| Identification | More | [Name]
Vitamin D2 | [CAS]
50-14-6 | [Synonyms]
5,7,10(19),22-CHOLESTATETRAEN-24BETA-METHYL-3BETA-OL-9,10-SECO
5,7,10(19),22-CHOLESTATETRAEN-24B-METHYL-3B-OL-9,10-SECO
9,10-secoergosta-5,7,10,22-tetraen-3-ol
CALCIFEROL
CALCIFEROL ERGOSTEROL
CALCIFEROL RESIN
ERCALCIOL
ERGOCALCIFEROL
ERGOCALCIFEROLUM
ERGOCALCIFEROL-WATER SOLUBLE
ERGOSTEROL IRRADIATED
'ERGOSTEROL IRRADIATED'
IRRADIATED ERGOSTEROL
IRRADIATED VITAMIN D2
MYKOSTIN
OLEOVITAMIN D2
OSTELIN-800
VIOSTEROL
VITAMIN D
VITAMIN D2 | [EINECS(EC#)]
200-014-9 | [Molecular Formula]
C28H44O | [MDL Number]
MFCD00166988 | [Molecular Weight]
396.65 | [MOL File]
50-14-6.mol |
| Chemical Properties | Back Directory | [Appearance]
Crystalline | [Melting point ]
114-118 °C(lit.)
| [alpha ]
82 º (c=3, in acetone 25 ºC) | [Boiling point ]
460.3°C (rough estimate) | [density ]
0.9784 (rough estimate) | [vapor pressure ]
7 x l0-7 Pa (20 °C), est.) | [refractive index ]
1.5100 (estimate) | [Fp ]
14 °C | [storage temp. ]
2-8°C
| [solubility ]
H2O: 200 mg/mL, clear to hazy
| [form ]
powder
| [pka]
14.74±0.20(Predicted) | [color ]
white to yellowish | [optical activity]
[α]20/D +105±2°, c = 4% in ethanol | [Water Solubility ]
Soluble in ethanol, water, methanol, dimethylformamide, and dimethyl sulfoxide. | [Usage]
The synthetic form of vitamin D. Prepared from ergosterol by UV irradiation in a suitable solvent. Commercial solutions are usually made with propylene glycol or sesame oil. Antirachitic | [Merck ]
10018 | [BRN ]
1916682 | [BCS Class]
3 | [Stability:]
Light Sensitive | [InChIKey]
MECHNRXZTMCUDQ-RKHKHRCZSA-N | [LogP]
10.440 (est) | [Uses]
Vitamin d2 is fat-soluble, and is stable unless oxidized. It is necessary for growth and maintenance of teeth and bones and the normal utilization of calcium and phosphorus; it is used medicinally in the treatment of rickets and as a dietary supplement. Its sources include fish liver and vitamin d-fortified milk. | [CAS DataBase Reference]
50-14-6(CAS DataBase Reference) | [NIST Chemistry Reference]
Ergocalciferol(50-14-6) | [Storage Precautions]
Moisture sensitive;Light sensitive;Store under nitrogen;Air sensitive | [EPA Substance Registry System]
50-14-6(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T+,T | [Risk Statements ]
R22:Harmful if swallowed.
R48/25:Toxic: danger of serious damage to health by prolonged exposure if swallowed .
R26:Very Toxic by inhalation.
R24/25:Toxic in contact with skin and if swallowed .
R40:Limited evidence of a carcinogenic effect.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S22:Do not breathe dust . | [RIDADR ]
UN 2811 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
KE1050000
| [F ]
1-8-10 | [TSCA ]
Yes | [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
29362910 | [Safety Profile]
Poison by ingestion,
intraperitoneal, intravenous, and
intramuscular routes. An experimental
teratogen. Human systemic effects by
ingestion: anorexia, nausea or vomiting, and
weight loss. Experimental reproductive
effects. When heated to decomposition it
emits acrid smoke and irritating fumes. | [Hazardous Substances Data]
50-14-6(Hazardous Substances Data) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Chloroform-->Pyridine-->Cyclohexane-->PASSION FLOWER OIL-->Silica glass-->3,5-Dinitrobenzoyl chloride-->Ergosterol | [Preparation Products]
25-HYDROXYVITAMIN D2-->VitaMin D2 Tosylate-->(1R,3aR,7aR)-1-((2R,5S)-5,6-diMethylheptan-2-yl)-7a-Methyloctahydro-1H-inden-4-ol-->Vitamin D2 SO2 Adduct-->(3S)-1,3-Bis-O-tert-ButyldiMethylsilyl 3-Hydroxy VitaMin D2 SO2 Adduct (Mixture of DiastereoMers)-->tert-Butyl-dimethyl-{3-[7a-methyl-1-(1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-ylidenemethyl]-2,2-dioxo-2,3,4,5,6,7-hexahydro-1H-2l6-benzo[c]thiophen-5-yloxy}-silane |
| Hazard Information | Back Directory | [General Description]
Odorless white crystals. Used as a dietary supplement and food additive. | [Reactivity Profile]
Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides. | [Health Hazard]
Ergocalciferol poisoning disturbs calcium metabolism and causes kidney damage. Ergocalciferol in a single acute ingestion presents no toxic hazards. Daily ingestion in excess of 5000 units/day in children or 7500 units/day in adults will produce toxic symptoms associated with hypervitaminosis D. Those with hypercalcemia are at a greater risk. | [Potential Exposure]
Used as a nutrient and/or dietary supplement food additive | [Fire Hazard]
Shows signs of decomposition when stored for a few days at room temperature. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts
the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from
exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has
stopped and CPR if heart action has stopped. Transfer
promptly to a medical facility. When this chemical has
been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit | [Shipping]
UN2811 Toxic solids, organic, n.o.s., Hazard
Class: 6.1; Labels: 6.1-Poisonous materials, Technical
Name Required. UN3249 Medicine, solid, toxic, n.o.s.,
Hazard Class: 6.1; Labels: 6.1-Poisonous materials | [Incompatibilities]
Dust may be combustible and may form
explosive mixture with air. Incompatible with oxidizers
(chlorates, nitrates, peroxides, permanganates, perchlorates,
chlorine, bromine, fluorine, etc.); contact may cause fires
or explosions. Keep away from alkaline materials, strong
bases, strong acids, oxoacids, and epoxides. | [Waste Disposal]
Dispose of contents and container to an approved waste disposal plant. All federal,
state, and local environmental regulations must be
observed. It is inappropriate and possibly dangerous to the
environment to dispose of expired or waste drugs and pharmaceuticals by flushing them down the toilet or discarding
them to the trash. Household quantities of expired or waste
pharmaceuticals may be mixed with wet cat litter or coffeegrounds, double-bagged in plastic, discard in trash. Larger
quantities shall carefully take into consideration applicable
DEA, EPA, and FDA regulations. If possible return the
pharmaceutical to the manufacturer for proper disposal
being careful to properly label and securely package the
material. Alternatively, the waste pharmaceutical shall be
labeled, securely packaged and transported by a state
licensed medical waste contractor to dispose by burial in a
licensed hazardous or toxic waste landfill or incinerator. | [Definition]
ChEBI: A vitamin D supplement and has been isolated from alfalfa. | [Brand name]
Deltalin (Lilly); Drisdol(Sanofi Aventis). | [Biochem/physiol Actions]
Ergocalciferol (vitamin D2) and 25-Hydroxycholecalciferol (vitamin D3) are the two form 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. | [Metabolic pathway]
Ergocalciferol (vitamin D2) is a product made by the UV irradiation of
yeast ergosterol. It is a common form of vitamin D and it has very similar
biological activity to that of cholecalciferol (vitamin D3) in the treatment of
the vitamin D deficiency diseases (e.g. rickets). The bioactive form of this
vitamin is also the 1,25-dihydroxy-derivative and this has equal antirachitic
activity to that of the cholecalciferol analogue (Jones et al., 1975). | [storage]
Store at 2-8°C | [Purification Methods]
It is converted into its 3,5-dinitrobenzoyl ester and crystallised repeatedly from acetone. The ester is then saponified and the free vitamin is isolated. [Laughland & Phillips Anal Chem 28 817 1956, Beilstein 6 IV 4404.] | [Degradation]
It is unstable in light and air and in acidic media.
It is inactivated within a few days under normal exposure conditions. This
is due to oxidation and fragmentation of the triene functionality. Ergocalciferol
is slightly more unstable, probably because of the additional
alkene group in the side chain. One of the several degradation products of
ergocalciferol has been identified as the ketone (8, shown in Scheme 1)
formed by the loss of the methano-cyclohexanol function (Stewart et al.,
1984). | [Toxicity evaluation]
Excess vitamin D in the form of 1,25-dihydroxycalciferol results
in hypercalcemia and hypercalciuria, due to increased calcium
absorption, bone demineralization, and hyperphosphatemia. |
| Questions And Answer | Back Directory | [Description]
Ergocalciferol, also under the name vitamin D2, is a type of vitamin D found in plants and yeast. It has no antirachitic activity. It helps the body to absorb calcium and phosphorus. It is used as a dietary supplement. It is used in the treatment of hypoparathyroidism (a condition in which not enough parathyroid hormone can be produced by the body), refractory rickets (softening and weakening of bones that does not respond to treatment, it is also known as vitamin D resistant rickets), and familial hypophosphatemia (rickets or osteomalacia caused by an inherited condition with a decreased ability to break down vitamin D in the body). Ergocalciferol is also used as a rodenticide.
| [Vitamin D]
Vitamin D refers to a group of fat-soluble steroid compounds with anti-rickets effect and is called anti-rickets vitamin. It is known currently about at least ten or more sterols substance with vitamin D activity. They are mainly presented in the vegetable oil or yeast ergosterol solid which subject to sunlight or ultraviolet irradiation to generate vitamin D2 which is also called as calciferol or ergocalciferol. Therefore, ergosterol is also called as original vitamin D2; the other is from that the human body can convert the cholesterol to the 7-dihydro-cholesterol to be stored in the skin with the later being able to be converted to vitamin D3 upon sunlight and ultraviolet radiation. Vitamin D3 is also known as cholecalciferol and therefore the 7-dehydrocholesterol is also known as original vitamin D3. Vitamin D2 has a very similar structure with vitamin D3 and both of them are the B ring open-ring derivatives of precursor sterols with the difference of them being laid in a extra double bond and a methyl group in the side chain of vitamin D2.
Both vitamin D2 and vitamin D3 are colorless or white crystals and are not foul with the melting point being 115~118 ℃ and 84~85 ℃, respectively. They are insoluble in water and easily soluble in alcohol, ether, acetone, and slightly soluble in vegetable oil. They are unstable in air and sunlight and are easily inactivated in moist air. However, vitamin D3 is relatively more stable than vitamin D2. These two have similar physiological roles in the human body with the major role being maintain the normal metabolism of calcium and phosphorus, promoting the deposition of calcium and phosphorus into the bone and tissue and thus it can be used in prevention and treatment of metabolic bone disease such as rickets and osteomalacia.
Vitamin D2 and D3 have the same effects on mammals and cows and pigs. However, vitamin D3 has a ten times stronger activity on poultry (birds) than vitamin D2.
Vitamin D deficiency can reduce the intestinal absorption of calcium and cause the decomposition of bone calcium and phosphorus. Young livestock will get osteomalacia and adult animals are prone to osteoporosis. Vitamin D deficiency can also lead to animal sternum and spine deformation and that layers give birth to soft-shell eggs. Because vitamin D control the absorption of calcium, phosphorus, too much absorption of vitamin D in the diet can cause high blood calcium, so that excess calcium can be deposited in the heart, blood vessels, joints, pericardium or intestinal wall, leading to heart failure, joint stiffness or intestines disorders.
Sunbathing is the most economical source of getting vitamin D. The ergosterol or 7-dehydrocholesterol can be converted into vitamin D inside animal body upon ultraviolet radiation. The hay, yeast, corn leaves, barley, oats, wheat under sunshine and yeast which has been subject to ultraviolet treatment is a good source of vitamin D. Animal products can directly provide vitamin D for the livestock, such as eggs, milk. Cod liver oil is rich in vitamin D levels. Reared animals and animal with insufficient sunlight need to have their daily feed supplied with additional vitamin D.
The above information is edited by the Chemicalbook of Dai Xiongfeng.
| [Chemical Properties]
It is white needle crystal or crystalline powder and is odorless and tasteless. Its melting point is 115-118 ℃ (decomposition), Its specific rotation is [α]20D+102.5°(ethanol). The ethanol solution of this product has maximum absorption at 265nm wavelength. It is soluble in ethanol (1: 2), diethyl ether (1: 2), acetone (1:10) and chloroform (1: 0.7) but insoluble in water. Moreover, it has a lower activity in case of light or oxygen.
| [Uses]
It can be applied to biochemical studies; its clinical drug belongs to a lipid-soluble vitamin which can promote the intestinal absorption of calcium and phosphorus which plays a role of facilitating the calcification of bone. It is clinically used for prevention and treatment of rickets in children and adult osteomalacia.
Vitamin D2 can maintain the normal metabolism of calcium and phosphorus and can also promote the body's absorption of calcium and phosphorus. Upon its deficiency, the children are easy to get rickets. China ruled that it can be applied for strengthening margarine with the usage amount being 125~156 μg/kg; its usage amount in fortified dairy is 63~125μg/kg; the usage amount in strengthening infant and children food used is 50~100μg/kg; the usage amount in strengthening milk or milk beverage is 10~40μg/kg; the maximal allowable usage amount in the strengthening solid drinks and ice cream is 10~20μg/kg.
It is mainly applied to the prevention and treatment of rickets, osteomalacia, and infant tetany psychosis.
| [Toxicity]
Acute toxicity dose: 100 mg/d (adult, orally). Mouse lethal dose of 20mg/kg (6 Day). Excess can easily cause poisoning.
GRAS (FDA, §182.5950, 2000).
LD50: 42mg/kg (rat, oral).
| [Limited use]
GB 14880-94 (μg/kg): liquid milk from 10 to 20; margarine: 125 to 156; dairy products: 63 to 125; milk and milk drinks: 10 to 40; infant and children food: 50 to 115.
GB 2760-2002 (pg/kg): solid drink, ice cream, 10 to 20; arrowroot flour: 50 to 100; Soy milk, soy flour, 15 to 60; soy milk, soy milk, 3 to 15; jelly: 10 to 40; instant breakfast cereals, 12.5 to 37.5; puffed food sandwich from 10 to 60.
FDA, §184.1950 (IU/100g; 2001): breakfast cereals 350; 90 granular and pasty products; milk 42; 89 dairy products.
| [Production method]
Dissolve the ergosterol dissolved in ethanol and go through ring-opening under UV illumination; the reaction was further concentrated under reduced pressure, frozen, filtered, and filtered of liquid nitrogen, and concentrated under reduced pressure to dryness to obtain the crude oil of vitamin D2 with distillation to obtain the refined products.
Vitamin D2 is naturally presented in the liver, egg yolk and milk; the production method of the industry starts with extracting the ergocalciferol from vegetable oil or yeast extract in the body. Further dissolve it in chloroform or cyclohexane, and then convert it to the vitamin D2 through ultraviolet radiation on the quartz glass flask.
Ergosterol ethanol solution is subject to ultraviolet radiation with the 9’, 10’ bond breakage to obtain the vitamin D2 crude product; the later one further has esterification with 3, 5-nitrobenzoyl chloride and undergoes alkaline hydrolysis to get the purified product.
| [References]
- https://en.wikipedia.org/wiki/Ergocalciferol
- https://pubchem.ncbi.nlm.nih.gov/compound/ergocalciferol
- https://www.drugs.com
- https://medlineplus.gov
- https://www.webmd.com
|
|
|