Retinol

Base Information

• Chemical Name: Retinol
• CAS No.: 68-26-8
• Deprecated CAS: 13123-33-6,17104-91-5,5979-23-7,1341-18-0,1406-67-3,53637-36-8,5979-23-7
• Molecular Formula: C20H30O
• Molecular Weight: 286.458
• Hs Code.: 29362100
• European Community (EC) Number: 200-683-7,234-328-2
• NSC Number: 758150,122759
• UNII: G2SH0XKK91
• DSSTox Substance ID: DTXSID3023556
• Nikkaji Number: J490.500H,J540.270K,J641.040E,J641.434F,J641.435D,J1.417F
• Wikipedia: Retinol,Vitamin_A
• Wikidata: Q424976
• NCI Thesaurus Code: C68302
• RXCUI: 11246
• Pharos Ligand ID: LKB2KDK4XY9M
• Metabolomics Workbench ID: 29025
• ChEMBL ID: CHEMBL986
• Mol file: 68-26-8.mol

Synonyms:11-cis-Retinol;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)-Isomer;All Trans Retinol;All-Trans-Retinol;Aquasol A;Retinol;Vitamin A;Vitamin A1

Chemical Property of Retinol

Chemical Property:

• Appearance/Colour: yellow to orange crystalline solid
• Vapor Pressure: 7.35E-09mmHg at 25°C
• Melting Point: 63.5 ºC
• Refractive Index: 1.641
• Boiling Point: 421.2 ºC at 760 mmHg
• PKA: 14.09±0.10(Predicted)
• Flash Point: 147.3 ºC
• PSA: 20.23000
• Density: 0.954 g/cm³
• LogP: 5.51030
• Storage Temp.: 2-8°C
• Sensitive.: Moisture & Light Sensitive
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: Practically insoluble inwaterorglycerol; soluble in absolute alcohol,methanol,℃hloroform, ether, fats and oils.
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 286.229665576
• Heavy Atom Count: 21
• Complexity: 496

Purity/Quality:

99.3% ^*data from raw suppliers

Vitamin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N,F
• Hazard Codes: Xn,N,F,T
• Statements: 22-38-67-65-62-51/53-48/20-11-43-61-63-36/38
• Safety Statements: 36/37-61-62-45-53-16-33-29-9-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Vitamins and Derivatives
• Drug Classes: Vitamins (Vitamin A)
• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/CO)/C)/C
• Recent ClinicalTrials: Quintuple Method for Treatment of Multiple Refractory Colorectal Liver Metastases
• Recent EU Clinical Trials: Vitamin D and atopic allergy
• Recent NIPH Clinical Trials: HELIOS-B: A Study to Evaluate Vutrisiran in Patients with Transthyretin Amyloidosis with Cardiomyopathy
• Description: Human vitamin A is derived from the natural food. Natural vitamin A exists in dif ferent forms. In animal tissues, vitamin A is present in the form of retinoids. However, in plants, the form of vitamin A 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 vitamin A in the human body. Therefore, food is the main source of vitamin A.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 vitamin A supplementation. The traditional Chinese medicine books also recorded that nourishing the liver can improve eyesight. Researches on the therapy of vitamin A deficient-diseases are mainly related to nourishing the liver and kidney, supplementing essence and blood, and activating qi
• Physical properties: Vitamin A1 (VA1), Molecular formula, C20H30O; MW, 286.45; CAS, 68-26-8. Melting point: 62–64 °C. Boiling point: 137–138 °CVA2, Molecular formula, C20H28O; MW, 284.44; Melting point: 17–19 °C.
• Uses: Vitamin A1 (retinal) 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. mucolytic vitamin A (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 it is stable in the absence of air. Sources include liver, fortified margarine, egg, and milk. Vitamin A palmitate can be found in frozen egg substitute. Occurs preformed only in animals; metabolized from carotenoids, such β-carotene, in the intestinal mucosa. Dietary sources include liver, milk, butter, cheese, eggs and fish liver oils or as carotenoi s from fruits and vegetables. Stored primarily in the liver in esterified form; transported in the blood by retinol binding protein (RBP). Nutritional factor. Atracurium Besilate intermediate retinol is a retinoid considered to be a skin revitalizer. It 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. It is able to alter the behavior of aged cells so they act in a more youthful manner. It 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.
• Indications: Vitamin A, or retinol, is essential for the proper maintenance of the functional and structural integrity of epithelial cells, and it plays a major role in epithelial differentiation. Bone development and growth in children have also been linked to adequate vitamin A intake. Vitamin A, when reduced to the aldehyde 11-cis-retinal, combines with opsin to produce the visual pigment rhodopsin. This pigment is present in the rods of the retina and is partly responsible for the process of dark adaptation.
• Clinical Use: Principal dietary sources of vitamin A are milk fat (cheese and butter) and eggs. Since it 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 vitamin A deficiency include cessation of growth and skin changes due to hyperkeratosis. Since vitamin A is a fat-soluble vitamin, any disease that results in fat malabsorption and impaired liver storage brings with it the risk of vitamin A 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.

Technology Process of Retinol

There total 178 articles about Retinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

tert-butyldimethylsilyl (7E,9Z,11E,13E)-retinyl ether (210700-52-0) → 9-cis-retinol (68-26-8,2052-63-3,6018-74-2,17706-49-9,22737-96-8,29444-25-5,34218-73-0,39815-04-8,69686-68-6,69686-69-7,74743-94-5,84415-27-0,84415-28-1,85354-09-2,85354-10-5,93380-02-0,98462-62-5,137121-52-9,22737-97-9)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1.5h;

DOI:10.1021/jo991757f

Reference yield: 90.0%

(9Ξ)-O-acetyl-retinol (200720-67-8,64536-04-5) → 9-cis-retinol (68-26-8,2052-63-3,6018-74-2,17706-49-9,22737-96-8,29444-25-5,34218-73-0,39815-04-8,69686-68-6,69686-69-7,74743-94-5,84415-27-0,84415-28-1,85354-09-2,85354-10-5,93380-02-0,98462-62-5,137121-52-9,22737-97-9)

Guidance literature:

(9Ξ)-O-acetyl-retinol; With sodium hydroxide; In ethanol; water; at 40 ℃; for 0.5h; Inert atmosphere; Darkness;

With pyridine; In Methyl formate; at 0 ℃; for 2h; Reagent/catalyst; Catalytic behavior;

DOI:10.1039/c9dt02189b

Reference yield: 77.0%

1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene (103905-07-3) → 2-cis-Vitamin-A (2052-63-3) + 9-cis-retinol (68-26-8,2052-63-3,6018-74-2,17706-49-9,22737-96-8,29444-25-5,34218-73-0,39815-04-8,69686-68-6,69686-69-7,74743-94-5,84415-27-0,84415-28-1,85354-09-2,85354-10-5,93380-02-0,98462-62-5,137121-52-9,22737-97-9) + 11-cis-retinol (22737-96-8) + RETINOL (68-26-8)

Guidance literature:

With potassium methanolate; In cyclohexane; at 38 ℃; for 2h;

DOI:10.1021/jo00370a017

upstream raw materials:

all-trans-Retinal

all-trans-methyl retinoate

Kitol

(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol

Downstream raw materials:

2-[2-(6,7-Dimethoxy-4-methyl-3-oxo-3,4-dihydro-quinoxalin-2-yl)-ethyl]-5-hydroxymethyl-6-methyl-8-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione

retinyl carbocation

retinol radical anion

5,6-Epoxyretinol

Refernces

• 1、 Birge et al.. "". . p. 1533,1534. Retrieved 1978.
• 2、 Hu, Meng-Yang,Huang, Qiang,Su, Yu-Xuan,Sun, Wei,Wang, Wei-Na,Zhu, Shou-Fei. "Iron-Catalyzed Vinylzincation of Terminal Alkynes". . . Retrieved 2022/01/08.
• 3、 Li, Yang,Lan, Haichuang,Yan, Xia,Shi, Xiaotao,Liu, Xiao,Xiao, Shuzhang. "Mimicking light-sensing chromophore in visual pigments and determination isomerization site". . . Retrieved 2020/01/02.