Ergocalciferol

"Calcidol" redirects here. For the form of vitamin D3 sometimes called "calcidiol", see Cholecalciferol.

Ergocalciferol
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
CAS number	50-14-6 Y
PubChem	5280793
ChemSpider	4444351 Y
UNII	VS041H42XC Y
DrugBank	DB00153
KEGG	C05441 Y
ChEBI	CHEBI:28934 Y
ChEMBL	CHEMBL1536 Y
Jmol-3D images	Image 1
SMILES 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
InChI 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 Y Key: MECHNRXZTMCUDQ-RKHKHRCZSA-N Y 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
Properties
Molecular formula	C28H44O
Molar mass	396.65 g/mol
Melting point	114-118 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Ergocalciferol is a form of vitamin D, also called vitamin D₂. It is marketed under various names including Deltalin (Eli Lilly and Company), Drisdol (Sanofi-Synthelabo) and Calcidol (Patrin Pharma). It is created from viosterol, which in turn is created when ultraviolet light activates ergosterol (which is found in fungi and named as a sterol from ergot) and so comes only from plants.

Ergocalciferol is widely used as a Vitamin D supplement, and a 2011 clinical guideline^[1] considers it to be as effective as cholecalciferol (Vitamin D₃), which is produced naturally by the skin when it is exposed to ultraviolet light. However there is now conflicting evidence regarding how similarly D₂ and D₃ behave in the body and whether they are equally potent. Some studies suggest D₃ is more potent^[2][3], but others have found that they are equally effective^[4][5].

References

1. ^ Holick, M. F.; Binkley, N. C.; Bischoff-Ferrari, H. A.; Gordon, C. M.; Hanley, D. A.; Heaney, R. P.; Murad, M. H.; Weaver, C. M. (2011). "Evaluation, Treatment, and Prevention of Vitamin D Deficiency: An Endocrine Society Clinical Practice Guideline". Journal of Clinical Endocrinology & Metabolism 96 (7): 1911. doi:10.1210/jc.2011-0385. PMID 21646368.  edit
2. ^ Houghton, L.; Vieth, R. (2006). "The case against ergocalciferol (vitamin D2) as a vitamin supplement". The American Journal of Clinical Nutrition 84 (4): 694–697. PMID 17023693.  edit
3. ^ Trang, H. M.; Cole, D. E.; Rubin, L. A.; Pierratos, A.; Siu, S.; Vieth, R. (1998). "Evidence that vitamin D3 increases serum 25-hydroxyvitamin D more efficiently than does vitamin D2". The American journal of clinical nutrition 68 (4): 854–858. PMID 9771862.  edit
4. ^ Holick, M. F.; Biancuzzo, R. M.; Chen, T. C.; Klein, E. K.; Young, A.; Bibuld, D.; Reitz, R.; Salameh, W. et al. (2007). "Vitamin D2 is as Effective as Vitamin D3 in Maintaining Circulating Concentrations of 25-Hydroxyvitamin D". Journal of Clinical Endocrinology & Metabolism 93 (3): 677. doi:10.1210/jc.2007-2308. PMC 2266966. PMID 18089691. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2266966.  edit
5. ^ Biancuzzo, R. M.; Young, A.; Bibuld, D.; Cai, M. H.; Winter, M. R.; Klein, E. K.; Ameri, A.; Reitz, R. et al. (2010). "Fortification of orange juice with vitamin D2 or vitamin D3 is as effective as an oral supplement in maintaining vitamin D status in adults". American Journal of Clinical Nutrition 91 (6): 1621–1626. doi:10.3945/ajcn.2009.27972. PMC 2869510. PMID 20427729. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2869510.  edit

External links

• NIST Chemistry WebBook page for ergocalciferol