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Cholecalciferol

C27H44O organic

Properties

StateSolid (white to yellowish crystalline powder)
ColorWhite to yellowish
SolubilityInsoluble in water; soluble in ethanol, acetone, ether, and fats/oils
Melting Point83-86°C
Boiling PointDecomposes before boiling

About Cholecalciferol

Cholecalciferol is a secosteroid — a steroid where one of the rings has been broken open — and the broken ring (the B ring of the parent cholesterol skeleton) is what makes it a vitamin D rather than a regular steroid. The biosynthesis runs in your skin: 7-dehydrocholesterol absorbs a UVB photon between 290 and 315 nm, the B ring undergoes a six-electron pericyclic ring-opening to give pre-vitamin D3, and that thermally isomerizes over the next few hours to cholecalciferol via a [1,7]-sigmatropic hydrogen shift. The product itself is hormonally inactive — it has to be hydroxylated twice to do anything. The first hydroxylation runs in the liver via CYP2R1 and CYP27A1 to give 25-hydroxyvitamin D (calcidiol), which is the metabolite measured in your blood test because it has a half-life of about three weeks and reflects long-term status. The second hydroxylation runs in the kidney via CYP27B1 under tight PTH and FGF23 control to give 1,25-dihydroxyvitamin D (calcitriol), which is the actual hormone. Calcitriol binds the vitamin D receptor (a nuclear hormone receptor in the same family as the thyroid and retinoic acid receptors), heterodimerizes with RXR, and activates transcription of calcium-binding protein, the epithelial Ca2+ channel TRPV6, and a few hundred other genes that handle Ca2+ and phosphate handling. Deficiency gives rickets in kids and osteomalacia in adults — soft bones — and remained a major public health problem in northern latitudes until milk fortification rolled out in the US starting in the 1930s.

Where you'll encounter it

If you've ever had a 25-OH vitamin D blood test come back below 30 ng/mL, the supplement your doctor handed you is cholecalciferol, almost always made by UV-irradiating 7-dehydrocholesterol extracted from sheep's wool lanolin. The lanolin connection is why D3 is technically not vegan — the vegan alternative is ergocalciferol (D2) made by UV-irradiating ergosterol from yeast, but D2 raises serum 25-OH-D less efficiently than D3 at the same dose. In a clinical lab, the LC-MS/MS method for measuring 25-OH-D simultaneously quantifies the D2 and D3 forms and reports total — important because vegan patients on D2 supplements can look deficient on assays that don't distinguish.

Common Uses

  • Oral supplement for treating and preventing 25-OH-D deficiency at doses from 600 to 50,000 IU per dose
  • Fortification of milk, breakfast cereals, orange juice, and infant formula to public health targets
  • Treatment for nutritional rickets in children and osteomalacia in adults at prescription doses
  • Adjunctive therapy for chronic kidney disease patients alongside calcium and phosphate management
  • Veterinary feed additive for poultry, swine, and dairy cattle to prevent rickets and milk fever
  • Reference compound in LC-MS/MS clinical assays for serum 25-hydroxyvitamin D quantification
  • Active ingredient in some rodenticides (very high doses cause fatal hypercalcemia in rodents)
  • Research substrate for studying vitamin D receptor-mediated transcriptional regulation

Safety Information

Acute toxicity from a single dose is essentially impossible at supplement levels — the LD50 in rats is around 42 mg/kg, which would be roughly 3 grams in an adult human, equivalent to 120 million IU. Chronic supplementation above 10,000 IU/day eventually causes hypervitaminosis D: serum 25-OH-D climbs above 150 ng/mL, calcitriol-driven calcium absorption pushes serum calcium above 11 mg/dL, and you get nausea, polyuria, kidney stones, and metastatic calcification of soft tissues including the kidneys and arteries. The Tolerable Upper Intake Level set by the IOM is 4000 IU/day for adults, with a no-observed-adverse-effect level around 10,000 IU/day. Sun exposure cannot cause toxicity because previtamin D3 photoisomerizes to inactive lumisterol and tachysterol once skin levels saturate — the skin self-regulates. The OSHA-relevant occupational hazard is dust exposure during pharmaceutical manufacturing; the manufacturing limit is typically set at 0.1 mg/m3.

This safety summary is for educational reference only and may not be complete. It is not a substitute for Safety Data Sheets (SDS), medical advice, or professional chemical safety guidance. Always consult appropriate SDS and qualified professionals before handling chemicals.

Constituent Elements

Frequently Asked Questions

What is the molar mass of cholecalciferol?
C27H44O comes out to 384.638 g/mol: 27 carbons at 12.011 (324.297), 44 hydrogens at 1.008 (44.352), and one oxygen at 15.999. The unit conversion that matters in clinical work is between mass and IU: 1 microgram of cholecalciferol equals 40 IU, so a typical 1000 IU supplement contains 25 micrograms of D3. The dosing convention in IU rather than mass is a holdover from when the activity assay was a rat-line bioassay rather than a chemical quantification.
How does the body produce vitamin D from sunlight?
UVB photons in the 290-315 nm window — the same band that gets you sunburned — trigger a six-electron electrocyclic ring-opening of 7-dehydrocholesterol in the basal layer of your epidermis, giving previtamin D3. That intermediate spontaneously rearranges over hours via a [1,7]-sigmatropic hydrogen shift to cholecalciferol, which then leaves the skin bound to vitamin D-binding protein. The two activating hydroxylations happen sequentially in liver (CYP2R1, giving 25-OH-D) and kidney (CYP27B1, giving 1,25-(OH)2-D, the active hormone). Skin synthesis is highly latitude-dependent: north of 40 degrees latitude, you produce essentially no vitamin D from October through March because the UVB simply doesn't reach the surface.
What is the difference between vitamin D2 and D3?
D3 (cholecalciferol) has a 27-carbon side chain matching cholesterol; D2 (ergocalciferol) has 28 carbons with an extra methyl and a double bond inherited from the ergosterol precursor in yeast. Both go through the same liver and kidney hydroxylation pathway, but D3 raises serum 25-OH-D about 1.7x more efficiently per IU than D2 — probably because D2's side chain is a worse substrate for vitamin D-binding protein in plasma, so it gets cleared faster. Most prescription guidelines now specifically recommend D3 except for vegan patients.