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79-81-2

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79-81-2 Usage

Chemical Properties

95.0-100.5% Absorbance @325 nm ≥0.85%

Uses

Different sources of media describe the Uses of 79-81-2 differently. You can refer to the following data:
1. antihypertensive
2. all-trans-Retinyl Palmitate is an ester derivative of Retinol (R252000). all-trans-Retinyl Palmitate is used as a vitamin supplement in the treatment of Vitamin A deficiency. all-trans-Retinyl Palmita te is used as an antioxidant and a source of vitamin A added to low fat milk and other dairy products. all-trans-Retinyl Palmitate is also a constituent of some topically applied skin care products
3. retinyl palmitate is a skin conditioner. This retinoid is considered a milder version of retinoic acid, given its conversion properties. once on the skin, it converts to retinol, which in turn converts to retinoic acid. Physiologically, it is credited with increasing R epidermal thickness, stimulating the production of more epidermal protein, and increasing skin elasticity. Cosmetically, retinyl palmitate is used to reduce the number and depth of fine lines and wrinkles, and prevent skin roughness resulting from uV exposure. Secondary reactions such as erythema, dryness, or irritation are not associated with retinyl palmitate. It is even more effective when used in combination with glycolic acid because it achieves greater penetration. In the united States, its maximum usage level in cosmetic formulations is 2 percent. Retinyl palmitate is the ester of retinol and palmitic acid.
4. vitamin A palmitate is known as a skin “normalizer.” It acts as an antikeratinizing agent, helping the skin stay soft and plump, and improving its water-barrier properties. Because of its impact on the skin’s water-barrier properties, it is useful against dryness, heat, and pollution. It is also an anti-oxidant and is suggested for use in sunscreens. Clinical studies with vitamin A palmitate indicate a significant change in skin composition, with increases in collagen, DnA, skin thickness, and elasticity. Vitamin A palmitate’s stability is superior to retinol.

General Description

Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards.Retinyl palmitate belongs to a category of compounds called retinoids, which are chemically similar to vitamin A. It exhibits a beneficial effect on vision, skin and immune function, inhibits cell proliferation and prevents cancer. It is an important dietary as well as a therapeutic compound.

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Review: Vitamin A metabolism.

Safety Profile

Mildly toxic by ingestion. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

Purification Methods

The palmitate is separated from retinol by column chromatography on water-deactivated alumina with hexane containing a very small percentage of acetone. It is also chromatographed on TLC silica gel G, using pet ether/isopropyl ether/acetic acid/water (180:20:2:5) or pet ether/acetonitrile/acetic acid/water (190:10:1:15) to develop the chromatogram. It is then recrystallised from propylene at low temperature (below -47o). [Beilstein 6 IV 4135.]

Check Digit Verification of cas no

The CAS Registry Mumber 79-81-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 7 and 9 respectively; the second part has 2 digits, 8 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 79-81:
(4*7)+(3*9)+(2*8)+(1*1)=72
72 % 10 = 2
So 79-81-2 is a valid CAS Registry Number.
InChI:InChI=1/C36H58O3/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-25-34(37)39-35(38)29-31(3)23-20-22-30(2)26-27-33-32(4)24-21-28-36(33,5)6/h20,22-23,26-27,29H,7-19,21,24-25,28H2,1-6H3/b23-20+,27-26+,30-22+,31-29+

79-81-2 Well-known Company Product Price

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  • Supelco

  • (46959-U)  Retinolpalmitate  analytical standard

  • 79-81-2

  • 46959-U

  • 300.69CNY

  • Detail
  • Sigma-Aldrich

  • (PHR1235)    pharmaceutical secondary standard; traceable to USP

  • 79-81-2

  • PHR1235-1G

  • 732.19CNY

  • Detail
  • USP

  • (1602502)  Retinyl palmitate  United States Pharmacopeia (USP) Reference Standard

  • 79-81-2

  • 1602502-4X50MG

  • 4,647.24CNY

  • Detail

79-81-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 15, 2017

Revision Date: Aug 15, 2017

1.Identification

1.1 GHS Product identifier

Product name all-trans-retinyl palmitate

1.2 Other means of identification

Product number -
Other names Retinyl palmitate

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:79-81-2 SDS

79-81-2Synthetic route

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
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%
hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

Retinol acetate
127-47-9

Retinol acetate

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With sodium hydroxide In methanol at 55℃; under 11.2511 - 16.5017 Torr; for 3h; Concentration; Pressure; Large scale;96%
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%
4-palmitoyloxy-2-methyl-2-buten-1-al

4-palmitoyloxy-2-methyl-2-buten-1-al

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
62285-98-7

5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 5℃; for 3h; Wittig Olefination; Inert atmosphere;91.3%
4-palmitoyloxy-2-methyl-2-buten-1-al

4-palmitoyloxy-2-methyl-2-buten-1-al

[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride
53282-28-3

[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With potassium hydroxide In isopropyl alcohol at 5 - 20℃; for 2h; Wittig Olefination; Inert atmosphere;90.8%
diethyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonate
186194-14-9

diethyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonate

2-methyl-4-palmitoyloxy-2-butenal

2-methyl-4-palmitoyloxy-2-butenal

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Stage #1: diethyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonate With sodium t-butanolate In toluene at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2-methyl-4-palmitoyloxy-2-butenal In toluene for 3h; Reagent/catalyst; Solvent; Inert atmosphere;
89%
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
pyridine
110-86-1

pyridine

RETINOL
68-26-8

RETINOL

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With 1,2-dichloro-ethane
pyridine
110-86-1

pyridine

(+/-)-9-palmitoyloxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(2ξ.5c.7c)-ol-(4)

(+/-)-9-palmitoyloxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(2ξ.5c.7c)-ol-(4)

toluene
108-88-3

toluene

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
at 90 - 95℃;
(+/-)-9-palmitoyloxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(2ξ.5c.7c)-ol-(4)

(+/-)-9-palmitoyloxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(2ξ.5c.7c)-ol-(4)

iodine
7553-56-2

iodine

petroleum ether

petroleum ether

retinyl palmitate
79-81-2

retinyl palmitate

4-palmitoyloxy-2-methyl-2-buten-1-al

4-palmitoyloxy-2-methyl-2-buten-1-al

3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,4-pentadienylphosphonic acid,diethyl ester
128759-92-2

3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,4-pentadienylphosphonic acid,diethyl ester

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With sodium t-butanolate In water; N,N-dimethyl-formamide; toluene
Retinol acetate
127-47-9

Retinol acetate

1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With Candida sp.99-125 lipase immobilized on SBA-15 In hexane at 30℃; for 6h; Enzymatic reaction;75.2 %Chromat.
With novozyme 435 In toluene at 20℃; for 20h; Schlenk technique; Inert atmosphere; Enzymatic reaction;
farnesyl alcohol
82010-11-5

farnesyl alcohol

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: TEMPOL; copper(l) chloride / N,N-dimethyl-formamide / 2 h / 30 °C
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.5 h / 50 °C
3.1: sulfuric acid / 1,2-dichloro-ethane / 0 - 5 °C
4.1: triphenylphosphine / methanol / 1 h / 45 °C
4.2: 1 h / 45 °C
5.1: toluene / 1 h / 35 °C
View Scheme
(2E)-farnesal
80442-43-9

(2E)-farnesal

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 0.5 h / 50 °C
2.1: sulfuric acid / 1,2-dichloro-ethane / 0 - 5 °C
3.1: triphenylphosphine / methanol / 1 h / 45 °C
3.2: 1 h / 45 °C
4.1: toluene / 1 h / 35 °C
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid / 1,2-dichloro-ethane / 0 - 5 °C
2.1: triphenylphosphine / methanol / 1 h / 45 °C
2.2: 1 h / 45 °C
3.1: toluene / 1 h / 35 °C
View Scheme
(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

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triphenylphosphine / methanol / 1 h / 45 °C
1.2: 1 h / 45 °C
2.1: toluene / 1 h / 35 °C
View Scheme
2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene
59633-88-4

2-(bromomethyl)-1,3,3-trimethylcyclohex-1-ene

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere
2.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
3.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
3.2: 3 h / 20 - 25 °C
4.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
5.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere
2.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
5.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
C28H32P(1+)*Cl(1-)

C28H32P(1+)*Cl(1-)

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
2.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
2.2: 3 h / 20 - 25 °C
3.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
4.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
4.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
diethyl [(2,2,6-trimethylcyclohexyl)methyl]phosphonate

diethyl [(2,2,6-trimethylcyclohexyl)methyl]phosphonate

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere
2.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
2.2: 3 h / 20 - 25 °C
3.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
4.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere
2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
4.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide
56013-01-5

triphenyl((2,6,6-trimethylcyclohex-1-enyl)methyl)phosphonium bromide

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
2.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
2.2: 3 h / 20 - 25 °C
3.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
4.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
2.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
2.2: 3 h / 20 - 25 °C
3.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
4.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene
3917-38-2

3-methyl-5-acetoxy-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
1.2: 3 h / 20 - 25 °C
2.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
3.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
1.2: 3 h / 20 - 25 °C
2.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
3.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-chloro-penta-2,4-diene
55732-70-2

5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-chloro-penta-2,4-diene

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
2: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
3-methyl-5-bromo-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene
38987-92-7

3-methyl-5-bromo-1-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,3-pentadiene

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
2: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
3,7-dimethylocta-1,6-dien-3-ol
78-70-6

3,7-dimethylocta-1,6-dien-3-ol

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: hydrogen bromide; sodium hydroxide / water; dichloromethane / 2 h / 30 - 35 °C / Inert atmosphere
1.2: 2 h / 35 - 40 °C
2.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere
3.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
4.2: 3 h / 20 - 25 °C
5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
6.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: hydrogen bromide; sodium hydroxide / water; dichloromethane / 2 h / 30 - 35 °C / Inert atmosphere
1.2: 2 h / 35 - 40 °C
2.1: hexane / 4 h / 50 - 55 °C / Inert atmosphere
3.1: potassium hydroxide / isopropyl alcohol / 1 h / -5 - 5 °C / Inert atmosphere
4.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
4.2: 3 h / 20 - 25 °C
5.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
6.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide; thionyl chloride / 1,2-dichloro-ethane; water / 3 h / 40 - 45 °C
1.2: 5 h / 70 - 75 °C
2.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere
3.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
4.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
4.2: 3 h / 20 - 25 °C
5.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
6.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
1,3,3-trimethyl-2-chloromethylcyclohexene

1,3,3-trimethyl-2-chloromethylcyclohexene

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere
2.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
5.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: acetonitrile / 4 h / 60 - 65 °C / Inert atmosphere
2.1: sodium ethanolate / N,N-dimethyl-formamide / 5 h / -5 - 10 °C / Inert atmosphere
3.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
3.2: 3 h / 20 - 25 °C
4.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
5.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: 4 h / 105 - 110 °C / Inert atmosphere
2.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere
3.1: potassium hydroxide / water; dichloromethane / 3 h / 10 - 15 °C
3.2: 3 h / 20 - 25 °C
4.1: isopropyl alcohol / 5 h / 55 - 60 °C / Inert atmosphere
5.1: potassium hydroxide / isopropyl alcohol / 2 h / 5 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 5 steps
1.1: 4 h / 105 - 110 °C / Inert atmosphere
2.1: sodium methylate / N,N-dimethyl-formamide / 1 h / 0 - 15 °C / Inert atmosphere
3.1: sodium hydroxide / water; dichloromethane / 3 h / 15 - 20 °C
3.2: 3 h / 20 - 25 °C
4.1: acetonitrile / 5 h / 50 - 55 °C / Inert atmosphere
5.1: sodium ethanolate / N,N-dimethyl-formamide / 3 h / -5 - 5 °C / Inert atmosphere
View Scheme
1-hexadecylcarboxylic acid
57-10-3

1-hexadecylcarboxylic acid

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium chloride; di-tert-butyl dicarbonate / ethyl acetate / 5 h / 25 - 35 °C
2.1: selenium(IV) oxide; tert.-butylhydroperoxide / 18 h / 25 - 30 °C / Inert atmosphere
3.1: sodium t-butanolate / toluene / 0.5 h / 0 °C / Inert atmosphere
3.2: 3 h / Inert atmosphere
View Scheme
3-methyl-2-buten-1-ol
556-82-1

3-methyl-2-buten-1-ol

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: magnesium chloride; di-tert-butyl dicarbonate / ethyl acetate / 5 h / 25 - 35 °C
2.1: selenium(IV) oxide; tert.-butylhydroperoxide / 18 h / 25 - 30 °C / Inert atmosphere
3.1: sodium t-butanolate / toluene / 0.5 h / 0 °C / Inert atmosphere
3.2: 3 h / Inert atmosphere
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

Hexadecanoic acid 2-hexadecanoyloxymethyl-3,6-dimethyl-5-[(1Z,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-6-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-cyclohex-3-enylmethyl ester

Hexadecanoic acid 2-hexadecanoyloxymethyl-3,6-dimethyl-5-[(1Z,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-6-[(1E,3E,5E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hexa-1,3,5-trienyl]-cyclohex-3-enylmethyl ester

Conditions
ConditionsYield
at 80℃; for 120h; Kinetics; Further Variations:; Solvents; Temperatures; Dimerization;
retinyl palmitate
79-81-2

retinyl palmitate

13-cis-retinoic acid
4759-48-2

13-cis-retinoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: aq. 5percent KOH / ethanol / 0.5 h / Heating
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

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

all-trans-retinoic-acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

20,14-retro-Retinoic acid
138093-35-3

20,14-retro-Retinoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
View Scheme
Multi-step reaction with 4 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) n-BuLi, diisopropylamine / 1.) THF, hexane, 0 deg C, 10 min, 2.) THF, hexane, -60 deg C, 5 min
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

14-ethyl-20,14-retro-retinoic acid
138093-38-6

14-ethyl-20,14-retro-retinoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

14-isopropyl-20,14-retro-retinoic acid
138093-39-7

14-isopropyl-20,14-retro-retinoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

methyl 14-ethyl-20,14-retro-retinoate
138093-44-4

methyl 14-ethyl-20,14-retro-retinoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
5: 77 percent / diethyl ether / 20 h / 0 °C
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

methyl 14-isopropyl-20,14-retro-retinoate
138093-45-5

methyl 14-isopropyl-20,14-retro-retinoate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
5: 89 percent / diethyl ether / 0.5 h / 0 °C
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

13-cis-14-Ethylretinoic acid
138231-98-8

13-cis-14-Ethylretinoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
5: 77 percent / diethyl ether / 20 h / 0 °C
6: 1.) MeONa, 2.) 10percent aq. KOH / 1.) MeOH, reflux, 7 h, 2.) EtOH, reflux
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

14-Ethylretinoic acid
138093-41-1

14-Ethylretinoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
5: 77 percent / diethyl ether / 20 h / 0 °C
6: 1.) MeONa, 2.) 10percent aq. KOH / 1.) MeOH, reflux, 7 h, 2.) EtOH, reflux
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

13-cis-14-Isopropylretinoic acid
138231-99-9

13-cis-14-Isopropylretinoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
5: 89 percent / diethyl ether / 0.5 h / 0 °C
6: 1.) NaH, 2.) 20percent aq. KOH, 18-crown-6 / 1.) DMF, 50 deg C, 90 min, 2.) EtOH, reflux
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

14-Isopropylretinoic acid
138093-42-2

14-Isopropylretinoic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
5: 89 percent / diethyl ether / 0.5 h / 0 °C
6: 1.) NaH, 2.) 20percent aq. KOH, 18-crown-6 / 1.) DMF, 50 deg C, 90 min, 2.) EtOH, reflux
View Scheme
retinyl palmitate
79-81-2

retinyl palmitate

(2Z,4E,6E,8E)-2-Ethyl-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester
138232-01-6

(2Z,4E,6E,8E)-2-Ethyl-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / aq. 10percent KOH / propan-2-ol; ethanol / 1.25 h / 90 °C
2: 58 percent / MnO2, NaCN / acetonitrile; acetic acid / 62 h / 20 °C
3: 77 percent / aq. 5percent KOH / ethanol / 0.5 h / Heating
4: 1.) lithium diisopropylamide, HMPA / 1.) THF, hexane, -60 deg C, 5 min, 2.) THF, hexane, -70 deg C, 45 min
5: 77 percent / diethyl ether / 20 h / 0 °C
6: MeONa / methanol / 7 h / Heating
View Scheme

79-81-2Relevant articles and documents

Antioxidant activity and synergism of butylhydroxytoluene in processes of oxidation of retinol esters

Finkel'shtein,Mednikova,Alekseev,Kozlov

, p. 100 - 104 (1977)

-

Synthesis method of 4-palmitoyloxy-2-methyl-2-butenal and synthesis method of vitamin A palmitate

-

, (2021/04/10)

The invention discloses a synthesis method of a vitamin A palmitate intermediate 4-palmitoyloxy-2-methyl-2-butenal, application of the vitamin A palmitate intermediate 4-palmitoyloxy-2-methyl-2-butenal in vitamin A palmitate synthesis, and a method for synthesizing vitamin A palmitate by using the intermediate. According to the method, in the process of introducing aldehyde group, solvent-free reaction conditions are adopted, so that the use of organic solvents is avoided while the reaction yield is increased, the production cost is reduced, the operation is simple and convenient, and the method is suitable for industrial large-scale production.

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.

Synthesis method of vitamin A higher fatty acid ester

-

Paragraph 0034; 0035; 0036; 0037, (2016/11/09)

The invention discloses a synthesis method of vitamin A higher fatty acid ester, which includes the following steps: a) performing an esterification reaction to vitamin A alcohol and higher fatty acid anhydride in an organic solvent under catalysis of an alkaline metal oxide; and b) performing after treatment after the reaction is finished to obtain the vitamin A higher fatty acid ester. The method is less in reaction by-products, is high in product purity and is good in product quality. The product is more than 97.5% in content and is more than 96.5% in yield through high performance liquid chromatography detection. The vitamin A higher fatty acid ester enables storage, transportation and application of vitamin A to be more convenient. An analytic method in pharmacopeia proves that vitamin A palmitate is 1750000-1780000 IU/g in biological titer and is more than 97.5% in content through the high performance liquid chromatography detection, so that the vitamin A palmitate can be marketed as commodity directly, and is widely applied in the fields of medicines, feed additives and food additives.

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