Product Name

  • Name

    Triamcinolone

  • EINECS 204-718-7
  • CAS No. 124-94-7
  • Density 1.42 g/cm3
  • Solubility 79.99mg/L(25 oC)
  • Melting Point 262-263 °C(lit.)
  • Formula C21H27FO6
  • Boiling Point 587.5 °C at 760 mmHg
  • Molecular Weight 394.44
  • Flash Point 309.1 °C
  • Transport Information
  • Appearance
  • Safety 22-36
  • Risk Codes 40
  • Molecular Structure Molecular Structure of 124-94-7 (Triamcinolone)
  • Hazard Symbols HarmfulXn
  • Synonyms 11b,16a,17a,21-Tetrahydroxy-9a-fluoro-1,4-pregnadiene-3,20-dione;9-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione;9a-Fluoro-16a-hydroxyprednisolone;Adcortyl;CL 19823;Cinolone;Fluoxyprednisolone;Kenacort;Ledercort;Mycolog;NSC13397;Omicilon;Polcortolon;Rodinolone;Triamcinlon;Triamcinolone;Tricortale;Volon;
  • PSA 115.06000
  • LogP 0.62050

Synthetic route

(11β,16α)-21-acetyloxy-9-fluoro-11,16,17-trihydroxypegna-1,4-diene-3,20-dione
3859-65-2

(11β,16α)-21-acetyloxy-9-fluoro-11,16,17-trihydroxypegna-1,4-diene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
With sodium hydroxide In methanol; dichloromethane at -7 - -3℃; Inert atmosphere;85.29%
C28H38O9

C28H38O9

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Stage #1: C28H38O9 With hydrogen fluoride In chloroform; water at -40℃;
Stage #2: With toluene-4-sulfonic acid at 40℃;
81%
isoflupredone
338-95-4

isoflupredone

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
mit Hilfe von Streptomyces roseochromogenus;
16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione
4001-36-9

16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
With potassium hydroxide
triamcinolone diacetate
67-78-7

triamcinolone diacetate

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
With potassium hydroxide
16β,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione
98422-57-2, 114417-77-5

16β,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CH2Cl2; THF; HF
2: SeO2
3: methanol.KOH
View Scheme
16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione
2967-24-0

16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregn-4-ene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: SeO2
2: methanol.KOH
View Scheme
16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione
98422-57-2, 114417-77-5

16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: CHCl3; HF
2: mit Hilfe von Nocardia corallina
3: methanol.KOH
View Scheme
11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione
1171-81-9

11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: mit Hilfe von Corynebacterium simplex oder Nocardia corallina
2: pyridine
3: SOCl2; pyridine
4: aqueous HClO4; dioxane
5: potassium acetate; ethanol
6: CHCl3; HF
7: methanol.KOH
View Scheme
16α,21-Diacetoxy-9α-fluoro-11β,17α-dihydroxpregn-4-ene-3,20-dione
426-39-1

16α,21-Diacetoxy-9α-fluoro-11β,17α-dihydroxpregn-4-ene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: mit Hilfe von Nocardia corallina
2: methanol.KOH
View Scheme
desonide
13951-70-7

desonide

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: pyridine
2: SOCl2; pyridine
3: aqueous HClO4; dioxane
4: potassium acetate; ethanol
5: CHCl3; HF
6: methanol.KOH
View Scheme
21-acetoxy-pregna-4,9(11),16-triene-3,20-dinone
23460-76-6

21-acetoxy-pregna-4,9(11),16-triene-3,20-dinone

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: KMnO4
2: pyridine
3: aqueous HClO4; dioxane
4: potassium acetate; ethanol / Behandeln einer Loesung des Reaktionsprodukts in Pyridin mit Acetanhydrid
5: CHCl3; HF
6: mit Hilfe von Nocardia corallina
7: methanol.KOH
View Scheme
21-Acetoxy-16α,17α-dihydroxy-4,9(11)-pregnadien-3,20-dion
74220-43-2

21-Acetoxy-16α,17α-dihydroxy-4,9(11)-pregnadien-3,20-dion

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: pyridine
2: aqueous HClO4; dioxane
3: potassium acetate; ethanol / Behandeln einer Loesung des Reaktionsprodukts in Pyridin mit Acetanhydrid
4: CHCl3; HF
5: mit Hilfe von Nocardia corallina
6: methanol.KOH
View Scheme
16α,21-diacetoxy-17-hydroxy-pregna-1,4,9(11)-triene-3,20-dione
95943-95-6

16α,21-diacetoxy-17-hydroxy-pregna-1,4,9(11)-triene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: aqueous HClO4; dioxane
2: potassium acetate; ethanol
3: CHCl3; HF
4: methanol.KOH
View Scheme
16α,21-diacetoxyprednisolone
98422-55-0

16α,21-diacetoxyprednisolone

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SOCl2; pyridine
2: aqueous HClO4; dioxane
3: potassium acetate; ethanol
4: CHCl3; HF
5: methanol.KOH
View Scheme
16α,21-diacetoxy-11β,17-dihydroxy-pregn-4-ene-3,20-dione
7333-34-8

16α,21-diacetoxy-11β,17-dihydroxy-pregn-4-ene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: SeO2
2: SOCl2; pyridine
3: aqueous HClO4; dioxane
4: potassium acetate; ethanol
5: CHCl3; HF
6: methanol.KOH
View Scheme
16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
91160-85-9

16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: potassium acetate; ethanol / Behandeln einer Loesung des Reaktionsprodukts in Pyridin mit Acetanhydrid
2: CHCl3; HF
3: mit Hilfe von Nocardia corallina
4: methanol.KOH
View Scheme
16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione
91160-86-0

16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium acetate; ethanol
2: CHCl3; HF
3: methanol.KOH
View Scheme
16α,21-diacetoxy-17-hydroxy-pregna-4,9(11)-diene-3,20-dione
98632-54-3

16α,21-diacetoxy-17-hydroxy-pregna-4,9(11)-diene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: aqueous HClO4; dioxane
2: potassium acetate; ethanol / Behandeln einer Loesung des Reaktionsprodukts in Pyridin mit Acetanhydrid
3: CHCl3; HF
4: mit Hilfe von Nocardia corallina
5: methanol.KOH
View Scheme
16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregna-1,4-diene-3,20-dione
96670-24-5

16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregna-1,4-diene-3,20-dione

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CHCl3; HF
2: methanol.KOH
View Scheme
triamcinolone phosphate
894767-41-0

triamcinolone phosphate

triamcinolone
124-94-7

triamcinolone

C23H26O5

C23H26O5

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: formic acid; potassium permanganate / acetone; water / 1 h / -7 - -3 °C
2: hydrogen fluoride / -30 - -25 °C
3: sodium hydroxide / methanol; dichloromethane / -7 - -3 °C / Inert atmosphere
View Scheme
C23H28O7

C23H28O7

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogen fluoride / -30 - -25 °C
2: sodium hydroxide / methanol; dichloromethane / -7 - -3 °C / Inert atmosphere
View Scheme
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
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

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; perchloric acid / acetone / -10 - -5 °C
1.2: 33 - 37 °C
2.1: formic acid; potassium permanganate / acetone; water / 1 h / -7 - -3 °C
3.1: hydrogen fluoride / -30 - -25 °C
4.1: sodium hydroxide / methanol; dichloromethane / -7 - -3 °C / Inert atmosphere
View Scheme
17-acetyl-10,13-dimethyl-6,7,8,10,12,13,14,15-octahydrocyclopenta[a]phenathren-3
117048-56-3

17-acetyl-10,13-dimethyl-6,7,8,10,12,13,14,15-octahydrocyclopenta[a]phenathren-3

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium hydroxide / methanol / Darkness; Cooling with ice
1.2: 20 °C
2.1: potassium permanganate; formic acid / acetone / -5 - 5 °C
3.1: triethylamine; dmap / chloroform
4.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
5.1: hydrogen fluoride / chloroform; water / -40 °C
5.2: 40 °C
View Scheme
C24H32O4

C24H32O4

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium permanganate; formic acid / acetone / -5 - 5 °C
2.1: triethylamine; dmap / chloroform
3.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
4.1: hydrogen fluoride / chloroform; water / -40 °C
4.2: 40 °C
View Scheme
C24H34O6

C24H34O6

triamcinolone
124-94-7

triamcinolone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: triethylamine; dmap / chloroform
2.1: 5,5-dibromohydantoin; perchloric acid / acetone / -5 - 5 °C
3.1: hydrogen fluoride / chloroform; water / -40 °C
3.2: 40 °C
View Scheme
triamcinolone
124-94-7

triamcinolone

acetone
67-64-1

acetone

triamcinolone acetonide
76-25-5

triamcinolone acetonide

Conditions
ConditionsYield
With boron trifluoride diethyl etherate at -10 - 0℃;93%
With hydrogenchloride for 1h; Heating;52%
With methanesulfonic acid at 50℃; for 2h; Temperature;
formic acid
64-18-6

formic acid

triamcinolone
124-94-7

triamcinolone

9α-Fluor-16α,21-bis(formyloxy)-11β,17α-dihydroxy-1,4-pregnadien-3,20-dion
2878-64-0

9α-Fluor-16α,21-bis(formyloxy)-11β,17α-dihydroxy-1,4-pregnadien-3,20-dion

Conditions
ConditionsYield
for 16h; Ambient temperature;90%
triamcinolone
124-94-7

triamcinolone

9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione
337-02-0

9α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione

Conditions
ConditionsYield
With Wilkinson's catalyst; hydrogen In ethanol; toluene at 20℃; under 760 Torr; for 48h; Catalytic hydrogenation;88%
(tris(triphenylphosphine)rhodium) chloride In ethanol; dichloromethane; toluene
triamcinolone
124-94-7

triamcinolone

9α-fluoro-11β,16α,17α-trihydroxy-17β-hydroxymethyl-D-homoandrosta-1,4-diene-3,17a-dione
130063-07-9

9α-fluoro-11β,16α,17α-trihydroxy-17β-hydroxymethyl-D-homoandrosta-1,4-diene-3,17a-dione

Conditions
ConditionsYield
With titanium(IV) isopropylate In N,N-dimethyl-formamide at 55 - 60℃; for 4h;69%
triamcinolone
124-94-7

triamcinolone

9α-fluoro-11β,16α,17α-trihydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid
159210-07-8

9α-fluoro-11β,16α,17α-trihydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Conditions
ConditionsYield
With dihydrogen peroxide; potassium carbonate In methanol; N,N-dimethyl-formamide for 23h;45%
triamcinolone
124-94-7

triamcinolone

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

2-((8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl methanesulfonate

2-((8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl methanesulfonate

Conditions
ConditionsYield
at 7 - 8℃;40%
triamcinolone
124-94-7

triamcinolone

tert-butyl (3-(4-formylbenzyl)phenyl)carbamate

tert-butyl (3-(4-formylbenzyl)phenyl)carbamate

(6aS,6bR,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-(4-(3-aminobenzyl)phenyl)-6b-fluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2’,1‘:4,5]indeno[1,2-d][1,3]dioxol-4-one

(6aS,6bR,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-(4-(3-aminobenzyl)phenyl)-6b-fluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2’,1‘:4,5]indeno[1,2-d][1,3]dioxol-4-one

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; magnesium sulfate In acetonitrile at -10℃;39%
triamcinolone
124-94-7

triamcinolone

sodium(4-((3-((tert-butoxycarbonyl)amino)phenyl)thio)phenyl)(hydroxy)methane sulfonate

sodium(4-((3-((tert-butoxycarbonyl)amino)phenyl)thio)phenyl)(hydroxy)methane sulfonate

(6aS,6bR,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-(4-((3-aminophenyl)thio)phenyl)-6b-fluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4-one

(6aS,6bR,7S,8aS,8bS,10R,11aR,12aS,12bS)-10-(4-((3-aminophenyl)thio)phenyl)-6b-fluoro-7-hydroxy-8b-(2-hydroxyacetyl)-6a,8a-dimethyl-1,2,6a,6b,7,8,8a,8b,11a,12,12a,12b-dodecahydro-4H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-4-one

Conditions
ConditionsYield
With perchloric acid In tetrahydrofuran at 20 - 25℃; for 2h;25.8%
triamcinolone
124-94-7

triamcinolone

A

9α-fluoro-11β,16α,17α-trihydroxy-17β-hydroxymethyl-D-homoandrosta-1,4-diene-3,17a-dione
130063-07-9

9α-fluoro-11β,16α,17α-trihydroxy-17β-hydroxymethyl-D-homoandrosta-1,4-diene-3,17a-dione

B

(11β,16β,17α)-9-fluoro-11,16,17-trihydroxy-17-(hydroxymethyl)-D-homoandrosta-1,4-diene-3,17a-dione
156352-67-9

(11β,16β,17α)-9-fluoro-11,16,17-trihydroxy-17-(hydroxymethyl)-D-homoandrosta-1,4-diene-3,17a-dione

Conditions
ConditionsYield
With edetate disodium; sodium carbonate In methanol for 22h; Mechanism; Ambient temperature; also in the presence of transition metal salts, also triamcinolone 21 acetate;A n/a
B 22%
triamcinolone
124-94-7

triamcinolone

(11β,16β,17α)-9-fluoro-11,16,17-trihydroxy-17-(hydroxymethyl)-D-homoandrosta-1,4-diene-3,17a-dione
156352-67-9

(11β,16β,17α)-9-fluoro-11,16,17-trihydroxy-17-(hydroxymethyl)-D-homoandrosta-1,4-diene-3,17a-dione

Conditions
ConditionsYield
With edetate disodium; sodium carbonate In methanol for 22h;22%
triamcinolone
124-94-7

triamcinolone

16α,17-((Ξ)-ethylLiDenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
3869-38-3

16α,17-((Ξ)-ethylLiDenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With perchloric acid; paracetaldehyde anschliessend Acetylierung und Hydrolyse;
triamcinolone
124-94-7

triamcinolone

triamcinolone acetonide
76-25-5

triamcinolone acetonide

Conditions
ConditionsYield
With perchloric acid; acetone
With hydrogenchloride; acetone
triamcinolone
124-94-7

triamcinolone

16α,17-((Ξ)-sec-butylidenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
3793-07-5

16α,17-((Ξ)-sec-butylidenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With perchloric acid; butanone
triamcinolone
124-94-7

triamcinolone

16α,17-(1-ethyl-propylidenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
3924-70-7

16α,17-(1-ethyl-propylidenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With perchloric acid; pentan-3-one
triamcinolone
124-94-7

triamcinolone

9-fluoro-11β,21-dihydroxy-16α,17-((Ξ)-1-phenyl-ethylLiDenedioxy)-pregna-1,4-diene-3,20-dione
3092-82-8

9-fluoro-11β,21-dihydroxy-16α,17-((Ξ)-1-phenyl-ethylLiDenedioxy)-pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With perchloric acid; acetophenone
triamcinolone
124-94-7

triamcinolone

cyclohexanone
108-94-1

cyclohexanone

16α,17-cyclohexyLiDenedioxy-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
2794-88-9

16α,17-cyclohexyLiDenedioxy-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione

Conditions
ConditionsYield
With perchloric acid
triamcinolone
124-94-7

triamcinolone

1-aminoguanidine hydrochloride
1937-19-5

1-aminoguanidine hydrochloride

C23H35FN8O4

C23H35FN8O4

Conditions
ConditionsYield
With hydrogenchloride In methanol
Trimethyl orthoacetate
1445-45-0

Trimethyl orthoacetate

triamcinolone
124-94-7

triamcinolone

16α-Acetoxy-9α-fluor-11β,17α,21-trihydroxy-pregna-1,4-dien-3,20-dion
3925-42-6

16α-Acetoxy-9α-fluor-11β,17α,21-trihydroxy-pregna-1,4-dien-3,20-dion

Conditions
ConditionsYield
(i) aq. HClO4, MeOH, dioxane, (ii) aq. oxalic acid, MeOH; Multistep reaction;
trimethyl orthovalerate
13820-09-2

trimethyl orthovalerate

triamcinolone
124-94-7

triamcinolone

Pentanoic acid (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-16-yl ester

Pentanoic acid (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-16-yl ester

Conditions
ConditionsYield
(i) aq. HClO4, MeOH, dioxane, (ii) aq. oxalic acid, MeOH; Multistep reaction;
triamcinolone
124-94-7

triamcinolone

(trimethoxymethyl)cyclopentane
51354-79-1

(trimethoxymethyl)cyclopentane

Cyclopentanecarboxylic acid (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-16-yl ester

Cyclopentanecarboxylic acid (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,17-dihydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-16-yl ester

Conditions
ConditionsYield
(i) aq. HClO4, MeOH, dioxane, (ii) aq. oxalic acid, MeOH; Multistep reaction;
triamcinolone
124-94-7

triamcinolone

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

A

16,17-(1,3-dimethyl-butylidenedioxy)-9-fluoro-11,21-dihydroxy-pregna-1,4-diene-3,20-dione
2794-91-4

16,17-(1,3-dimethyl-butylidenedioxy)-9-fluoro-11,21-dihydroxy-pregna-1,4-diene-3,20-dione

B

stereoisomer(ic) of mp: 188 degree

stereoisomer(ic) of mp: 188 degree

Conditions
ConditionsYield
With perchloric acid stereoisomer(ic) of mp: 258 degree;
triamcinolone
124-94-7

triamcinolone

4-methyl-2-pentanone
108-10-1

4-methyl-2-pentanone

A

16,17-(1,3-dimethyl-butylidenedioxy)-9-fluoro-11,21-dihydroxy-pregna-1,4-diene-3,20-dione
2794-91-4

16,17-(1,3-dimethyl-butylidenedioxy)-9-fluoro-11,21-dihydroxy-pregna-1,4-diene-3,20-dione

B

stereoisomer(ic) of mp: 258 degree

stereoisomer(ic) of mp: 258 degree

Conditions
ConditionsYield
With perchloric acid stereoisomer(ic) of mp: 188 degree;
triamcinolone
124-94-7

triamcinolone

Pentanedioic acid mono-[2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxa-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl] ester
409094-09-3

Pentanedioic acid mono-[2-((4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-fluoro-5-hydroxy-4a,6a,8,8-tetramethyl-2-oxo-2,4a,4b,5,6,6a,9a,10,10a,10b,11,12-dodecahydro-7,9-dioxa-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl] ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / HCl / 1 h / Heating
2: 83 percent / pyridine / 18 h / 20 °C
View Scheme

Triamcinolone Chemical Properties

Molecular Formula: C21H27FO6
Molar mass: 394.44 g/mol
EINECS: 204-718-7
Density: 1.42 g/cm3
Flash Point: 309.1 °C
Index of Refraction: 1.617
Boiling Point: 587.5 °C at 760 mmHg
Vapour Pressure: 3E-16 mmHg at 25°C
Melting point: 260-263 ºC (dec.)
Synonyms of Triamcinolone (124-94-7): (8S,9R,10S,11S,13S,14S,16R,17S)-9-fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one ;  (1R,2S,10S,11S,13R,14S,15S,17S)-1-fluoro-13,14,17-trihydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one
Structure of Triamcinolone (124-94-7):

XLogP3-AA: 1.2
H-Bond Donor: 4
H-Bond Acceptor: 7
IUPAC Name: (8S,9R,10S,11S,13S,14S,16R,17S)-9-Fluoro-11,16,17-trihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES: CC12CC(C3(C(C1CC(C2(C(=O)CO)O)O)CCC4=CC(=O)C=CC43C)F)O
Isomeric SMILES: C[C@]12C[C@@H]([C@]3([C@H]([C@@H]1C[C@H]([C@@]2(C(=O)CO)O)O)CCC4=CC(=O)C=C[C@@]43C)F)O
InChI: InChI=1S/C21H27FO6/c1-18-6-5-12(24)7-11(18)3-4-13-14-8-15(25)21(28,
17(27)10-23)19(14,2)9-16(26)20(13,18)22/h5-7,13-16,23,25-26,28H,3-4,8-10H2,1-2H3/t13-,14-,15+,16-,18-,19-,20-,21-/m0/s1 
InChIKey: GFNANZIMVAIWHM-OBYCQNJPSA-N

Triamcinolone Uses

 Triamcinolone (124-94-7) is used in the post-operative period of certain cosmetic surgery procedures, notably rhinoplasty. Injected into the subcutaneous area, it may help to alleviate stubborn swelling, scar tissue, and inflamed sebaceous cysts.It is occasionally used to treat lichen planus and severe cases of hayfever, and may also be used to treat diabetic retinopathy.It is highly effective in the most severe cases of eczema, but may require a waiting period before subsequent treatments.Inaddition, it can be used in case of severe arthritis, Lumbago sciatica.

Triamcinolone Toxicity Data With Reference

1.    

oms-hmn-orl 428 µg/kg

    ARDEAC    Archives of Dermatology. 103 (1971),39.
2.    

scu-rat LD50:99 mg/kg

    TXAPA9    Toxicology and Applied Pharmacology. 8 (1966),250.

Triamcinolone Safety Profile

Poison by subcutaneous route. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits toxic fumes of F. An anti-inflammatory and antiallergic agent.
 

Hazard Codes: Xn
Risk Statements:
40:  Limited evidence of a carcinogenic effect
Safety Statements:
22:  Do not breathe dust
36:  Wear suitable protective clothing

Triamcinolone Specification

Triamcinolone (124-94-7) (trade names Kenalog, Aristocort, Nasacort, Tri-Nasal, Triderm, Azmacort, Trilone, Volon A, Tristoject, Fougera, Tricortone,Triesence) is a synthetic corticosteroid given orally, by inhalation, injection, or as a topical ointment or cream.
Its side effects include nosebleeds, a sore throat, increased headache, coughing, and runny nose. White patches in the throat or nose indicates a serious side effect. Symptoms of an allergic reaction include itch, rash, severe dizziness, swelling, trouble breathing.

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