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(24S)-24,25-Dihydroxyvitamin D3

Inactive form of vitamin D3 CAS# 55700-58-8

(24S)-24,25-Dihydroxyvitamin D3

2D Structure

Catalog No. BCC1290----Order now to get a substantial discount!

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(24S)-24,25-Dihydroxyvitamin D3

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Chemical Properties of (24S)-24,25-Dihydroxyvitamin D3

Cas No. 55700-58-8 SDF Download SDF
PubChem ID 6439679 Appearance Powder
Formula C27H44O3 M.Wt 416.64
Type of Compound N/A Storage Desiccate at -20°C
Synonyms (24S)-24,25-Dihydroxycholecalciferol
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (3S,6R)-6-[(1R,3aS,4E,7aR)-4-[(2Z)-2-[(5R)-5-hydroxy-2-methylidenecyclohexylidene]ethylidene]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-1-yl]-2-methylheptane-2,3-diol
SMILES CC(CCC(C(C)(C)O)O)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)C
Standard InChIKey FCKJYANJHNLEEP-XUCUACLUSA-N
Standard InChI InChI=1S/C27H44O3/c1-18-8-12-22(28)17-21(18)11-10-20-7-6-16-27(5)23(13-14-24(20)27)19(2)9-15-25(29)26(3,4)30/h10-11,19,22-25,28-30H,1,6-9,12-17H2,2-5H3/b20-10+,21-11-/t19-,22-,23-,24+,25+,27-/m1/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of (24S)-24,25-Dihydroxyvitamin D3

Description(24S)-24,25-Dihydroxycholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. IC50 value: Target: Vitamin D3 analog 1α-Hydroxyvitamin D3 (alfacalcidol) is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3. Other analogues of cholecalciferol result from different hydroxylations. 24S,25-Dihydroxyvitamin D3 should not be confused with 24R,25-Dihydroxyvitamin D3.

References:
[1]. Yamada S, Ino E, Takayama H et al. Differences in the side-chain metabolism of vitamin D3 between chickens and rats. Proc Natl Acad Sci U S A. 1985 Nov;82(22):7485-9. [2]. Kobayashi N, Higashi T, Saito K et al. Specificity of polyclonal antibodies raised against a novel 24,25-dihydroxyvitamin D3-bovine serum albumin conjugant linked through the C-11alpha or C-3 position. J Steroid Biochem Mol Biol. 1997 May;62(1):79-87. [3]. Larsson D, Nemere I, Sundell K. Putative basal lateral membrane receptors for 24,25-dihydroxyvitamin D(3) in carp and Atlantic cod enterocytes: characterization of binding and effects on intracellular calcium regulation. J Cell Biochem. 2001 Aug 1-9;83(2):171-86. [4]. Nemere I, Yazzie-Atkinson D, Johns DO, Larsson D. Biochemical characterization and purification of a binding protein for 24,25-dihydroxyvitamin D3 from chick intestine. J Endocrinol. 2002 Jan;172(1):211-9.

(24S)-24,25-Dihydroxyvitamin D3 Dilution Calculator

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(24S)-24,25-Dihydroxyvitamin D3 Molarity Calculator

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Preparing Stock Solutions of (24S)-24,25-Dihydroxyvitamin D3

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.4002 mL 12.0008 mL 24.0015 mL 48.0031 mL 60.0038 mL
5 mM 0.48 mL 2.4002 mL 4.8003 mL 9.6006 mL 12.0008 mL
10 mM 0.24 mL 1.2001 mL 2.4002 mL 4.8003 mL 6.0004 mL
50 mM 0.048 mL 0.24 mL 0.48 mL 0.9601 mL 1.2001 mL
100 mM 0.024 mL 0.12 mL 0.24 mL 0.48 mL 0.6 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on (24S)-24,25-Dihydroxyvitamin D3

Cholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs. 1α-Hydroxyvitamin D3 (alfacalcidol) is a synthetic analog that is metabolized to 1,25-dihydroxycholecalciferol, the biologically active form of vitamin D3. Other analogues of cholecalciferol result from different hydroxylations. 24S,25-Dihydroxyvitamin D3 should not be confused with 24R,25-Dihydroxyvitamin D3.

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References on (24S)-24,25-Dihydroxyvitamin D3

Naturally occurring 24,25-dihydroxyvitamin D3 is a mixture of both C-24R and C-24S epimers.[Pubmed:6091567]

Arch Biochem Biophys. 1984 Oct;234(1):97-104.

Tritium-labeled 24,25-dihydroxyvitamin D3 was prepared both in vitro, by using chick kidney homogenates, and in vivo in rats from [26,27-methyl-3H]25-hydroxyvitamin D3. These compounds were mixed with synthetic 24(R),25- and 24(S),25-dihydroxyvitamin D3, converted to the corresponding trimethylsilyl ether derivatives, and analyzed by a high-pressure liquid chromatography procedure that separates the derivatized isomers. The tritium-labeled 24,25-dihydroxyvitamin D3 derivatives were found to be a mixture of both the 24(R) and 24(S) epimers; the ratio was found to be 96.4:3.6 in chick kidney homogenates and 96.8:3.2 in the serum of rats under physiological conditions. In addition, nonradioactive 24,25-dihydroxyvitamin D3 isolated from the serum of rats given large doses of vitamin D3 was shown to be an 89.5:10.5 mixture of the 24(R) and 24(S) isomers. When 25-hydroxy-24-oxo-vitamin D3 was utilized as a substrate, it was found to be more selectively reduced to 24(S),25-dihydroxyvitamin D3 than 24(R),25-dihydroxyvitamin D3 by the renal enzyme. The 24(S),25-dihydroxyvitamin D3 has been identified by ultraviolet absorption spectrophotometry, cochromatography with an authentic standard, and mass spectrometry. The reduced metabolites of 25-hydroxy-24-oxo-vitamin D3 were a 1:50 mixture of the 24(R) and 24(S) epimers. There are two known metabolic pathways leading to 24,25-dihydroxyvitamin D3 from 25-hydroxyvitamin D3; one is 24(R)-hydroxylation of 25-hydroxyvitamin D3 and the other is reduction of 25-hydroxy-24-oxo-vitamin D3. In contrast, 24(S),25-dihydroxyvitamin D3 is produced only by reduction of 25-hydroxy-24-oxo-vitamin D3 in the kidney. Therefore, naturally occurring 24,25-dihydroxyvitamin D3 is a mixture of the 24(R) and 24(S) isomers, and not just the 24(R) isomer as reported previously.

Description

(24S)-24,25-Dihydroxycholecalciferol is an inactive form of vitamin D3 which undergoes various levels of hydroxylation to form active vitamin D3 analogs.

Keywords:

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