9-cis-Retinol

Base Information

• Chemical Name: 9-cis-Retinol
• CAS No.: 22737-97-9
• Molecular Formula: C₂₀H₃₀O
• Molecular Weight: 286.458
• UNII: 035JKP3HXH
• DSSTox Substance ID: DTXSID201317690
• Nikkaji Number: J1.321.775K
• Wikidata: Q27147725
• Metabolomics Workbench ID: 29032
• ChEMBL ID: CHEMBL4802238
• Mol file: 22737-97-9.mol

Synonyms:9-cis-Retinol;9-cis retinol;Zuretinol;22737-97-9;Retinol, 9-cis-;9-cis-Vitamin A Alcohol;9Z-retinol;UNII-035JKP3HXH;035JKP3HXH;(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol;(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol;(9cis)-retinol;(7Z,9Z)-Retinol;ZURETINOL [WHO-DD];SCHEMBL254333;CHEMBL4802238;CHEBI:78272;FPIPGXGPPPQFEQ-MKOSUFFBSA-N;DTXSID201317690;LMPR01090009;Q27147725

Chemical Property of 9-cis-Retinol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 82-830C
• Boiling Point: 421.2°Cat760mmHg
• PKA: 14.09±0.10(Predicted)
• Flash Point: 147.3°C
• PSA: 20.23000
• Density: 0.954g/cm³
• LogP: 5.51030
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Sparingly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 286.229665576
• Heavy Atom Count: 21
• Complexity: 496

Purity/Quality:

97% ^*data from raw suppliers

9-cisRetinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CCO)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C\C=C\C(=C\CO)\C)/C

Technology Process of 9-cis-Retinol

There total 39 articles about 9-cis-Retinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

tert-butyldimethylsilyl (7E,9Z,11E,13E)-retinyl ether (210700-52-0) → 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)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 1.5h;

DOI:10.1021/jo991757f

Reference yield: 90.0%

(9Ξ)-O-acetyl-retinol (200720-67-8,64536-04-5) → 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)

Guidance literature:

(9Ξ)-O-acetyl-retinol; With sodium hydroxide; In ethanol; water; at 40 ℃; for 0.5h; Inert atmosphere; Darkness;

With pyridine; In Methyl formate; at 0 ℃; for 2h; Reagent/catalyst; Catalytic behavior;

DOI:10.1039/c9dt02189b

Reference yield: 77.0%

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) → 2-cis-Vitamin-A (2052-63-3) + 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) + 11-cis-retinol (22737-96-8) + RETINOL (68-26-8)

Guidance literature:

With potassium methanolate; In cyclohexane; at 38 ℃; for 2h;

DOI:10.1021/jo00370a017

upstream raw materials:

[7t,9c,11t,13t]retinoic acid methyl ester

2-cis-Vitamin-A

acetic anhydride

1-acetoxy-6-chloro-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-9-phenylsulfonyl-2,7-nonadiene

Downstream raw materials:

9-cis-retinoic acid

9-cis vitamin A aldehyde

11-cis-retinol

ethyl retinoate