Ergocalciferol

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Ergocalciferol
Skeletal formula of ergocalciferol
Ball-and-stick model of the ergocalciferol molecule
Names
IUPAC name
(3β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-ol
Other names
Drisdol (Sanofi-Synthelabo), Calcidol (Patrin Pharma)
Identifiers
50-14-6 YesY
ChEBI CHEBI:28934 YesY
ChEMBL ChEMBL1536 YesY
ChemSpider 4444351 YesY
DrugBank DB00153 YesY
Jmol 3D model Interactive image
KEGG C05441 YesY
PubChem 5280793
UNII VS041H42XC YesY
  • InChI=1S/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1 YesY
    Key: MECHNRXZTMCUDQ-RKHKHRCZSA-N YesY
  • InChI=1/C28H44O/c1-19(2)20(3)9-10-22(5)26-15-16-27-23(8-7-17-28(26,27)6)12-13-24-18-25(29)14-11-21(24)4/h9-10,12-13,19-20,22,25-27,29H,4,7-8,11,14-18H2,1-3,5-6H3/b10-9+,23-12+,24-13-/t20-,22+,25-,26+,27-,28+/m0/s1
    Key: MECHNRXZTMCUDQ-RKHKHRCZBW
  • O[C@@H]1CC(\C(=C)CC1)=C\C=C2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](/C=C/[C@H](C)C(C)C)C)C
Properties
C28H44O
Molar mass 396.65 g/mol
Melting point 114 to 118 °C (237 to 244 °F; 387 to 391 K)
Pharmacology
ATC code A11CC01
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Ergocalciferol (vitamin D2) is a form of vitamin D. Ergocalciferol is a secosteroid formed by a photochemical bond breaking of a steroid, specifically, by the action of ultraviolet light on ergosterol. Viosterol, the name given to early preparations of irradiated ergosterol, is essentially synonymous with ergocalciferol.[1][2]

Ergocalciferol may be used as a vitamin D supplement, and a 2011 clinical guideline[3] considered it to be as effective as cholecalciferol (vitamin D3) which is produced naturally by the skin when exposed to ultraviolet light. It is manufactured and marketed under various names, including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo) and Calcidol (Patrin Pharma).

Sources

Lichen

  • Cladina arbuscula specimens grown under different natural conditions: The contents of vitamin D3 range from 0.67 to 2.04 μg/g dry matter in the thalli of C. arbuscula specimens grown under different natural conditions, while provitamin D3 could not be detected. The ranges for provitamin D2 and vitamin D2 were 89-146 and 0.22-0.55 μg/g dry matter, respectively, while the contents of provitamin D3 were below the detection limit (0.01 μg/g dry matter).[4]

Fungus, from USDA nutrient database (per 100g) [5]

  • Mushrooms, portobello, exposed to ultraviolet light, raw: Vitamin D (D2 + D3): 11.2 µg (446 IU)
  • Mushrooms, portobello, exposed to ultraviolet light, grilled: Vitamin D (D2 + D3): 13.1 µg (524 IU)
  • Mushrooms, shiitake, dried: Vitamin D (D2 + D3): 3.9 μg (154 IU)
  • Mushrooms, shiitake, raw: Vitamin D (D2 + D3): 0.4 μg (18 IU)
  • Mushrooms, portobello, raw: Vitamin D (D2 + D3): 0.3 μg (10 IU)

Plantae

  • Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 μg (192 IU) vitamin D2, 0.1 μg (4 IU) vitamin D3[6]

Ergocalciferol is produced in fungi synthetically through irradiation of ergosterol.[7] Human bioavailability of vitamin D2 from vitamin D2-enhanced button mushrooms via UV-B irradiation is effective in improving vitamin D status and not different from a vitamin D2 supplement.[8] Vitamin D2 from UV-irradiated yeast baked into bread is bioavailable.[9] By visual assessment or using a chromometer, no significant discoloration of irradiated mushrooms, as measured by the degree of "whiteness", was observed.[10] Claims that a normal serving of mushrooms treated with ultraviolet light provides the equivalent of 3,500 International Units of vitamin D when exposed to ultraviolet light after harvest have gained popular attention.[11]

Research concerning efficacy of vitamin D2 and D3

Conflicting evidence exists for how similarly D2 and D3 behave in the body and whether they are equally active or efficient in production of 1,25-hydroxyvitamin D (1,25(OH)D), the active hormone. Some preliminary studies indicate D3 is more potent,[12][13] while others report equal efficacy.[3][14][15] Both forms appear to have similar efficacy in ameliorating rickets[16] and reducing the incidence of falls in elderly patients.[17]

The metabolism of each appears to be different, with the vitamin D binding protein possibly having greater affinity for 25(OH)D3 than for 25(OH)D2, as shown in one study.[12] Cholecalciferol (vitamin D3) is sensitive to UV radiation and rapidly, but reversibly, forms other sterols which can further irreversibly convert to ergosterol.[citation needed]

Preliminary research

One study found low vitamin D2 levels in patients with Alzheimer's disease,[18] but this observational study did not prove cause or effect related to ergocalciferol and vitamin D2 deficiency in the diet.

References

  1. ↑ Science Service (1930) Viosterol official name for irradiated ergosterol, J. Chem. Educ. 7(1) 166, DOI: 10.1021/ed007p166, see [pubs.acs.org/doi/abs/10.1021/ed007p166, accessed 10 July 2014.
  2. ↑ See "Viosterol" and "Calciferol" at Merriam-Webster Medical Dictionary, e.g., [1] and [2], accessed 10 July 2014.
  3. ↑ 3.0 3.1 Lua error in package.lua at line 80: module 'strict' not found.
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  12. ↑ 12.0 12.1 Lua error in package.lua at line 80: module 'strict' not found.
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  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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External links


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