Cholecalciferol
From Wikipedia, the free encyclopedia
| Cholecalciferol | |
|---|---|
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| IUPAC name | (3β,5Z,7E)-9,10-secocholesta- 5,7,10(19)-trien-3-ol |
| Other names | vitamin D3, activated 7-dehydrocholesterol. |
| Identifiers | |
| CAS number | [67-97-0] |
| EINECS number | |
| SMILES | CC(C)CCC[C@@H](C)[C@H] 1CCC2C(\CCCC12C)=C\ C=C3\C[C@@H](O)CCC3=C |
| Properties | |
| Molecular formula | C27H44O |
| Molar mass | 384.64 g/mol |
| Appearance | White, needle-like crystals |
| Melting point |
83–86 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Cholecalciferol is a form of Vitamin D, also called vitamin D3. It is structurally similar to steroids such as testosterone, cholesterol, and cortisol (though vitamin D3 itself is a secosteroid).
1g of pure vitamin D3 is 40 000 000 (40x106) IU, or in other words, one IU is 0.025 μg.
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[edit] Forms
Cholecalciferol has several forms:
- Calciol [1], is an inactive, unhydroxylated form of vitamin D3)
- calcidiol (also called 25-hydroxyvitamin D3), is the blood calcium form
- calcitriol (also called 1,25-dihydroxyvitamin D3), is the active form of D3.
[edit] Metabolism
7-Dehydrocholesterol is the precursor of vitamin D3 and only forms the vitamin after being exposed to solar UV radiation. This creates calciol.
Calciol is then hydroxylated in the liver to become calcidiol.
Next, calcidiol is once again hydroxylated, this time in the kidney, and becomes calcitriol. Calcitriol is the active hormone form of vitamin D3; for this reason vitamin D is often referred to as a prohormone.
[edit] As food fortification
Cholecalciferol is the form of vitamin D normally added during fortification of foods.[citation needed] Cholecalciferol is produced industrially by the irradiation of 7-dehydrocholesterol extracted from lanolin found in sheep's wool. In products where animal products are not desired, the alternative is to use ergocalciferol (also known as vitamin D2) derived from the fungal sterol ergosterol.
[edit] Dose
Healthy individuals absorb cholecalciferol and ergocalciferol approximately equally well[2], and while initial reports suggested that vitamin D3 was more potent in humans, the same journal has published newer research which contradicts those initial reports.[2] [3] The human body does not tolerate vitamin D3 as well as vitamin D2[citation needed], limiting the maximum efficacy of vitamin D3 supplementation compared to vitamin D2. Cholecalciferol is synthesized by the bone marrow of the skeletal system. Hepatic synthesis of 25-hydroxycholecalciferol is only loosely regulated, and blood levels of this molecule largely reflect the amount of amount of vitamin D produced in the skin or ingested. In contrast, the activity of 1-alpha-hydroxylase in the kidney is tightly regulated and serves as the major control point in production of the active hormone.
[edit] Stability
Cholecalciferol is very sensitive to UV radiation and will rapidly, but reversibly break down to form supra-sterols, which can further irreversibly convert to tachysterol.
[edit] See also
- Hypervitaminosis D, Vitamin D poisoning
- Ergocalciferol, vitamin D2.
- 25-Hydroxyvitamin D3 1-alpha-Hydroxylase, a kidney enzyme that converts calcidiol to calcitriol.
[edit] References
- ^ online medical dictionary
- ^ a b Armas L, Hollis B, Heaney R (2004). "Vitamin D2 is much less effective than vitamin D3 in humans". J Clin Endocrinol Metab 89 (11): 5387–91. doi:. PMID 15531486 Cholecalciferol is synthesized by the bone marrow of the skeletal system..
- ^ "Vitamin D2 is as effective as vitamin D3 in maintaining circulating concentrations of 25-hydroxyvitamin-D "Context: Two reports suggested that vitamin D2 is less effective than vitamin D3 in maintaining vitamin D status"" (2007). J Clin Endocrinol Metab.
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