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32222-06-3

Basic Information
CAS No.: 32222-06-3
Name: Calcitriol
Article Data: 55
Cas Database
Molecular Structure:
Molecular Structure of 32222-06-3 (Calcitriol)
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
Solubility: N/A
Appearance: white crystalline powder
Hazard Symbols: VeryT+,HarmfulXn
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
Synthetic route
57102-09-7

[2H]-Pre-1,25-D3

32222-06-3

calcitriol

Conditions
ConditionsYield
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.);

C30H52O3Si

32222-06-3

calcitriol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0 - 20℃; for 10h; Inert atmosphere;100%
873567-12-5

(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

32222-06-3

calcitriol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 2h;95%

C45H86O3Si3

A

2-methylene-19-nor-(20S)-1α,25-dihydroxyvitamin D3

B

1α,25-dihydroxy-2-methylene-19-nor-vitamin D3

C

32222-06-3

calcitriol

Conditions
ConditionsYield
With AG 50W-X4 resin In methanol; benzene at 20℃; for 19h;A 95%
B n/a
C n/a

C51H98O3Si3

32222-06-3

calcitriol

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 24h;81%

1α-[(triethylsilyl)oxy]-24-(tert-butoxycarbonyl)-25,26,27-trisnorvitamin D3 triethylsilyl ether

32222-06-3

calcitriol

Conditions
ConditionsYield
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%
917-54-4

methyllithium

77531-53-4

1α-Hydroxy-25-oxo-27-norvitamin D3

32222-06-3

calcitriol

Conditions
ConditionsYield
In diethyl ether at -78℃; for 0.333333h;80%
73837-24-8

(1S),3(R)-9,10-secocholesta-5(E),7(E),10(19)-triene-1,3,25-triol

32222-06-3

calcitriol

Conditions
ConditionsYield
With 9-acetylanthracene In ethanol Inert atmosphere; UV-irradiation; Cooling with ice;78%
With 9-acetylanthracene In methanol at 0℃; for 2h; Irradiation;66%
140710-96-9

(1S),3(R)-bis<(tert-butyldimethylsilyl)oxy>-9,10-secocholesta-5(Z),7(E),10(19)-trien-25-ol

32222-06-3

calcitriol

Conditions
ConditionsYield
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;

(1R,3R)-5-{(Z)-2-[(1R,3aR,7aR)-1-((R)-5-Hydroxy-1,5-dimethyl-hexyl)-7a-methyl-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl]-vinyl}-4-methyl-cyclohex-4-ene-1,3-diol

32222-06-3

calcitriol

Conditions
ConditionsYield
In acetone at 80℃; for 4h;70%
Downstream Products
73837-24-8
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    Product Name: Calcitriol Synonyms: VITAMIN D3, 1ALPHA,25-DIHYDROXY;(5z,7e)-(1s,3r)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol;9,10-SECOCHOLESTA-5Z,7E,10(19)-TRIENE-1ALPHA,3BETA,25-TRIOL;1,25-(OH)2

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Specification

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
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.

Or

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.

5. Safety information of Calcitriol
A deadly poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental teratogenic and reproductive effects. Mutation data reported. Enhances intestinal calcium transport and bone mineral mobilization. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: VeryT+,HarmfulXn
Risk Statements: 26/27/28-63-36/37/38-20/21/22
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed. 
R63:Possible risk of harm to the unborn child. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 36/37/39-45-36-26
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36:Wear suitable protective clothing. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 1
WGK Germany: 3
RTECS: FZ4645000
F: 8-10-19
HazardClass: 6.1(a)
PackingGroup: I

6. Uses of Calcitriol
Calcitriol is used to manufacture the antineoplastic or antipsoriatic drug. Calcitriol also called 1,25-dihydroxycholecalciferol or 1,25-dihydroxyvitamin D3 is the hormonally active form of vitamin D with three hydroxyl groups (abbreviated 1,25-(OH)2D3 or simply 1,25(OH)2D). It increases the level of calcium (Ca2+) in the blood by increasing the uptake of calcium from the gut into the blood, and possibly increasing the release of calcium into the blood from bone.