11-cis-Retinol

Base Information

• Chemical Name: 11-cis-Retinol
• CAS No.: 22737-96-8
• Molecular Formula: C20H30O
• Molecular Weight: 286.458
• DSSTox Substance ID: DTXSID401317284
• Nikkaji Number: J641.433H
• Wikidata: Q27070756
• Metabolomics Workbench ID: 29028
• Mol file: 22737-96-8.mol

Synonyms:11-cis-Retinol;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)-Isomer;All Trans Retinol;All-Trans-Retinol;Aquasol A;Retinol;Vitamin A;Vitamin A1

Chemical Property of 11-cis-Retinol

Chemical Property:

• Vapor Pressure: 7.35E-09mmHg at 25°C
• Boiling Point: 421.2°C at 760 mmHg
• 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 (Slightly), 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:

99% ^*data from raw suppliers

11-cis-Retinol,>85% ^*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
• Uses: A metabolite of Vitamin A (R252000(M)).

Technology Process of 11-cis-Retinol

There total 99 articles about 11-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 vitamin A aldehyde

(11Z)-retinal

RETINOL

9-cis-retinoic acid

Refernces

• 1、 Sperling,Rafferty. "". . p. 591,592,593,594. Retrieved 1969.
• 2、 Kahremany, Shirin,Sander, Christopher Lane,Tochtrop, Gregory P.,Kubas, Adam,Palczewski, Krzysztof. "Z -isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis". supporting information. p. 8125 - 8139. Retrieved 2019/09/19.
• 3、 Sato, Shinya,Fukagawa, Takashi,Tachibanaki, Shuji,Yamano, Yumiko,Wada, Akimori,Kawamura, Satoru. "Substrate specificity and subcellular localization of the aldehyde-Alcohol redox-Coupling reaction in carp cones". . p. 36589 - 36597. Retrieved 2014/01/17.