(1R,3S,5E)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Base Information

• Chemical Name: (1R,3S,5E)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
• CAS No.: 41294-56-8
• Molecular Formula: C27H44O2
• Molecular Weight: 400.645
• Hs Code.: 29361000
• European Community (EC) Number: 255-297-1,688-308-7
• UNII: 9H9H4DCC8T
• DSSTox Substance ID: DTXSID101031732
• Nikkaji Number: J9.282G,J3.276.012K
• Wikipedia: Alfacalcidol
• NCI Thesaurus Code: C80258
• Metabolomics Workbench ID: 35782
• ChEMBL ID: CHEMBL3350876
• Mol file: 41294-56-8.mol

Synonyms:1 alpha-hydroxycholecalciferol;1 alpha-hydroxyvitamin D3;1-alpha-oxycholecalciferol;1-hydroxycholecalciferol;1-hydroxycholecalciferol, (1alpha,3alpha-(5Z,7E))-isomer;1-hydroxycholecalciferol, (1beta)-(5Z)-isomer;1-hydroxycholecalciferol, (1beta,3beta-(5E,7E))-isomer;1-hydroxycholecalciferol, aluminum salt;1alpha-OHD3;alfacalcidol;AlfaD;alphacalcidol;Bondiol;Eenalfadrie;EinsAlpha;Etalpha;Oksidevit;One-Alpha;Un-Alfa

Chemical Property of (1R,3S,5E)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.62E-13mmHg at 25°C
• Melting Point: 134-136 °C
• Refractive Index: 1.534
• Boiling Point: 531.5 °C at 760 mmHg
• PKA: 14.43±0.40(Predicted)
• Flash Point: 222.6 °C
• PSA: 40.46000
• Density: 1.01 g/cm³
• LogP: 6.58980
• Storage Temp.: −20°C
• Solubility.: Practically insoluble in water, freely soluble in ethanol (96 per cent), soluble in fatty oils.
• XLogP3: 6.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 643

Purity/Quality:

99% ^*data from raw suppliers

Alfacalcidol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T+, Xi
• Hazard Codes: T+,Xi
• Statements: 26/27/28-36/37/38
• Safety Statements: 28-36/37-45-36-26

MSDS Files:

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CC(C3=C)O)O)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C\3/C[C@H](C[C@@H](C3=C)O)O)C
• Recent ClinicalTrials: Alfacalcidol Supplementation on Levator Ani Muscle Strength of Menopausal Pelvic Organ Prolapse Patients
• Recent EU Clinical Trials: Treatment of primary minimal change nephropathy.
• Recent NIPH Clinical Trials: Investigation of clinical effect of vitamin D supplement therapy for pancreatic cancer
• Description: Alfacalcidol is a vitamin D analog. It is important for the regulation of the bone metabolism. Alfacaldidol is a regulator of calcium and phosphorus metabolism, which helps calcium and phosphorus to be absorbed more effectively in the intestines. Thus, alfacalcidol is used to treat renal (kidney) bone diseases, rickets, osteoporosis, and patients with high or low activity of the parathyroid gland. Also, it is used to maintain normal calcium levels within the body. Alfacalcidol has significant effects on the immune system, including regulatory T cells. Alfacalcidol is furthermore used as a poultry feed additive to prevent tibial dyschondroplasia and increases phytate bioavailability.
• Indications: Symptoms alfacalcidol can be used to improve chronic renal insufficiency, hypoparathyroidism, vitamin D-dependent rickets, a softening of bone disease caused by vitamin D metabolism, such as hypocalcemia, hand, foot cramps, pain , bone disease and osteoporosis embolism.
• Drug Interactions: Using Alfacalcidol and magnesium formulation (magnesium oxide, magnesium carbonate, etc.) sometimes causes hypermagnesemia. Using Alfacalcidol and Cardiac preparations may cause cardiac arrhythmia. Using Alfacalcidol and vitamin D and its derivatives (calcitriol) , it is possible to cause hypercalcemia. Using Alfacalcidol and calcium , Thiazide diuretics, digitalis drugs , can cause hypercalcemia. And barbiturates, anti-seizure drugs may reduce the efficacy of the drug. Gastrointestinal absorption inhibitors can reduce the absorption of the drug. Combination with large doseas of Phosphorus compounds, can induce hyperphosphatemia. When Alfacalcidol and calcium preparations (calcium lactate, calcium carbonate, etc.) are used together, there may be hypercalcemia.
• Uses: For the treatment of osteoporosis, vitamin D-dependent rickets and osteomalacia A synthetic analog of Calcitiol (the hormonal form of vitamin D3), which shows identical potency with respect to stimulation of intestinal calcium absorption and bone mineral mobilization. Vitamin D source
• Therapeutic Function: Calcium regulator, Vitamin
• Clinical Use: Vitamin D analogue: Increase serum calcium levels Suppression of PTH production
• Drug interactions: Potentially hazardous interactions with other drugs Carbamazepine, fosphenytoin, phenytoin, phenobarbital and primidone may increase metabolism of alfacalcidol, necessitating larger doses than normal to produce the desired effect.

Technology Process of (1R,3S,5E)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

There total 109 articles about (1R,3S,5E)-5-[(2E)-2-[(1R,3aS,7aR)-7a-methyl-1-[(2R)-6-methylheptan-2-yl]-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol 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: 98.0%

1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene (108887-35-0) → 1α-hydroxyvitamin D3 (41294-56-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1248/cpb.48.215

Reference yield: 94.0%

(1R,3aS,7aR)-1-((R)-1,5-Dimethyl-hexyl)-7a-methyl-4-[2-[(3S,5R)-2-methylene-3,5-bis-triisopropylsilanyloxy-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-octahydro-indene (873567-11-4) → 1α-hydroxyvitamin D3 (41294-56-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 1h;

DOI:10.1021/ol052489c

Reference yield: 79.0%

(1R,3aS,7aR)-4-[2-[(3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene (138924-22-8) → 1α-hydroxyvitamin D3 (41294-56-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 40h; Ambient temperature;

upstream raw materials:

1α-hydroxyprecalciferol₃

1α,3β-bis(tert-butyldimethylsilyloxy)-9,10-secocholesta-5,7,10(19)-triene

(1R,3aS,7aR)-4-[2-[(3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-1-((R)-1,5-dimethyl-hexyl)-7a-methyl-octahydro-indene

(1S)-1-methoxymethoxyvitamin D₃

Downstream raw materials:

1α-Hydroxyvitamin-D₃ 1-butyrate

1α-hydroxyprecalciferol₃

calcitriol

Refernces

Synthesis of Retiferol RAD1 and RAD2, the Lead Representatives of a New Class of des-CD Analogs of Cholecalciferol

10.1006/bioo.1995.1002

The study investigates the design and total convergent synthesis of new analogs of cholecalciferol (vitamin D) with the CD-ring system replaced by a two-carbon aliphatic spacer. The researchers aimed to simplify the structure of vitamin D-based therapeutics by identifying the essential structural parts responsible for its activity. The key chemicals involved include vitamin D derivatives, such as vitamin D3 and 1α-hydroxyvitamin D3, which serve as precursors for the ring fragments. The chain fragment is derived from S-(-)-β-citronellol, a natural monoterpene. The synthesized compounds, RAD and RAD2, are designed as des-CD analogs of 25-OH-D3 and 1,25-(OH)2D3, respectively, with an unnatural configuration at C-20. The study employs various reagents and conditions, such as imidazole, t-BuMe2SiCl, MCPBA, lithium triethylborohydride, and pyridinium chlorochromate, to achieve the desired modifications and coupling of the ring and chain fragments. The results provide insights into the potential for developing more effective therapeutic agents based on the simplified structure of vitamin D.

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