(11β,16α)-21-acetyloxy-9-fluoro-11,16,17-trihydroxypegna-1,4-diene-3,20-dione
triamcinolone
Conditions | Yield |
---|---|
With sodium hydroxide In methanol; dichloromethane at -7 - -3℃; Inert atmosphere; | 85.29% |
triamcinolone
Conditions | Yield |
---|---|
Stage #1: C28H38O9 With hydrogen fluoride In chloroform; water at -40℃; Stage #2: With toluene-4-sulfonic acid at 40℃; | 81% |
Conditions | Yield |
---|---|
mit Hilfe von Streptomyces roseochromogenus; |
16β,21-diacetoxy-9-fluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione
triamcinolone
Conditions | Yield |
---|---|
With potassium hydroxide |
Conditions | Yield |
---|---|
With potassium hydroxide |
16β,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione
triamcinolone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: CH2Cl2; THF; HF 2: SeO2 3: methanol.KOH View Scheme |
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: CHCl3; HF 2: mit Hilfe von Nocardia corallina 3: methanol.KOH View Scheme |
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: mit Hilfe von Nocardia corallina 2: methanol.KOH View Scheme |
desonide
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CHCl3; HF 2: methanol.KOH View Scheme |
triamcinolone phosphate
triamcinolone
triamcinolone
Conditions | Yield |
---|---|
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 |
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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
triamcinolone
Conditions | Yield |
---|---|
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 |
triamcinolone
Conditions | Yield |
---|---|
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 |
triamcinolone
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
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
triamcinolone
9α-Fluor-16α,21-bis(formyloxy)-11β,17α-dihydroxy-1,4-pregnadien-3,20-dion
Conditions | Yield |
---|---|
for 16h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
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
9α-fluoro-11β,16α,17α-trihydroxy-17β-hydroxymethyl-D-homoandrosta-1,4-diene-3,17a-dione
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In N,N-dimethyl-formamide at 55 - 60℃; for 4h; | 69% |
triamcinolone
9α-fluoro-11β,16α,17α-trihydroxy-3-oxoandrosta-1,4-diene-17β-carboxylic acid
Conditions | Yield |
---|---|
With dihydrogen peroxide; potassium carbonate In methanol; N,N-dimethyl-formamide for 23h; | 45% |
Conditions | Yield |
---|---|
at 7 - 8℃; | 40% |
triamcinolone
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; magnesium sulfate In acetonitrile at -10℃; | 39% |
triamcinolone
Conditions | Yield |
---|---|
With perchloric acid In tetrahydrofuran at 20 - 25℃; for 2h; | 25.8% |
triamcinolone
A
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
Conditions | Yield |
---|---|
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
(11β,16β,17α)-9-fluoro-11,16,17-trihydroxy-17-(hydroxymethyl)-D-homoandrosta-1,4-diene-3,17a-dione
Conditions | Yield |
---|---|
With edetate disodium; sodium carbonate In methanol for 22h; | 22% |
triamcinolone
16α,17-((Ξ)-ethylLiDenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid; paracetaldehyde anschliessend Acetylierung und Hydrolyse; |
Conditions | Yield |
---|---|
With perchloric acid; acetone | |
With hydrogenchloride; acetone |
triamcinolone
16α,17-((Ξ)-sec-butylidenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid; butanone |
triamcinolone
16α,17-(1-ethyl-propylidenedioxy)-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid; pentan-3-one |
triamcinolone
9-fluoro-11β,21-dihydroxy-16α,17-((Ξ)-1-phenyl-ethylLiDenedioxy)-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid; acetophenone |
triamcinolone
cyclohexanone
16α,17-cyclohexyLiDenedioxy-9-fluoro-11β,21-dihydroxy-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid |
Conditions | Yield |
---|---|
With hydrogenchloride In methanol |
Trimethyl orthoacetate
triamcinolone
16α-Acetoxy-9α-fluor-11β,17α,21-trihydroxy-pregna-1,4-dien-3,20-dion
Conditions | Yield |
---|---|
(i) aq. HClO4, MeOH, dioxane, (ii) aq. oxalic acid, MeOH; Multistep reaction; |
trimethyl orthovalerate
triamcinolone
Conditions | Yield |
---|---|
(i) aq. HClO4, MeOH, dioxane, (ii) aq. oxalic acid, MeOH; Multistep reaction; |
triamcinolone
(trimethoxymethyl)cyclopentane
Conditions | Yield |
---|---|
(i) aq. HClO4, MeOH, dioxane, (ii) aq. oxalic acid, MeOH; Multistep reaction; |
triamcinolone
4-methyl-2-pentanone
A
16,17-(1,3-dimethyl-butylidenedioxy)-9-fluoro-11,21-dihydroxy-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid stereoisomer(ic) of mp: 258 degree; |
triamcinolone
4-methyl-2-pentanone
A
16,17-(1,3-dimethyl-butylidenedioxy)-9-fluoro-11,21-dihydroxy-pregna-1,4-diene-3,20-dione
Conditions | Yield |
---|---|
With perchloric acid stereoisomer(ic) of mp: 188 degree; |
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
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 52 percent / HCl / 1 h / Heating 2: 83 percent / pyridine / 18 h / 20 °C View Scheme |
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 (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.
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. |
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 (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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