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68-26-8 Usage

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

Chemical Properties

Yellow-Orange Powder

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.

Originator

Acon ,Endo

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 vitamin A and water-soluble vitamin B.preventedIn 1919, the researchers demonstrated that fat-soluble vitamin A 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 vitamin A. It exists in cod liver oil and prevents the occurrence of eye dryness and night blindness.

Uses

Different sources of media describe the Uses of 68-26-8 differently. You can refer to the following data:
1. 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.
2. mucolytic
3. 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.
4. 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.
5. Atracurium Besilate intermediate
6. 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.

Definition

ChEBI: A retinol in which all four exocyclic double bonds have E- (trans-) geometry.

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.

Manufacturing Process

Manufacturing process for Vitamin A 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 Vitamin A 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 Vitamin A acetate fraction was sufficiently pure to become crystallized from pentane at -15°C when seeded with a pure Vitamin A acetate crystal. When the Vitamin A acetate was converted to the alcohol form of Vitamin A, 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.

Brand name

Avibon.

World Health Organization (WHO)

Vitamin A, a fat-soluble vitamin, is used in the treatment and prevention of vitamin A deficiency resulting from inadequate dietary intake. It has been demonstrated to be teratogenic at high doses (more than 25,000 IU per day). Daily dosages of less than 10000 IU seem to be free of this risk. Retinol (vitamin A) is listed in the WHO Model List of Essential Drugs.

Synthesis Reference(s)

Tetrahedron, 51, p. 2435, 1995 DOI: 10.1016/0040-4020(94)01108-C

General Description

Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain. Retinol is biologically active in a wide range of processes.

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. Its deficiency leads to xerosis and follicular hyperkeratosis.

Pharmacology

Intake of vitamin A precursors, such as carotenoids, retinyl esters, retinol, and reti nal, can maintain the epithelial cell differentiation, normal proliferation, and visual function. All of these substances can be metabolized into retinol, retinal, and reti noic acid. But unlike retinol and retinal, retinoic acid cannot be reduced to retinol and retinal. Intake of retinoic acid can only maintain the systemic function of vita min A.Visual and vitamin A. 11-cis-retinal plays an important role as a photographic group of retinal cones and visual pigments in rod cells. 11-cis-retinal would be transformed into all-trans-retinal form under the light induction. The dissociation of all-trans retinal and opsin was coupled with the nerve stimulation of the brain’s visual center. By a series of biochemical processes, nerve impulses format in the rod cells at the end of synapse, and then the optic nerve conducts the nerve impulses along. The visual process is a component renewable cycle, and all-trans-retinal can be enzymatically modified to 11-cis form in dark conditions.The systemic effects of vitamin A. Vitamin A not only significantly affects visual function but also has a greater physiological impact than visual function. Vitamin A deficiency destroys the visual cycle, leads to dark adaptation damage (night blind ness or nyctalopia), and destroys systemic function which is necessary to maintain life (e.g., corneal injury, infection, and hypoplasia). Vitamin A deficiency can lead to animal death.Vitamin A functions in reproduction and embryonic development. Vitamin A plays an important role in the reproductive process of sperm production and ovula tion, but its biochemical basis is unclear. Vitamin A plays a key role in the develop ment of embryos and organism and maintenance of tissue function. The main organs affected by vitamin A deficiency are the heart, eye tissue, circulatory system, geni tourinary system, and respiratory system. Vitamin A is necessary for embryonic development.Vitamin A functions on immune function. The lymphoid organs, cell distribu tion, histology, lymphocytes, and other characteristics will change when the ani mals lack vitamin A. Vitamin A deficiency can lead to immune function decrease, induce inflammation, and exacerbate inflammatory symptomsVitamin A functions in dermatology. Vitamin A plays an important role in main taining healthy skin. Vitamin A deficiency disrupts human keratin cell terminal dif ferentiation and makes the skin rough, dry, scaly, and clogged It is reported that vitamin A can degrade malignant melanoma and T-cell lymphoma epidermal transfer, reduce the oil secretion of the common acne and the number of bacteria in the epidermis and capillaries, and inhibit immune response of monocytes and neutrophils.Vitamin A plays an important role as an important function material in the body system, such as hematopoietic function, bone development, tumor prevention, and so on. Therefore, supplement of vitamin A is necessary for health requirements

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.

Side effects

Acute hypervitaminosis A results in drowsiness, headache, vomiting, papilledema, and a bulging fontanel in infants. The symptoms of chronic toxicity include scaly skin, hair loss, brittle nails, and hepatosplenomegaly. Anorexia, irritability, and swelling of the bones have been seen in children. Retardation of growth also may occur. Liver toxicity has been associated with excessive vitamin A intake. Vitamin A is teratogenic in large amounts, and supplements should not be given during a normal pregnancy. The IOM has reported the UL of vitamin A to be 3,000 μg/day.

Safety Profile

Moderately toxic by ingestion. Human teratogenic effects by ingestion: developmental abnormalities of the craniofacial area and urogenital system. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

Purify retinol by chromatography on columns of water-deactivated alumina and elute with 3-5% acetone in hexane. Separate the isomers by TLC plates on silica gel G, developed with pet ether (low boiling)/methyl heptanone (11:2). Store it in the dark, under N2, at 0o, or in Et2O, Me2CO or EtOAc. [See Gunghaly et al. Arch Biochem Biophys 38 75 1952, Beilstein 6 IV 4133.]

Toxicity evaluation

The exact mechanism leading to toxicity is not known. Both acute and chronic toxicity may occur. Acute and Short-Term Toxicity (or Exposure) Human Acute toxicity is uncommon in adults. However, vitamin A ingestions of greater than 1 million IU in adults and greater than 300 000 IU in children have resulted in the development of increased intracranial pressure (symptoms described include headache, dizziness, vomiting, visual changes, and bulging fontanel in infants). Acute ingestions of greater than 12 000 IU per kilogram are also considered toxic. Chronic Toxicity (or Exposure) Human Toxicity is more frequently seen with chronic ingestion of high doses of 30 000–50 000 IU per day. Vitamin A toxicity in children develops following chronic ingestion of 410 times the recommended daily allowance for weeks to months. Malnutrition and individual tolerance may also be factors in predisposition to toxicity. Signs and symptoms of toxicity include vomiting, anorexia, agitation, fatigue, double vision, headache, bone pain, alopecia, skin lesions, increased intracranial pressure, and papilledema. Hepatic toxicity typically requires months or years of daily high doses of vitamin A. There are no known cases of vitamin A toxicity associated with beta-carotene ingestion.

Check Digit Verification of cas no

The CAS Registry Mumber 68-26-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 8 respectively; the second part has 2 digits, 2 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 68-26:
(4*6)+(3*8)+(2*2)+(1*6)=58
58 % 10 = 8
So 68-26-8 is a valid CAS Registry Number.
InChI:InChI=1/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/b9-6u,12-11+,16-8+,17-13u

68-26-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Price
  • Detail
  • Sigma

  • (95144)  Retinol  BioXtra, ≥97.5% (HPLC), ~3100 U/mg

  • 68-26-8

  • 95144-250MG

  • 1,235.52CNY

  • Detail
  • Sigma

  • (95144)  Retinol  BioXtra, ≥97.5% (HPLC), ~3100 U/mg

  • 68-26-8

  • 95144-1G

  • 4,119.57CNY

  • Detail
  • Sigma

  • (R7632)  Retinol  synthetic, ≥95% (HPLC), crystalline

  • 68-26-8

  • R7632-25MG

  • 435.24CNY

  • Detail
  • Sigma

  • (R7632)  Retinol  synthetic, ≥95% (HPLC), crystalline

  • 68-26-8

  • R7632-100MG

  • 636.48CNY

  • Detail
  • Sigma

  • (R7632)  Retinol  synthetic, ≥95% (HPLC), crystalline

  • 68-26-8

  • R7632-250MG

  • 1,353.69CNY

  • Detail
  • Sigma

  • (R7632)  Retinol  synthetic, ≥95% (HPLC), crystalline

  • 68-26-8

  • R7632-500MG

  • 1,950.39CNY

  • Detail
  • Sigma

  • (R7632)  Retinol  synthetic, ≥95% (HPLC), crystalline

  • 68-26-8

  • R7632-1G

  • 3,056.04CNY

  • Detail

68-26-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name all-trans-Retinol

1.2 Other means of identification

Product number -
Other names VITAMIN A

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:68-26-8 SDS

68-26-8Synthetic route

ethenol
557-75-5

ethenol

(+/-)-7-hydroxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraene-(1.3.5.8)
39668-33-2

(+/-)-7-hydroxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraene-(1.3.5.8)

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With hydrogenchloride In toluene at 50℃; for 1h; Temperature;95%
9-(2,6,6-Trimethyl-cyclohex-1-enyl)-5-phenyl-sulphonyl-3,7-dimethyl-1-acetoxy-nona-2,6,8-triene
50465-60-6

9-(2,6,6-Trimethyl-cyclohex-1-enyl)-5-phenyl-sulphonyl-3,7-dimethyl-1-acetoxy-nona-2,6,8-triene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With sodium ethanolate In ethanol Heating;94%
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal
3917-41-7

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

(E)-4-chloro-3-methyl-2-buten-1-ol
53170-97-1

(E)-4-chloro-3-methyl-2-buten-1-ol

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: (E)-4-chloro-3-methyl-2-buten-1-ol With triphenylphosphine In methanol at 45℃; for 1h;
Stage #2: (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal With sodium hydroxide In methanol; water at 45℃; for 1h; Reagent/catalyst;
90%
tert-Butyl-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-diphenyl-silane
138922-13-1

tert-Butyl-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-diphenyl-silane

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran84%
Retinol acetate
127-47-9

Retinol acetate

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at -15℃; for 0.75h; Inert atmosphere;83%
With water
With methyllithium In diethyl ether at -15℃; for 2h;600 mg
(E,E)-(5-hydroxy-3-methylpenta-1,3-dienyl)boronic acid
120040-83-7

(E,E)-(5-hydroxy-3-methylpenta-1,3-dienyl)boronic acid

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene
138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); TlOH In tetrahydrofuran for 0.5h; Ambient temperature;83%
(2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol
1430344-83-4

(2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene
138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: (2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.5h; Hiyama Coupling; Inert atmosphere;
Stage #2: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 0 - 25℃; for 3.5h; Hiyama Coupling; Inert atmosphere;
82%
Stage #1: (2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Hiyama Coupling; Inert atmosphere; Darkness;
Stage #2: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran for 1h; Hiyama Coupling; Inert atmosphere; Darkness;
77%
tBDMS-retinol
118353-70-1

tBDMS-retinol

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride80%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Ambient temperature;80%
Retinol acetate
127-47-9

Retinol acetate

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

A

retinyl palmitate
79-81-2

retinyl palmitate

B

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21 In toluene at 20℃; for 15h; Product distribution / selectivity; Enzymatic reaction;A 78%
B n/a
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

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

A

2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

C

11-cis-retinol
22737-96-8

11-cis-retinol

D

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h;A n/a
B n/a
C n/a
D 77%
With potassium methanolate In cyclohexane at 38℃; for 2h; Title compound not separated from byproducts;
ethyl (all-E)-retinoate
3899-20-5

ethyl (all-E)-retinoate

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With diisobutylaluminium hydride76%
trans-tetrahydropyran-2-yl retinyl ether
138842-95-2

trans-tetrahydropyran-2-yl retinyl ether

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With methanol; chloro-trimethyl-silane; water In tetrahydrofuran for 0.0833333h;74%
With chloro-trimethyl-silane; water In methanol for 0.166667h; Inert atmosphere;74%
With chloro-trimethyl-silane; water In methanol for 0.166667h;74%
Retinol acetate
127-47-9

Retinol acetate

Thioctic acid
1077-28-7, 62-46-4

Thioctic acid

A

retinyl lipoate

retinyl lipoate

B

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21 In toluene at 20℃; for 21h; Product distribution / selectivity; Enzymatic reaction; Sonication;A 71%
B n/a
linoleic acid
60-33-3

linoleic acid

Retinol acetate
127-47-9

Retinol acetate

A

retinyl linoleate

retinyl linoleate

B

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21 In toluene at 20℃; for 2 - 50h; Product distribution / selectivity; Enzymatic reaction;A 71%
B n/a
With Novozyme 435 (from Candida antarctica immobilized on acrylic resin) In toluene at 20 - 50℃; for 1 - 2h; Product distribution / selectivity; Enzymatic reaction;
With Lipozyme TI IM; Amberlyst A-21 In toluene at 20℃; for 45h; Product distribution / selectivity; Enzymatic reaction;
cis-Octadecenoic acid
112-80-1

cis-Octadecenoic acid

Retinol acetate
127-47-9

Retinol acetate

A

retinyl stearate
631-88-9

retinyl stearate

B

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21 In toluene at 20℃; for 15h; Product distribution / selectivity; Enzymatic reaction;A 69%
B n/a
formaldehyd
50-00-0

formaldehyd

trimethylaluminum
75-24-1

trimethylaluminum

1-((E,E,E)-3-methyl-1,3,5-octatrien-7-ynyl)-2,6,6-trimethyl-1-cyclohexene
111917-89-6

1-((E,E,E)-3-methyl-1,3,5-octatrien-7-ynyl)-2,6,6-trimethyl-1-cyclohexene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Multistep reaction.;67%
2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene
138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

(2E,4E)-3-methyl-5-(tri-n-butylstannyl)penta-2,4-dien-1-ol
128426-10-8

(2E,4E)-3-methyl-5-(tri-n-butylstannyl)penta-2,4-dien-1-ol

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With 1-methyl-pyrrolidin-2-one; tris-(dibenzylideneacetone)dipalladium(0); triphenyl-arsane at 25℃; for 0.166667h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere;
Stage #2: (2E,4E)-5-(tri-n-butylstannyl)-3-methylpenta-2,4-dien-1-ol at 25℃; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere;
60%
all-trans-Retinal
116-31-4

all-trans-Retinal

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With diisobutylaluminium hydride
With triethylaluminum
With sodium tetrahydroborate In ethanol Ambient temperature; 2-3 h;
all-trans-methyl retinoate
339-16-2

all-trans-methyl retinoate

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

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

benzoyl chloride
98-88-4

benzoyl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

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

acetyl chloride
75-36-5

acetyl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

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

butyryl chloride
141-75-3

butyryl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

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

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
retinoyl fluoride
83802-77-1

retinoyl fluoride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With lithium aluminium tetrahydride Yield given;
Acetic acid (2Z,6E)-9-benzenesulfonyl-3,7-dimethyl-8-(tetrahydro-pyran-2-yloxy)-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl ester
103905-07-3, 105615-50-7

Acetic acid (2Z,6E)-9-benzenesulfonyl-3,7-dimethyl-8-(tetrahydro-pyran-2-yloxy)-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl ester

A

2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

B

11,13-Di-cis-vitamin A
17706-49-9

11,13-Di-cis-vitamin A

C

(9Z,13Z)-retinol
29444-25-5

(9Z,13Z)-retinol

D

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h; Yield given. Title compound not separated from byproducts;
With potassium methanolate In cyclohexane at 38℃; for 2h; Title compound not separated from byproducts;
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

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

B

11-cis-retinol
22737-96-8

11-cis-retinol

C

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h;
acetic anhydride
108-24-7

acetic anhydride

RETINOL
68-26-8

RETINOL

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
In hexane at 35℃; for 1h; Solvent; Temperature;99.5%
In hexane at 35℃; for 1h;99.5%
With triethylamine In hexane at 25℃; for 24h; Inert atmosphere; Darkness;76%
RETINOL
68-26-8

RETINOL

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
In toluene at 35℃; for 1h;99%
With pyridine In 1,2-dichloro-ethane
undecanoic acid anhydride
2082-77-1

undecanoic acid anhydride

RETINOL
68-26-8

RETINOL

vitamin-A undecanoate

vitamin-A undecanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;98.73%
RETINOL
68-26-8

RETINOL

propionic acid
802294-64-0

propionic acid

vitamin A Propionate
7069-42-3

vitamin A Propionate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In cyclohexane at 70℃; for 2h;98%
palmitic anhydride
623-65-4

palmitic anhydride

RETINOL
68-26-8

RETINOL

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h; Solvent;97.62%
pentadecanoic acid anhydride
59252-34-5

pentadecanoic acid anhydride

RETINOL
68-26-8

RETINOL

vitamin-A pentadecanoate

vitamin-A pentadecanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;97.48%
RETINOL
68-26-8

RETINOL

myristic anhydride
626-29-9

myristic anhydride

vitamin-A myristate

vitamin-A myristate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;97.09%
tridecanoic acid anhydride
53517-88-7

tridecanoic acid anhydride

RETINOL
68-26-8

RETINOL

vitamin-A tridecanoate

vitamin-A tridecanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;97.01%
RETINOL
68-26-8

RETINOL

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

bromoacetic acid retinol ester
81112-43-8

bromoacetic acid retinol ester

Conditions
ConditionsYield
Novozym 435 In toluene at 20℃; for 26h; Inert atmosphere;97%
lauric anhydride
645-66-9

lauric anhydride

RETINOL
68-26-8

RETINOL

Retinyl laurate
1259-24-1

Retinyl laurate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;96.85%
capric anhydride
2082-76-0

capric anhydride

RETINOL
68-26-8

RETINOL

vitamin-A decanoate
79279-28-0

vitamin-A decanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;96.73%
hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

RETINOL
68-26-8

RETINOL

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
at 60℃; under 0.750075 Torr; for 3h; Temperature; Large scale;94%
retinol anhydride

retinol anhydride

RETINOL
68-26-8

RETINOL

retinoic anhydride
58175-89-6

retinoic anhydride

Conditions
ConditionsYield
With triethylamine In dichloromethane92%
RETINOL
68-26-8

RETINOL

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride; oxygen; bis-(3-methyl-1-imidazolyl)ethylene tetrafluoroborate In hexane at 50℃; under 760.051 Torr; for 3h; Reagent/catalyst; Darkness;90.2%
Multi-step reaction with 2 steps
1: MnO2 / CH2Cl2 / 2 h / Ambient temperature
2: 80 percent / AgO, NaCN / methanol / 18 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / MnO2 / CH2Cl2 / Ambient temperature
2: AgO / CNNa / methanol
View Scheme
RETINOL
68-26-8

RETINOL

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane Ambient temperature;90%
With manganese(IV) oxide; sodium carbonate In dichloromethane for 4h; Inert atmosphere;90%
With manganese(IV) oxide90%
4-Phenyl-1,2,4-triazolidine-3,5-dione
4233-33-4

4-Phenyl-1,2,4-triazolidine-3,5-dione

RETINOL
68-26-8

RETINOL

5-Hydroxymethyl-6-methyl-8-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
135154-45-9

5-Hydroxymethyl-6-methyl-8-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione

Conditions
ConditionsYield
In dichloromethane at -78℃;90%
RETINOL
68-26-8

RETINOL

4-<2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalyl)ethyl>-1,2,4-triazoline-3,5-dione
132788-52-4

4-<2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalyl)ethyl>-1,2,4-triazoline-3,5-dione

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
135154-50-6

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

Conditions
ConditionsYield
In dichloromethane at -78℃;90%
In dichloromethane at 0℃; for 1h;
RETINOL
68-26-8

RETINOL

A

13-cis-vitamin A aldehyde
472-86-6

13-cis-vitamin A aldehyde

B

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane for 12h; Inert atmosphere; Fluorescence light;A 8%
B 90%
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

RETINOL
68-26-8

RETINOL

vitamin A methacrylate

vitamin A methacrylate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In Petroleum ether at 50℃;89%
With dicyclohexyl-carbodiimide In Petroleum ether at 50℃;89%
With dicyclohexyl-carbodiimide In Petroleum ether at 50℃;89%
succinic acid anhydride
108-30-5

succinic acid anhydride

RETINOL
68-26-8

RETINOL

retinyl monosuccinate
13241-44-6

retinyl monosuccinate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 12h; Ambient temperature;88%
With dmap In dichloromethane at 20℃;85%
With dmap; triethylamine In dichloromethane at 20℃; for 12h;3.4 g
With 1-pentyl-3-methylimidazolium nitrate at 50℃; for 3h; Darkness; Inert atmosphere; Green chemistry;
RETINOL
68-26-8

RETINOL

pivalaldehyde
630-19-3

pivalaldehyde

A

2,2-dimethyl-propanol-1
75-84-3

2,2-dimethyl-propanol-1

B

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With aluminum isopropoxide In waterA n/a
B 87%
With aluminum isopropoxide In water
2,2-dimethyl-4-pentenal
5497-67-6

2,2-dimethyl-4-pentenal

RETINOL
68-26-8

RETINOL

A

2,2-dimethylpent-4-en-1-ol
3420-42-6

2,2-dimethylpent-4-en-1-ol

B

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With aluminum isopropoxide In waterA n/a
B 87%
triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
In methanol at 20℃; for 1h;86%

68-26-8Relevant articles and documents

-

Embree,Shantz

, p. 910,912 (1943)

-

Human and rodent aldo-keto reductases from the AKR1B subfamily and their specificity with retinaldehyde

Ruiz, F. Xavier,Moro, Armando,Gallego, Oriol,Ardèvol, Albert,Rovira, Carme,Petrash, J. Mark,Parés, Xavier,Farrés, Jaume

, p. 199 - 205 (2011)

NADP(H)-dependent cytosolic aldo-keto reductases (AKR) are mostly monomeric enzymes which fold into a typical (α/β)8-barrel structure. Substrate specificity and inhibitor selectivity are determined by interaction with residues located in three highly variable loops (A, B, and C). Based on sequence identity, AKR have been grouped into families, namely AKR1-AKR15, containing multiple subfamilies. Two human enzymes from the AKR1B subfamily (AKR1B1 and AKR1B10) are of special interest. AKR1B1 (aldose reductase) is related to secondary diabetic complications, while AKR1B10 is induced in cancer cells and is highly active with all-trans-retinaldehyde. Residues interacting with all-trans-retinaldehyde and differing between AKR1B1 and AKR1B10 are Leu125Lys and Val131Ala (loop A), Leu301Val, Ser303Gln, and Cys304Ser (loop C). Recently, we demonstrated the importance of Lys125 as a determinant of AKR1B10 specificity for retinoids. Residues 301 and 304 are also involved in interactions with substrates or inhibitors, and thus we checked their contribution to retinoid specificity. We also extended our study with retinoids to rodent members of the AKR1B subfamily: AKR1B3 (aldose reductase), AKR1B7 (mouse vas deferens protein), AKR1B8 (fibroblast-growth factor 1-regulated protein), and AKR1B9 (Chinese hamster ovary reductase), which were tested against all-trans isomers of retinaldehyde and retinol. All enzymes were active with retinaldehyde, but with kcat values (0.02-0.52 min -1) much lower than that of AKR1B10 (27 min-1). None of the enzymes showed oxidizing activity with retinol. Since these enzymes (except AKR1B3) have Lys125, other residues should account for retinaldehyde specificity. Here, by using site-directed mutagenesis and molecular modeling, we further delineate the contribution of residues 301 and 304. We demonstrate that besides Lys125, Ser304 is a major structural determinant for all-trans-retinaldehyde specificity of AKR1B10.

Preparation method of vitamin A and vitamin A ester

-

, (2020/04/02)

The invention provides a novel method for preparing vitamin A and vitamin A ester with farnesene as a raw material. The method comprises the following steps: reacting farnesene with acetoacetate underthe action of a catalyst to obtain farnesyl keto ester; carrying out a cyclization reaction and a dehydrogenation reaction on farnesene acetone, and then reacting a reaction product with vinyl magnesium halide to generate vinyl alcohol; carrying out a rearrangement reaction on vinyl alcohol to obtain vitamin A; and subjecting the vitamin A to an esterification reaction to obtain the vitamin A ester. The method avoids the defects of the existing processes, and the process line of the method is economical and effective.

Method for preparing vitamin A and vitamin A ester

-

, (2020/04/17)

The invention provides a novel method for preparing vitamin A and vitamin A ester by taking farnesol as a raw material. The method comprises the following steps: carrying out oxidation reaction on farnesol and oxygen under the action of a catalyst and a cocatalyst to generate farnesal; carrying out dehydrogenation reaction on farnesal to generate dehydrofarnesal; carrying out cyclization reactionon the dehydrofarnesal under the catalysis of acid to generate a cyclized intermediate; carrying out a reaction on the cyclized intermediate with chloroisopentenol to generate vitamin A; carrying outan esterification reaction on vitamin A to generate vitamin A ester. The method avoids the defects of an existing process, and the process line is economical and effective.

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