E5750

Sigma-Aldrich

Ergocalciferol

40,000,000 USP units/g

Synonym(s):
Ergosterol irradiated, Ercalciol, Calciferol, Vitamin D2, Irradiated ergosterol
Empirical Formula (Hill Notation):
C28H44O
CAS Number:
Molecular Weight:
396.65
Beilstein/REAXYS Number:
1916682
EC Number:
MDL number:
eCl@ss:
34058017
PubChem Substance ID:
NACRES:
NA.79

Quality Level

biological source

synthetic (organic)

assay

≥97%

form

powder

specific activity

40,000,000 USP units/g

application(s)

HPLC: suitable

color

white to off-white

mp

114-118 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)[C@@H](C)/C=C/[C@@H](C)[C@@]1([H])CC[C@@]([C@]1(C)CCC/2)([H])C2=C\C=C(C[C@@H](O)CC3)/C3=C

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

InChI key

MECHNRXZTMCUDQ-RKHKHRCZSA-N

Gene Information

human ... VDR(7421)

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General description

Vitamin D2 or ergocalciferol is available through dietary supplements or plant sources. It is a provitamin, which is fat-soluble.

Application

Ergocalciferol has been used as a component of the diet for rats, to study its bioavailability from ultraviolet-irradiated D2-rich yeast. It has also been used as a standard for identification and quantification of vitamins, as part of a study to determine the nutritional composition of food fishes.

Packaging

1, 5, 25 g in ampule
Sealed ampule.

Biochem/physiol Actions

Ergocalciferol is used for antirachitic treatment. Vitamin D has an active role in bone mineralization. Severe deficiency of this vitamin has been associated with osteomalacia and rickets.
Ergocalciferol (vitamin D2) and 25-Hydroxycholecalciferol (vitamin D3) are the two forms of vitamin D, which are activated in vivo by hydroxylation. Vitamin D2 and D3 may be used in a wide range of studies to assess their effects on function such as immune function and calcium homeostasis.

Quantity

1 USP unit = 1 I.U.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2811 6.1 / PGII

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Nutritional composition of food fishes and their importance in providing food and nutritional security
Mohanty BP, et al.
Food Chemistry, 293 (2019)
Hypoparathyroidism and Other Causes of Hypocalcemia
Luciano M
Encyclopedia of Endocrine Diseases (2018)
Vitamin D: The Biotechnology of Ergosterol
Vandamme EJ
Biotechnology of microbial enzymes (1989)
Poor bioavailability of vitamin D2 from ultraviolet-irradiated D2-rich yeast in rats
Itkonen ST, et al.
Nutrition Research (New York, N.Y.), 59, 36-43 (2018)
Rock E
Food for the Ageing Population (2009)
Articles
Vitamin D2 (ergocalciferol) is naturally synthesized from ergosterol by invertebrates, fungi, and plants in response to ultraviolet B irradiation, while vitamin D3 synthesis (cholecalciferol) is uniquely initiated in the skin of vertebrates. During sun exposure, ultraviolet B photons are absorbed by 7-dehydrocholesterol, which is found within the plasma membranes of epidermal and dermal skin layers. This reaction yields an unstable derivative of 7-dehydrocholesterol, named precholecalcitrol, which rapidly rearranges to vitamin D3. Vitamin D binding protein (DBP) is a carrier protein responsible for drawing vitamin D3 from the plasma membrane into the dermal capillaries within the extracellular space.
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