Triamcinolone acetonide supplier

Name
Triamcinolone acetonide
EINECS 200-948-7
CAS No. 76-25-5
Article Data22
CAS DataBase
Density 1.33 g/cm³
Solubility Soluble in DMSO or ethanol. Slightly soluble in water.
Melting Point 274-278°C (dec.)
Formula C₂₄H₃₁FO₆
Boiling Point 576.9 °C at 760 mmHg
Molecular Weight 434.505
Flash Point 302.7 °C
Transport Information
Appearance White solid
Safety 53-45
Risk Codes 61
Molecular Structure
Hazard Symbols
Synonyms Aristocort A;Azmacort;Berlicort;Extracort;Kenacort 80;Kenacort A 40;Kenalog;Kenalog 10;Kenalog 40;Ledercort Cream;Lichtena;Nasacort;Respicort;Rineton;TAC 3;Tamceton;Tramacin;Tri-Nasal;Triacet;Triamcinolone 16,17-acetonide;Triamcort-Depot;Triamhexal;Trianopollon;Tricinolon;Vetalog;Vetazine;Volon A;Volonimat;Triamcinalone acetonide;Pregna-1,4-diene-3,20-dione,9-fluoro-11,21-dihydroxy-16,17-[(1-methylethylidene)bis(oxy)]-, (11b,16a)-;9-Fluoro-11b,16a,17,21-tetrahydroxypregna-1,4-diene-3,20-dione-16,17-acetonide;9a-Fluoro-11b,21-dihydroxy-16a,17a-isopropylidenedioxy-1,4-pregnadiene-3,20-dione;9a-Fluoro-16a-hydroxyprednisolone 16a,17a-acetonide;Adcortyl A;Aristocort acetonide;
PSA 93.06000
LogP 2.41880

Synthetic route

: 124-94-7
triamcinolone

: 67-64-1
acetone

: 76-25-5
triamcinolone acetonide

Conditions

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;

: 64089-14-1
11β-trimethylsiloxy-21-acetoxy-16α,17α-isopropylidenedioxy-9α-fluoro-pregna-1,4-diene-3,20-dione

A triamcinolone acetonide, 21-acetate: triamcinolone acetonide, 21-acetate

B: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
With sodium carbonate In aqueous hydrofluoric acid	A 80% B n/a

: C24H30O6

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
With hydrogen fluoride In chloroform at -40℃;	76%

: 1524-86-3
16α-17-[(1-methylethylidene)bis(oxy)]-11β,21-dihydroxy-9-fluoro-4-ene-pregna-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 70h; Heating;	40%

: 124-94-7
triamcinolone

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
With perchloric acid; acetone
With hydrogenchloride; acetone

: 13951-70-7
desonide

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: pyridine 2: SOCl2; pyridine 3: aqueous HClO4; dioxane 4: potassium acetate; ethanol 5: CHCl3; HF 6: methanol.KOH 7: acetone; hydrochloric acid View Scheme

: 23460-76-6
21-acetoxy-pregna-4,9(11),16-triene-3,20-dinone

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 8 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 8: acetone; hydrochloric acid View Scheme

: 74220-43-2
21-Acetoxy-16α,17α-dihydroxy-4,9(11)-pregnadien-3,20-dion

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 7 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 7: acetone; hydrochloric acid View Scheme

: 95943-95-6
16α,21-diacetoxy-17-hydroxy-pregna-1,4,9(11)-triene-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: aqueous HClO4; dioxane 2: potassium acetate; ethanol 3: CHCl3; HF 4: methanol.KOH 5: acetone; hydrochloric acid View Scheme

: 98422-55-0
16α,21-diacetoxyprednisolone

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: SOCl2; pyridine 2: aqueous HClO4; dioxane 3: potassium acetate; ethanol 4: CHCl3; HF 5: methanol.KOH 6: acetone; hydrochloric acid View Scheme

: 7333-34-8
16α,21-diacetoxy-11β,17-dihydroxy-pregn-4-ene-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: SeO2 2: SOCl2; pyridine 3: aqueous HClO4; dioxane 4: potassium acetate; ethanol 5: CHCl3; HF 6: methanol.KOH 7: acetone; hydrochloric acid View Scheme

: 91160-85-9
16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 5 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 5: acetone; hydrochloric acid View Scheme

: 91160-86-0
16α,21-diacetoxy-9-bromo-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium acetate; ethanol 2: CHCl3; HF 3: methanol.KOH 4: acetone; hydrochloric acid View Scheme

: 98632-54-3
16α,21-diacetoxy-17-hydroxy-pregna-4,9(11)-diene-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 6 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 6: acetone; hydrochloric acid View Scheme

: 67-78-7
triamcinolone diacetate

: 76-25-5
triamcinolone acetonide

Conditions

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

: 96670-24-5
16α,21-diacetoxy-9,11β-epoxy-17-hydroxy-9β-pregna-1,4-diene-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: CHCl3; HF 2: methanol.KOH 3: acetone; hydrochloric acid View Scheme

: C23H26O5

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: formic acid; potassium permanganate / acetone; water / 1 h / -7 - -3 °C 2.1: hydrogen fluoride / -30 - -25 °C 2.2: -50 - -45 °C 3.1: sodium hydroxide / methanol; dichloromethane / -7 - -3 °C / Inert atmosphere View Scheme

: C23H28O7

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen fluoride / -30 - -25 °C 1.2: -50 - -45 °C 2.1: sodium hydroxide / methanol; dichloromethane / -7 - -3 °C / Inert atmosphere View Scheme

: 3870-07-3
(11β,16α,17α)-21-acetyloxy-9-fluoro-11-hydroxy-16,17-<1-methylethylidenebis(oxy)>pregna-1,4-diene-3,20-dione

: 76-25-5
triamcinolone acetonide

Conditions

Conditions	Yield
With sodium hydroxide In methanol; dichloromethane at -7 - -3℃; Inert atmosphere;	43 g

: 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

: 76-25-5
triamcinolone acetonide

Conditions

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 3.2: -50 - -45 °C 4.1: sodium hydroxide / methanol; dichloromethane / -7 - -3 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1.1: formic acid / acetone / 0.08 h / -5 - 0 °C 1.2: 0.17 h / -5 - 0 °C 2.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / N,N-dimethyl-formamide / 2 h / -5 - 0 °C 3.1: sodium hydroxide / water; dichloromethane; methanol / 1 h / -5 - 0 °C / Inert atmosphere 4.1: hydrogen fluoride / water / 6.33 h / -40 - 0 °C View Scheme

: 124-63-0
methanesulfonyl chloride

: 76-25-5
triamcinolone acetonide

: 2967-04-6
triamcinolone acetonide mesylate

Conditions

Conditions	Yield
With pyridine at 0℃; for 0.5h; Sealed tube;	100%

: 108-55-4
glutaric anhydride,

: 76-25-5
triamcinolone acetonide

: 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

Conditions	Yield
With pyridine at 20℃; for 18h;	83%
With dmap In acetone at 20℃; for 0.4h;	32%

: 98-91-9
thiobenzoic acid

: 76-25-5
triamcinolone acetonide

: 21-S-benzoylthio-9α-fluoro-16α,17-O-isopropylidene-11β,16α,17α-trihydroxy-1,4-pregnadiene-3,20-dione

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 2h; Mitsunobu reaction;	82%

: 186581-53-3, 908094-01-9
diazomethane

: 108-30-5
succinic acid anhydride

: 108-24-7
acetic anhydride

: 76-25-5
triamcinolone acetonide

A: 1'-(21-Acetyl-triamcinolone-acetonide-11)-4'-methyl succinate

B: 1'-(11-Acetyl-triamcinolone-acetonide-21)-4'-methyl succinate

Conditions

Conditions	Yield
Yield given. Multistep reaction. Title compound not separated from byproducts;

...Expand

: 108-30-5
succinic acid anhydride

: 108-24-7
acetic anhydride

: 76-25-5
triamcinolone acetonide

A: 21-Acetyl-11-hemisuccinoyl-triamcinolone-acetonide

B: 11-Acetyl-21-hemisuccinoyl-triamcinolone-acetonide

Conditions

Conditions	Yield
With pyridine 1.) reflux, 4 h, 2.) r.t., overnight; Yield given. Multistep reaction. Title compound not separated from byproducts;

...Expand

: 108-30-5
succinic acid anhydride

: 76-25-5
triamcinolone acetonide

A: 11-Hemisuccinoyl-triamcinolone-acetonide

B: 21-Hemisuccinoyl-triamcinolone-acetonide

Conditions

Conditions	Yield
With pyridine for 4h; Heating; Title compound not separated from byproducts;

...Expand

: 76-25-5
triamcinolone acetonide

A: 165739-48-0
9α-fluoro-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-dien-3-one

B: 389119-96-4
9α-fluoro-17β-hydroperoxy-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-dien-3-one

C: 389119-95-3
9α-fluoro-11β,21-dihydroxy-16α,17α-(1,1-dimethylmethylenedioxy)-1,5-cyclopregna-3-en-2,20-dione

Conditions

Conditions	Yield
With oxygen; 1-dodecylthiol In acetonitrile Quantum yield; Further Variations:; Solvents; Reagents; irradiation wavelength; Irradiation;

...Expand

: 76-25-5
triamcinolone acetonide

A: 165739-48-0
9α-fluoro-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-dien-3-one

B: 389119-95-3
9α-fluoro-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 for 0.666667h; Irradiation;	A 60 % Turnov. B 11 % Turnov.

: 76-25-5
triamcinolone acetonide

: 389119-96-4
9α-fluoro-17β-hydroperoxy-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-dien-3-one

Conditions

Conditions	Yield
With oxygen In isopropyl alcohol for 0.916667h; Irradiation;	60 % Turnov.

: 76-25-5
triamcinolone acetonide

: 389119-95-3
9α-fluoro-11β,21-dihydroxy-16α,17α-(1,1-dimethylmethylenedioxy)-1,5-cyclopregna-3-en-2,20-dione

Conditions

Conditions	Yield
In acetonitrile for 2h; Irradiation;	70 % Turnov.

: 76-25-5
triamcinolone acetonide

A: 165739-48-0
9α-fluoro-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-dien-3-one

B: 389119-96-4
9α-fluoro-17β-hydroperoxy-11β-hydroxy-16α,17α-(1-methylethylidenedioxy)androsta-1,4-dien-3-one

C: 11β,21-dihydroxy-16α,17α-(1-methylethylidenedioxy)-9α-fluoro-1,5-cyclopregn-3-ene-2,20-dione

Conditions

Conditions	Yield
With phosphate-buffered saline; oxygen In methanol at 20℃; Product distribution; Quantum yield; Further Variations:; Solvents; Reagents; irradiation wavelength; Irradiation;	A 15 % Chromat. B 30 % Chromat. C 15 % Chromat.

...Expand

: 76-25-5
triamcinolone acetonide

: C44H53FN4O13

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 83 percent / pyridine / 18 h / 20 °C 2.1: carbonyldiimidazole / tetrahydrofuran / 4 h / 20 °C 2.2: 43 percent / DMAP / tetrahydrofuran / 96 h / 20 °C View Scheme

: 76-25-5
triamcinolone acetonide

: 9α-fluoro-11β,16α-dihydroxyandrosta-1,4-diene-3,17-dione

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 60 percent Turnov. / O2 / propan-2-ol / 0.92 h / Irradiation 2: 94 percent / triphenylphosphine / CH2Cl2 / 2 h View Scheme

: 76-25-5
triamcinolone acetonide

: 158952-15-9
9α-fluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-17β-(methylthio)androsta-1,4-dien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 68 percent / K2CO3, air / methanol / 1 h 2: 1.) molecular sieves (4 Angstroem), Et3N / 1.) THF, 25 deg C, 0.5 h, 2.) THF, 90 min 3: molecular sieves (4 Angstroem) / toluene / 20 °C 4: -8 °C / Irradiation View Scheme

: 76-25-5
triamcinolone acetonide

: 9α-fluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-17β-(methylsulphonyl)androsta-1,4-dien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 68 percent / K2CO3, air / methanol / 1 h 2: 1.) molecular sieves (4 Angstroem), Et3N / 1.) THF, 25 deg C, 0.5 h, 2.) THF, 90 min 3: molecular sieves (4 Angstroem) / toluene / 20 °C 4: -8 °C / Irradiation 5: 16 percent / 3-chloroperoxybenzoic acid / CHCl3 / 25 °C View Scheme

: 76-25-5
triamcinolone acetonide

: 9α-Fluoro-11β-hydroxy-16α,17α-isopropylidenedioxy-17β-(2-pyridylthio)androsta-1,4-dien-3-one

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 68 percent / K2CO3, air / methanol / 1 h 2: 1.) molecular sieves (4 Angstroem), Et3N / 1.) THF, 25 deg C, 0.5 h, 2.) THF, 90 min 3: molecular sieves (4 Angstroem) / toluene / 20 °C 4: 7 percent / CH2Cl2 / 20 °C / Irradiation View Scheme

Triamcinolone acetonide Consensus Reports

Reported in EPA TSCA Inventory.

Triamcinolone acetonide Specification

1. Introduction of Triamcinolone acetonide

Triamcinolone acetonide, with the Systematic Name of (4aS,4bR,5S,6aS,6bS,9aR,10aS,10bS)-4b-Fluoro-5-hydroxy-6b-(hydroxyacetyl)-4a,6a,8,8-tetramethyl-4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-dodecahydro-2H-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxol-2-one, is one kind of white solid. For being incompatible with strong oxidizing agents, it belongs to the Product Categories which include Biochemistry; Steroids; Steroids (Others); Intermediates & Fine Chemicals; Pharmaceuticals. Besides, its Classification Code are including Adrenal Cortex Hormones; Anti-Inflammatory Agents; Drug / Therapeutic Agent; Glucocorticoid; Glucocorticoids; Hormones; Hormones, Hormone Substitutes, and Hormone Antagonists; Human Data; Immunologic Factors; Immunosuppressive agents; Mutation data; Reproductive Effect.

2. Properties of Triamcinolone acetonide

Triamcinolone acetonide has the below properties: (1)Molar Refractivity: 109.41 cm³; (2)Molar Volume: 324.8 cm³; (3)Surface Tension: 54.5 dyne/cm; (4)Density: 1.33 g/cm³; (5)Flash Point: 302.7 °C; (6)Enthalpy of Vaporization: 99.19 kJ/mol; (7)Boiling Point: 576.9 °C at 760 mmHg; (8)Vapour Pressure: 1.04E-15 mmHg at 25 °C; (9)Appearance: White Solid; (10)Melting Point: 274-278 °C (dec.).

3. Toxicity of Triamcinolone acetonide

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
man	TDLo	intramuscular	571ug/kg (0.571mg/kg)	VASCULAR: SHOCK SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Annals of Pharmacotherpy. Vol. 28, Pg. 1310, 1994.
mouse	LD50	intraperitoneal	105mg/kg (105mg/kg)		Drugs in Japan Vol. 6, Pg. 516, 1982.
mouse	LD50	oral	5gm/kg (5000mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 2117, 1979.
mouse	LD50	subcutaneous	132mg/kg (132mg/kg)		Drugs in Japan Vol. 6, Pg. 516, 1982.
rat	LD50	subcutaneous	13100ug/kg (13.1mg/kg)		Drugs of the Future. Vol. 6, Pg. 44, 1981.
women	TDLo	parenteral	4mg/kg (4mg/kg)	BEHAVIORAL: MUSCLE WEAKNESS VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION	Netherlands Journal of Medicine. Vol. 56, Pg. 12, 2000.

4. Safety Information of Triamcinolone acetonide

Poison by subcutaneous and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and toxic fumes of F⁻.
Hazard Codes: Toxic T
Risk Statements: 61
R61:May cause harm to the unborn child.
Safety Statements: 53-45
S53:Avoid exposure - obtain special instructions before use.
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS: TU3920000

5. Use and Preparation of Triamcinolone acetonide

Aristocort acetonide can be used as adrenal cortical hormone medicines and also used in neurodermatitis, eczema, psoriasis, joint pain, bronchial asthma and other illnesses.

Product Name

Triamcinolone acetonide

Synthetic route

Triamcinolone acetonide Consensus Reports

Triamcinolone acetonide Specification

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