mg/kg) | BEHAVIORAL: ATAXIA SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 4175, 1983. |
rat | LD50 | intraperitoneal | > 5mg/kg (5mg/kg) | GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" KIDNEY, URETER, AND BLADDER: OTHER CHANGES BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 4175, 1983. |
rat | LD50 | intravenous | 105ug/kg (.105mg/kg) | Japanese Kokai Tokyo Koho Patents. Vol. #94-247858, | |
rat | LD50 | oral | 620ug/kg (.62mg/kg) | Japanese Kokai Tokyo Koho Patents. Vol. #94-247858, | |
rat | LD50 | subcutaneous | 66ug/kg (.066mg/kg) | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 4175, 1983. | |
rat | LD50 | subcutaneous | 66ug/kg (.066mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: ATAXIA | Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 11, Pg. 4175, 1983. |
1. | dns-mus:fbr 2 µg/L | CNREA8 Cancer Research. 46 (1986),604. | ||
2. | scu-rat LD50:66 µg/kg | YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. 11 (1983),4175. | ||
3. | orl-mus LD50:1350 µg/kg | YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. 11 (1983),4175. | ||
4. | ipr-mus LD50:1900 µg/kg | YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. 11 (1983),4175. | ||
5. | scu-mus LD50:145 µg/kg | YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. 11 (1983),4175. |