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112965-21-6

Basic Information
CAS No.: 112965-21-6
Name: Calcipotriene
Article Data: 10
Cas Database
Molecular Structure:
Molecular Structure of 112965-21-6 (Calcipotriene)
Formula: C27H40O3
Molecular Weight: 412.613
Synonyms: 9,10-Secochola-5,7,10(19),22-tetraene-1,3,24-triol,24-cyclopropyl-, (1a,3b,5Z,7E,22E,24S)- (9CI);Calciptriol;Daivonex;Dovonex;MC 903;PRI 2201;Psorcutan;
EINECS: 601-218-4
Density: 1.12 g/cm3
Melting Point: 166-168 ºC
Boiling Point: 582 ºC at 760 mmHg
Flash Point: 250.6 ºC
Solubility: N/A
Appearance: white crystalline solid
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 26
Transport Information: N/A
PSA: 60.69000
LogP: 5.09060
Synthetic route
112875-61-3

(1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene

112965-21-6

calcipotriene

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃;87%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃; for 0.833333h;73%
With tetrabutyl ammonium fluoride In tetrahydrofuran at 40℃; for 2h;
With tetrabutyl ammonium fluoride In tetrahydrofuran at 60℃;
Stage #1: (1S,3R)-bis(tert-butyldimethylsilyloxy)-20(R)-(3'(S)-cyclopropyl-3'-hydroxyprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene With tetrabutyl ammonium fluoride In tetrahydrofuran at 60 - 65℃; for 2h;
Stage #2: With water; sodium hydrogencarbonate In tetrahydrofuran; ethyl acetate for 0.25h;
765-43-5

Cyclopropyl methyl ketone

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature
2: 84 percent
3: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
5: N-methylmorpholine N-oxide, selenium dioxide
6: imidazole / dimethylformamide
7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 7 steps
1: 87 percent / bromine / methanol / 0.5 h / Ambient temperature
2: 84 percent
3: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
4: dimethylsulfoxide / 4 h / 105 °C
5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
69267-75-0

2-bromo-1-cyclopropylethan-1-one

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 84 percent
2: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
4: N-methylmorpholine N-oxide, selenium dioxide
5: imidazole / dimethylformamide
6: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
7: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
8: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 6 steps
1: 84 percent
2: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
3: dimethylsulfoxide / 4 h / 105 °C
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
7691-76-1

1-cyclopropyl-2-(triphenyl-λ5-phosphanylidene)ethan-1-one

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
2: N-methylmorpholine N-oxide, selenium dioxide
3: imidazole / dimethylformamide
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: dimethylsulfoxide / 4 h / 105 °C
2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
3: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
112828-12-3

3(R)-(tert-butyldimethylsilyloxy)-20(S)-formyl-9,10-secopregna-5(Z),7(E),10(19)-triene

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 6 steps
2: N-methylmorpholine N-oxide, selenium dioxide
3: imidazole / dimethylformamide
4: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
5: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
6: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
87680-65-7

(S)-3-[(1R,3aS,7aR)-7a-Methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-(4E)-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2λ6-benzo[c]thiophen-5-ol

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
3: NaHCO3 / aq. ethanol / Heating
5: N-methylmorpholine N-oxide, selenium dioxide
6: imidazole / dimethylformamide
7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 9 steps
1: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
2: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
3: NaHCO3 / aq. ethanol / Heating
5: N-methylmorpholine N-oxide, selenium dioxide
6: imidazole / dimethylformamide
7: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
8: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
9: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
112849-18-0

20(R),3(R)-(tert-butyldimethylsilyloxy)-20-(3'-cyclopropyl-3'-oxoprop-1'(E)-enyl)-9,10-secopregna-5(Z),7(E),10(19)-triene

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: N-methylmorpholine N-oxide, selenium dioxide
2: imidazole / dimethylformamide
3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
4: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
5: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme

(E)-(R)-4-{(1R,3aS,7aR)-4-[2-[(R)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-1-cyclopropyl-pent-2-en-1-one

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: imidazole / dimethylformamide
2: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
3: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
112849-15-7

(2-cyclopropyl-2-oxoethyl) (triphenyl)phosphonium bromide

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
3: N-methylmorpholine N-oxide, selenium dioxide
4: imidazole / dimethylformamide
5: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
6: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
7: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 5 steps
1: 86 percent / 2N sodium hydroxide / H2O; CH2Cl2
2: dimethylsulfoxide / 4 h / 105 °C
3: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
4: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
5: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
247900-07-8

(7Z)-Vitamin D2

112965-21-6

calcipotriene

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: liq. SO2 / 0.5 h / Heating
2: 42 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
4: NaHCO3 / aq. ethanol / Heating
6: N-methylmorpholine N-oxide, selenium dioxide
7: imidazole / dimethylformamide
8: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
9: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
10: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
Multi-step reaction with 10 steps
1: liq. SO2 / 0.5 h / Heating
2: 52 percent / imidazole / dimethylformamide / 1.5 h / 20 °C
3: 1.) ozone 2.) PPh3 / 1.) CH2Cl2, MeOH, -60 deg C 2.) CH2Cl2, MeOH, -60 to 0 deg C
4: NaHCO3 / aq. ethanol / Heating
6: N-methylmorpholine N-oxide, selenium dioxide
7: imidazole / dimethylformamide
8: 33 percent / NaBH4, CeCl3*6H2O / methanol / further reag.: (S)-BINAL-H
9: anthracene, triethylamine / toluene / 1 h / 20 °C / Irradiation
10: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.83 h / 60 °C
View Scheme
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Specification

The Calcipotriene, with the CAS registry number 112965-21-6, is also known as (1S,3S,5Z)-5-[(2E)-2-[(1R,3aR,7aR)-1-[(E,2S)-5-Cyclopropyl-5-hydroxy-pent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidene-cyclohexane-1,3-diol.It belongs to the product categories of Intermediates & Fine Chemicals;Pharmaceuticals;Isotope Labelled Compounds.This chemical's molecular formula is C27H40O3  and molecular weight is 412.61. What's more,Its systematic name is Calcipotriol.It is a topical dermatologic for the treatment of moderate plaque psoriasis. It is White Crystalline Solid.

Physical properties about Calcipotriene are:(1)ACD/LogP: 5.018; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.02; (4)ACD/LogD (pH 7.4): 5.02; (5)ACD/BCF (pH 5.5): 3834.42; (6)ACD/BCF (pH 7.4): 3834.42; (7)ACD/KOC (pH 5.5): 12788.11; (8)ACD/KOC (pH 7.4): 12788.11; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 8; (12)Index of Refraction: 1.579; (13)Molar Refractivity: 122.172 cm3; (14)Molar Volume: 367.238 cm3; (15)Surface Tension: 48.1889991760254 dyne/cm; (16)Density: 1.124 g/cm3; (17)Flash Point: 250.613 °C; (18)Enthalpy of Vaporization: 99.905 kJ/mol; (19)Boiling Point: 581.963 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Uses of Calcipotriene: It is an antipsoriatic. A vitamin D3 analogue with low calcemic activity.Vitamin D 3 analog that displays minimal effects on calcium homeostasis. Regulates cell differentiation and proliferation; exhibits antiproliferative activity against human HL-60, HL60/MX2, MCF-7, T47D, SCC-25 and mouse WEHI-3 cancer cell lines.

You can still convert the following datas into molecular structure:
(1)SMILES:O[C@@H]1CC(\C(=C)[C@@H](O)C1)=C\C=C2/CCC[C@]4([C@H]2CC[C@@H]4[C@@H](/C=C/[C@@H](O)C3CC3)C)C;
(2)Std. InChI:InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1;
(3)Std. InChIKey:LWQQLNNNIPYSNX-UROSTWAQSA-N;

The toxicity data of Calcipotriene as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 skin > 1500ug/kg (1.5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

MUSCULOSKELETAL: OTHER CHANGES

GASTROINTESTINAL: NAUSEA OR VOMITING
Journal of Toxicological Sciences. Vol. 21(Suppl,
man TDLo skin 11gm/kg/11W-I (11000mg/kg)   British Medical Journal. Vol. 306, Pg. 896, 1993.
rat LD50 skin > 15mg/kg (15mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA
Journal of Toxicological Sciences. Vol. 21(Suppl,
rat LD50 subcutaneous 2190ug/kg (2.19mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Toxicological Sciences. Vol. 21(Suppl,
women TDLo skin 10gm/kg/6W-I (10000mg/kg)   British Medical Journal. Vol. 306, Pg. 896, 1993.