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Retinyl acetate
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Name

Retinyl acetate

 EINECS 204-844-2
CAS No. 127-47-9 Density 0.968 g/cm3
PSA 26.30000 LogP 6.08110
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 N/A 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;

Article Data 79

Retinyl acetate Synthetic route

108-24-7

acetic anhydride

68-26-8

RETINOL

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

argon

127-47-9

Retinol acetate

Conditions
ConditionsYield
In N-methyl-acetamide95.8%
In N-methyl-acetamide94.1%
In N-methyl-acetamide93.9%
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

argon

127-47-9

Retinol acetate

Conditions
ConditionsYield
In N-methyl-acetamide94.9%
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

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%
1660-94-2

Tetraethyl methylenediphosphonate

26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

14398-40-4

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

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%
14918-80-0

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

1062-12-0

β-Jonylidenaethyl-triphenyl-phosphonium-chlorid

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%
26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

53282-28-3

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

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%
26586-02-7

(E)-4-acetoxy-2-methylcrotonaldehyde

62285-98-7

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

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%
475558-35-1

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

127-47-9

Retinol acetate

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

127-47-9

Retinol acetate

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

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 cm3  
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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