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Retinol is derived from the natural food.
Retinol exists in dif ferent forms.
In animal tissues, Retinol is present in the form of retinoids.
CAS: 68-26-8
MF: C20H30O
MW: 286.45
EINECS: 200-683-7
Synonyms
Vitamin A1 alcohol;Vitamin A1 alcohol, all-trans-;Vitamin A1, all-trans-;vitamina1alcohol;vitamina1alcohol,alltrans;Vitavel A;Vitamin A (all-trans-Retinol);VITAMIN-A-ALCOHOL SOLUTION, IN HEXANE (0 .25 MG/ML), 1X2 ML
However, in plants, the form of Retinol called carotenoids is contained in the green, orange, and yellow plant tissue.
Vitamin A compounds such as retinol, reti nal, carotene, and so on from these foods can be converted to Retinol in the human body.
Therefore, food is the main source of Retinol.
As early as 1000 years ago, the Qian Jin Yao Fang written by Sun Simiao in Tang Dynasty recorded that animal liver can cure night blindness.
This is the early recognition in Retinol supplementation.
The traditional Chinese medicine books also recorded that nourishing the liver can improve eyesight.
Retinol, also called vitamin A1, is a fat-soluble vitamin in the Retinol family that is found in food and used as a dietary supplement.
Retinol or other forms of Retinol are needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development.
Dietary sources include fish, dairy products, and meat.
As a supplement Retinol is used to treat and prevent vitamin A deficiency, especially that which results in xerophthalmia.
Retinol is taken by mouth or by injection into a muscle.
As an ingredient in skin-care products, Retinol is used to reduce wrinkles and other effects of skin aging.
Retinol at normal doses is well tolerated.
High doses may cause enlargement of the liver, dry skin, and hypervitaminosis A.
High doses during pregnancy may harm the fetus.
The body converts retinol to retinal and retinoic acid, through which it acts.
Retinol was discovered in 1909, isolated in 1931, and first made in 1947.
Retinol is on the World Health Organization's List of Essential Medicines.
Retinol is available as a generic medication and over the counter.
In 2021, Retinol was the 298th most commonly prescribed medication in the United States, with more than 500,000 prescriptions.
All-trans-retinol is a form of Retinol that is an important component of the visual system and helps maintain healthy skin.
Retinol is found in many animal products and can be taken as a dietary supplement.
Retinol can react with other chemicals to form all-trans-retinoic acid, which has been shown to inhibit the growth of human carcinoma cells in culture by binding to the ATP binding cassette transporter.
All-trans-retinol also inhibits the uptake of retinaldehyde and retinoic acid into cells, which may be due to its ability to bind to cell membranes or react with chemical inhibitors.
History
The vitamin research is the great achievement in the development of life sciences, while human beings only took half a century to discover and understand vitamins.
However, everything is still very difficult for scientists in the early stage of vitamin discovery.
From 1913 to 1915, Elmer McCollum and Marguerite Davis indicated that the growth rate was maintained by at least two different kinds of growth factors: one can be separated from eggs or butter, and the other one which multiple neuritis of chicks and pigeons can be extracted by water; thus they were named fat-soluble Retinol and water-soluble vitamin B.prevented
In 1919, the researchers demonstrated that fat-soluble Retinol not only sup ported the rate of growth but also prevented eye dryness and night blindness in the process of property study.
In 1920, Dr. J.C. Drummond named this active lipid as Retinol.
Retinol exists in cod liver oil and prevents the occurrence of eye dryness and night blindness.
Retinol Chemical Properties
Melting point: 61-63 °C(lit.)
Boiling point: 368.81°C (rough estimate)
density: 0.9933 (rough estimate)
refractive index: 1.641
Fp: -26 °C
storage temp.: -20°C
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: 14.09±0.10(Predicted)
form: crystalline
color: yellow to orange
PH: 6.5-7.5 (20°C, 100g/L in H2O)
biological source: synthetic
Water Solubility: Practically insoluble inwaterorglycerol; soluble in absolute alcohol,methanol,℃hloroform, ether, fats and oils.
Sensitive: Moisture & Light Sensitive
Merck: 13,10073
BRN: 403040
Specific Activity: ~3100U/mg
Stability: Stable, but light and air sensitive. Incompatible with strong acids, strong oxidizing agents.
Cosmetics Ingredients Functions SKIN CONDITIONING - MISCELLANEOUS
InChI: 1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChIKey: FPIPGXGPPPQFEQ-OVSJKPMPSA-N
LogP: 5.680
CAS DataBase Reference: 68-26-8(CAS DataBase Reference)
EPA Substance Registry System: Retinol (68-26-8)
Physical properties
Retinol, Molecular formula, C20H30O; MW, 286.45; CAS, 68-26-8.
Melting point: 62–64 °C.
Boiling point: 137–138 °C
VA2, Molecular formula, C20H28O; MW, 284.44; Melting point: 17–19 °C.
Uses
Retinol is the fat-soluble vitamin a which is required for new cell growth and prevention of night blindness.
There is no appreciable loss by heating or freezing, and Retinol is stable in the absence of air.
Sources include liver, fortified margarine, egg, and milk.
Retinol can be found in frozen egg substitute.
Retinol is produced from (3-carotene, which can be obtained by fermentation of corn, soybean meal, kerosene, thiamin, and oc-ionone.
The dry-mass after fermentation contains 120 to 150 g product/kg.
Retinol is a retinoid considered to be a skin revitalizer.
Retinol is reported to enhance skin radiance and treat conditions associated with chronological aging, such as wrinkles and fine lines, as well as dermatological disorders, including acne, follicular and lesion papules, actinic keratosis, oily skin, and rosacea.
According to clinical dermatologists, retinol is one of the few substances with a demonstrated ability to reduce and prevent fine lines and wrinkles.
Retinol is able to alter the behavior of aged cells so they act in a more youthful manner.
Retinol is considered necessary for normal epidermal cell growth and differentiation and stimulates the production of new blood vessels in the skin, improving skin tone.
In addition, retinol has anti-oxidant capacities and protects dermal fibers by counteracting the increased activity of enzymes that degrade collagen and elastin when the skin is exposed to uV rays.
Retinol can be drying to the skin when used for a prolonged period of time or in concentrations that are too high.
A weaker retinoid than retinoic acid, retinol converts to retinoic acid once on the skin.
When compared to retinoic acid, retinol has an increased penetration potential and is less irritating, making it an effective ingredient for anti-aging products.
The anti-aging benefits of topically treating skin with retinol are based on its penetration ability, which allows it to reach the sites in the skin requiring treatment. When used on sensitive skin for a prolonged period of time or in concentrations that are too high, retinol can cause dermatitis.
Medical uses
Retinol is used to treat vitamin A deficiency.
Three approaches may be used when populations have low vitamin A levels:
Through dietary modification involving the adjustment of menu choices of affected persons from available food sources to optimize vitamin A content.
Enriching commonly eaten and affordable foods with vitamin A, a process called fortification.
Retinol involves the addition of synthetic vitamin A to staple foods like margarine, bread, flour, cereals, and infant formula during processing.
By giving high doses of vitamin A to the targeted deficient population, a method known as supplementation.
In regions where deficiency is common, a single large dose is recommended to those at high risk twice a year.
Retinol is also used to reduce the risk of complications in measles patients.
Clinical Use
Principal dietary sources of Retinol are milk fat (cheese and butter) and eggs.
Since Retinol is stored in the liver, inclusion of liver in the diet also provides vitamin A.
A plant pigment, carotene, is a precursor for vitamin A and is present in highly pigmented vegetables, such as carrots, rutabaga, and red cabbage.
An early sign of hypovitaminosis A is night blindness.
This condition is related to the role of vitamin A as the prosthetic group of the visual pigment rhodopsin.
The night blindness may progress to xerophthalmia (dryness and ulceration of the cornea) and blindness.
Other symptoms of Retinol deficiency include cessation of growth and skin changes due to hyperkeratosis.
Since Retinol is a fat-soluble vitamin, any disease that results in fat malabsorption and impaired liver storage brings with it the risk of Retinol deficiency; these conditions include biliary tract disease, pancreatic disease, sprue, and hepatic cirrhosis.
One group at great risk are children from low-income families, who are likely to lack fresh vegetables (carotene) and dairy products (vitamin A) in the diet.
Biochem/physiol Actions
Retinol and its derivatives exhibit anti-aging properties.
Retinol is used for treating wrinkles and signs of aging.
However, due to its photo instability and skin irritation potency, it is hardly used in cosmetic formulations.
Retinol is also used as a therapeutic for dermatoses.
Retinol's deficiency leads to xerosis and follicular hyperkeratosis.
Manufacturing Process
Manufacturing process for Retinol includes these steps as follows: Step A: Synthesis of Preparation of ethyl ether of ethynyl-β-ionol;Step B: Coupling Reaction; Step C:Semi-Hydrogenation of Coupling Product;Step D:Hydrolysis of Semi-Hydrogenated Coupling Product.
Separation of Retinol from the product obtained was achieved by acetylating the total reaction product using pyridine-acetic anhydride at room temperature and chromatographing on alumina neutralized with acetic acid.
A fairly clean separation was achieved.
The Retinol acetate fraction was sufficiently pure to become crystallized from pentane at -15°C when seeded with a pure Vitamin A acetate crystal.
When the Retinol acetate was converted to the alcohol form of Retinol, the final product showed the characteristic infrared and ultraviolet absorption curves for Vitamin A.
Similar results were obtained using as co-solvents (with the liquid ammonia) ethylene diamine and ether; pentane; tetrahydrofuran; diethylamine and hexamethylphosphoramide.
