Ergocalciferol

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
CAS Number	50-14-6 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28934 Y
ChEMBL	ChEMBL1536 Y
ChemSpider	4444351 Y
DrugBank	DB00153 Y
ECHA InfoCard	100.000.014
KEGG	C05441 Y
PubChem CID	5280793
UNII	VS041H42XC Y
CompTox Dashboard (EPA)	DTXSID5020233
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
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
Properties
Chemical formula	C28H44O
Molar mass	396.65 g/mol
Melting point	114–118 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) 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), discontinued Drisdol (Sanofi-Synthelabo), and Calcidol (Patrin Pharma). Created from viosterol when ultraviolet light activates ergosterol (found in fungi, it is named as a sterol from ergot), with fungi as the primary plant source.

Ergocalciferol may be used as a vitamin D supplement, and a 2011 clinical guideline^[1] considered it to be as effective as cholecalciferol (vitamin D₃), which is produced naturally by the skin when exposed to ultraviolet light. Conflicting evidence exists for how similarly D₂ and D₃ behave in the body and whether they are equally active, with some studies suggesting D₃ is more potent,^[2][3] while others report equal efficacy.^[4][5][1] Cholecalciferol (vitamin D₃) is sensitive to UV radiation and rapidly, but reversibly, forms other sterols which can further irreversibly convert to ergosterol.^{[citation needed]}

Sources

Lichen

• Cladina arbuscula specimens grown under different natural conditions: The contents of vitamin D3 range from 0.67 to 2.04 μg g⁻¹ 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⁻¹ dry matter, respectively, while the contents of provitamin D3 were below the detection limit (0.01 microg g(-1) dry matter).^[6]

Fungus, from USDA nutrient database^[7]

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

Plantae

• Alfalfa (Medicago sativa subsp. sativa), shoot: 4.8 mcg (192 IU) vitamin D₂, 0.1 mcg (4 IU) vitamin D₃^[8]

Vitamin D₂ (ergocalciferol) is produced in fungus synthetically from radiating an ergosterol.^[9] 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 to a vitamin D₂ supplement.^[10] Vitamin D₂ from UV-irradiated yeast baked into bread is bioavailable.^[11] By visual assessment or using a chromometer, no significant discoloration of irradiated mushrooms, as measured by the degree of "whiteness", was observed.^[12] Claims have been made that a normal serving (approx. 3 oz or 1/2 cup, or 60 grams) of mushrooms treated with ultraviolet light provides vitamin D content to levels of 3,476 IU if exposed to just 5 minutes of UV light after being harvested.^[13]