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25-Hydroxyvitamin D3

25-Hydroxyvitamin D3 structure

CAS No:
19356-17-3
Formula:
C27H44O2
Chemical Name:
25-Hydroxyvitamin D3
Synonyms:
1H-Indene-1-pentanol,4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-α,α,ε,7a-tetramethyl-,(εR,1R,3aS,4E,7aR)-;9,10-Secocholesta-5,7,10(19)-triene-3β,25-diol;9,10-Secocholesta-5,7,10(19)-triene-3,25-diol,(3β,5Z,7E)-;(εR,1R,3aS,4E,7aR)-4-[(2Z)-2-[(5S)-5-Hydroxy-2-methylenecyclohexylidene]ethylidene]octahydro-α,α,ε,7a-tetramethyl-1H-indene-1-pentanol;25-Hydroxycholecalciferol;Cholecalciferol,25-hydroxy-;25-Hydroxyvitamin D3;5,6-cis-25-Hydroxyvitamin D3;Calcifediol;25-Hydroxyvitamin D;Calcidiol;Ro 8-8892;Calderol;Hidroferol;U 32070E;25-HCC;Dedrogyl;Didrogyl;Rovimix Hy-D;Hy-D;25-Hydroxyl-vitamin D3;Rayaldee;25631-40-7;1384584-62-6
Categories:
Active Pharmaceutical Ingredients > Vitamins and Minerals Medicines

Description

Calcifediol is a major circulating metabolite of vitamin D3, acting as a competitive inhibitor with an apparent Ki of 3.9 μM, suppresses PTH secretion and mRNA (ED50=2 nM).

25-Hydroxyvitamin D3 Basic Attributes

Molecular Weight：

400.64

Exact Mass：

400.64

EC Number：

242-990-9

DSSTox ID：

DTXSID0022721|DTXSID30274318

Characteristics

PSA：

40.5 Å²

XLogP3：

Appearance：

Solid

Density：

1.0±0.1 g/cm3

Melting Point：

74-76oC

Boiling Point：

529.2°C at 760 mmHg

Flash Point：

14 °C

Refractive Index：

1.536

Water Solubility：

Insoluble

Storage Conditions：

−20°C

Safety Information

Packing level：

Ⅱ

Hazard category：

6.1

Transport codes：

UN 2811 6.1/PG 2

wgk germany：

hazard class code：

28-48/25-26-24/25-11

safety instructions：

28-36/37-45-16-7

Marks：

T+,F

Precautionary statement(s)：

P260-P280-P284-P301 + P310-P310

Hazard Statements：

H301 + H311-H330-H372

GHS Classification：

|Danger|H301+H311 (90.48%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]|P260, P264, P270, P271, P280, P284, P301+P310, P302+P352, P304+P340, P310, P312, P314, P320, P321, P322, P330, P361, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 42 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

25-Hydroxyvitamin D3 Use and Manufacturing

Methods of Manufacturing

To a solution of 4-[4-[2-[4-(l, l-dimethylpiperidin-l-ium-4-yl)triazol-l- yl]ethoxy]phenyl]-l, 2, 4-triazolidine-3, 5-dione;2, 2, 2-trifluoroacetate (15.4 mg, 30 pmol) in 1.5 mL dry DMF was added l, 3-dibromo-5, 5-dimethyl-hydantoin (9.43 mg, 33 Limol). The event of the oxidation reaction was indicated by an instant color change from colorless into red. After 60 min, 45 mg of 44% sulfuric acid coated silica was added and the suspension is stirred for 30 min. The solution was filtrated and added to 25-hydroxy vitamin D3 (13.0 mg, 30 pmol) to facilitate the conjugation reaction, which was indicated by an instant color change from red into yellow. The reaction mixture was concentrated in vacuo and the crude product was purified by RP-HPLC. Lyophilization affored the product 25-hydroxy vitamin D3-conjugate (0.86 mg) as a colorless solid. ESI-MS: m/z= 798.6 (C46H68N705 [M]+, calc.: 798.5); MW = 913.1 g/mol (C46H68N705 C2HF302).10 g of calcifediol and 0.078 g of diphenyl diselenide were placed in a 1000 ml flask at room temperature, and dissolved by adding 250 ml of n-hexane and 250 ml of ethyl acetate. The samples were taken at a temperature of 30 minutes, 60 minutes, 90 minutes, and 120 minutes with a 250 watt tungsten halogen lamp, and the progress of the reaction was analyzed by HPLC. As shown in Table 2 below, the results showed that the reaction was completed in 1.5 hours, and the conversion was 70%.At room temperature, calcifediol (20.32 g) and vitamin D3 (19.23 g) powders were weighed and completely dissolved in 500 mL of acetonitrile solution to form an unsaturated solution of calcifediol and vitamin D3. The unsaturated solution was cooled from room temperature to -20 degrees Celsius, and after standing for 24 hours, a eutectic powder of calcifediol and vitamin D3 was precipitated. The suspension was centrifuged and filtered to obtain a eutectic (31.35 g) of calcifediol and vitamin D3.

Uses

A metabolite of Vitamin D. The principal circulating form of vitamin D3, formed in the liver by hydroxylation at C-25. Calcium regulator.

Computed Properties

Molecular Weight:400.6
XLogP3:6.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:6
Exact Mass:400.334130642
Monoisotopic Mass:400.334130642
Topological Polar Surface Area:40.5
Heavy Atom Count:29
Complexity:655
Undefined Atom Stereocenter Count:5
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

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