Fluocinolone acetonide supplier

Name
Fluocinolone acetonide
EINECS 200-668-5
CAS No. 67-73-2
Article Data15
CAS DataBase
Density 1.36 g/cm³
Solubility Soluble in water (partly), DMSO, alcohol, chloroform and methanol.
Melting Point 267-269 °C(lit.)
Formula C₂₄H₃₀F₂O₆
Boiling Point 578.5 °C at 760 mmHg
Molecular Weight 452.495
Flash Point 303.7 °C
Transport Information
Appearance Crystalline Solid
Safety 26-36-22
Risk Codes 20/21/22-36/37/38-40
Molecular Structure
Hazard Symbols Xi; Xn
Synonyms Pregna-1,4-diene-3,20-dione,6a,9-difluoro-11b,16a,17,21-tetrahydroxy-, cyclic 16,17-acetal with acetone(6CI,8CI);16a,17a-Isopropylidene-6a,9a-difluoro-1,4-pregnadiene-11b,16a,17a,21-tetrol-3,20-dione;6a,9-Difluoro-11b,21-dihydroxy-16a,17a-(isopropylidenedioxy)pregna-1,4-diene-3,20-dione;6a,9a-Difluoro-16a,17a-isopropylidenedioxy-D1-hydrocortisone;6a,9a-Difluoro-16a-hydroxyprednisolone16,17-acetonide;6a-Fluorotriamcinolone acetonide;Coriphate;Cortiplastol;Dermalar;Dermatin;Dermatin (steroid);Fluocinolone 16,17-acetonide;Fluovitef;Fluvean;Jellin;Localyn;NSC 92339;Percutina;Sinaflan;Sinalar;Synaflan;Synamol;Synandrone;Synemol;Synsac;Pregna-1,4-diene-3,20-dione,6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (6a,11b,16a)-;
PSA 93.06000
LogP 2.36680

Synthetic route

: 356-12-7
fluocinonide

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water at 0 - 5℃; Inert atmosphere;	99.4%
With sodium hydroxide; sodium sulfite In dichloromethane; water at 5 - 15℃; for 1.5h; Reagent/catalyst; Temperature; Inert atmosphere;	91%
With sodium methylate; sodium hydroxide In dichloromethane Inert atmosphere;	83.6%

: 11β,21-diacetoxy-6α,9α-difluoro-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
With water; potassium carbonate In methanol	80%
With potassium carbonate In methanol; water

: 64-17-5
ethanol

: 1217194-25-6
(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-phenoxypropionate)

A: 67-73-2
fluocinolone Acetonide

B: 42412-84-0
ethyl 2-phenoxypropionate

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water

...Expand

: 3932-49-8
21-acetoxy-6α,9α-difluoro-11β-hydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; dmap 2: benzeneseleninic anhydride / toluene / 7 h / Reflux 3: potassium carbonate / methanol; water View Scheme

: 11β,21-diacetoxy-6α,9α-difluoro-16α,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: benzeneseleninic anhydride / toluene / 7 h / Reflux 2: potassium carbonate / methanol; water View Scheme

: 1217194-25-6
(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-phenoxypropionate)

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
With ethanol; sodium hydrogencarbonate In water Kinetics;

: 1269666-11-6
(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-ethoxypropionate)

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
With ethanol; sodium hydrogencarbonate In water Kinetics;

: 1269666-13-8
(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-ethoxybutyrate)

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
With ethanol; sodium hydrogencarbonate In water Kinetics;

: 1269666-10-5
(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-methoxypropionate)

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
With ethanol; sodium hydrogencarbonate In water Kinetics;

: 1269666-12-7
(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-methoxybutyrate)

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
With ethanol; sodium hydrogencarbonate In water Kinetics;

: 7753-60-8
anecortave

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 10 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 10.1: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 10 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
10.1: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere
View Scheme

: 4380-55-6
pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 9 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 9.1: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 9 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
9.1: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere
View Scheme

: 38680-83-0
21-acetyloxy-9β,11β-epoxy-17α-hydroxy-1,4-diene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 8 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 8: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 8 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
8: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere
View Scheme

: C30H33NO9

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 7 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 7: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 7 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
7: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere
View Scheme

: 3802-45-7
21-acetyloxy-9β,11β-epoxy-6α-fluoro-17α-hydroxy-1,4-diene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 6 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 6: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 6 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
6: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere
View Scheme

: 72498-89-6
17α, 21-diacetyloxy-9β,11β-epoxy-6α-fluoro-1,4-diene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogen fluoride; N,N-dimethyl acetamide / water / -15 °C 2: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere 3: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 4: perchloric acid / 25 - 30 °C 5: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

: 17α,21-diacetyloxy-11β-hydroxy-6α, 9α-difluoro-1,4-diene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium acetate / N,N-dimethyl-formamide / 8 h / 90 - 100 °C / Inert atmosphere 2: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 3: perchloric acid / 25 - 30 °C 4: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

: 2326-26-3
acetic acid 2-((6S,8S,9R,10S,11S,13S,14S)-6,9-difluoro-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15-decahydro-3H-cyclopenta[a]phenanthrene-17-yl)-2-oxo-ethyl ester

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: formic acid; potassium permanganate / acetone / 0.33 h / -5 - 0 °C 2: perchloric acid / 25 - 30 °C 3: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

: 4306-83-6
21-acetyloxy-11β,16α,17α-trihydroxy-6α,9α-difluoro-1,4-diene-3,20-dione

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: perchloric acid / 25 - 30 °C 2: sodium hydroxide / water; dichloromethane / 0 - 5 °C / Inert atmosphere View Scheme

: 37413-91-5
2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; perchloric acid / acetone; water / 2 h / -10 - -5 °C 1.2: 12 h / -5 - 35 °C 2.1: methanesulfonic acid / 3 h / 85 °C 2.2: 12 h / -10 - -5 °C 2.3: 1 h / -10 - -5 °C 3.1: hydrogen fluoride / 4 h / -30 - -25 °C 3.2: 2 h / -50 - -45 °C 4.1: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 2 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; perchloric acid / acetone; water / 2 h / -10 - -5 °C
1.2: 12 h / -5 - 35 °C
2.1: methanesulfonic acid / 3 h / 85 °C
2.2: 12 h / -10 - -5 °C
2.3: 1 h / -10 - -5 °C
3.1: hydrogen fluoride / 4 h / -30 - -25 °C
3.2: 2 h / -50 - -45 °C
4.1: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 2 °C / Inert atmosphere
View Scheme

: C23H26O5

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: methanesulfonic acid / 3 h / 85 °C 1.2: 12 h / -10 - -5 °C 1.3: 1 h / -10 - -5 °C 2.1: hydrogen fluoride / 4 h / -30 - -25 °C 2.2: 2 h / -50 - -45 °C 3.1: sodium hydroxide / methanol; dichloromethane / 2 h / -5 - 2 °C / Inert atmosphere View Scheme

: C26H32O7

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine; 4-nitro-benzoyl chloride; toluene-4-sulfonic acid / acetonitrile / 60 °C 2: 1-ethyl-3-methylimidazole hydrogen fluoride / 25 °C 3: sodium hydroxide; sodium methylate / dichloromethane / Inert atmosphere View Scheme

: C26H31FO7

: 67-73-2
fluocinolone Acetonide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1-ethyl-3-methylimidazole hydrogen fluoride / 25 °C 2: sodium hydroxide; sodium methylate / dichloromethane / Inert atmosphere View Scheme

: 67-73-2
fluocinolone Acetonide

: 108-24-7
acetic anhydride

: 356-12-7
fluocinonide

Conditions

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

: 67-73-2
fluocinolone Acetonide

: 106915-70-2
C24H30(3)H2F2O6

Conditions

Conditions	Yield
With Wilkinson's catalyst; tritium In tetrahydrofuran; toluene	100%
With Wilkinson's catalyst; tritium In tetrahydrofuran; toluene

: 67-73-2
fluocinolone Acetonide

: 124-63-0
methanesulfonyl chloride

: 3793-01-9
6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With pyridine at 0℃; for 0.5h;	99%

: 67-73-2
fluocinolone Acetonide

: 108-24-7
acetic anhydride

: 11β,21-diacetoxy-6α,9α-difluoro-16α,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.5h;	99%
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at 20℃; for 0.5h;	99%
With pyridine; dmap at 20℃; for 22h; Inert atmosphere; Heating;	86%

: 67-73-2
fluocinolone Acetonide

: 327185-94-4
6α,9α-difluoro-11β,20,21-trihydroxy-16α,17α-isopropylidenedioxypregnane-1,4-dien-3-one

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran at 20℃; for 18h;	99%

: 67-73-2
fluocinolone Acetonide

: 13242-30-3
2-((2S,6aS,6bR,7S,8aS,8bS,11aR,12aS,12bS)-2,6b-difluoro-7-hydroxy-6a,8a,10,10-tetramethyl-4-oxo-2,4,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-1H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-8b-yl)-2-oxoacetaldehyde

Conditions

Conditions	Yield
With copper diacetate In methanol at 20℃;	98%
With copper diacetate In methanol at 20℃;	98%
With copper diacetate; oxygen In methanol

: 67-73-2
fluocinolone Acetonide

: 6α,9α-Difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-21-trifluoro-methanesulfonyloxy-pregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With pyridine; trifluoromethanesulfonic acid anhydride In diethyl ether; dichloromethane	96%

: 67-73-2
fluocinolone Acetonide

: 807-38-5, 67438-36-2
6α,9α-difluoro-11β,16α,17α,21-tetra-hydroxypregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
With tetrafluoroboric acid In water at 22℃; for 2h;	94.5%
With tetrafluoroboric acid In water at 25℃; for 48h;	60.3%
With tetrafluoroboric acid In water at 25℃; for 48h;	60.3%
With tetrafluoroboric acid In water at 25℃; for 48h;	60.3%
With tetrafluoroboric acid; water at 20℃; for 7h;

: 67-73-2
fluocinolone Acetonide

: 65751-34-0
11β-hydroxy-16α,17α-isopropylidenedioxy-3-oxo-6α,9α-difluoroandrosta-1,4-diene-17β-carboxylic acid

Conditions

Conditions	Yield
With periodic acid In 1,4-dioxane; water at 20℃; for 4.5h; Product distribution / selectivity;	92%
With sodium hydroxide; air In methanol; dichloromethane for 3h; Ambient temperature;	77.6%
With air; potassium carbonate In methanol at 20℃; for 16h;	75%

: 67-73-2
fluocinolone Acetonide

: 122-35-0
2-phenoxypropanoic acid chloride

: 1217194-25-6
(6α,11β,16α)-6,9-difluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]pregna-1,4-diene-3,20-dione-21-(2'-phenoxypropionate)

Conditions

Conditions	Yield
With triethylamine at 0 - 20℃; for 4.08333h; Inert atmosphere;	89%
With triethylamine In dichloromethane at 0 - 20℃; for 4h;

: 67-73-2
fluocinolone Acetonide

: 7693-46-1
4-Nitrophenyl chloroformate

: 1308322-37-3
C31H33F2NO10

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃;	83%

: 67-73-2
fluocinolone Acetonide

: (4aS,4bR,5S,6aS,6bR,9aR,10aS,10bS,12S)-4b,12-Difluoro-5,7-dihydroxy-4a,6a-dimethyl-4b,5,6,6a,6b,7,9a,10,10a,10b,11,12-dodecahydro-4aH-9-oxa-pentaleno[2,1-a]phenanthrene-2,8-dione

Conditions

Conditions	Yield
With sodium hydride Rearrangement;	81%

: 67-73-2
fluocinolone Acetonide

: 123-72-8
butyraldehyde

: (1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

Conditions

Conditions	Yield
With perchloric acid; silica gel In n-heptane at 0 - 20℃;	78%
With perchloric acid; silica gel In n-heptane at 0 - 20℃; for 0.166667h;	16%
Stage #1: fluocinolone Acetonide; butyraldehyde With silica gel In n-heptane at 10 - 20℃; for 0.166667h; Stage #2: With perchloric acid In n-heptane at 10 - 20℃;	16%
Stage #1: fluocinolone Acetonide; butyraldehyde With silica gel In n-heptane at 10 - 20℃; for 0.166667h; Stage #2: With perchloric acid In n-heptane at 0 - 20℃; for 12h;	16%

: 67-73-2
fluocinolone Acetonide

: 9α-fluoro-21-hydroxy-16α,17α-(1,1-dimethylmethylenedioxy)-1β,11β-oxy-pregna-3,5-dien-2,20-dione

Conditions

Conditions	Yield
In acetonitrile Irradiation;	76%

: 67-73-2
fluocinolone Acetonide

: 106931-78-6
21-oic acid of Fluocinolone Acetonide

Conditions

Conditions	Yield
Stage #1: fluocinolone Acetonide With copper diacetate Stage #2: With 3-chloro-benzenecarboperoxoic acid for 18h;	70%
Multi-step reaction with 2 steps 1: O2, Cu(OAc)2 / methanol 2: NaClO2, KH2PO4 / tetrahydrofuran; 2-methyl-propan-2-ol; H2O View Scheme

: 67-73-2
fluocinolone Acetonide

: C22H28F2O6

Conditions

Conditions	Yield
With oxygen In methanol Irradiation;	60%

: 67-73-2
fluocinolone Acetonide

: 6α,9α-difluoro-11β,21-dihydroxy-16α,17α-(1,1-dimethylmethylenedioxy)-1,5-cyclopregna-3-en-2,20-dione

Conditions

Conditions	Yield
In acetonitrile for 2.5h; Irradiation;	50%

: 67-73-2
fluocinolone Acetonide

: 123-72-8
butyraldehyde

: 51547-52-5
(1S,2S,4R,6R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.02'9.04,8.013'18]icosa-14,17-dien-16-one

Conditions

Conditions	Yield
With perchloric acid; fine sand In n-heptane
With sand; 70percent HClO4 In n-heptane

: 67-73-2
fluocinolone Acetonide

A: 6α,9α-difluoro-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-dien-3-one

B: 6α,9α-difluoro-11β,21-dihydroxy-16α,17α-(1,1-dimethylmethylenedioxy)-1,5-cyclopregna-3-en-2,20-dione

Conditions

Conditions	Yield
In acetonitrile Quantum yield; Further Variations:; irradiation wavelength; UV-irradiation;
In acetonitrile Quantum yield; Further Variations:; irradiation wavelength; Irradiation;
In acetonitrile for 2h; Irradiation;	A 80 % Turnov. B 5 % Turnov.

: 67-73-2
fluocinolone Acetonide

: methylthiomethyl 6α,9-difluoro-11β-hydroxy-3,20-dioxo-16α,17-isopropylidenedioxypregn-1,4-diene-21-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: cupric acetate monohydrate 1.2: 70 percent / m-chloroperbenzoic acid / 18 h 2.1: triethylamine View Scheme

: 67-73-2
fluocinolone Acetonide

: 193408-59-2
16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-methylsulfonyloxypregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sand; 70percent HClO4 / heptane 2: 97 percent / pyridine / 2 h View Scheme

: 67-73-2
fluocinolone Acetonide

: 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-[(3R)-2-oxotetrahydrofuran-3-ylsulfanyl]pregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sand; 70percent HClO4 / heptane 2.1: 97 percent / pyridine / 2 h 3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 3.2: 16 percent / tetrahydrofuran / 19 h / 0 - 21 °C View Scheme

: 67-73-2
fluocinolone Acetonide

: 16α,17α-[(R)-butylidenedioxy]-6α,9α-difluoro-11β-hydroxy-21-[(3S)-2-oxotetrahydrofuran-3-ylsulfanyl]pregna-1,4-diene-3,20-dione

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sand; 70percent HClO4 / heptane 2.1: 97 percent / pyridine / 2 h 3.1: NaH / tetrahydrofuran / 0.5 h / 0 °C 3.2: 26 percent / tetrahydrofuran / 19 h / 0 - 21 °C View Scheme

: 67-73-2
fluocinolone Acetonide

: 327185-95-5
6α,9α-difluoro-17β-formyl-11β-hydroxy-16α,17α-isopropylidenedioxyandrosta-1,4-dien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 99 percent / NaBH4 / tetrahydrofuran / 18 h / 20 °C 2: 100 percent / aq. NaIO4 / ethanol / 4 h / 20 °C View Scheme

: 67-73-2
fluocinolone Acetonide

: 327185-96-6
6α,9α-difluoro-11β-hydroxy-17β-hydroxymethyl-16α,17α-isopropylidenedioxyandrosta-1,4-dien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / NaBH4 / tetrahydrofuran / 18 h / 20 °C 2: 100 percent / aq. NaIO4 / ethanol / 4 h / 20 °C 3: 45 percent / NaBH4 / ethanol / 0.5 h / 0 °C View Scheme

: 67-73-2
fluocinolone Acetonide

: 6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-17β-[(2-oxotetrahydrofuran-4-ylsulfanyl)methyl]androsta-1,4-dien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 99 percent / NaBH4 / tetrahydrofuran / 18 h / 20 °C 2.1: 100 percent / aq. NaIO4 / ethanol / 4 h / 20 °C 3.1: 45 percent / NaBH4 / ethanol / 0.5 h / 0 °C 4.1: 93 percent / pyridine / CH2Cl2 / 1.5 h / 0 °C 5.1: NaH / tetrahydrofuran / 0.08 h 5.2: 21 percent / tetrahydrofuran / 18 h / 20 °C View Scheme

: 67-73-2
fluocinolone Acetonide

: 6α,9α-difluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-17β-[(2-oxotetrahydrofuran-3-ylsulfanyl)methyl]androsta-1,4-dien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: 99 percent / NaBH4 / tetrahydrofuran / 18 h / 20 °C 2.1: 100 percent / aq. NaIO4 / ethanol / 4 h / 20 °C 3.1: 45 percent / NaBH4 / ethanol / 0.5 h / 0 °C 4.1: 93 percent / pyridine / CH2Cl2 / 1.5 h / 0 °C 5.1: NaH / tetrahydrofuran / 0.08 h 5.2: 43 percent / tetrahydrofuran / 16 h / 20 °C View Scheme

Fluocinolone acetonide Consensus Reports

EPA Genetic Toxicology Program.

Fluocinolone acetonide Specification

1. Introduction of Fluocinolone acetonide

The Fluocinolone acetonide is a kind of crystalline solid, and it belongs to the following product categories which include Organics; Alkaloids; Biochemistry; Quinoline Alkaloids; Intermediates & Fine Chemicals; Pharmaceuticals; Steroids. What's more, it is a corticosteroid primarily used in dermatology to reduce skin inflammation and relieve itching. And it is a synthetic hydrocortisone derivative.

2. Properties of Fluocinolone acetonide

The physical properties of Fluocinolone acetonide are as followings: (1)ACD/LogP: 2.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.24; (4)ACD/LogD (pH 7.4): 2.24; (5)ACD/BCF (pH 5.5): 29.91; (6)ACD/BCF (pH 7.4): 29.91; (7)ACD/KOC (pH 5.5): 396.28; (8)ACD/KOC (pH 7.4): 396.28; (9)#H bond acceptors: 6; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 71.06 Å²; (13)Index of Refraction: 1.577; (14)Molar Refractivity: 109.5 cm³; (15)Molar Volume: 330.3 cm³; (16)Polarizability: 43.41×10^-24cm³; (17)Surface Tension: 52.7 dyne/cm; (18)Density: 1.36 g/cm³; (19)Flash Point: 303.7 °C; (20)Enthalpy of Vaporization: 99.42 kJ/mol; (21)Boiling Point: 578.5 °C at 760 mmHg; (22)Vapour Pressure: 8.57E-16 mmHg at 25°C.

3. Structure Descriptors of Fluocinolone acetonide

You could convert the following datas into the molecular structure:
(1)SMILES: O=C\1\C=C5/[C@@](/C=C/1)(C)[C@]2(F)[C@H]([C@H]3[C@](C[C@@H]2O)([C@@]4(OC(O[C@@H]4C3)(C)C)C(=O)CO)C)C[C@@H]5F
(2)InChI: InChI=1/C24H30F2O6/c1-20(2)31-19-9-13-14-8-16(25)15-7-12(28)5-6-21(15,3)23(14,26)17(29)10-22(13,4)24(19,32-20)18(30)11-27/h5-7,13-14,16-17,19,27,29H,8-11H2,1-4H3/t13-,14-,16-,17-,19+,21-,22-,23-,24+/m0/s1
(3)InChIKey: FEBLZLNTKCEFIT-VSXGLTOVBO

4. Toxicity of Fluocinolone acetonide

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Source
guinea pig	LD50	subcutaneous	> 3170mg/kg (3170mg/kg)	Drugs in Japan Vol. 6, Pg. 694, 1982.
mouse	LD50	intraperitoneal	103mg/kg (103mg/kg)	Drugs in Japan Vol. 6, Pg. 694, 1982.
mouse	LD50	oral	> 4gm/kg (4000mg/kg)	Drugs in Japan Vol. 6, Pg. 694, 1982.
mouse	LD50	subcutaneous	200mg/kg (200mg/kg)	Drugs in Japan Vol. 6, Pg. 694, 1982.
rat	LD50	intraperitoneal	42mg/kg (42mg/kg)	Drugs in Japan Vol. 6, Pg. 694, 1982.
rat	LD50	oral	> 4gm/kg (4000mg/kg)	Drugs in Japan Vol. 6, Pg. 694, 1982.
rat	LD50	subcutaneous	108mg/kg (108mg/kg)	Drugs in Japan Vol. 6, Pg. 694, 1982.

5. Safety Information of Fluocinolone acetonide

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin, and it is also harmful by inhalation, in contact with skin and if swallowed. What's more, there's limited evidence of a carcinogenic effect. Therefore, you had better take the following instructions: Do not breathe the dust; Wear suitable protective clothing, and in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Product Name

Fluocinolone acetonide

Synthetic route

Fluocinolone acetonide Consensus Reports

Fluocinolone acetonide Specification

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