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| CAS No.: | 127-47-9 |
|---|---|
| Name: | Retinyl acetate |
| Article Data: | 79 |
| Molecular Structure: | |
|
|
|
| Formula: | C22H32O2 |
| Molecular Weight: | 328.495 |
| 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; |
| EINECS: | 204-844-2 |
| Density: | 0.968 g/cm3 |
| Melting Point: | 57-58 ºC |
| Boiling Point: | 440.5 ºC at 760 mmHg |
| Flash Point: | 124.8 ºC |
| Solubility: | soluble in water |
| Appearance: | crystalline |
| Hazard Symbols: |
 Xn, Xi
|
| Risk Codes: | 38-63-36/37/38 |
| Safety: | 36/37-45-37/39-26 |
| PSA: | 26.30000 |
| LogP: | 6.08110 |
| 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% |
Retinol acetate
| Conditions | Yield |
|---|---|
| In N-methyl-acetamide | 95.8% |
| In N-methyl-acetamide | 94.1% |
| In N-methyl-acetamide | 93.9% |
| 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
Retinol acetate
| 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
(E)-4-acetoxy-2-methylcrotonaldehyde
(E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)-2-butenal
Retinol acetate
| 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
β-Jonylidenaethyl-triphenyl-phosphonium-chlorid
Retinol acetate
| 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
[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride
Retinol acetate
| 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
5-(2,6,6-trimethylcyclohexenyl)-3-methyl-2,4-pentadienyltriphenylphosphonium bromide
Retinol acetate
| 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
Retinol acetate
| Conditions | Yield |
|---|---|
| With sodium hydroxide In ethanol for 15h; Heating; | 82% |
| Conditions | Yield |
|---|---|
| With ammonia In water at 50℃; for 0.5h; Product distribution / selectivity; Wittig Reaction; | 77% |
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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 (CAS NO.127-47-9) is used for vitamin A deficiency.
| 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. |
Hazard Codes: 
Xn,
Xi
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 (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.
