67-78-7

Basic information

• Product Name: Triamcinolone diacetate
• Synonyms: (11beta,16alpha)-16,21-Bis(acetyloxy)-9-fluoro-11,17-dihydroxypregna-1,4-diene-3,20-dione;16-(Acetyloxy)-9-fluoro-11,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl acetate;21-diacetate;9-alpha-Fluoro-16-alpha-hydroxyprednisolone diacetate;9-alpha-fluoro-16-alpha-hydroxyprednisolonediacetate;9-Fluoro-11-beta,16-alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 16,21-diacetate;9-fluoro-11-beta,16-alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione16,21;Aristocort diacetate
• CAS NO: 67-78-7
• Molecular Formula: C₂₅H₃₁FO₈
• Molecular Weight: 478.51
• EINECS: 200-669-0
• Product Categories: Steroid and Hormone;KENACORT
• Mol File: 67-78-7.mol
• Article Data: 0

Chemical Properties

• Melting Point: 186-188 C
• Boiling Point: 608.5 °C at 760 mmHg
• Flash Point: 321.8 °C
• Appearance: /
• Density: 1.2087 (estimate)
• Vapor Pressure: 2.4E-17mmHg at 25°C
• Refractive Index: 1.573
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly, Heated), DMSO (Slightly), Methanol (Slightly)
• PKA: 11.21±0.70(Predicted)
• Water Solubility: 48mg/L(25 oC)
• CAS DataBase Reference: Triamcinolone diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Triamcinolone diacetate(67-78-7)
• EPA Substance Registry System: Triamcinolone diacetate(67-78-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 67-78-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Originator

Aristocort,Lederle,US,1959

Uses

Different sources of media describe the Uses of 67-78-7 differently. You can refer to the following data:
1. A glucocorticoid that inhibits prolyl hydroxylase activity and used as an antiasthmatic and antiallergic drug.
2. A glucocorticoid that inhibits prolyl hydroxylase activity, Triamcinolone diacetate can be used as an antiasthmatic and antiallergic drug.
3. antiinflammatory

Manufacturing Process

To a solution of 16α,21-diacetoxy-11β,17α-dihydroxy-9α-fluoro-4-pregnene- 3,20-dione (1.0 g) in tertiary-butanol (160 ml) and glacial acetic acid (1.6 ml) was added 600 mg of selenium dioxide, the mixture swept with nitrogen and kept at 70°C for 24 hours, selenium dioxide (350 mg) added, and the mixture swept with nitrogen and allowed to stand for another 24 hours. The reaction mixture was filtered, and the filtrate was evaporated to dryness under reduced pressure. The material so obtained was dissolved in ethyl acetate, washed with saturated sodium bicarbonate, water, cold freshly prepared ammonium sulfide solution, cold dilute ammonia water, cold dilute hydrochloric acid, and finally with water. After treatment with anhydrous sodium sulfate and activated charcoal, filtration through diatomaceous earth and evaporation to dryness under reduced pressure, 850 mg of a tan glass was obtained. Paper strip chromatographic analysis showed predominantly product plus a small amount of starting material. The 850 mg was chromatographed on 320 g of diatomaceous earth containing 160 ml of stationary phase of a solvent system composed of 3,4,3,2-ethyl acetate-petroleum ether (boiling point 90°C to 100°C), methanol, and water, respectively. The column dimensions were 3.8 cm x 78 cm with 460 ml hold back volume. The fifth and sixth hold back volumes were combined and evaporated under reduced pressure to 250 mg of product which, after a single crystallization from acetone petroleum ether, gave 173 mg, melting point 150°C to 190°C. Paper strip chromatography showed a single spot having the same polarity as an authentic sample of 16α,21-diacetoxy-11β,17α-dihydroxy-9α-fluoro-1,4-pregnadiene-3,20-dione. A further crystallization from the same solvent pair gave 134 mg, melting point 185°C to 189°C, bubbles to 230°C.

Therapeutic Function

Glucocorticoid

Safety Profile

An experimental teratogen. Whenheated to decomposition it emits toxic fumes of F-.

InChI:InChI=1/C25H31FO8/c1-13(27)33-12-20(31)25(32)21(34-14(2)28)10-18-17-6-5-15-9-16(29)7-8-22(15,3)24(17,26)19(30)11-23(18,25)4/h7-9,17-19,21,30,32H,5-6,10-12H2,1-4H3/t17?,18?,19-,21+,22-,23-,24-,25+/m0/s1

Synthetic route

16α,21-Diacetoxy-9α-fluoro-11β,17α-dihydroxpregn-4-ene-3,20-dione (426-39-1) → triamcinolone diacetate (67-78-7)

Conditions	Yield
With selenium(IV) oxide
mit Hilfe von Nocardia corallina;

16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregna-1,4-diene-3,20-dione (96670-24-5) → triamcinolone diacetate (67-78-7)

Conditions	Yield
With chloroform; hydrogen fluoride

16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione (98422-57-2, 114417-77-5) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: CHCl3; HF 2: mit Hilfe von Nocardia corallina View Scheme

11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione (1171-81-9) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 6 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 View Scheme

desonide (13951-70-7) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine 2: SOCl2; pyridine 3: aqueous HClO4; dioxane 4: potassium acetate; ethanol 5: CHCl3; HF View Scheme

21-acetoxy-pregna-4,9(11),16-triene-3,20-dinone (23460-76-6) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 6 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 View Scheme

21-Acetoxy-16α,17α-dihydroxy-4,9(11)-pregnadien-3,20-dion (74220-43-2) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 5 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 View Scheme

16α,21-diacetoxy-17-hydroxy-pregna-1,4,9(11)-triene-3,20-dione (95943-95-6) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: aqueous HClO4; dioxane 2: potassium acetate; ethanol 3: CHCl3; HF View Scheme

16α,21-diacetoxyprednisolone (98422-55-0) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: SOCl2; pyridine 2: aqueous HClO4; dioxane 3: potassium acetate; ethanol 4: CHCl3; HF View Scheme

16α,21-diacetoxy-11β,17-dihydroxy-pregn-4-ene-3,20-dione (7333-34-8) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 5 steps 1: SeO2 2: SOCl2; pyridine 3: aqueous HClO4; dioxane 4: potassium acetate; ethanol 5: CHCl3; HF View Scheme

16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione (91160-85-9) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium acetate; ethanol / Behandeln einer Loesung des Reaktionsprodukts in Pyridin mit Acetanhydrid 2: CHCl3; HF 3: mit Hilfe von Nocardia corallina View Scheme

16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione (91160-86-0) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium acetate; ethanol 2: CHCl3; HF View Scheme

16α,21-diacetoxy-17-hydroxy-pregna-4,9(11)-diene-3,20-dione (98632-54-3) → triamcinolone diacetate (67-78-7)

Conditions	Yield
Multi-step reaction with 4 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 View Scheme

triamcinolone diacetate (67-78-7) → triamcinolone (124-94-7)

Conditions	Yield
With potassium hydroxide

triamcinolone diacetate (67-78-7) → 16α,21-diacetoxy-9-fluoro-17-hydroxy-pregna-1,4-diene-3,11,20-trione (1868-22-0)

Conditions	Yield
With pyridine; chromium(VI) oxide
With chromium(VI) oxide; sulfuric acid; acetone

triamcinolone diacetate (67-78-7) → triamcinolone acetonide (76-25-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol.KOH 2: acetone; hydrochloric acid View Scheme

Upstream product

• 96670-24-5 16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregna-1,4-diene-3,20-dione 
• 98632-54-3 16α,21-diacetoxy-17-hydroxy-pregna-4,9(11)-diene-3,20-dione 
• 91160-86-0 16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione 
• 91160-85-9 16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 7333-34-8 16α,21-diacetoxy-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 98422-55-0 16α-21-diacetoxyprednisolone 
• 95943-95-6 16α,21-diacetoxy-17-hydroxy-pregna-1,4,9(11)-triene-3,20-dione 
• 74220-43-2 21-Acetoxy-16α,17α-dihydroxy-4,9(11)-pregnadien-3,20-dion 
• 23460-76-6 21-acetoxy-pregna-4,9⁽¹¹⁾,16-triene-3,20-dinone 
• 13951-70-7 desonide 
• 1171-81-9 11β,16α,17,21-tetrahydroxy-pregn-4-ene-3,20-dione 
• 98422-57-2 16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregn-4-ene-3,20-dione 
• 426-39-1 16α,21-Diacetoxy-9α-fluoro-11β,17α-dihydroxpregn-4-ene-3,20-dione 

Downstream Products

• 76-25-5 triamcinolone acetonide 
• 1868-22-0 16α,21-diacetoxy-9-fluoro-17-hydroxy-pregna-1,4-diene-3,11,20-trione 
• 124-94-7 triamcinolone