Product Name

  • Name

    Retinyl acetate

  • EINECS 204-844-2
  • CAS No. 127-47-9
  • Article Data79
  • CAS DataBase
  • Density 0.968 g/cm3
  • Solubility soluble in water
  • Melting Point 57-58 ºC
  • Formula C22H32O2
  • Boiling Point 440.5 ºC at 760 mmHg
  • Molecular Weight 328.495
  • Flash Point 124.8 ºC
  • Transport Information
  • Appearance crystalline
  • Safety 36/37-45-37/39-26
  • Risk Codes 38-63-36/37/38
  • Molecular Structure Molecular Structure of 127-47-9 (Retinyl acetate)
  • Hazard Symbols HarmfulXn,IrritantXi
  • Synonyms Retinol,acetate, all-trans- (8CI);Myvak;Myvax;Vitamin A acetate;Vitamin A1 acetate;all-trans-Retinol acetate;all-trans-Retinyl acetate;all-trans-Vitamin Aacetate;trans-Retinol acetate;trans-Retinyl acetate;
  • PSA 26.30000
  • LogP 6.08110

Synthetic route

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%
(2Z,4Z)-3,7-dimethyl-6-hydroxy-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-nona-2,4,6,8-tetraenyl acetate

(2Z,4Z)-3,7-dimethyl-6-hydroxy-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-nona-2,4,6,8-tetraenyl acetate

argon

argon

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
In N-methyl-acetamide95.8%
In N-methyl-acetamide94.1%
In N-methyl-acetamide93.9%
phosphorus pentaoxide
337913-25-4

phosphorus pentaoxide

(2Z,4Z)-3,7-dimethyl-6-hydroxy-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-nona-2,4,6,8-tetraenyl acetate

(2Z,4Z)-3,7-dimethyl-6-hydroxy-9-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)-nona-2,4,6,8-tetraenyl acetate

argon

argon

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
In N-methyl-acetamide94.9%
(+/-)-(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

(+/-)-(E,E,E)-9-(acetyloxy)-3,7-dimethyl-1-<2,6,6-trimethyl-1-cyclohexen-1-yl>-1,5,7-nonatrien-4-one

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

Tetraethyl methylenediphosphonate

(E)-4-acetoxy-2-methylcrotonaldehyde
26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

(E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal
14398-40-4

(E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

3-methyl-4-oxobut-2-enyl acetate

β-Jonylidenaethyl-triphenyl-phosphonium-chlorid
1062-12-0

β-Jonylidenaethyl-triphenyl-phosphonium-chlorid

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

(E)-4-acetoxy-2-methylcrotonaldehyde

[(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

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

(E)-4-acetoxy-2-methylcrotonaldehyde

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

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

1-acetoxy-5.9-dibensenesulfonyl-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6-nonadiene

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 15h; Heating;82%
(E)-4-acetoxy-2-methylcrotonaldehyde
26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

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

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

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With ammonia In water at 50℃; for 0.5h; Product distribution / selectivity; Wittig Reaction;77%
Conditions
ConditionsYield
With erythrosine B In methanol; n-heptane at 15℃; for 4h; Irradiation;76.8%
7,8-dihydroretinyl acetate

7,8-dihydroretinyl acetate

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

acetyl chloride

1,3,3-trimethyl-2-[(2E,4E,6E)-3,7-dimethyl-2,4,6,8-nonatetraenyl]cyclohexene
388075-89-6

1,3,3-trimethyl-2-[(2E,4E,6E)-3,7-dimethyl-2,4,6,8-nonatetraenyl]cyclohexene

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

(2E,6E,8E)-4-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,6,8-nonatrienyl acetate

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With 2,6-dichloro-benzonitrile In hexane at 25℃; for 6h;31%
(E)-4-acetoxy-2-methylcrotonaldehyde
26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,diethyl ester
128759-88-6

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

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With dimethyl sulfoxide In tetrahydrofuran; hexane; water7.1%
In di-isopropyl ether; water7.9%
In N-methyl-acetamide; water; toluene7%
3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,dimethyl ester

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

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

(E)-4-acetoxy-2-methylcrotonaldehyde
26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,diethyl ester
128759-88-6

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

sodium t-butanolate
865-48-5

sodium t-butanolate

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
In N-methyl-acetamide; toluene6.9%
pyridine
110-86-1

pyridine

RETINOL
68-26-8

RETINOL

acetyl chloride
75-36-5

acetyl chloride

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With 1,2-dichloro-ethane
With diethyl ether
3-methyl-4-oxobut-2-enyl acetate
14918-80-0

3-methyl-4-oxobut-2-enyl acetate

1,5,5-trimethyl-6-(3-methyl-penta-2,4-dienylidene)-cyclohexene
55497-46-6

1,5,5-trimethyl-6-(3-methyl-penta-2,4-dienylidene)-cyclohexene

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With triphenylphosphine hydrochloride
acetic anhydride
108-24-7

acetic anhydride

1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene
105096-76-2

1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene

A

Retinol acetate
127-47-9

Retinol acetate

B

9-cis-Vitamin-A-acetat
29584-22-3

9-cis-Vitamin-A-acetat

C

11-cis-Vitamin-A-acetat
29443-87-6

11-cis-Vitamin-A-acetat

D

(7E,9E,11E,13Z)-retinyl acetate
34356-31-5

(7E,9E,11E,13Z)-retinyl acetate

Conditions
ConditionsYield
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

acetic anhydride

1-acetoxy-6-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene
103905-08-4

1-acetoxy-6-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene

A

Retinol acetate
127-47-9

Retinol acetate

C

(7E,9E,11E,13Z)-retinyl acetate
34356-31-5

(7E,9E,11E,13Z)-retinyl acetate

Conditions
ConditionsYield
With potassium methanolate; triethylamine 1.) cyclohexane, 38 deg C, 2 h, 2.) hexane; Yield given. Multistep reaction;
acetic anhydride
108-24-7

acetic anhydride

1-acetoxy-6-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene
103905-09-5

1-acetoxy-6-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene

A

Retinol acetate
127-47-9

Retinol acetate

B

9-cis-Vitamin-A-acetat
29584-22-3

9-cis-Vitamin-A-acetat

C

11-cis-Vitamin-A-acetat
29443-87-6

11-cis-Vitamin-A-acetat

D

(7E,9E,11E,13Z)-retinyl acetate
34356-31-5

(7E,9E,11E,13Z)-retinyl acetate

Conditions
ConditionsYield
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

10,15-dihydroxy-9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohex-6-enyl)-8,11,13-nonatriene

A

Retinol acetate
127-47-9

Retinol acetate

B

(7E,9E,11E,13Z)-retinyl acetate
34356-31-5

(7E,9E,11E,13Z)-retinyl acetate

C

(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

(3E,5E,7E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-triene-1,2-diol

D

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 (2Z,4Z,6E)-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienyl ester

E

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,5Z,7Z)-2-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester

F

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,5E,7E)-2-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester

Conditions
ConditionsYield
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

Acetic acid (2Z,4Z,6E)-8-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienyl ester

A

Retinol acetate
127-47-9

Retinol acetate

B

(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

(3E,5E,7E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-triene-1,2-diol

C

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 (2Z,4Z,6E)-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienyl ester

D

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,5E,7E)-2-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester

E

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,5Z,7Z)-2-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester

F

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

Acetic acid (3E,5E,7E)-2-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trienyl ester

Conditions
ConditionsYield
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

1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene

A

Retinol acetate
127-47-9

Retinol acetate

B

9-cis-Vitamin-A-acetat
29584-22-3

9-cis-Vitamin-A-acetat

C

11-cis-Vitamin-A-acetat
29443-87-6

11-cis-Vitamin-A-acetat

D

(7E,9E,11E,13Z)-retinyl acetate
34356-31-5

(7E,9E,11E,13Z)-retinyl acetate

Conditions
ConditionsYield
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)

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

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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

3,7-dimethyl-9-<2,6,6-trimethyl-cyclohex-1-enyl>-nona-2c,4c,7ξ-triene-1,6-diol

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
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-4-oxobut-2-enyl acetate

3-methyl-5t-<2,6,6-trimethyl-cyclohex-1-enyl>-penta-2t,4-dien-1-ol

3-methyl-5t-<2,6,6-trimethyl-cyclohex-1-enyl>-penta-2t,4-dien-1-ol

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
With triphenylphosphine hydrochloride
pyridine
110-86-1

pyridine

(+/-)-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

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

toluene
108-88-3

toluene

Retinol acetate
127-47-9

Retinol acetate

Conditions
ConditionsYield
at 90 - 95℃;
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%
Retinol acetate
127-47-9

Retinol acetate

beta-carotene
7235-40-7

beta-carotene

Conditions
ConditionsYield
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 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
Retinol acetate
127-47-9

Retinol acetate

9-cis-Vitamin-A-acetat
29584-22-3

9-cis-Vitamin-A-acetat

Conditions
ConditionsYield
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

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
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
Retinol acetate
127-47-9

Retinol acetate

A

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 (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

B

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

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
ConditionsYield
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

Retinol acetate

A

Hexahydrovitamin A acetate
113563-63-6

Hexahydrovitamin A acetate

B

9,13-Dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,13-nonadien-15-ol acetate
113563-62-5

9,13-Dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,13-nonadien-15-ol acetate

Conditions
ConditionsYield
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

ethyl 4-pentenoate

Retinol acetate
127-47-9

Retinol acetate

A

(1E,3E)-3-methyl-1-[2,6,6-trimethylcyclohex-1-enyl]hexa-1,3,5-triene
43219-55-2

(1E,3E)-3-methyl-1-[2,6,6-trimethylcyclohex-1-enyl]hexa-1,3,5-triene

B

ethyl (11Z)-13-nor-13,14-dihydroretinoate

ethyl (11Z)-13-nor-13,14-dihydroretinoate

C

ethyl (11E)-13-nor-13,14-dihydroretinoate
1332483-21-2

ethyl (11E)-13-nor-13,14-dihydroretinoate

Conditions
ConditionsYield
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

Retinol acetate

(2E,4EZ)-N-(4-hexyloxyphenyl)-3-methylhexa-2,4-dienamide
1332483-19-8

(2E,4EZ)-N-(4-hexyloxyphenyl)-3-methylhexa-2,4-dienamide

N-(4-hexyloxyphenyl)retinamide
1332483-22-3

N-(4-hexyloxyphenyl)retinamide

Conditions
ConditionsYield
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

Retinol acetate

(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

(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-amine

Conditions
ConditionsYield
Stage #1: Retinol acetate With sodium hydroxide
Stage #2: With manganese(IV) oxide In hexane Further stages;
23.5%
Retinol acetate
127-47-9

Retinol acetate

N-(4-hydroxyphenyl)sorbamide

N-(4-hydroxyphenyl)sorbamide

N-(4-hydroxyphenyl)-13-apo-β-caroten-13-amide
1332483-33-6

N-(4-hydroxyphenyl)-13-apo-β-caroten-13-amide

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

Retinyl acetate Chemical Properties


IUPAC Name: [(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate
Molecular Formula: C22H32O2
Molecular Weight: 328.49 g/mol
SMILES: O=C(OCC=C(C=CC=C(C=C/C1=C(/CCCC1(C)C)C)C)C)C Copy 
InChI: InChI=1/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3
EINECS: 204-844-2
Classification Code: Adjuvants, immunologic; Anticarcinogenic agents; Antineoplastic Agents; Immunologic Factors; Mutation data; Protective Agents; Reproductive Effect; Tumor data
Melting Point: 57-58 °C
storage temperature: 2-8 °C
solubility: absolute ethanol: 25 mg/mL
Water Solubility: soluble
Index of Refraction: 1.531 
Molar Refractivity: 105 cm3 
Molar Volume: 339 cm 
Surface Tension: 35.3 dyne/cm 
Density: 0.968 g/cm3 
Flash Point: 124.8 °C 
Enthalpy of Vaporization: 69.76 kJ/mol 
Boiling Point: 440.5 °C at 760 mmHg 
Vapour Pressure of Retinyl acetate (CAS NO.127-47-9): 5.86E-08 mmHg at 25 °C

Retinyl acetate Uses

 Retinyl acetate (CAS NO.127-47-9) is used for vitamin A deficiency.

Retinyl acetate Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intravenous 432mg/kg (432mg/kg)   United States Patent Document. Vol. #3878202,
mouse LD50 oral 4100mg/kg (4100mg/kg)   Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982.

Retinyl acetate Safety Profile

Hazard Codes: HarmfulXn,IrritantXi
Risk Statements: 38-63-36/37/38 
R38:Irritating to skin. 
R63:Possible risk of harm to the unborn child. 
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 36/37-45-37/39-26 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S37/39:Wear suitable gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 2
RTECS of Retinyl acetate (CAS NO.127-47-9): VH6825000

Retinyl acetate Specification

 Retinyl acetate (CAS NO.127-47-9), its Synonyms are Acetic acid, retinyl ester ; Vitamin A acetate ; Retinol, acetate, all-trans- ; Vitamin A alcohol acetate ; Vitamin A ester ; Vitamin A1 acetate ; Retinol, acetate, all-trans- (8CI) ; all-trans-Retinylacetate ; all-trans-Vitamin A acetate . It is crystalline.

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