(4R,8S,9S,11S,12R,13S)-12-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

Base Information

• Chemical Name: (4R,8S,9S,11S,12R,13S)-12-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one
• CAS No.: 76-25-5
• Molecular Formula: C24H31FO6
• Molecular Weight: 434.505
• Hs Code.: 29372290
• NSC Number: 757366
• ChEMBL ID: CHEMBL275338
• Mol file: 76-25-5.mol

Synonyms:(4R,8S,9S,11S,12R,13S)-12-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one;Spectrum_000224;Spectrum2_000843;Spectrum3_001370;Spectrum4_000364;Spectrum5_001457;BSPBio_002900;KBioGR_000827;KBioSS_000704;DivK1c_000606;SPECTRUM1500587;SPBio_000825;CHEMBL275338;SCHEMBL13234864;HMS501O08;KBio1_000606;KBio2_000704;KBio2_003272;KBio2_005840;KBio3_002120;NINDS_000606;HMS1921G09;HMS2092O13;Pharmakon1600-01500587;CCG-39546;NSC757366;NSC-757366;IDI1_000606;NCGC00178399-01;SBI-0051542.P002;AB00052114_02;SR-05000002093;SR-05000002093-1;BRD-A92439610-001-02-4;BRD-A92439610-001-03-2

Chemical Property of (4R,8S,9S,11S,12R,13S)-12-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

Chemical Property:

• Appearance/Colour: White solid
• Vapor Pressure: 1.04E-15mmHg at 25°C
• Melting Point: 274-278°C (dec.)
• Refractive Index: 1.588
• Boiling Point: 576.9 °C at 760 mmHg
• PKA: 12.87±0.10(Predicted)
• Flash Point: 302.7 °C
• PSA: 93.06000
• Density: 1.33 g/cm³
• LogP: 2.41880
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, sparingly soluble in ethanol (96 per cent).
• Water Solubility.: Soluble in DMSO or ethanol. Slightly soluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 434.21046687
• Heavy Atom Count: 31
• Complexity: 925

Purity/Quality:

99.00% ^*data from raw suppliers

Triamcinolone acetonide ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 61
• Safety Statements: 53-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(OC2CC3C4CCC5=CC(=O)C=CC5(C4(C(CC3(C2(O1)C(=O)CO)C)O)F)C)C
• Isomeric SMILES: C[C@]12C[C@@H]([C@]3(C(C1C[C@@H]4[C@]2(OC(O4)(C)C)C(=O)CO)CCC5=CC(=O)C=C[C@@]53C)F)O
• Uses: It is adrenal cortex hormones drugs used for treating diseases such as neurodermatitis, eczema, psoriasis, joint pain, and asthma. antiinflammatory Triamcinolone acetonide is a topical and systemic corticosteroid belonging to the group-B (triamcinolone acetonide) type of steroids.
• Description: Triamcinolone acetonide is a synthetic corticosteroid. It decreases cytokine levels, the firing rate of sensory neurons, and mechanical hypersensitivity in a rat spinal nerve ligation model when used at a dose of 1.5 mg/kg prior to and following surgery for three days. Triamcinolone acetonide also decreases outflow facility in a mouse model of steroid-induced glaucoma when 20 μl of a 40 mg/ml suspension is administered subconjunctivally. Formulations containing triamcinolone acetonide are used in the treatment of diabetic macular edema.
• Indications: Triamcinolone acetonide (Aristocort, Kenalog) is a synthetic fluorinated corticosteroid.
• Therapeutic Function: Glucocorticoid
• Clinical Use: Triamcinolone acetonide frequently is used by inhalation for the treatment of lung diseases (e.g., asthma).

Technology Process of (4R,8S,9S,11S,12R,13S)-12-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one

There total 43 articles about (4R,8S,9S,11S,12R,13S)-12-Fluoro-11-hydroxy-8-(2-hydroxyacetyl)-6,6,9,13-tetramethyl-5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.5%

C24H30O6 (39672-75-8) → triamcinolone acetonide (76-25-5,911437-91-7)

Guidance literature:

With hydrogen fluoride; In N,N-dimethyl-formamide; at -25 - -15 ℃; for 5h; Temperature;

Reference yield: 93.0%

triamcinolone (124-94-7) + acetone (67-64-1) → triamcinolone acetonide (76-25-5,911437-91-7)

Guidance literature:

With boron trifluoride diethyl etherate; at -10 - 0 ℃;

Reference yield: 80.0%

11β-trimethylsiloxy-21-acetoxy-16α,17α-isopropylidenedioxy-9α-fluoro-pregna-1,4-diene-3,20-dione (64089-14-1) → triamcinolone acetonide, 21-acetate + triamcinolone acetonide (76-25-5,911437-91-7)

Guidance literature:

With sodium carbonate; In aqueous hydrofluoric acid;

upstream raw materials:

triamcinolone

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

acetone

9β,11β-epoxy-21-hydroxy-16α,17-(isopropylidenedioxy)pregn-4-ene-3,30-dione

Downstream raw materials:

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

2,2'-oxybis-acetic acid

triamcinolone acetonide acetate

21-Hemisuccinoyl-triamcinolone-acetonide

Refernces

• 1、 -. "Preparation method of triamcinolone acetonide". Paragraph 0023; 0025; 0030-0031; 0036-0037; 0042. . Retrieved 2021/10/11.
• 2、 -. "Synthesis method and application of 9-fluorosteroid compound". Paragraph 0089-0096; 0137-0139. . Retrieved 2021/01/15.