50-14-6 Usage
Uses
Used in Pharmaceutical Industry:
Vitamin D2 is used as an antirachitic vitamin for the prevention and treatment of rickets in children and adult osteomalacia. It is also used in the treatment of hypoparathyroidism, refractory rickets, and familial hypophosphatemia.
Used in Food and Beverage Industry:
Vitamin D2 is used as a dietary supplement and food additive to maintain the normal metabolism of calcium and phosphorus and promote the body's absorption of these minerals. It is used in fortified margarine, dairy products, infant and children's food, milk or milk beverages, solid drinks, and ice cream.
Used in Rodenticide Industry:
Vitamin D2 is also used as a rodenticide due to its toxicity to rodents when ingested in large quantities.
Used in Research and Development:
Vitamin D2 is applied in biochemical studies and is a subject of research interest for its metabolism and action differences compared to vitamin D3 in mammals.
Used in Dietary Supplements:
Vitamin D2 is used as a dietary supplement to support the growth and maintenance of teeth and bones, as well as the normal utilization of calcium and phosphorus. It is sourced from fish liver and vitamin D-fortified milk.
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 lookchem of Dai Xiongfeng.
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
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
Vitamin D2 poisoning disturbs calcium metabolism and causes kidney damage. Vitamin D2 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.
Fire Hazard
Shows signs of decomposition when stored for a few days at room temperature.
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.
Potential Exposure
Used as a nutrient and/or dietary supplement food additive
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).
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 50-14-6 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 50-14:
(4*5)+(3*0)+(2*1)+(1*4)=26
26 % 10 = 6
So 50-14-6 is a valid CAS Registry Number.
InChI:InChI=1/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/t20-,22+,25-,26+,27-,28+/m0/s1
50-14-6Relevant articles and documents
Preparation method of vitamin D2
-
Paragraph 0089; 0091; 0098-0099; 0108; 0115-0116; 0125; 0132, (2021/05/12)
The invention belongs to the technical field of medicine synthesis, and particularly relates to a preparation method of vitamin D2. Compared with the prior art, the method has the following beneficial effects: the invention provides a technical scheme for synthesizing vitamin D2 through photochemical reaction, thermal isomerization reaction, esterification reaction and saponification reaction by taking ergosterol as an initial raw material, and according to the technical scheme, the effect of high yield of the vitamin D2 is achieved by comprehensively optimizing an organic solvent system in which photochemical reaction is carried out and the temperature of thermal isomerization reaction and washing a saponification product by adopting a proper washing solution.
Production process of vitamin D2
-
Paragraph 0026; 0027; 0028; 0029; 0030; 0031; 0032; 0033, (2017/05/19)
The invention discloses a production process of vitamin D2. The process includes the steps of: S1) light irradiation and thermal-isomerization reaction; S2) chromatographic eluting separation; S3) freezing crystallization separation; S4) drying, mixing and packaging. Compared with the prior art, the process is modified in synthetic process conditions, so that the process is improved in productivity and total yield of the product reaches more than 90%. The thermal-isomerization reaction and a pressure-reduced concentration step are combined, so that the process is simplified and is reduced in energy consumption. A synthesis reaction zone and a purifying separation zone are completely separated, so that process maintenance and process management are convenient. In addition, in the purifying process, a chromatographic crystallization method is employed directly instead of a process comprising chromatography, esterification and hydrolytic crystallization in the prior art, so that usage of toxic organic reagents is avoided, and the process is energy-saving, reduces consumption and is environment-friendly. In the production process of the vitamin D2, tail oil and tail materials contain lumisterol, tachysterol and other derivative products, so that it is valuable to deeply research and develop a high-value medicine intermediate.
Continuous-flow synthesis of activated vitamin D3 and its analogues
Fuse, Shinichiro,Mifune, Yuto,Tanabe, Nobutake,Takahashi, Takashi
experimental part, p. 5205 - 5211 (2012/08/08)
An efficient, two-stage, continuous-flow synthesis of 1α,25-(OH) 2-vitamin D3 (activated vitamin D3) and its analogues was achieved. The developed method afforded the desired products in satisfactory yields using a high-intensity and economical light source, i.e., a high-pressure mercury lamp. In addition, our method required neither intermediate purification nor high-dilution conditions. The Royal Society of Chemistry 2012.
(20S)-1alpha-hydroxy-2-methylene-19-nor-vitamin D3 and its uses
-
, (2008/06/13)
The compound (20S)-1α-hydroxy-2 methylene-19 nor-vitamin D3 and pharmaceutical uses therefor are described herein. This compound exhibits pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the tretment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. This compound also has very significant calcemic activity and therefore may be used to treat immune disorders in humans as well as metabolic bone diseases such as osteoporosis.
(20S) 1alpha-hydroxy-2alpha-methyl and 2beta-methyl-19-nor-vitamin D3 and their uses
-
, (2008/06/13)
This invention discloses (20S)-1α-hydroxy-2α-methyl-19-nor-vitamin D3 and (20S)-1α-hydroxy-2β-methyl-19-nor-vitamin D3 and pharmaceutical uses therefor. These compounds exhibit pronounced activity in arresting the proliferation of undifferentiated cells and inducing their differentiation to the monocyte thus evidencing use as an anti-cancer agent and for the treatment of skin diseases such as psoriasis as well as skin conditions such as wrinkles, slack skin, dry skin and insufficient sebum secretion. These compounds also have very significant calcemic activity and therefore may be used to treat immune disorders in humans as well as metabolic bone diseases such as osteoporosis.
VITAMIN D DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
-
, (2008/06/13)
A process for producing hydroxyvitamin D derivatives, characterized by converting a hydrogen atom or atoms at the 2-position, 24-position, 25-position and/or 26-position of a vitamin D into a hydroxyl group or groups in a solution containing a microorganism that belongs to the genus Nocardia, Streptomyces,Sphingomonas or Amycolata which has an ability to hydroxylate vitamin Ds or an enzyme produced by that microorganism, and optionally under the coexistence of a cyclodextrin; and novel vitamin D3 derivatives obtained by that process.
Vitamin D3 derivative and treating agent for inflammatory respiratory disease using same
-
, (2008/06/13)
Compounds expressed by the following general formula (1), 1[wherein, R01 and R02 are each independently a hydrogen atom or a protecting group for a hydroxyl group; Z is one out of the following formulae (1-1), (1-2), (1-3), (1-4) and (1-5)]. 2The compounds can be used as active ingredients of treating agents for inflammatory respiratory diseases, malignant tumors, rheumatoid arthritis, osteoporosis, diabetes mellitus, hypertension, alopecia, acne, psoriasis, dermatitis, hypercalcemia, hypoparathyroidism and metabolic disorder of cartilage.
Scalp life conditioner
-
, (2008/06/13)
The present invention is an improved scalp conditioner for conditions related to flaky and inflamed scalp that are commonly associated with dandruff, seborrhea, psoriasis and burns from the use of alkaline based products. The method involves administering the product to the scalp of the head and gently massaging the scalp. It can be administered several times per week.
The modified Julia olefination in vitamin D2 synthesis
Blakemore,Kocienski,Marzcak,Wicha
, p. 1209 - 1215 (2007/10/03)
A partial synthesis of vitamin D2 employing fragments derived from a new improved degradation procedure is described. The 7,8-double bond of the vitamin D triene system was synthesised via the modified Julia olefination. The new procedure is more efficient than the classical Julia olefination.
