13-cis-Retinal

Base Information

• Chemical Name: 13-cis-Retinal
• CAS No.: 472-86-6
• Deprecated CAS: 18800-92-5,69686-71-1
• Molecular Formula: C20H28 O
• Molecular Weight: 284.442
• Hs Code.: 2912299000
• European Community (EC) Number: 207-456-1
• UNII: IBP64540CD
• DSSTox Substance ID: DTXSID0025997
• Nikkaji Number: J1.321.770J
• Wikidata: Q27070771
• Metabolomics Workbench ID: 29041
• ChEMBL ID: CHEMBL1579130
• Mol file: 472-86-6.mol

Synonyms:13-cis-retinal

Chemical Property of 13-cis-Retinal

Chemical Property:

• Vapor Pressure: 2.61E-07mmHg at 25°C
• Melting Point: 65-69°C
• Refractive Index: 1.54
• Boiling Point: 421.4°C at 760 mmHg
• Flash Point: 205.4°C
• PSA: 17.07000
• Density: 0.948g/cm³
• LogP: 5.71690
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 284.214015512
• Heavy Atom Count: 21
• Complexity: 522

Purity/Quality:

98%,99%, ^*data from raw suppliers

13-cis-Retinal ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 20/21/22-38
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C\C=O)/C)/C
• Uses: An isomer of all-trans-Retinal (R240000).

Technology Process of 13-cis-Retinal

There total 86 articles about 13-cis-Retinal 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: 29.0%

all-trans-Retinal (116-31-4) → 9-cis vitamin A aldehyde (514-85-2) + (11Z)-retinal (564-87-4) + 13-cis-vitamin A aldehyde (472-86-6) + 7-cis-retinal (24315-14-8)

Guidance literature:

In chloroform; for 3h; Product distribution; Irradiation; effects of various solvents and phosphatidyl choline, dipalmitoylphosphatidylcholine vesicles on product/yield distribution;

DOI:10.1246/bcsj.62.2589

Reference yield: 23.19%

all-trans-Retinal (116-31-4) → 9-cis vitamin A aldehyde (514-85-2) + (11Z)-retinal (564-87-4) + 13-cis-vitamin A aldehyde (472-86-6) + 9-cis,13-cis-retinal (23790-80-9)

Guidance literature:

With iodine; In n-heptane; at 50 ℃; Product distribution; other reagent;

DOI:10.1021/ja00347a058

Reference yield: 10.0%

12,14-retro-retinol (74916-02-2) → 9-cis vitamin A aldehyde (514-85-2) + 13-cis-vitamin A aldehyde (472-86-6) + all-trans-Retinal (116-31-4) + 9-cis,13-cis-retinal (23790-80-9)

Guidance literature:

With iodine; dimethyl sulfoxide; dicyclohexyl-carbodiimide;

upstream raw materials:

2-cis-Vitamin-A

9-cis vitamin A aldehyde

(11Z)-retinal

all-trans-Retinal

Downstream raw materials:

9-cis vitamin A aldehyde

all-trans-Retinal

7-cis,9-cis,13-cis-retinal

7,9,13-tricis-retinal

Refernces

• 1、 Yamaguchi, Shoichi,Hamaguchi, Hiro-O. "Femtosecond ultraviolet-visible absorption study of all-trans→13-cis9-cis photoisomerization of retinal". . p. 1397 - 1408. Retrieved 1998.
• 2、 Simmons, Charles J.,Liu, Robert S. H.,Denny, Marlene,Seff, Karl. "The Crystal Structure of 13-cis-Retinal. The Molecular Structures of its 6-s-cis and 6-s-trans Conformers". . p. 2197 - 2205. Retrieved 1981.
• 3、 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.
• 4、 Sacolick, Davidson A.,Curley, Robert W.. "An improved synthesis of retinal (Vitamin A Aldehyde)". . p. 325 - 327. Retrieved 2013/07/26.