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
• Article Data: 49

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

Description

Retinyl acetate (retinol acetate, vitamin A acetate) is a natural form of vitamin A. It is the acetate ester of retinol. It consists of yellow crystals which are greasy or sticky. It has a mild, characteristic odor. It has potential antineoplastic and chemo-preventive activities. It can be used to fortify food with vitamin A. As vitamin A acetate can induce cell differentiation and inhibit cell proliferation, it is used in skin-conditioning agent.

Reference

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

Chemical Properties

Crystalline

Uses

Different sources of media describe the Uses of 127-47-9 differently. You can refer to the following data:
1. vitamin precursor
2. Essential micronutrient
3. Retinyl acetate has been used: a control diet to study its effect at different developmental periods in fish larvae to study its inhibitory effects on Mycobacterium avium?subspecies?paratuberculosis?(MAP) strains as an internal standard in high performance liquid chromatography (HPLC) to quantify vitamin A in fortified milk

General Description

Retinyl acetate is suitable for use in the retention identification of the analyte when using HPLC and GC. Not intended for use as an activity reference standard. It has been thoroughly evaluated to ensure the utmost quality. Neat, unless otherwise noted. Certificate of Composition provided with the purchase.

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

• 388075-88-5 (2E,6E)-3,7-dimethyl-1-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatriene-4-ol 
• 59830-43-2 1-hydroxy-3,7-dimethyl-4-(phenylsulfonyl)-9-(2,6,6-trimethylcyclohexen-1-yl)-none-2,6,8-triene 
• 68-26-8 RETINOL 
• 388075-82-9 (2E,6E,8E)-4-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatriene acetate 
• 388075-80-7 2-[(E)-3-methoxy-3-methyl-1,4-pentadienyl]-1,3,3-trimethylcyclohexene 
• 14398-40-4 (E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal 
• 59057-30-6 (1E)-1-(2,6,6-trimethylcyclohex-1-enyl)-3-methyl-1,4-pentadien-3-ol 
• 26586-02-7 (E)-4-acetoxy-2-methylcrotonaldehyde 
• 1115-08-8 3-methyl-1,4-pentadiene 
• 475558-35-1 1-acetoxy-5.9-dibensenesulfonyl-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6-nonadiene 
• 388075-83-0 (2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate 
• 75-36-5 acetyl chloride 
• 388075-89-6 1,3,3-trimethyl-2-[(2E,4E,6E)-3,7-dimethyl-2,4,6,8-nonatetraenyl]cyclohexene 
• 62417-05-4 (+/-)-9-acetoxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(2ξ.5c.7c)-ol-(4) 

Downstream Products

• 801-72-9 5,6-epoxyretinyl acetate 
• 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 
• 38699-13-7 8'-acetoxy-all-trans-8'-apo-β-carotene 
• 1109-11-1 trans-apo-8'-carotenic acid ethyl ester 
• 5056-11-1 Torularhodin-ethylester 

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

A whey protein isolate (WPI) and native phosphocaseins (PC) at pH 6.5–6.6 were processed with retinyl acetate (RAC) using pressure-assisted technological tools to improve RAC embedding through processing-induced protein structural changes. To this end, protein-RAC dispersions were submitted to ...detailed

Original articleA new model of detrusor overactivity in conscious rats induced by Retinyl acetate (cas 127-47-9) instillation09/10/2019

IntroductionA credible animal overactive bladder model used in basic research is an indispensable harbinger of safe and ethical clinical trials on human subjects. Our objective was to develop a new animal model of a hyperactive bladder that will be void of inflammatory urothelium lesions and dis...detailed

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

ObjectiveThe purpose of this study is to elucidate the behavior of retinyl acetate in penetrating human skin without the presence of enhancers by using confocal Raman spectroscopy and molecular dynamics simulation.detailed

Relevant articles and documents

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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 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.