Vitamin D2
[CAS# 50-14-6]

Identification

• Classification: API >> Vitamins and minerals >> Vitamin AD drugs
• Name: Vitamin D2
• Synonyms: Calciferol; Ergocalciferol; Oleovitamin D2; 9,10-Secoergosta-5,7,10,22-tetraen-3-ol
• Molecular Formula: C₂₈H₄₄O
• Molecular Weight: 396.65
• CAS Registry Number: 50-14-6
• EC Number: 200-014-9
• SMILES: C[C@H](/C=C/[C@H](C)C(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C/3\C[C@H](CCC3=C)O)C

Properties

• Melting point: 115-119 ºC
• alpha: 82 º (c=3, in acetone 25 ºC)
• Density: 1.0±0.1 g/cm³ Calc.^*
• Boiling point: 504.2±29.0 ºC 760 mmHg (Calc.)^*
• Flash point: 218.2±16.5 ºC (Calc.)^*
• Index of refraction: 1.53 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS06;GHS08 Danger
• Hazard Statements: H300-H300-H301-H310-H311-H330-H372-H413
• Precautionary Statements: P260-P262-P264-P270-P271-P273-P280-P284-P301+P316-P302+P352-P304+P340-P316-P319-P320-P321-P330-P361+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	2	H330
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	3	H311
Acute toxicity	Acute Tox.	2	H300
Acute toxicity	Acute Tox.	2	H310
Chronic hazardous to the aquatic environment	Aquatic Chronic	4	H413
Specific target organ toxicity - single exposure	STOT SE	1	H370

• Transport Information: UN 2811

Discovory and Applicatios

Vitamin D2, also known as ergocalciferol, is one of the two main forms of vitamin D, the other being vitamin D3 (cholecalciferol). It is a fat-soluble secosteroid that plays a crucial role in maintaining calcium and phosphorus balance in the body, which is vital for bone health and overall metabolic function. Vitamin D2 is primarily obtained from plant-based sources and fungi, whereas vitamin D3 is synthesized in the skin upon exposure to sunlight.

The discovery of vitamin D and its importance in bone health dates back to the early 20th century. In 1922, the American biochemist Elmer McCollum identified vitamin D as a substance essential for the prevention of rickets, a disease characterized by weak and deformed bones due to calcium deficiency. Vitamin D2 was first isolated from ergosterol, a compound found in yeast, in 1928. The structure of ergocalciferol was elucidated in the 1930s, paving the way for further research into its role in human health.

Vitamin D2 is synthesized in fungi and yeast when exposed to ultraviolet (UV) light. Ergosterol, the precursor molecule, undergoes photochemical conversion to ergocalciferol under UV radiation. This process is similar to the way that 7-dehydrocholesterol in the human skin is converted to vitamin D3 through sunlight exposure. Because of this, vitamin D2 is often considered the plant-based or fungal form of vitamin D, whereas vitamin D3 is considered the animal-based form, found in sources like fatty fish, liver, and egg yolks.

Once ingested, vitamin D2 is converted into its active form in the liver and kidneys. It undergoes hydroxylation, first in the liver to form 25-hydroxyvitamin D2 (calcidiol), and then in the kidneys to form 1,25-dihydroxyvitamin D2 (calcitriol), the active hormone. This active form of vitamin D2 helps regulate the absorption of calcium and phosphorus in the intestines, promoting healthy bone mineralization. It also plays a role in immune system function and the regulation of cell growth.

The primary application of vitamin D2 is in the prevention and treatment of vitamin D deficiency, which can lead to bone disorders like rickets in children and osteomalacia or osteoporosis in adults. Vitamin D deficiency is a global health concern, particularly in regions with limited sunlight, where individuals may not produce sufficient vitamin D3 from sunlight exposure. In these cases, supplementation with vitamin D2 is often recommended. It is commonly used in dietary supplements, fortified foods, and as a prescription medication for individuals with low vitamin D levels.

One of the most well-known uses of vitamin D2 is in the fortification of milk and other dairy products. Since vitamin D is essential for calcium absorption, fortifying milk with vitamin D2 has been a public health measure aimed at preventing rickets and promoting bone health in populations with inadequate sun exposure. In some countries, vitamin D2 is added to a variety of foods, including breakfast cereals, orange juice, and plant-based milk alternatives like soy and almond milk, to help prevent deficiency.

Vitamin D2 is also used in clinical settings to manage conditions related to vitamin D deficiency. It is prescribed to patients who have conditions such as osteomalacia, osteoporosis, or hypoparathyroidism, where there is impaired calcium regulation. Vitamin D2 supplementation can help improve calcium balance and bone health in these patients. Additionally, it has been used in the treatment of chronic kidney disease (CKD), where the kidneys are unable to convert vitamin D to its active form effectively.

However, there are some limitations to the use of vitamin D2. Studies have shown that vitamin D3 is more effective than vitamin D2 in raising and maintaining blood levels of 25-hydroxyvitamin D. This is because vitamin D3 has a higher binding affinity to vitamin D receptors and is more stable in the body than vitamin D2. As a result, vitamin D3 is often preferred in supplementation for long-term use. Despite this, vitamin D2 remains an important option for individuals who follow vegetarian or vegan diets or for those who prefer plant-based sources of vitamin D.

The safety profile of vitamin D2 is generally good when taken within recommended doses. Excessive intake can lead to vitamin D toxicity, also known as hypervitaminosis D, which can result in elevated calcium levels, kidney stones, and other complications. As with any supplement, it is important to follow dosage guidelines and consult with a healthcare provider before taking vitamin D2, particularly in individuals with underlying health conditions such as kidney disease or hypercalcemia.

In conclusion, vitamin D2 is an essential nutrient that plays a vital role in calcium and phosphorus metabolism, bone health, and immune function. It is commonly used in the prevention and treatment of vitamin D deficiency, with applications in dietary supplementation and fortified foods. While vitamin D3 is often preferred for long-term use due to its superior efficacy, vitamin D2 remains a valuable option, especially for those following plant-based diets or requiring specific forms of supplementation.

References

1986. Isolation and identification of 1,24,25-trihydroxyvitamin D2, 1,24,25,28-tetrahydroxyvitamin D2, and 1,24,25,26-tetrahydroxyvitamin D2: new metabolites of 1,25-dihydroxyvitamin D2 produced in the rat kidney. Biochemistry, 25(22).
DOI: 10.1021/bi00366a051

1987. Growth Retardation Induced in Rat Fetuses by Maternal Fasting and Massive Doses of Ergocalciferol. The Journal of Nutrition, 117(2).
DOI: 10.1093/jn/117.2.342

1987. Synthesis of 25-hydroxy-[26,27-3H]vitamin D2, 1,25-dihydroxy-[26,27-3H]vitamin D2 and their (24R)-epimers. Analytical Biochemistry, 160(2).
DOI: 10.1016/0003-2697(87)90657-9