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CAS No.: | 356-12-7 |
---|---|
Name: | Fluocinonide |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C26H32F2O7 |
Molecular Weight: | 494.533 |
Synonyms: | Pregna-1,4-diene-3,20-dione,6a,9-difluoro-11b,16a,17,21-tetrahydroxy-, cyclic 16,17-acetal withacetone, 21-acetate (7CI,8CI);Biscosal;Dermaplus;Flucinar;Fluocinolide acetate;Fluocinolone acetonide 21-acetate;Fluocinolone acetonide acetate;Lidex;Lidex E;Metosyn;NSC101791;Straderm;Topsym;Topsymin;Topsyn;Vanos; |
EINECS: | 206-597-6 |
Density: | 1.34 g/cm3 |
Melting Point: | 309 °C |
Boiling Point: | 591.1 °C at 760 mmHg |
Flash Point: | 311.3 °C |
Solubility: | 0.53mg/L(25 oC) |
Appearance: | white crystalline powder |
Hazard Symbols: | T+ |
Risk Codes: | 28-63 |
Safety: | 22-25-28-36/37/39-45 |
Transport Information: | UN 2811 6.1/PG 2 |
PSA: | 99.13000 |
LogP: | 2.93760 |
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.0833333h; | 100% |
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 1.16667h; | 59% |
With trimethylsilyl trifluoromethanesulfonate In dichloromethane |
fluocinonide
Conditions | Yield |
---|---|
With 1-ethyl-3-methylimidazole hydrogen fluoride at 25℃; Reagent/catalyst; Temperature; | 98.2% |
21-acetyloxy-11β,16α,17α-trihydroxy-6α,9α-difluoro-1,4-diene-3,20-dione
acetone
fluocinonide
Conditions | Yield |
---|---|
With perchloric acid at 25 - 30℃; | 87.3% |
With toluene-4-sulfonic acid at 35℃; Reagent/catalyst; Temperature; Inert atmosphere; | 6.9 g |
With methanesulfonic acid at 50℃; for 1.5h; Temperature; |
21-acetoxy-6α,9α-difluoro-11β-hydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione
fluocinonide
Conditions | Yield |
---|---|
With pyridine; selenium(IV) oxide In tert-butyl alcohol Reflux; | |
With selenium(IV) oxide In pyridine; tert-butyl alcohol at 95℃; |
Conditions | Yield |
---|---|
With pyridine; dmap at 20℃; for 4h; Inert atmosphere; Heating; |
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: D-glucose / aq. phosphate buffer 2.1: perchloric acid / acetone; water / 0.17 h / 0 - 5 °C 2.2: 1 h / 0 - 5 °C 2.3: 2 h / 0 - 35 °C 3.1: pyridine; toluene-4-sulfonic acid; Isopropenyl acetate / acetonitrile; methanol / 3 h / 80 °C / Inert atmosphere 4.1: SelectfluorTM / acetonitrile / 8.5 h 5.1: toluene-4-sulfonic acid / 12 h / 70 °C 6.1: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C 7.1: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere 8.1: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 9.1: perchloric acid / 25 - 30 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: perchloric acid / acetone; water / 0.17 h / 0 - 5 °C 1.2: 1 h / 0 - 5 °C 1.3: 2 h / 0 - 35 °C 2.1: pyridine; toluene-4-sulfonic acid; Isopropenyl acetate / acetonitrile; methanol / 3 h / 80 °C / Inert atmosphere 3.1: SelectfluorTM / acetonitrile / 8.5 h 4.1: toluene-4-sulfonic acid / 12 h / 70 °C 5.1: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C 6.1: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere 7.1: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 8.1: perchloric acid / 25 - 30 °C View Scheme |
21-acetyloxy-9β,11β-epoxy-17α-hydroxy-1,4-diene-3,20-dione
fluocinonide
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: pyridine; toluene-4-sulfonic acid; Isopropenyl acetate / acetonitrile; methanol / 3 h / 80 °C / Inert atmosphere 2: SelectfluorTM / acetonitrile / 8.5 h 3: toluene-4-sulfonic acid / 12 h / 70 °C 4: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C 5: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere 6: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 7: perchloric acid / 25 - 30 °C View Scheme |
fluocinonide
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: SelectfluorTM / acetonitrile / 8.5 h 2: toluene-4-sulfonic acid / 12 h / 70 °C 3: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C 4: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere 5: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 6: perchloric acid / 25 - 30 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: toluene-4-sulfonic acid / 12 h / 70 °C 2: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C 3: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere 4: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 5: perchloric acid / 25 - 30 °C View Scheme |
The Fluocinolide with CAS registry number of 356-12-7 is also known as Topsymin. The systematic name is 2-[(4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS,12S)-4b,12-Difluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-6bH-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-6b-yl]-2-ox oethyl acetate. It belongs to product categories of Steroids. Its EINECS registry number is 206-597-6 . In addition, the formula is C26H32F2O7 and the molecular weight is 494.52. This chemical is a white crystalline powder and used for atopic dermatitis, eczema and so on.
Physical properties about Fluocinolide are: (1)ACD/LogP: 3.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.36; (4)ACD/LogD (pH 7.4): 3.36; (5)ACD/BCF (pH 5.5): 209.69; (6)ACD/BCF (pH 7.4): 209.69; (7)ACD/KOC (pH 5.5): 1597.31; (8)ACD/KOC (pH 7.4): 1597.3; (9)#H bond acceptors: 7; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.56; (13)Molar Refractivity: 119.09 cm3; (14)Molar Volume: 368 cm3; (15)Surface Tension: 49.9 dyne/cm; (16)Density: 1.34 g/cm3; (17)Flash Point: 311.3 °C; (18)Enthalpy of Vaporization: 101.2 kJ/mol; (19)Boiling Point: 591.1 °C at 760 mmHg; (20)Vapour Pressure: 1.97E-16 mmHg at 25 °C.
Preparation of Fluocinolide: it is prepared by reaction of acetic acid anhydride with fluocinolon-acetonid. The reaction needs reagent trimethylsilyl trifluoromethanesulfonate and solvent CH2Cl2 at the temperature of 20 °C for 5 minutes. The yield is about 100%.
When you are using this chemical, please be cautious about it. As a chemical, it is very toxic if swallowed and has possible risk of harm to the unborn child. During using it, wear suitable protective clothing, gloves and eye/face protection. Besides, do not breathe dust and avoid contact with eyes. In case of accident or if you feel unwell seek medical advice immediately.
You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC(=O)OCC(=O)C12C(CC3C1(CC(C4(C3CC(C5=CC(=O)C=CC54C)F)F)O)C)OC(O2)(C)C
2. Isomeric SMILES: CC(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@]4([C@H]3C[C@@H](C5=CC(=O)C=C[C@@]54C)F)F)O)C)OC(O2)(C)C
3. InChI: InChI=1S/C26H32F2O7/c1-13(29)33-12-20(32)26-21(34-22(2,3)35-26)10-15-16-9-18(27)17-8-14(30)6-7-23(17,4)25(16,28)19(31)11-24(15,
26)5/h6-8,15-16,18-19,21,31H,9-12H2,1-5H3/t15-,16-,18-,19-,21+,23-,24-,25-,26+/m0/s1
4. InChIKey: WJOHZNCJWYWUJD-IUGZLZTKSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | subcutaneous | > 3170mg/kg (3170mg/kg) | Drugs in Japan Vol. 6, Pg. 694, 1982. | |
mouse | LD50 | intraperitoneal | 160mg/kg (160mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 17, Pg. 849, 1975. | |
mouse | LD50 | oral | > 6gm/kg (6000mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 386, 1975. | |
mouse | LD50 | subcutaneous | 165mg/kg (165mg/kg) | Yakkyoku. Pharmacy. Vol. 26, Pg. 741, 1975. | |
rat | LD50 | intraperitoneal | 300ug/kg (0.3mg/kg) | Drugs in Japan Vol. 6, Pg. 694, 1982. | |
rat | LD50 | oral | 14mg/kg (14mg/kg) | Drugs in Japan Vol. 6, Pg. 694, 1982. | |
rat | LD50 | subcutaneous | 720ug/kg (0.72mg/kg) | Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 6, Pg. 386, 1975. |