Product Name

  • Name

    VITAMIN A

  • EINECS 200-683-7
  • CAS No. 68-26-8
  • Article Data126
  • CAS DataBase
  • Density 0.954 g/cm3
  • Solubility Practically insoluble inwaterorglycerol; soluble in absolute alcohol,methanol,℃hloroform, ether, fats and oils.
  • Melting Point 63.5 ºC
  • Formula C20H30O
  • Boiling Point 421.2 ºC at 760 mmHg
  • Molecular Weight 286.458
  • Flash Point 147.3 ºC
  • Transport Information UN 1208 3/PG 2
  • Appearance yellow to orange crystalline solid
  • Safety 36/37-61-62
  • Risk Codes R22-38-67-65-62-51/53-48/20-11
  • Molecular Structure Molecular Structure of 68-26-8 (VITAMIN A)
  • Hazard Symbols HarmfulXn,DangerousN,FlammableF
  • Synonyms Retinol,all-trans- (8CI);2,4,6,8-Nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-,(all-E)-;A-Mulsal;A-Vi-Pel;Acon;Agiolan;Alcovit A;Alphalin;Anatola;Anti-Infective vitamin;Aoral;Apostavit;Aquasol A Parenteral;Avibon;Avitol;Axerophthol;Biosterol;Disatabs Tabs;Dofsol;Epiteliol;Lard Factor;NSC 122759;Oleovitamin a;Ophthalamin;PlivitA;Retinol 50C;Tegosphere VitA;Thalasphere;Veroftal;Vi-Dom-A;Vitamin Aalcohol, all-trans-;Vitamin A1 alcohol;Vitamin A1, all-trans-;Vitpex;all-trans-Retinol;all-trans-Vitamin A;all-trans-Vitamin A alcohol;trans-VitaminA alcohol;
  • PSA 20.23000
  • LogP 5.51030

Synthetic route

ethenol
557-75-5

ethenol

(+/-)-7-hydroxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraene-(1.3.5.8)
39668-33-2

(+/-)-7-hydroxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraene-(1.3.5.8)

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With hydrogenchloride In toluene at 50℃; for 1h; Temperature;95%
9-(2,6,6-Trimethyl-cyclohex-1-enyl)-5-phenyl-sulphonyl-3,7-dimethyl-1-acetoxy-nona-2,6,8-triene
50465-60-6

9-(2,6,6-Trimethyl-cyclohex-1-enyl)-5-phenyl-sulphonyl-3,7-dimethyl-1-acetoxy-nona-2,6,8-triene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With sodium ethanolate In ethanol Heating;94%
(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal
3917-41-7

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

(E)-4-chloro-3-methyl-2-buten-1-ol
53170-97-1

(E)-4-chloro-3-methyl-2-buten-1-ol

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: (E)-4-chloro-3-methyl-2-buten-1-ol With triphenylphosphine In methanol at 45℃; for 1h;
Stage #2: (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal With sodium hydroxide In methanol; water at 45℃; for 1h; Reagent/catalyst;
90%
tert-Butyl-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-diphenyl-silane
138922-13-1

tert-Butyl-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-diphenyl-silane

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran84%
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
(E,E)-(5-hydroxy-3-methylpenta-1,3-dienyl)boronic acid
120040-83-7

(E,E)-(5-hydroxy-3-methylpenta-1,3-dienyl)boronic acid

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene
138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); TlOH In tetrahydrofuran for 0.5h; Ambient temperature;83%
(2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol
1430344-83-4

(2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene
138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: (2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.5h; Hiyama Coupling; Inert atmosphere;
Stage #2: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 0 - 25℃; for 3.5h; Hiyama Coupling; Inert atmosphere;
82%
Stage #1: (2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Hiyama Coupling; Inert atmosphere; Darkness;
Stage #2: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran for 1h; Hiyama Coupling; Inert atmosphere; Darkness;
77%
tBDMS-retinol
118353-70-1

tBDMS-retinol

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride80%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Ambient temperature;80%
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
1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene
103905-07-3

1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene

A

2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

C

11-cis-retinol
22737-96-8

11-cis-retinol

D

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h;A n/a
B n/a
C n/a
D 77%
With potassium methanolate In cyclohexane at 38℃; for 2h; Title compound not separated from byproducts;
ethyl (all-E)-retinoate
3899-20-5

ethyl (all-E)-retinoate

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With diisobutylaluminium hydride76%
trans-tetrahydropyran-2-yl retinyl ether
138842-95-2

trans-tetrahydropyran-2-yl retinyl ether

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With methanol; chloro-trimethyl-silane; water In tetrahydrofuran for 0.0833333h;74%
With chloro-trimethyl-silane; water In methanol for 0.166667h; Inert atmosphere;74%
With chloro-trimethyl-silane; water In methanol for 0.166667h;74%
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
formaldehyd
50-00-0

formaldehyd

trimethylaluminum
75-24-1

trimethylaluminum

1-((E,E,E)-3-methyl-1,3,5-octatrien-7-ynyl)-2,6,6-trimethyl-1-cyclohexene
111917-89-6

1-((E,E,E)-3-methyl-1,3,5-octatrien-7-ynyl)-2,6,6-trimethyl-1-cyclohexene

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Multistep reaction.;67%
2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene
138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

(2E,4E)-3-methyl-5-(tri-n-butylstannyl)penta-2,4-dien-1-ol
128426-10-8

(2E,4E)-3-methyl-5-(tri-n-butylstannyl)penta-2,4-dien-1-ol

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With 1-methyl-pyrrolidin-2-one; tris-(dibenzylideneacetone)dipalladium(0); triphenyl-arsane at 25℃; for 0.166667h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere;
Stage #2: (2E,4E)-5-(tri-n-butylstannyl)-3-methylpenta-2,4-dien-1-ol at 25℃; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling); Inert atmosphere;
60%
all-trans-Retinal
116-31-4

all-trans-Retinal

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With diisobutylaluminium hydride
With triethylaluminum
With sodium tetrahydroborate In ethanol Ambient temperature; 2-3 h;
all-trans-methyl retinoate
339-16-2

all-trans-methyl retinoate

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol

benzoyl chloride
98-88-4

benzoyl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol

acetyl chloride
75-36-5

acetyl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol

butyryl chloride
141-75-3

butyryl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol
3230-76-0, 34255-07-7, 60102-36-5, 62653-03-6

(+/-)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2c,4c,7ξ-triene-1,6-diol

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With benzene weiteres Edukt: N.N-Dimethyl-anilin; ueber mehrere Stufen;
With benzene weiteres Edukt: Chinolin; ueber mehrere Stufen;
With benzene weiteres Edukt: Pyridin; ueber mehrere Stufen;
retinoyl fluoride
83802-77-1

retinoyl fluoride

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With lithium aluminium tetrahydride Yield given;
Acetic acid (2Z,6E)-9-benzenesulfonyl-3,7-dimethyl-8-(tetrahydro-pyran-2-yloxy)-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl ester
103905-07-3, 105615-50-7

Acetic acid (2Z,6E)-9-benzenesulfonyl-3,7-dimethyl-8-(tetrahydro-pyran-2-yloxy)-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl ester

A

2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

B

11,13-Di-cis-vitamin A
17706-49-9

11,13-Di-cis-vitamin A

C

(9Z,13Z)-retinol
29444-25-5

(9Z,13Z)-retinol

D

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h; Yield given. Title compound not separated from byproducts;
With potassium methanolate In cyclohexane at 38℃; for 2h; Title compound not separated from byproducts;
1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene
103905-07-3

1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene

B

11-cis-retinol
22737-96-8

11-cis-retinol

C

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h;
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%
RETINOL
68-26-8

RETINOL

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
In toluene at 35℃; for 1h;99%
With pyridine In 1,2-dichloro-ethane
undecanoic acid anhydride
2082-77-1

undecanoic acid anhydride

RETINOL
68-26-8

RETINOL

vitamin-A undecanoate

vitamin-A undecanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;98.73%
RETINOL
68-26-8

RETINOL

propionic acid
802294-64-0

propionic acid

vitamin A Propionate
7069-42-3

vitamin A Propionate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In cyclohexane at 70℃; for 2h;98%
palmitic anhydride
623-65-4

palmitic anhydride

RETINOL
68-26-8

RETINOL

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h; Solvent;97.62%
pentadecanoic acid anhydride
59252-34-5

pentadecanoic acid anhydride

RETINOL
68-26-8

RETINOL

vitamin-A pentadecanoate

vitamin-A pentadecanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;97.48%
RETINOL
68-26-8

RETINOL

myristic anhydride
626-29-9

myristic anhydride

vitamin-A myristate

vitamin-A myristate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;97.09%
tridecanoic acid anhydride
53517-88-7

tridecanoic acid anhydride

RETINOL
68-26-8

RETINOL

vitamin-A tridecanoate

vitamin-A tridecanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;97.01%
RETINOL
68-26-8

RETINOL

bromoacetic acid methyl ester
96-32-2

bromoacetic acid methyl ester

bromoacetic acid retinol ester
81112-43-8

bromoacetic acid retinol ester

Conditions
ConditionsYield
Novozym 435 In toluene at 20℃; for 26h; Inert atmosphere;97%
lauric anhydride
645-66-9

lauric anhydride

RETINOL
68-26-8

RETINOL

Retinyl laurate
1259-24-1

Retinyl laurate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;96.85%
capric anhydride
2082-76-0

capric anhydride

RETINOL
68-26-8

RETINOL

vitamin-A decanoate
79279-28-0

vitamin-A decanoate

Conditions
ConditionsYield
With aluminum oxide In Petroleum ether at 40℃; for 2h;96.73%
hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

RETINOL
68-26-8

RETINOL

retinyl palmitate
79-81-2

retinyl palmitate

Conditions
ConditionsYield
at 60℃; under 0.750075 Torr; for 3h; Temperature; Large scale;94%
retinol anhydride

retinol anhydride

RETINOL
68-26-8

RETINOL

retinoic anhydride
58175-89-6

retinoic anhydride

Conditions
ConditionsYield
With triethylamine In dichloromethane92%
RETINOL
68-26-8

RETINOL

all-trans-retinoic-acid
302-79-4

all-trans-retinoic-acid

Conditions
ConditionsYield
With tris(triphenylphosphine)ruthenium(II) chloride; oxygen; bis-(3-methyl-1-imidazolyl)ethylene tetrafluoroborate In hexane at 50℃; under 760.051 Torr; for 3h; Reagent/catalyst; Darkness;90.2%
Multi-step reaction with 2 steps
1: MnO2 / CH2Cl2 / 2 h / Ambient temperature
2: 80 percent / AgO, NaCN / methanol / 18 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / MnO2 / CH2Cl2 / Ambient temperature
2: AgO / CNNa / methanol
View Scheme
RETINOL
68-26-8

RETINOL

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane Ambient temperature;90%
With manganese(IV) oxide; sodium carbonate In dichloromethane for 4h; Inert atmosphere;90%
With manganese(IV) oxide90%
4-Phenyl-1,2,4-triazolidine-3,5-dione
4233-33-4

4-Phenyl-1,2,4-triazolidine-3,5-dione

RETINOL
68-26-8

RETINOL

5-Hydroxymethyl-6-methyl-8-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
135154-45-9

5-Hydroxymethyl-6-methyl-8-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-2-phenyl-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione

Conditions
ConditionsYield
In dichloromethane at -78℃;90%
RETINOL
68-26-8

RETINOL

4-<2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalyl)ethyl>-1,2,4-triazoline-3,5-dione
132788-52-4

4-<2-(6,7-dimethoxy-4-methyl-3-oxo-3,4-dihydroquinoxalyl)ethyl>-1,2,4-triazoline-3,5-dione

2-[2-(6,7-Dimethoxy-4-methyl-3-oxo-3,4-dihydro-quinoxalin-2-yl)-ethyl]-5-hydroxymethyl-6-methyl-8-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione
135154-50-6

2-[2-(6,7-Dimethoxy-4-methyl-3-oxo-3,4-dihydro-quinoxalin-2-yl)-ethyl]-5-hydroxymethyl-6-methyl-8-[(1E,3E)-2-methyl-4-(2,6,6-trimethyl-cyclohex-1-enyl)-buta-1,3-dienyl]-5,8-dihydro-[1,2,4]triazolo[1,2-a]pyridazine-1,3-dione

Conditions
ConditionsYield
In dichloromethane at -78℃;90%
In dichloromethane at 0℃; for 1h;
RETINOL
68-26-8

RETINOL

A

13-cis-vitamin A aldehyde
472-86-6

13-cis-vitamin A aldehyde

B

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With manganese(IV) oxide In dichloromethane for 12h; Inert atmosphere; Fluorescence light;A 8%
B 90%
poly(methacrylic acid)
79-41-4

poly(methacrylic acid)

RETINOL
68-26-8

RETINOL

vitamin A methacrylate

vitamin A methacrylate

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In Petroleum ether at 50℃;89%
With dicyclohexyl-carbodiimide In Petroleum ether at 50℃;89%
With dicyclohexyl-carbodiimide In Petroleum ether at 50℃;89%
succinic acid anhydride
108-30-5

succinic acid anhydride

RETINOL
68-26-8

RETINOL

retinyl monosuccinate
13241-44-6

retinyl monosuccinate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 12h; Ambient temperature;88%
With dmap In dichloromethane at 20℃;85%
With dmap; triethylamine In dichloromethane at 20℃; for 12h;3.4 g
With 1-pentyl-3-methylimidazolium nitrate at 50℃; for 3h; Darkness; Inert atmosphere; Green chemistry;
RETINOL
68-26-8

RETINOL

pivalaldehyde
630-19-3

pivalaldehyde

A

2,2-dimethyl-propanol-1
75-84-3

2,2-dimethyl-propanol-1

B

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With aluminum isopropoxide In waterA n/a
B 87%
With aluminum isopropoxide In water
2,2-dimethyl-4-pentenal
5497-67-6

2,2-dimethyl-4-pentenal

RETINOL
68-26-8

RETINOL

A

2,2-dimethylpent-4-en-1-ol
3420-42-6

2,2-dimethylpent-4-en-1-ol

B

all-trans-Retinal
116-31-4

all-trans-Retinal

Conditions
ConditionsYield
With aluminum isopropoxide In waterA n/a
B 87%
triphenylphosphine hydrobromide
6399-81-1

triphenylphosphine hydrobromide

RETINOL
68-26-8

RETINOL

Conditions
ConditionsYield
In methanol at 20℃; for 1h;86%

Retinol Chemical Properties

The Molecular Structure of Vitamin A (CAS NO.68-26-8):

Empirical Formula: C20H30O
Molecular Weight: 286.4516 
IUPAC Name: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol 
Appearance: Yellow-Orange Powder
Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;Intracellular receptor
Nominal Mass: 286
Average Mass: 286.4516 
Monoisotopic Mass: 286.229666
Index of Refraction: 1.549
Molar Refractivity: 95.49 cm3
Molar Volume: 300 cm3
Surface Tension: 36.6 dyne/cm
Density: 0.954 g/cm3
Flash Point: 147.3 °C
Enthalpy of Vaporization: 77.99 kJ/mol
Boiling Point: 421.2 °C at 760 mmHg
Vapour Pressure: 7.35E-09 mmHg at 25°C 
Stability: Stable, but light and air sensitive. Incompatible with strong acids, strong oxidizing agents
InChI: InChI=1/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
Smiles: C=1(C(CCCC1C)(C)C)\C=C\C(=C\C=C\C(=C\CO)C)C 
Melting Point: 63.5 °C
log P (octanol-water): 5.68  
Water Solubility: 0.671 mg/L at 25 °C 
Henry's Law Constant: 1.16E-04 atm-m3/mole at 25 °C 
Atmospheric OH Rate Constant: 4.00E-10 cm3/molecule-sec at 25 °C 

Retinol History

  Vitamin A (CAS NO.68-26-8) was first synthesized in 1947 by two Dutch chemists, David Adriaan van Dorp and Jozef Ferdinand Arens. The discovery of vitamin A may have stemmed from research dating back to 1906, indicating that factors other than carbohydrates, proteins, and fats were necessary to keep cattle healthy.By 1917 one of these substances was independently discovered by Elmer McCollum at the University of Wisconsin-Madison, and Lafayette Mendel and Thomas Burr Osborne at Yale University. Since "water-soluble factor B" ( Vitamin B ) had recently been discovered, the researchers chose the name "fat-soluble factor A" (vitamin A).

Retinol Uses

 Vitamin A (CAS NO.68-26-8) is important in vision and bone growth,and appears to function in maintaining normal skin health.It is used in medicine and feed industry.

Retinol Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 912ku/kg/2Y-I (912000iu/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LIVER: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
New England Journal of Medicine. Vol. 294, Pg. 805, 1976.
child TDLo oral 5475ku/kg/1Y- (5475000iu/kg) LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION

GASTROINTESTINAL: OTHER CHANGES

MUSCULOSKELETAL: OTHER CHANGES
Clinical Pediatrics Vol. 21, Pg. 435, 1982.
infant LDLo oral 442ku/kg/11D- (442000iu/kg) BEHAVIORAL: ANOREXIA (HUMAN

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Archives of Pathology and Laboratory Medicine. Vol. 108, Pg. 838, 1984.
man TDLo oral 1217ku/kg/1Y- (1217000iu/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"

BLOOD: HEMORRHAGE

BLOOD: CHANGES IN SPLEEN
Liver Annual. Vol. 12, Pg. 381, 1992.
mouse LD50 intraperitoneal 1510mg/kg (1510mg/kg)   Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982.
mouse LD50 oral 1510mg/kg (1510mg/kg)   "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984.
rat LD50 oral 2gm/kg (2000mg/kg)   Acta Dermato-Venereologica, Supplementum. Vol. 74, Pg. 29, 1975.
women TDLo oral 91000iu/kg/26 (91000iu/kg) BEHAVIORAL: ANOREXIA (HUMAN

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Medicine. Vol. 97, Pg. 523, 1994.

Retinol Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Retinol Safety Profile

Moderately toxic by ingestion. Human teratogenic effects by ingestion: developmental abnormalities of the craniofacial area and urogenital system. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: HarmfulXnDangerousNFlammableF
Risk Statements: 22-38-67-65-62-51/53-48/20-11 
R22: Harmful if swallowed
R38: Irritating to skin
R67: Vapours may cause drowsiness and dizziness
R65: Harmful: may cause lung damage if swallowed
R62: Risk of impaired fertility
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
R48/20: Harmful: danger of serious damage to health by prolonged exposure through inhalation
R11: Highly flammable
Safety Statements: 36/37-61-62 
S36/37: Wear suitable protective clothing and gloves
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
S62: If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label
RIDADR: UN 1208 3/PG 2
WGK Germany: 3
RTECS: VH6750000
F: 8-10-16-23 
F 8: Photosensitive
F 10: Keep under argon
F 16: Decomposes easily
F 23: Sensitive to air

Retinol Specification

 Vitamin A (CAS NO.68-26-8) is also called as Retinol [INN:BAN] ; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol ; 2,4,6,8-Nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- ; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclchexen-1-yl)-2,4,6,8-nonatetraen-1-ol ; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)- ; A-Mulsal ; A-Sol ; A-Vi-Pel ; A-Vitan ; ACON ; ATAV ; Afaxin ; Agiolan ; Agoncal ; Alcovit A ; All-trans retinol ; Alphalin ; Alphasterol ; Anatola ; Anatola A ; Anti-infective vitamin ; Antixerophthalmic vitamin ; Antixerophthalmisches Vitamin ; Aoral ; Apexol ; Apostavit ; Aquasol A ; Aquasynth ; Atars ; Avibon ; Avita ; Avitol ; Axerol ; Axerophthol ; Axerophtholum ; BRN 0403040 ; Bentavit A ; Biosterol ; Chocola A ; Del-VI-A ; Disatabs Tabs ; Dofsol ; Dohyfral A ; EINECS 200-683-7 ; Epiteliol ; HI-A-Vita ; HSDB 815 ; Homagenets Aoral ; Lard factor ; Myvpack ; NSC 122759 ; Nio-A-let ; Oleovitamin A ; Ophthalamin ; Plivit A ; Prepalin ; Retinol ; Retinol, all trans- ; Retinolo ; Retinolo [DCIT] ; Retinolum ; Retinolum [INN-Latin] ; Retrovitamin A ; Sehkraft A ; Solu-A ; Super A ; Testavol ; Testavol S ; UNII-81G40H8B0T ; UNII-G2SH0XKK91 ; VI-alpha ; Vaflol ; Vafol ; Veroftal ; Vi-Dom-A ; Vi-alpha ; Vi-alpha; Vi-alpha ; Vio-A ; Vitamin A alcohol (VAN) ; Vitamin A alcohol, all-trans- ; Vitamin A1 ; Vitamin A1 alcohol ; Vitamin A1 alcohol, all trans ; Vitamin A1, all-trans- ; Wachstumsvitamin ; all-trans-Retinol ; all-trans-Retinyl alcohol ; all-trans-Vitamin A ; all-trans-Vitamin A alcohol ; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonate-traen-1-ol ; Alcohol 9,13-dimethyl-7-(1,1,5-trimethyl-6-cyclohexen-5-yl)-7,9,11,13-nonatetraen-15-ol  .

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