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% |
Retinol acetate
Conditions | Yield |
---|---|
With erythrosine B In methanol; n-heptane at 15℃; for 4h; Irradiation; | 76.8% |
Retinol acetate
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
1,3,3-trimethyl-2-[(2E,4E,6E)-3,7-dimethyl-2,4,6,8-nonatetraenyl]cyclohexene
Retinol acetate
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
Retinol acetate
Conditions | Yield |
---|---|
With 2,6-dichloro-benzonitrile In hexane at 25℃; for 6h; | 31% |
(E)-4-acetoxy-2-methylcrotonaldehyde
3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,diethyl ester
Retinol acetate
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% |
(E)-4-acetoxy-2-methylcrotonaldehyde
3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienylphosphonic acid,diethyl ester
sodium t-butanolate
Retinol acetate
Conditions | Yield |
---|---|
In N-methyl-acetamide; toluene | 6.9% |
Conditions | Yield |
---|---|
With 1,2-dichloro-ethane | |
With diethyl ether |
3-methyl-4-oxobut-2-enyl acetate
1,5,5-trimethyl-6-(3-methyl-penta-2,4-dienylidene)-cyclohexene
Retinol acetate
Conditions | Yield |
---|---|
With triphenylphosphine hydrochloride |
acetic anhydride
1-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-phenylsulfonyl-2,6,8-nonatriene
A
Retinol acetate
B
9-cis-Vitamin-A-acetat
C
11-cis-Vitamin-A-acetat
D
(7E,9E,11E,13Z)-retinyl acetate
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
1-acetoxy-6-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene
A
Retinol acetate
C
(7E,9E,11E,13Z)-retinyl acetate
Conditions | Yield |
---|---|
With potassium methanolate; triethylamine 1.) cyclohexane, 38 deg C, 2 h, 2.) hexane; Yield given. Multistep reaction; |
acetic anhydride
1-acetoxy-6-bromo-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene
A
Retinol acetate
B
9-cis-Vitamin-A-acetat
C
11-cis-Vitamin-A-acetat
D
(7E,9E,11E,13Z)-retinyl acetate
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
A
Retinol acetate
B
(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
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
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
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
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
A
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
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
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
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
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
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
A
Retinol acetate
B
9-cis-Vitamin-A-acetat
C
11-cis-Vitamin-A-acetat
D
(7E,9E,11E,13Z)-retinyl acetate
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane at 38℃; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Retinol acetate
Conditions | Yield |
---|---|
With iodine; Petroleum ether; Tocopherol bei Siedetemperatur; | |
With pyridine; toluene; trichlorophosphate at 90 - 95℃; Durchleiten von Stickstoff; |
Retinol acetate
Conditions | Yield |
---|---|
Acetylierung und aufeinanderfolgendes Behandeln mit HCl und mit NaHCO3 ; | |
Acetylierung und aufeinanderfolgendes Behandeln mit HCl und mit NaHCO3 ; |
Conditions | Yield |
---|---|
With triphenylphosphine hydrochloride |
pyridine
(+/-)-9-acetoxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatrien-(2ξ.5c.7c)-ol-(4)
toluene
trichlorophosphate
Retinol acetate
Conditions | Yield |
---|---|
at 90 - 95℃; |
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 55℃; under 11.2511 - 16.5017 Torr; for 3h; Concentration; Pressure; Large scale; | 96% |
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% |
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
9-cis-Vitamin-A-acetat
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
1-hexadecylcarboxylic acid
A
retinyl palmitate
B
RETINOL
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 |
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 |
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
Retinol acetate
A
retinyl stearate
B
RETINOL
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
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
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
A
Hexahydrovitamin A acetate
B
9,13-Dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-8,13-nonadien-15-ol acetate
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
Retinol acetate
A
(1E,3E)-3-methyl-1-[2,6,6-trimethylcyclohex-1-enyl]hexa-1,3,5-triene
C
ethyl (11E)-13-nor-13,14-dihydroretinoate
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
(2E,4EZ)-N-(4-hexyloxyphenyl)-3-methylhexa-2,4-dienamide
N-(4-hexyloxyphenyl)retinamide
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
(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 | Yield |
---|---|
Stage #1: Retinol acetate With sodium hydroxide Stage #2: With manganese(IV) oxide In hexane Further stages; | 23.5% |
Retinol acetate
N-(4-hydroxyphenyl)-13-apo-β-caroten-13-amide
Conditions | Yield |
---|---|
With Hoveyda-Grubbs catalyst second generation In toluene at 20℃; Inert atmosphere; optical yield given as %de; diastereoselective reaction; | 13% |
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.
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