127-47-9

Basic information

• Product Name: Retinyl acetate
• Synonyms: RETINYL ACETATE;RETINOL ACETATE;RETINOL ACETATE ALL TRANS;RETINOL ACETATE, WATER SOLUBLE;VITAMIN A ACETATE, ALL TRANS;VITAMIN A ACETATE 1500;VITAMIN A ACETATE;TRANS-RETINOL ACETATE
• CAS NO: 127-47-9
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.49
• EINECS: 204-844-2
• Product Categories: Retinoids;Vitamins and derivatives;Vitamin Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;Vitamin series;Inhibitors
• Mol File: 127-47-9.mol

Chemical Properties

• Melting Point: 57-58 °C
• Boiling Point: 406.22°C (rough estimate)
• Flash Point: 14℃
• Appearance: /solid or viscous liquid
• Density: 1.0474 (rough estimate)
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.547-1.555
• Storage Temp.: 2-8°C
• Solubility: absolute ethanol: 25 mg/mL
• Water Solubility: soluble
• Sensitive: Light & Air Sensitive & Hygrosco
• Stability: Hygroscopic, Light Sensitive
• Merck: 14,10013
• BRN: 1915439
• CAS DataBase Reference: Retinyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Retinyl acetate(127-47-9)
• EPA Substance Registry System: Retinyl acetate(127-47-9)

Safety Data

• Hazard Codes: Xn,Xi,T,F
• Statements: 38-63-36/37/38-53-61-11
• Safety Statements: 36/37-45-37/39-26-53-16
• RIDADR: UN1170 - class 3 - PG 2 - Ethanol
• WGK Germany: 2
• RTECS: VH6825000
• F: 1-8-10
• TSCA: Yes
• Hazardous Substances Data: 127-47-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Retinyl acetate is used as a vitamin precursor for its essential micronutrient properties, playing a crucial role in maintaining overall health and well-being.
Used in Food Fortification:
Retinyl acetate is used as a fortifying agent for food products, particularly to enhance the vitamin A content, which is essential for proper growth, development, and immune function.
Used in Skincare Products:
Retinyl acetate is used as a skin-conditioning agent due to its ability to induce cell differentiation and inhibit cell proliferation, making it beneficial for maintaining healthy skin.
Used in Research and Analysis:
Retinyl acetate has been used in various research applications, such as a control diet to study its effects at different developmental periods in fish larvae, and to study its inhibitory effects on Mycobacterium avium subspecies paratuberculosis (MAP) strains.
Used in Chromatography:
Retinyl acetate is used as an internal standard in high-performance liquid chromatography (HPLC) to quantify vitamin A in fortified milk, ensuring accurate and reliable results in the analysis of vitamin A content.
Used in Analytical Chemistry:
Retinyl acetate is suitable for use in the retention identification of the analyte when using high-performance liquid chromatography (HPLC) and gas chromatography (GC), providing a reliable reference for quality assurance in these analytical techniques.

Reference

Volker Bühler, Vademecum for Vitamin Formulations, 2001, ISBN 3-8047-1834-5

Flammability and Explosibility

Notclassified

Biochem/physiol Actions

Retinyl esters provide pools of vitamin A that are converted into retinol and other retinoids as required. Retinyl acetate is used in a wide range of biological applications. It acts as a chemopreventive agent. Retinyl acetate also has antineoplastic property.

Safety Profile

Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. Questionable carcinogen with experimental neoplastigenic data. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes. See also VITAMIN A.

Purification Methods

The acetate is separated from retinol by column chromatography, then crystallised from MeOH. [Kofler and Rubin Vitamins and Hormones (NY) 18 315 1960 for purification methods]. Store it in the dark, under N2 or Ar, at 0o. [Beilstein 6 IV 4135.]

InChI:InChI=1/C22H30O3/c1-16(9-7-10-17(2)15-21(24)25-19(4)23)12-13-20-18(3)11-8-14-22(20,5)6/h7,9-10,12-13,15H,8,11,14H2,1-6H3/b10-7+,13-12+,16-9+,17-15+

Synthetic route

acetic anhydride (108-24-7) + RETINOL (68-26-8) → Retinol acetate (127-47-9)

Conditions	Yield
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%

(2Z,4Z)-3,7-dimethyl-6-hydroxy-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-nona-2,4,6,8-tetraenyl acetate + argon → Retinol acetate (127-47-9)

Conditions	Yield
In N-methyl-acetamide	95.8%
In N-methyl-acetamide	94.1%
In N-methyl-acetamide	93.9%

phosphorus pentaoxide (337913-25-4) + (2Z,4Z)-3,7-dimethyl-6-hydroxy-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-nona-2,4,6,8-tetraenyl acetate + argon → Retinol acetate (127-47-9)

Conditions	Yield
In N-methyl-acetamide	94.9%

(+/-)-(E,E,E)-9-(acetyloxy)-3,7-dimethyl-1-<2,6,6-trimethyl-1-cyclohexen-1-yl>-1,5,7-nonatrien-4-one (120591-27-7) → Retinol acetate (127-47-9)

Conditions	Yield
With iridium on carbon; hydrogen In ethanol at 50℃; under 11251.1 - 15001.5 Torr; for 3h; Reagent/catalyst; Pressure; Temperature; Solvent; Autoclave; Inert atmosphere;	93%

Tetraethyl methylenediphosphonate (1660-94-2) + (E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + (E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal (14398-40-4) → Retinol acetate (127-47-9)

Conditions	Yield
Stage #1: Tetraethyl methylenediphosphonate With 18-crown-6 ether; potassium tert-butylate In toluene at 30℃; for 0.5h; [1,2]-Wittig Rearrangement; Inert atmosphere; Stage #2: (E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal In toluene at -5℃; for 4.5h; Stage #3: (E)-4-acetoxy-2-methylcrotonaldehyde In toluene at -40℃; for 1h; Reagent/catalyst; Solvent; Temperature;	93%

3-methyl-4-oxobut-2-enyl acetate (14918-80-0) + β-Jonylidenaethyl-triphenyl-phosphonium-chlorid (1062-12-0) → Retinol acetate (127-47-9)

Conditions	Yield
With 1-butyl-3-methylimidazolium imidazolide; sodium hydroxide In hexane; water at 43℃; for 2h; Reagent/catalyst; Temperature; Solvent; Autoclave; Inert atmosphere;	92.92%

(E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride (53282-28-3) → Retinol acetate (127-47-9)

Conditions	Yield
With potassium hydroxide In isopropyl alcohol at 0 - 10℃; for 2h; Wittig Olefination; Inert atmosphere;	92.8%
With potassium hydroxide In N,N-dimethyl-formamide; isopropyl alcohol at 0 - 10℃; for 2h; Inert atmosphere;	91.9%

(E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + 5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide (62285-98-7) → Retinol acetate (127-47-9)

Conditions	Yield
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 0℃; for 2h; Solvent; Temperature; Reagent/catalyst; Wittig Olefination; Inert atmosphere;	91%
With sodium ethanolate In N,N-dimethyl-formamide at -5 - 5℃; for 2h; Time; Inert atmosphere;	90.7%

1-acetoxy-5.9-dibensenesulfonyl-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6-nonadiene (475558-35-1) → Retinol acetate (127-47-9)

Conditions	Yield
With sodium hydroxide In ethanol for 15h; Heating;	82%

(E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium hydrogensulfate → Retinol acetate (127-47-9)

Conditions	Yield
With ammonia In water at 50℃; for 0.5h; Product distribution / selectivity; Wittig Reaction;	77%

(9Ξ,11Ξ,13Ξ)-O-acetyl-retinol (127-47-9, 22586-94-3, 29443-87-6, 29444-27-7, 29584-22-3, 34356-31-5, 63568-38-7, 98462-63-6, 137121-50-7, 137121-51-8, 137121-55-2) → Retinol acetate (127-47-9)

Conditions	Yield
With erythrosine B In methanol; n-heptane at 15℃; for 4h; Irradiation;	76.8%

7,8-dihydroretinyl acetate → Retinol acetate (127-47-9)

Conditions	Yield
With triethanolamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In ethyl acetate at 20 - 77℃; for 1h; Temperature; Solvent;	75%

acetyl chloride (75-36-5) + 1,3,3-trimethyl-2-[(2E,4E,6E)-3,7-dimethyl-2,4,6,8-nonatetraenyl]cyclohexene (388075-89-6) → Retinol acetate (127-47-9)

Conditions	Yield
Stage #1: 1,3,3-trimethyl-2-[(2E,4E,6E)-3,7-dimethyl-2,4,6,8-nonatetraenyl]cyclohexene With NMPA; lithium diisopropyl amide In tetrahydrofuran; hexane Stage #2: With sodium hydroxide; fluorodimethoxyborane diethyl etherate In tetrahydrofuran at 25℃; for 2h; Stage #3: acetyl chloride With pyridine In dichloromethane at 25℃; for 3h; Further stages.;	41%

(2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate (388075-83-0) → Retinol acetate (127-47-9)

Conditions	Yield
With 2,6-dichloro-benzonitrile In hexane at 25℃; for 6h;	31%

(E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,diethyl ester (128759-88-6) → Retinol acetate (127-47-9)

Conditions	Yield
With dimethyl sulfoxide In tetrahydrofuran; hexane; water	7.1%
In di-isopropyl ether; water	7.9%
In N-methyl-acetamide; water; toluene	7%

3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,dimethyl ester + methyl ethyl 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonate + (E)-4-acetoxy-2-methylcrotonaldehyde (26586-02-7) + 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,diethyl ester (128759-88-6) + sodium t-butanolate (865-48-5) → Retinol acetate (127-47-9)

Conditions	Yield
In N-methyl-acetamide; toluene	6.9%

pyridine (110-86-1) + RETINOL (68-26-8) + acetyl chloride (75-36-5) → Retinol acetate (127-47-9)

Conditions	Yield
With 1,2-dichloro-ethane
With diethyl ether

3-methyl-4-oxobut-2-enyl acetate (14918-80-0) + 1,5,5-trimethyl-6-(3-methyl-penta-2,4-dienylidene)-cyclohexene (55497-46-6) → Retinol acetate (127-47-9)

Conditions	Yield
With triphenylphosphine hydrochloride

acetic anhydride (108-24-7) + 1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene (105096-76-2) → Retinol acetate (127-47-9) + 9-cis-Vitamin-A-acetat (29584-22-3) + 11-cis-Vitamin-A-acetat (29443-87-6) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5)

Conditions	Yield
With potassium methanolate 1.) cyclohexane, 38 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

acetic anhydride (108-24-7) + 1-acetoxy-6-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene (103905-08-4) → Retinol acetate (127-47-9) + 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) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5)

Conditions	Yield
With potassium methanolate; triethylamine 1.) cyclohexane, 38 deg C, 2 h, 2.) hexane; Yield given. Multistep reaction;

acetic anhydride (108-24-7) + 1-acetoxy-6-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene (103905-09-5) → Retinol acetate (127-47-9) + 9-cis-Vitamin-A-acetat (29584-22-3) + 11-cis-Vitamin-A-acetat (29443-87-6) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5)

Conditions	Yield
With potassium methanolate 1.) cyclohexane, 38 deg C, 2 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

10,15-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohex-6-enyl)-8,11,13-nonatriene (3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6) → Retinol acetate (127-47-9) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5) + (3E,5E,7E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-triene-1,2-diol (139697-18-0) + Acetic acid (2Z,4Z,6E)-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienyl ester (59677-18-8, 59728-52-8, 139758-19-3) + Acetic acid (3E,5Z,7Z)-2-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester (62417-07-6, 139890-93-0) + Acetic acid (3E,5E,7E)-2-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester (62417-07-6, 139890-93-0)

Conditions	Yield
Product distribution; Mechanism; multistep reaction; dehydrochlorination;

Acetic acid (2Z,4Z,6E)-8-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienyl ester (139697-15-7, 139758-18-2) → Retinol acetate (127-47-9) + (3E,5E,7E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-triene-1,2-diol (139697-18-0) + Acetic acid (2Z,4Z,6E)-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienyl ester (59677-18-8, 59728-52-8, 139758-19-3) + Acetic acid (3E,5E,7E)-2-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester (62417-07-6, 139890-93-0) + Acetic acid (3E,5Z,7Z)-2-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester (139697-16-8, 139890-92-9) + Acetic acid (3E,5E,7E)-2-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester (139697-16-8, 139890-92-9)

Conditions	Yield
With hydrogenchloride at 35℃; for 3h; Rate constant; other 8- and 14-chloroacetates;

1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene (105096-76-2) → Retinol acetate (127-47-9) + 9-cis-Vitamin-A-acetat (29584-22-3) + 11-cis-Vitamin-A-acetat (29443-87-6) + (7E,9E,11E,13Z)-retinyl acetate (34356-31-5)

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

(+-)-9-acetoxy-3.7-dimethyl-1-<2.2.6-trimethyl-cyclohexen-(6)-yl>-nonatrien-(2ξ.5c.7ξ)-ol-(4) → Retinol acetate (127-47-9)

Conditions	Yield
With iodine; Petroleum ether; Tocopherol bei Siedetemperatur;
With pyridine; toluene; trichlorophosphate at 90 - 95℃; Durchleiten von Stickstoff;

3,7-dimethyl-9-<2,6,6-trimethyl-cyclohex-1-enyl>-nona-2c,4c,7ξ-triene-1,6-diol → Retinol acetate (127-47-9)

Conditions	Yield
Acetylierung und aufeinanderfolgendes Behandeln mit HCl und mit NaHCO3 ;
Acetylierung und aufeinanderfolgendes Behandeln mit HCl und mit NaHCO3 ;

3-methyl-4-oxobut-2-enyl acetate (14918-80-0) + 3-methyl-5t-<2,6,6-trimethyl-cyclohex-1-enyl>-penta-2t,4-dien-1-ol → Retinol acetate (127-47-9)

Conditions	Yield
With triphenylphosphine hydrochloride

pyridine (110-86-1) + (+/-)-9-acetoxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(2ξ.5c.7c)-ol-(4) (62417-05-4, 95404-32-3) + toluene (108-88-3) + trichlorophosphate (10025-87-3, 12599-09-6, 63736-95-8) → Retinol acetate (127-47-9)

Conditions	Yield
at 90 - 95℃;

hexadecanoic acid methyl ester (112-39-0) + Retinol acetate (127-47-9) → retinyl palmitate (79-81-2)

Conditions	Yield
With sodium hydroxide In methanol at 55℃; under 11.2511 - 16.5017 Torr; for 3h; Concentration; Pressure; Large scale;	96%

Retinol acetate (127-47-9) → beta-carotene (7235-40-7)

Conditions	Yield
Stage #1: Retinol acetate With sulfuric acid; triphenylphosphine In methanol at 0 - 5℃; for 10.5h; Stage #2: With palladium diacetate; β‐cyclodextrin In ethanol; dichloromethane; water under 16501.7 Torr; for 8h; Reagent/catalyst; Solvent; Pressure; Temperature; Autoclave;	90.6%
Stage #1: Retinol acetate With aniline In ethanol Stage #2: With hydrogenchloride; triphenylphosphine In ethanol; water at 10 - 25℃; for 26h; Reagent/catalyst; Solvent; Further stages;	58.75%

Retinol acetate (127-47-9) → RETINOL (68-26-8)

Conditions	Yield
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

Retinol acetate (127-47-9) → 9-cis-Vitamin-A-acetat (29584-22-3)

Conditions	Yield
In acetonitrile at 25℃; for 24h; UV-irradiation;	80%
With dichloro bis(acetonitrile) palladium(II); triethylamine In hexane at 65℃; for 20h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere;	n/a

Retinol acetate (127-47-9) + 1-hexadecylcarboxylic acid (57-10-3) → retinyl palmitate (79-81-2) + RETINOL (68-26-8)

Conditions	Yield
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

Retinol acetate (127-47-9) + Thioctic acid (1077-28-7, 62-46-4) → retinyl lipoate + RETINOL (68-26-8)

Conditions	Yield
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) + Retinol acetate (127-47-9) → retinyl linoleate + RETINOL (68-26-8)

Conditions	Yield
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) + Retinol acetate (127-47-9) → retinyl stearate (631-88-9) + RETINOL (68-26-8)

Conditions	Yield
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

Retinol acetate (127-47-9) → Acetic acid (4E,6E,8E)-(2S,3S)-2,3-dihydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-4,6,8-trienyl ester (166584-42-5) + Acetic acid (3E,5E,7E)-(1S,2S)-2-hydroxy-1-hydroxymethyl-2,6-dimethyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-octa-3,5,7-trienyl ester

Conditions	Yield
With potassium osmate(VI); Hydroquinone 1,4-phthalazinediyl diether; methanesulfonamide; potassium carbonate; potassium hexacyanoferrate(III) In water; tert-butyl alcohol at 0℃; for 4h; Yields of byproduct given;	A 63% B n/a

Retinol acetate (127-47-9) → Hexahydrovitamin A acetate (113563-63-6) + 9,13-Dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,13-nonadien-15-ol acetate (113563-62-5)

Conditions	Yield
With hydrogen; nickel In methanol for 0.5h; Ambient temperature; Yields of byproduct given;	A 62.5% B n/a
With hydrogen; nickel In methanol for 0.5h; Ambient temperature; Yield given. Yields of byproduct given;

ethyl 4-pentenoate (1968-40-7) + Retinol acetate (127-47-9) → (1E,3E)-3-methyl-1-[2,6,6-trimethylcyclohex-1-enyl]hexa-1,3,5-triene (43219-55-2) + ethyl (11Z)-13-nor-13,14-dihydroretinoate + ethyl (11E)-13-nor-13,14-dihydroretinoate (1332483-21-2)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In toluene at 20℃; for 96h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	A 33% B n/a C n/a

Retinol acetate (127-47-9) + (2E,4EZ)-N-(4-hexyloxyphenyl)-3-methylhexa-2,4-dienamide (1332483-19-8) → N-(4-hexyloxyphenyl)retinamide (1332483-22-3)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In dichloromethane; toluene at 20℃; for 96h; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	26%

Retinol acetate (127-47-9) → (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-amine (43219-27-8)

Conditions	Yield
Stage #1: Retinol acetate With sodium hydroxide Stage #2: With manganese(IV) oxide In hexane Further stages;	23.5%

Retinol acetate (127-47-9) + N-(4-hydroxyphenyl)sorbamide → N-(4-hydroxyphenyl)-13-apo-β-caroten-13-amide (1332483-33-6)

Conditions	Yield
With Hoveyda-Grubbs catalyst second generation In toluene at 20℃; Inert atmosphere; optical yield given as %de; diastereoselective reaction;	13%

Upstream product

• 56691-74-8 {[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene 
• 59057-30-6 (1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol 
• 138871-46-2 3-methyl-5-(2, 6, 6,-trimethyl-cyclohexen-1-yl)-1,3-pentadienylphosphonic acid diethyl ester 
• 26586-02-7 (E)-4-acetoxy-2-methylcrotonaldehyde 
• 138871-48-4 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1,4-pentadienylphosphonic acid, diethyl ester 
• 59830-43-2 1-hydroxy-3,7-dimethyl-4-(phenylsulfonyl)-9-(2,6,6-trimethylcyclohexen-1-yl)-none-2,6,8-triene 
• 59830-46-5 1-hydroxy-3,7-dimethyl-4-(p-trifluoromethylphenylsulfonyl)-9-(2,6,6-trimethylcyclohexen-1-yl)-nona-2,6,8-triene 
• 59830-45-4 1-hydroxy-3,7-dimethyl-4-(p-methoxyphenylsulfonyl)-9-(2,6,6-trimethylcyclohexen-1-yl)-nona-2,6,8-triene 
• 105096-76-2 1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene 
• 128759-88-6 3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,diethyl ester 
• 865-48-5 sodium t-butanolate 
• 751-83-7 [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium hydrogensulfate 
• 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 
• 103905-01-7 1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene 

Downstream Products

• 1224-78-8 anhydroretinol 
• 32450-56-9 retinyl methyl ether 
• 29584-22-3 9-cis-Vitamin-A-acetat 
• 34356-31-5 (7E,9E,11E,13Z)-retinyl acetate 
• 137121-55-2 Acetic acid (2E,4Z,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyl ester 
• 68-26-8 RETINOL 
• 20056-09-1 retinyl carbocation 
• 127-47-9 retinol acetate radical anion 
• 113563-63-6 Hexahydrovitamin A acetate 
• 113563-62-5 9,13-Dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,13-nonadien-15-ol acetate 
• 127-47-9 Retinol acetate 
• 7235-40-7 beta-carotene 
• 200720-67-8 (9Ξ)-O-acetyl-retinol 

Related news

Off-line coupling of pressurized liquid extraction and LC/ED for the determination of Retinyl acetate (cas 127-47-9) and tocopherols in infant formulas09/29/2019

An analytical methodology including pressurized liquid extraction (PLE) as sample treatment to isolate retinyl acetate and tocopherols from infant formulas has been developed. The milk extracts were kept at −18 °C for 30 min and after filtration could be injected directly into the chromatograph...detailed

Binding of Retinyl acetate (cas 127-47-9) to whey proteins or phosphocasein micelles: Impact of pressure-processing on protein structural changes and ligand embedding09/26/2019

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In vivo confocal Raman spectroscopy and molecular dynamics analysis of penetration of Retinyl acetate (cas 127-47-9) into stratum corneum09/09/2019

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Relevant articles and documents

PROCESS FOR PRODUCTION OF VITAMIN A

The present invention relates to a new process for the production of vitamin A and/or its derivatives.

PROCESS FOR PRODUCTION OF NEW SULFOLENIC INTERMEDIATES

The present invention relates to a new process for the production of new specific intermediates, which are preferably used in the production of vitamin A, vitamin A acetate, or β-carotene and derivatives thereof, e.g. canthaxanthin, astaxanthin or zeaxanthin.

Preparation method of vitamin A acetate

The invention provides a novel preparation method of vitamin A acetate, which comprises the following steps: 1-bromo-2-chloroethane is subjected to in-situ preparation of a Grignard reagent, then the Grignard reagent reacts with pentacarbaldehyde to prepare 3-methyl-6-chloro-2, 4-hexadienol acetate, and the 3-methyl-6-chloro-2, 4-hexadienol acetate is subjected to one-step in-situ Grignard reaction and beta-ionone reaction to obtain the vitamin A acetate. The process provides a C13 + C7 vitamin A acetate synthesis route, generation of triphenylphosphine oxide is avoided, modification solid acid is used for catalysis, VA deterioration is avoided, the yield of the vitamin A acetate is improved, the process cost is reduced, the reaction process is environmentally friendly, and industrial production is facilitated. The process cost is reduced, the reaction process is environment-friendly, and industrial production is facilitated.

Preparation method of vitamin A acetate

The invention provides a preparation method of vitamin A acetate, which comprises the following steps: reacting bromoethanol with acetone to obtain a ketal compound, preparing a Grignard reagent fromthe ketal compound, reacting the Grignard reagent with C5 aldehyde to obtain heptanol, reacting the heptanol with triphenylphosphine to prepare heptacarbon phosphine salt, and further reacting the heptacarbon phosphine salt with ionone to obtain the vitamin A acetate. According to the present invention, a C13 + C7 vitamin A acetate synthesis route is provided, such that the yield of the vitamin Aacetate is improved, the process cost is reduced, and the industrial production is easily achieved.

Preparation method of vitamin A acetate

The invention discloses a preparation method of vitamin A acetate. Thepreparation method is characterized in that raw materials including vinyl ionol, an organic phosphine compound and pentacarbonaldehyde react under the action of a catalyst to generate vitamin A acetate, and the vitamin A acetate is synthesized by adopting a one-step method. According to the invention, the problems of considerable byproducts, serious equipment corrosion and the like caused by a liquid acid catalyst in a reaction are avoided; and meanwhile, the defects of large dosage of a base catalyst, difficulty in waste alkali treatment and the like are overcome.

Preparation method of vitamin A acetate intermediate C15 and vitamin A acetate

The invention provides a preparation method of a vitamin A acetate intermediate C15 and vitamin A acetate. The method comprises the following steps: taking 1-halogenated-2-methyl-4-acetoxy-2-butene asa raw material, preparing a corresponding Wittig reagent through a substitution reaction with triphenylphosphine or triester phosphite, then carrying out a Wittig reaction with beta-cyclocitral, hydrolyzing an ester group under an alkaline condition, acidifying to obtain a corresponding halide, and carrying out a substitution reaction with triphenylphosphine or triester phosphite again to prepareC15. The vitamin A acetate can be prepared by carrying out a Wittig reaction on the obtained C15 and 2-methyl-4-acetoxy-2-butenal under an alkaline condition. The method has the advantages of singlereaction type, easy operation and realization of reaction conditions, safe and environment-friendly operation, simple post-treatment and low cost; and the reaction activity is strong, the reaction selectivity is high, the atom economy is high, and the target product yield and purity are high.

Preparation method of vitamin A and vitamin A ester

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

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.

ISOMERIZATION OF POLYUNSATURATED NON-AROMATIC COMPOUNDS

The invention relates to an improved process for isomerizing polyunsaturated non-aromatic compounds including acyclic conjugated polyenes and alicyclic conjugated polyenes. In particular it relates to an improved and safe process for forming a 11-E retinoid compounds in high yield by expending as few energy as possible and with avoiding at most possible side products or product mixtures. This is achieved by feeding at least one of retinoid compounds of formula 2 to 5, or at least one of retinoid compounds of formula 2 to 5 and retinoid compound of formula 1, an organic solvent and a photosensitizer into a reaction device and irradiating the thus obtained reaction mixture with visible monochromatic light, at least 90 % of the power of said monochromatic light and at most 100 % of said power being emitted in the range from 460 nm to 580 nm.

Preparation method of vitamin A acetate

The invention belongs to the field of organic synthesis and discloses a method for preparing vitamin A acetate. The method comprises the following steps that: in the presence of crown ether, a first Wittig reaction is carried out on C14 aldehyde trans-2-methyl-4-(2, 6, 6-trimethyl-1-cyclohexene)-2-butenal and C1 phosphate (tetraethyl methylenediphosphate or tetramethyl methylenediphosphate) in thepresence of organic alkali to obtain a material containing C15 phosphate, wherein R is selected from C1-C3 alkyl groups, preferably ethyl groups; and (2) the material containing C15 phosphate obtained in the step (1) and C5 aldehyde 2-methyl-4-acetoxy-2-butenal are subjected to a second Wittig reaction so as to obtain a reaction liquid containing the vitamin A acetate. The method has the advantages of environmental friendliness and high yield, and provides convenience for large-scale production of the vitamin A acetate.