Product Name

  • Name

    13-CIS-RETINOL

  • EINECS
  • CAS No. 2052-63-3
  • Article Data30
  • CAS DataBase
  • Density 0.954 g/cm3
  • Solubility
  • Melting Point 58-60°
  • Formula C20H30O
  • Boiling Point 421.2 °C at 760 mmHg
  • Molecular Weight 286.458
  • Flash Point 147.3 °C
  • Transport Information
  • Appearance
  • Safety 22-36/37
  • Risk Codes 38
  • Molecular Structure Molecular Structure of 2052-63-3 (13-CIS-RETINOL)
  • Hazard Symbols Xi
  • Synonyms (13Z)-Retinol;13-cis-Retinol;13-cis-Vitamin A;Neovitamin A;Neovitamin A1;neo-Retinol;
  • PSA 20.23000
  • LogP 5.51030

Synthetic route

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

B

9-cis-retinol
68-26-8, 2052-63-3, 6018-74-2, 17706-49-9, 22737-96-8, 29444-25-5, 34218-73-0, 39815-04-8, 69686-68-6, 69686-69-7, 74743-94-5, 84415-27-0, 84415-28-1, 85354-09-2, 85354-10-5, 93380-02-0, 98462-62-5, 137121-52-9, 22737-97-9

9-cis-retinol

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;
...Expand
9-(2',6',6'-trimethylcyclohex-1'-enyl)-8-acetoxy-3,7-dimethyl-9-(p-tolylsulfonyl)nona-2Z,4E,6E-trien-1-ol
181053-77-0

9-(2',6',6'-trimethylcyclohex-1'-enyl)-8-acetoxy-3,7-dimethyl-9-(p-tolylsulfonyl)nona-2Z,4E,6E-trien-1-ol

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

2-cis-Vitamin-A

Conditions
ConditionsYield
With methanol; potassium dihydrogenphosphate; sodium amalgam In diethyl ether for 0.5h; Ambient temperature;63%
With potassium dihydrogenphosphate; sodium amalgam In diethyl ether; ethanol at 20℃; for 0.5h;63%
(2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
16760-45-5

(2Z,4E,6E,8E)-methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
With lithium aluminium tetrahydride; diethyl ether at -50℃;
triethylsilyl ether of 13-cis-retinol
118304-60-2

triethylsilyl ether of 13-cis-retinol

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

2-cis-Vitamin-A

Conditions
ConditionsYield
With pyridine hydrogenfluoride; sodium fluoride Ambient temperature; Yield given;
With pyridine hydrogenfluoride; sodium fluoride In tetrahydrofuran; acetonitrile for 5h; Ambient temperature;
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

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

2-cis-Vitamin-A

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h;
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;
...Expand
O-all-trans-retinol

O-all-trans-retinol

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

2-cis-Vitamin-A

Conditions
ConditionsYield
With iodine; benzene Einwirkung von Tageslicht;
ethyl (2E,4E,6Z)-8-hydroxy-2,6-dimethylocta-2,4,6-trienoate
181053-78-1

ethyl (2E,4E,6Z)-8-hydroxy-2,6-dimethylocta-2,4,6-trienoate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 98 percent / imidazole / dimethylformamide / 1 h / 20 °C
2.1: 96 percent / LiAlH4; AlCl3 / diethyl ether / 3 h / 0 °C
3.1: 100 percent / MnO2 / hexane; CHCl3 / 12 h / 20 °C
4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
4.2: tetrahydrofuran; hexane / 3 h / -78 °C
5.1: 118.2 mg / tetrahydrofuran; hexane / -78 - 20 °C
6.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
7.1: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1: 98 percent
2: 96 percent / AlCl3, LiAlH4
3: 100 percent / MnO2
4: 1.) nBuLi
5: n-Bu4NF
6: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
ethyl (2E,4E,6Z)-8-tert-butyldimethylsiloxy-2,6-dimethylocta-2,4,6-trienoate
181053-73-6

ethyl (2E,4E,6Z)-8-tert-butyldimethylsiloxy-2,6-dimethylocta-2,4,6-trienoate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C
2.1: 98 percent / imidazole / dimethylformamide / 1 h / 20 °C
3.1: 96 percent / LiAlH4; AlCl3 / diethyl ether / 3 h / 0 °C
4.1: 100 percent / MnO2 / hexane; CHCl3 / 12 h / 20 °C
5.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
5.2: tetrahydrofuran; hexane / 3 h / -78 °C
6.1: 118.2 mg / tetrahydrofuran; hexane / -78 - 20 °C
7.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
8.1: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
(3E,6Z)-8-(tert-Butyl-dimethyl-silanyloxy)-2-(N,N-dimethyl-aminooxy)-2,6-dimethyl-octa-3,6-dienoic acid ethyl ester
181053-74-7

(3E,6Z)-8-(tert-Butyl-dimethyl-silanyloxy)-2-(N,N-dimethyl-aminooxy)-2,6-dimethyl-octa-3,6-dienoic acid ethyl ester

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1.1: methanol / 72 h / 20 °C
2.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C
3.1: 98 percent / imidazole / dimethylformamide / 1 h / 20 °C
4.1: 96 percent / LiAlH4; AlCl3 / diethyl ether / 3 h / 0 °C
5.1: 100 percent / MnO2 / hexane; CHCl3 / 12 h / 20 °C
6.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
6.2: tetrahydrofuran; hexane / 3 h / -78 °C
7.1: 118.2 mg / tetrahydrofuran; hexane / -78 - 20 °C
8.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
9.1: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
(2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trien-1-ol
181053-80-5

(2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trien-1-ol

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: 100 percent / MnO2 / hexane; CHCl3 / 12 h / 20 °C
2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
2.2: tetrahydrofuran; hexane / 3 h / -78 °C
3.1: 118.2 mg / tetrahydrofuran; hexane / -78 - 20 °C
4.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
5.1: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: 100 percent / MnO2
2: 1.) nBuLi
3: n-Bu4NF
4: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
(2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trienal
181053-76-9

(2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trienal

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
1.2: tetrahydrofuran; hexane / 3 h / -78 °C
2.1: 118.2 mg / tetrahydrofuran; hexane / -78 - 20 °C
3.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
4.1: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 1.) nBuLi
2: n-Bu4NF
3: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
ethyl (2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trienoate
181053-79-2

ethyl (2E,4E,6Z)-8-tert-butyldiphenylsiloxy-2,6-dimethylocta-2,4,6-trienoate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 96 percent / LiAlH4; AlCl3 / diethyl ether / 3 h / 0 °C
2.1: 100 percent / MnO2 / hexane; CHCl3 / 12 h / 20 °C
3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C
3.2: tetrahydrofuran; hexane / 3 h / -78 °C
4.1: 118.2 mg / tetrahydrofuran; hexane / -78 - 20 °C
5.1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
6.1: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: 96 percent / AlCl3, LiAlH4
2: 100 percent / MnO2
3: 1.) nBuLi
4: n-Bu4NF
5: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
9-(2',6',6'-trimethylcyclohex-1'-enyl)-8-acetoxy-1-tert-butyldiphenylsiloxy-3,7-dimethyl-9-(p-tolylsulfonyl)nona-2Z,4E,6E-triene
463302-50-3

9-(2',6',6'-trimethylcyclohex-1'-enyl)-8-acetoxy-1-tert-butyldiphenylsiloxy-3,7-dimethyl-9-(p-tolylsulfonyl)nona-2Z,4E,6E-triene

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
2: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: n-Bu4NF
2: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
(3E,5E,7Z)-9-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-1-(toluene-4-sulfonyl)-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trien-2-ol

(3E,5E,7Z)-9-(tert-Butyl-diphenyl-silanyloxy)-3,7-dimethyl-1-(toluene-4-sulfonyl)-1-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-3,5,7-trien-2-ol

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 118.2 mg / tetrahydrofuran; hexane / -78 - 20 °C
2: 99 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C
3: 63 percent / KH2PO4; Na/Hg / ethanol; diethyl ether / 0.5 h / 20 °C
View Scheme
β-cyclogeranyl p-tolyl sulfone

β-cyclogeranyl p-tolyl sulfone

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) nBuLi
2: n-Bu4NF
3: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
C20H39NO4Si
181053-72-5

C20H39NO4Si

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / n-Bu4NF
2: 98 percent
3: 96 percent / AlCl3, LiAlH4
4: 100 percent / MnO2
5: 1.) nBuLi
6: n-Bu4NF
7: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
[(2E)-3-ethoxycarbonylbut-2-enyl][1-isopropenyl-2-(tert-butyldimethylsiloxy)ethyl]dimethylammonium bromide

[(2E)-3-ethoxycarbonylbut-2-enyl][1-isopropenyl-2-(tert-butyldimethylsiloxy)ethyl]dimethylammonium bromide

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: KOEt / ethanol / 5 h / -70 °C
2: peracetic acid, Na2CO3 / CH2Cl2 / -60 °C
3: 100 percent / n-Bu4NF
4: 98 percent
5: 96 percent / AlCl3, LiAlH4
6: 100 percent / MnO2
7: 1.) nBuLi
8: n-Bu4NF
9: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
(2E,6Z)-8-(tert-Butyl-dimethyl-silanyloxy)-4-dimethylamino-2,6-dimethyl-octa-2,6-dienoic acid ethyl ester
181053-71-4

(2E,6Z)-8-(tert-Butyl-dimethyl-silanyloxy)-4-dimethylamino-2,6-dimethyl-octa-2,6-dienoic acid ethyl ester

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: peracetic acid, Na2CO3 / CH2Cl2 / -60 °C
2: 100 percent / n-Bu4NF
3: 98 percent
4: 96 percent / AlCl3, LiAlH4
5: 100 percent / MnO2
6: 1.) nBuLi
7: n-Bu4NF
8: 63 percent / Na/Hg, KH2PO4, MeOH / diethyl ether / 0.5 h / Ambient temperature
View Scheme
neryl acetate
141-12-8

neryl acetate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SeO2, salicylic acid, tert-butyl hydroperoxide / CH2Cl2 / 27 h / Ambient temperature
2: PDC / CH2Cl2 / 10 h / Ambient temperature
3: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
4: p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
5: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
Multi-step reaction with 4 steps
1: SeO2, salicylic acid, tert-butyl hydroperoxide / CH2Cl2 / 27 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
3: p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
4: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
3,7-dimethyl-2E,6-octadien-1-yl acetate
105-87-3

3,7-dimethyl-2E,6-octadien-1-yl acetate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: SeO2, salicylic acid, tert-butyl hydroperoxide / CH2Cl2 / 27 h / Ambient temperature
2: PDC / CH2Cl2 / 10 h / Ambient temperature
3: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
4: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
5: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
Multi-step reaction with 4 steps
1: SeO2, salicylic acid, tert-butyl hydroperoxide / CH2Cl2 / 27 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
3: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
4: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
8-hydroxygeranyl acetate
37905-03-6

8-hydroxygeranyl acetate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: PDC / CH2Cl2 / 10 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
3: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
4: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate
37905-02-5

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
2: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
3: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
(2'Z,6'E)-Essigsaeure-(8'-hydroxy-3',7'-dimethyl-2',6'-octadien-1'-yl)ester
70238-37-8

(2'Z,6'E)-Essigsaeure-(8'-hydroxy-3',7'-dimethyl-2',6'-octadien-1'-yl)ester

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: PDC / CH2Cl2 / 10 h / Ambient temperature
2: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
3: p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
4: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
{[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene
56691-74-8

{[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
2: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
3: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
2: p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
3: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
Multi-step reaction with 3 steps
1: n-BuLi / tetrahydrofuran / 5 h / -78 °C
2: p-toluenesulfonic acid / CH2Cl2
3: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
(2Z,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate
94853-00-6

(2Z,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1.) n-BuLi / 1.) THF, -78 deg C, 2 h, 2.) THF, -78 deg C, 3 h
2: p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
3: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
Multi-step reaction with 3 steps
1: n-BuLi / tetrahydrofuran / 5 h / -78 °C
2: p-toluenesulfonic acid / CH2Cl2
3: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
Acetic acid (2Z,6E)-9-benzenesulfonyl-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl ester
105615-49-4

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

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
2: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
Multi-step reaction with 2 steps
1: p-toluenesulfonic acid / CH2Cl2
2: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
1-acetoxy-8-hydroxy-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-9-(phenylsulfonyl)-2(E),6(E)-nonadiene
103905-01-7

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

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / p-toluenesulfonic acid / CH2Cl2 / 3 h / Ambient temperature
2: MeOK / cyclohexane / 2 h / 38 °C
View Scheme
5-hydroxy-4-methyl-5H-furan-2-one
40834-42-2

5-hydroxy-4-methyl-5H-furan-2-one

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

2-cis-Vitamin-A

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 1.) NaH / 1.) HMPA, 0 deg C, 1 h, 2.) 20 min
2: 1.) ethylmagnesium bromide / 1.) THF, room temperature, 1 h, 2.) 15 min
3: 75 percent / DIBAH / tetrahydrofuran; toluene / 0.5 h / -78 °C
4: 90 percent / H2 / Lindlar catalyst / methanol / 24 h
5: 80 percent / imidazole / dimethylformamide / 18 h / Ambient temperature
6: 90 percent / LiAlH4, TiCl3 / tetrahydrofuran / 0.5 h / Ambient temperature
7: sodium fluoride, pyridinium fluoride / tetrahydrofuran; acetonitrile / 5 h / Ambient temperature
View Scheme
Multi-step reaction with 7 steps
1: 85 percent / NaH / hexamethylphosphoric acid triamide
2: 90 percent / EtMgBr
3: 75 percent / DIBAL
4: 80 percent
5: 90 percent / H2 / Lindlar catalist
6: 90 percent / LiAlH4,TiCl3 / tetrahydrofuran / 0.5 h / Ambient temperature
7: NaF, pyridiniumfluoride / Ambient temperature
View Scheme
pyridine
110-86-1

pyridine

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

2-cis-Vitamin-A

acetyl chloride
75-36-5

acetyl chloride

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

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

Conditions
ConditionsYield
With 1,2-dichloro-ethane
...Expand
pyridine
110-86-1

pyridine

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

2-cis-Vitamin-A

n-hexadecanoyl chloride
112-67-4

n-hexadecanoyl chloride

9-Palmitoyloxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraen-(1.3t.5t.7c)
26771-20-0

9-Palmitoyloxy-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraen-(1.3t.5t.7c)

Conditions
ConditionsYield
With 1,2-dichloro-ethane
...Expand
2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

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

13-cis-vitamin A aldehyde

Conditions
ConditionsYield
With manganese(IV) oxide; Petroleum ether unter Lichtausschluss;
With manganese(IV) oxide
With manganese(IV) oxide In tetrachloromethane for 0.5h;
4-phenylazobenzoyl chloride
104-24-5

4-phenylazobenzoyl chloride

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

2-cis-Vitamin-A

9-(4-Phenylazo-benzoyloxy)-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraen-(1.3t.5t.7c)
50696-24-7, 50837-87-1, 105616-34-0

9-(4-Phenylazo-benzoyloxy)-3.7-dimethyl-1t-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraen-(1.3t.5t.7c)

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

2-cis-Vitamin-A

anthraquinone-2-carbonyl chloride
6470-87-7

anthraquinone-2-carbonyl chloride

O-(9.10-dioxo-9.10-dihydro-anthracenecarbonyl-(2))-[7t.9t.11t.13c]retinol
107892-29-5

O-(9.10-dioxo-9.10-dihydro-anthracenecarbonyl-(2))-[7t.9t.11t.13c]retinol

Conditions
ConditionsYield
With pyridine; dichloromethane
2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

acetic anhydride
108-24-7

acetic anhydride

A

9-cis-retinol
68-26-8, 2052-63-3, 6018-74-2, 17706-49-9, 22737-96-8, 29444-25-5, 34218-73-0, 39815-04-8, 69686-68-6, 69686-69-7, 74743-94-5, 84415-27-0, 84415-28-1, 85354-09-2, 85354-10-5, 93380-02-0, 98462-62-5, 137121-52-9, 22737-97-9

9-cis-retinol

B

9cis,13cis-retinyl acetate
29444-27-7

9cis,13cis-retinyl acetate

C

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

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

D

11,13-di-cis-Vitamin-A-acetat
63568-38-7

11,13-di-cis-Vitamin-A-acetat

Conditions
ConditionsYield
With triethylamine In hexane Yield given;
...Expand
2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

acetic anhydride
108-24-7

acetic anhydride

A

9cis,13cis-retinyl acetate
29444-27-7

9cis,13cis-retinyl acetate

B

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

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

C

11,13-di-cis-Vitamin-A-acetat
63568-38-7

11,13-di-cis-Vitamin-A-acetat

Conditions
ConditionsYield
With triethylamine In hexane Yield given;
...Expand
2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

propargyl bromide
106-96-7

propargyl bromide

2-((1E,3E,5E,7Z)-3,7-Dimethyl-9-prop-2-ynyloxy-nona-1,3,5,7-tetraenyl)-1,3,3-trimethyl-cyclohexene
173010-18-9

2-((1E,3E,5E,7Z)-3,7-Dimethyl-9-prop-2-ynyloxy-nona-1,3,5,7-tetraenyl)-1,3,3-trimethyl-cyclohexene

Conditions
ConditionsYield
With n-butyllithium 1.) benzene, hexane, 20 deg C, 5 min, 2.) benzene, DMF, hexane, RT, 4 h; Yield given. Multistep reaction;
hydrogenchloride
7647-01-0

hydrogenchloride

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

2-cis-Vitamin-A

anhydrovitamin-A1

anhydrovitamin-A1

Conditions
ConditionsYield
Kinetics; Dehydratisierung;
2-cis-Vitamin-A
2052-63-3

2-cis-Vitamin-A

iodine
7553-56-2

iodine

benzene
71-43-2

benzene

O--derivative of all-trans-retinol

O--derivative of all-trans-retinol

Conditions
ConditionsYield
Gleichgewichtsgemisch mit dem O--Derivat unter der Einwirkung von Tageslicht;
...Expand

Retinol, 13-cis- Specification

The Retinol, 13-cis- is an organic compound with the formula C20H30O. The IUPAC name of this chemical is (2Z,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol. With the CAS registry number 2052-63-3, it is also named as 13-cis-Retinol.

Physical properties about Retinol, 13-cis- are: (1)ACD/LogP: 6.84; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 6.84; (4)ACD/LogD (pH 7.4): 6.84; (5)ACD/BCF (pH 5.5): 93126.2; (6)ACD/BCF (pH 7.4): 93126.2; (7)ACD/KOC (pH 5.5): 125441.47; (8)ACD/KOC (pH 7.4): 125441.47; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.549; (14)Molar Refractivity: 95.49 cm3; (15)Molar Volume: 300 cm3; (16)Polarizability: 37.85×10-24cm3; (17)Surface Tension: 36.6 dyne/cm; (18)Density: 0.954 g/cm3; (19)Flash Point: 147.3 °C; (20)Enthalpy of Vaporization: 77.99 kJ/mol; (21)Boiling Point: 421.2 °C at 760 mmHg; (22)Vapour Pressure: 7.35E-09 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: OC/C=C(\C=C\C=C(/C=C/C1=C(/CCCC1(C)C)C)C)C
(2)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-
(3)InChIKey: FPIPGXGPPPQFEQ-BOOMUCAABT
(4)Std. InChI: InChI=1S/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-
(5)Std. InChIKey: FPIPGXGPPPQFEQ-BOOMUCAASA-N

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