Ergocalciferol (CHEM002129)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (4)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:10 UTC
Update Date2026-03-26 21:20:40 UTC
Accession NumberCHEM002129
Identification
Common NameErgocalciferol
ClassSmall Molecule
DescriptionErgocalciferol is a form of Vitamin D, also called vitamin D2. It is created from viosterol, which in turn is created when ultraviolet light activates ergosterol. Ergocalciferol is used in the treatment of hypcalcemia and in dialysis-dependent renal failure. Ergoalcifediol is a fat soluble steroid hormone precursor of vitamin D that contributes to the maintenance of normal levels of calcium and phosphorus in the bloodstream. Vitamin D2 is the form of vitamin D most commonly added to foods and nutritional supplements. Vitamin D2 must be transformed (hydroxylated) into one of two active forms via the liver or kidney. Once transformed, it binds to the vitamin D receptor that then leads to a variety of regulatory roles.
Contaminant Sources
  • Clean Air Act Chemicals
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Antihypocalcemic Agent
  • Antihypoparathyroid Agent
  • Antithyroid Agent
  • Bone Density Conservation Agent
  • Drug
  • Essential Vitamin
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Nutraceutical
  • Organic Compound
  • Vitamin
  • Vitamin D
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3beta,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
(5Z,7E,22E)-(3S)-9,10-Seco-5,7,10(19),22-ergostatetraen-3-olChEBI
(5Z,7E,22E)-(3S)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olChEBI
Activated ergosterolChEBI
CalciferolChEBI
ErcalciolChEBI
ErgocalciferolumChEBI
Oleovitamin D2ChEBI
ViosterolChEBI
Vitamina D2ChEBI
Vitamin D2Kegg
DrisdolKegg
(3b,5Z,7E,22E)-9,10-Secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(3Β,5Z,7E,22E)-9,10-secoergosta-5,7,10(19),22-tetraen-3-olGenerator
(+)-Vitamin D2HMDB
(5E,7E,22E)-9,10-Secoergosta-5,7,10,22-tetraen-3-olHMDB
22-Tetraen 3beta 9,10,secoergosta-5,7,10(19)-olHMDB
4-Methylene-3-[2-[tetrahydro-7a-methyl-1-(1,4,5-trimethyl-2-hexenyl)-4(3ah)-indanylidene]ethylidene]-cyclohexanolHMDB
9,10-Secoergosta-5,7,10(19),22-tetraen-3b-olHMDB
beta-OlHMDB
Buco-DHMDB
Calciferon 2HMDB
CondacapsHMDB
CondocapsHMDB
CondolHMDB
CrtronHMDB
CrystallinaHMDB
D-ArthinHMDB
D-TracettenHMDB
DaralHMDB
Davitamon DHMDB
DavitinHMDB
De-rat concentrateHMDB
DecapsHMDB
Dee-osterolHMDB
Dee-ronHMDB
Dee-ronalHMDB
Dee-roualHMDB
delta-ArthinHMDB
delta-TracettenHMDB
DeltalinHMDB
DeratolHMDB
DetalupHMDB
DiactolHMDB
Divit urtoHMDB
DoralHMDB
Ergocalciferol oilHMDB
ErgoroneHMDB
Ergosterol activatedHMDB
Ergosterol irradiatedHMDB
ErtronHMDB
FortodylHMDB
GeltabsHMDB
Hi-deratolHMDB
InfronHMDB
Irradiated ergosta-5,7,22-trien-3beta-olHMDB
MetadeeHMDB
Mina D2HMDB
MulsiferolHMDB
MykostinHMDB
Novovitamin-DHMDB
Oleovitamin DHMDB
OsteilHMDB
OstelinHMDB
RadiostolHMDB
RadsteinHMDB
RadsterinHMDB
Rodine CHMDB
Shock-ferolHMDB
Shock-ferol sterogylHMDB
SterogylHMDB
Synthetic vitamin DHMDB
Uvesterol DHMDB
Uvesterol-DHMDB
Vio DHMDB
Vio-DHMDB
ViostdrolHMDB
Viosterol in oilHMDB
Vitavel-DHMDB
CalciferolsHMDB
ErgocalciferolsHMDB
D2, VitaminHMDB
Vitamin D 2HMDB
ErgocalciferolChEBI
Chemical FormulaC28H44O
Average Molecular Mass396.648 g/mol
Monoisotopic Mass396.339 g/mol
CAS Registry Number50-14-6
IUPAC Name(1S,3Z)-3-{2-[(1R,3aS,4E,7aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-7a-methyl-octahydro-1H-inden-4-ylidene]ethylidene}-4-methylidenecyclohexan-1-ol
Traditional Nameergocalciferol
SMILESCC(C)[C@@H](C)\C=C\[C@@H](C)[C@@]1([H])CC[C@@]2([H])\C(CCC[C@]12C)=C\C=C1\C[C@@H](O)CCC1=C
InChI IdentifierInChI=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 KeyMECHNRXZTMCUDQ-RKHKHRCZSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as vitamin d and derivatives. Vitamin D and derivatives are compounds containing a secosteroid backbone, usually secoergostane or secocholestane.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassVitamin D and derivatives
Direct ParentVitamin D and derivatives
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
Biofluid LocationsNot Available
Tissue Locations
  • Adipose Tissue
  • Bladder
  • Brain
  • Fibroblasts
  • Gonads
  • Intestine
  • Kidney
  • Liver
  • Muscle
  • Nerve Cells
  • Pancreas
  • Placenta
  • Prostate
  • Skeletal Muscle
  • Skin
  • Spleen
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point116.5°C
Boiling PointNot Available
Solubility50 mg/L
Predicted Properties
PropertyValueSource
Water Solubility0.00043 g/LALOGPS
logP7.59ALOGPS
logP7.05ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)18.38ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity128.89 m³·mol⁻¹ChemAxon
Polarizability50.72 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-003u-3911000000-dba9e396497310b31715Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-003u-3911000000-dba9e396497310b31715Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f89-3019000000-8a847f6179b3a364ad05Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0udl-4103900000-4c6f376ae6706d7e8556Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0002-0129000000-77bd32807ec8ea97183bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0601-5902000000-ae4a4363ac10f9f0feb7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-05mo-9800000000-1ea9f4fa17117a9e6515Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-01ot-9801000000-17d2120d47f9c718ea95Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ot-9801000000-c10341d61ee2d6369219Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-1129000000-41a3f60b47798eb6bd6cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05ai-4694000000-95577608302dfef840b4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gx9-9464000000-f7bcbdb6e805513cd661Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-819b52cfd84baf07f550Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0009000000-5ed8b1f535a88d73555cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-3249000000-bf201c27d3bc67289adbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0398000000-dfcffd595ce9725ef52cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0uk9-4192000000-c93d9259f7db1789c50aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015c-9340000000-aa858d8ca84ec1673a55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0009000000-2f6aa9af0bd8878fb6c6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-0109000000-7977d6caa249a0925fb3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-1759000000-2c5dd594802c53ac80a1Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureOral, readily absorbed.
Mechanism of ToxicityVitamin D2 is the form of vitamin D most commonly added to foods and nutritional supplements. Vitamin D2 must be transformed (hydroxylated) into one of two active forms via the liver or kidney. Once transformed, it binds to the vitamin D receptor that then leads to a variety of regulatory roles. Vitamin D plays an important role in maintaining calcium balance and in the regulation of parathyroid hormone (PTH). It promotes renal reabsorption of calcium, increases intestinal absorption of calcium and phosphorus, and increases calcium and phosphorus mobilization from bone to plasma. Vitamin D2 and its analogs appear to promote intestinal absorption of calcium through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein. Activated ergocalciferol increases serum calcium and phosphate concentrations, primarily by increasing intestinal absorption of calcium and phosphate through binding to a specific receptor in the mucosal cytoplasm of the intestine. Subsequently, calcium is absorbed through formation of a calcium-binding protein. 25-hydroxyergocalciferol is the intermediary metabolite of ergocalciferol. Although this metabolite exhibits 2-5 times more activity than unactivated ergocalciferol in curing rickets and inducing calcium absorption and mobilization (from bone) in animals, this increased activity is still insufficient to affect these functions at physiologic concentrations. Activated ergocalciferol stimulate resorption of bone and are required for normal mineralization of bone. Physiological doses of ergocalciferol also promotes calcium reabsorption by the kidneys, but the significance of this effect is not known.
MetabolismWithin the liver, ergocalciferol is hydroxylated to ercalcidiol (25-hydroxyergocalciferol) by the enzyme 25-hydroxylase. Within the kidney, ercalcidiol serves as a substrate for 1-alpha-hydroxylase, yielding ercalcitriol (1,25-dihydroxyergocalciferol), the biologically active form of vitamin D2. Half Life: 19 to 48 hours (however, stored in fat deposits in body for prolonged periods).
Toxicity ValuesLD50 = 23.7 mg/kg (Orally in mice); LD50 = 10 mg/kg (Orally in rats ).
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor use in the management of hypocalcemia and its clinical manifestations in patients with hypoparathyroidism, as well as for the treatment of familial hypophosphatemia (vitamin D resistant rickets). This drug has also been used in the treatment of nutritional rickets or osteomalacia, vitamin D dependent rickets, rickets or osteomalacia secondary to long-term high dose anticonvulsant therapy, early renal osteodystrophy, osteoporosis (in conjunction with calcium), and hypophosphatemia associated with Fanconi syndrome (with treatment of acidosis).
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNausea, vomiting and diarrhea, weight loss, irritability, weakness, fatigue, lassitude, and headache.
TreatmentThe treatment of hypervitaminosis D with hypercalcemia consists in immediate withdrawal of the vitamin, a low calcium diet, generous intake of fluids, along with symptomatic and supportive treatment. Hypercalcemic crisis with dehydration, stupor, coma, and azotemia requires more vigorous treatment. The first step should be hydration of the patient. Intravenous saline may quickly and significantly increase urinary calcium excretion. A loop diuretic (furosemide or ethacrynic acid) may be given with the saline infusion to further increase renal calcium excretion. Other reported therapeutic measures include dialysis or the administration of citrates, sulfates, phosphates, corticosteroids, EDTA (ethylenediaminetetraacetic acid), and mithramycin via appropriate regimens. (23)
Concentrations
Not Available
DrugBank IDDB00153
HMDB IDHMDB0000900
FooDB IDFDB012811
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID2289183
BioCyc IDVITAMIN_D2
METLIN ID5856
PDB IDNot Available
Wikipedia LinkErgocalciferol
Chemspider ID4444351
ChEBI ID28934
PubChem Compound ID5280793
Kegg Compound IDC05441
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Charles W. Bishop, Glenville Jones, Ronald L. Horst, Nicholas J. Koszewski, Joyce C. Knutson, Raju Penmasta, Robert M. Moriarty, Stephen Strugnell, Timothy A. Reinhardt, Liang Guo, Sanjay K. Singhal, Lei Zhao, “Methods for preparation and use of 1A,24(S)-dihydroxy vitamin D2.” U.S. Patent US5789397, issued March, 1992.

MSDSLink
General References
1. Okabe, Masami. Vitamin D2 from ergosterol (9,10-secoergosta-5,7,10(19),22-tetraen-3-ol,(3b)- from ergosta-5,7,22-trien-3-ol,(3b)-). Organic Syntheses (1999), 76 275-286.
2. A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation)
3. Pirjo H. Mattila, Vieno I. Piironen, Esko J. Uusi-Rauva, and Pekka E. Koivistoinen. 1995. Contents of Cholecalciferol, Ergocalciferol, and Their 25-Hydroxylated Metabolites in Milk Products and Raw Meat and Liver As Determined by HPLC. J. Agric. Food Chem. 43 (9), pp 2394–2399
4. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=33&2
5. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1154&2
6. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1049&2
7. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1066&2
8. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1048&2
9. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1265&2
10. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=6&2
11. Fooddata+, The Technical University of Denmark (DTU): https://frida.fooddata.dk/ShowFood.php?foodid=1266&2
12. Okabe, Masami. Vitamin D2 from ergosterol (9,10-secoergosta-5,7,10(19),22-tetraen-3-ol,(3b)- from ergosta-5,7,22-trien-3-ol,(3b)-). Organic Syntheses (1999), 76 275-286.
13. Samanek AJ, Croager EJ, Gies P, Milne E, Prince R, McMichael AJ, Lucas RM, Slevin T: Estimates of beneficial and harmful sun exposure times during the year for major Australian population centres. Med J Aust. 2006 Apr 3;184(7):338-41.
14. Shepard RM, Horst RL, Hamstra AJ, DeLuca HF: Determination of vitamin D and its metabolites in plasma from normal and anephric man. Biochem J. 1979 Jul 15;182(1):55-69.
15. Bischoff HA, Borchers M, Gudat F, Duermueller U, Theiler R, Stahelin HB, Dick W: In situ detection of 1,25-dihydroxyvitamin D3 receptor in human skeletal muscle tissue. Histochem J. 2001 Jan;33(1):19-24.
16. Jorde R, Saleh F, Figenschau Y, Kamycheva E, Haug E, Sundsfjord J: Serum parathyroid hormone (PTH) levels in smokers and non-smokers. The fifth Tromso study. Eur J Endocrinol. 2005 Jan;152(1):39-45.
17. Bischoff-Ferrari HA, Borchers M, Gudat F, Durmuller U, Stahelin HB, Dick W: Vitamin D receptor expression in human muscle tissue decreases with age. J Bone Miner Res. 2004 Feb;19(2):265-9.
18. Young MV, Schwartz GG, Wang L, Jamieson DP, Whitlatch LW, Flanagan JN, Lokeshwar BL, Holick MF, Chen TC: The prostate 25-hydroxyvitamin D-1 alpha-hydroxylase is not influenced by parathyroid hormone and calcium: implications for prostate cancer chemoprevention by vitamin D. Carcinogenesis. 2004 Jun;25(6):967-71. Epub 2004 Jan 16.
19. Jones G, Strugnell SA, DeLuca HF: Current understanding of the molecular actions of vitamin D. Physiol Rev. 1998 Oct;78(4):1193-231.
20. Langman CB, Brooks ER: Renal osteodystrophy in children: a systemic disease associated with cardiovascular manifestations. Growth Horm IGF Res. 2006 Jul;16 Suppl A:S79-83. Epub 2006 Apr 18.
21. Reginster JY: The high prevalence of inadequate serum vitamin D levels and implications for bone health. Curr Med Res Opin. 2005 Apr;21(4):579-86.
22. Tuohimaa P, Tenkanen L, Ahonen M, Lumme S, Jellum E, Hallmans G, Stattin P, Harvei S, Hakulinen T, Luostarinen T, Dillner J, Lehtinen M, Hakama M: Both high and low levels of blood vitamin D are associated with a higher prostate cancer risk: a longitudinal, nested case-control study in the Nordic countries. Int J Cancer. 2004 Jan 1;108(1):104-8.
23. Malloy PJ, Xu R, Peng L, Clark PA, Feldman D: A novel mutation in helix 12 of the vitamin D receptor impairs coactivator interaction and causes hereditary 1,25-dihydroxyvitamin D-resistant rickets without alopecia. Mol Endocrinol. 2002 Nov;16(11):2538-46.
24. Boyle MP, Noschese ML, Watts SL, Davis ME, Stenner SE, Lechtzin N: Failure of high-dose ergocalciferol to correct vitamin D deficiency in adults with cystic fibrosis. Am J Respir Crit Care Med. 2005 Jul 15;172(2):212-7. Epub 2005 Apr 28.
25. Salle BL, Delvin EE, Lapillonne A, Bishop NJ, Glorieux FH: Perinatal metabolism of vitamin D. Am J Clin Nutr. 2000 May;71(5 Suppl):1317S-24S.
26. Bai S, Favus MJ: Vitamin D and calcium receptors: links to hypercalciuria. Curr Opin Nephrol Hypertens. 2006 Jul;15(4):381-5.
27. Vieth R: The role of vitamin D in the prevention of osteoporosis. Ann Med. 2005;37(4):278-85.
28. Robinson DM, Scott LJ: Spotlight on paricalcitol in secondary hyperparathyroidism. Treat Endocrinol. 2005;4(3):185-6.
29. Bouillon R, Verstuyf A, Zhao J, Tan BK, Van Baelen H: Nonhypercalcemic vitamin D analogs: interactions with the vitamin D-binding protein. Horm Res. 1996;45(3-5):117-21.
30. Moreira RO, Duarte MP, Farias ML: [Disturbances of calcium-PTH-vitamin D axis in chronic liver diseases]. Arq Bras Endocrinol Metabol. 2004 Aug;48(4):443-50. Epub 2005 Mar 7.
31. Shah N, Bernardini J, Piraino B: Prevalence and correction of 25(OH) vitamin D deficiency in peritoneal dialysis patients. Perit Dial Int. 2005 Jul-Aug;25(4):362-6.
32. Makishima M, Lu TT, Xie W, Whitfield GK, Domoto H, Evans RM, Haussler MR, Mangelsdorf DJ: Vitamin D receptor as an intestinal bile acid sensor. Science. 2002 May 17;296(5571):1313-6.
33. DeLuca HF: Overview of general physiologic features and functions of vitamin D. Am J Clin Nutr. 2004 Dec;80(6 Suppl):1689S-96S.
34. https://www.ncbi.nlm.nih.gov/pubmed/?term=24362707
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=24780068
36. https://www.ncbi.nlm.nih.gov/pubmed/?term=24854739