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E5750

Sigma-Aldrich

Ergocalciferol

40,000,000 USP units/g

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

biological source

synthetic (organic)

Quality Level

Assay

≥97%

form

powder

specific activity

40,000,000 USP units/g

technique(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.

Biochem/physiol Actions

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.
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.

Packaging

Sealed ampule.

Quantity

1 USP unit = 1 I.U.

Pictograms

Skull and crossbonesHealth hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 3 Dermal - Acute Tox. 3 Oral - STOT RE 1 Oral

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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