11-cis-Retinal

Base Information

• Chemical Name: 11-cis-Retinal
• CAS No.: 564-87-4
• Molecular Formula: C20H28O
• Molecular Weight: 284.442
• UNII: 91058V6HCH
• ChEMBL ID: CHEMBL1255087
• DSSTox Substance ID: DTXSID80415057
• Metabolomics Workbench ID: 29027
• Nikkaji Number: J1.631.404H,J1.631.405F
• Wikidata: Q17002962
• Wikipedia: 11-cis_retinal
• Mol file: 564-87-4.mol

Synonyms:11 cis Retinal;11 trans Retinal;11-cis-Retinal;11-trans-Retinal;3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-Nonatetraenal;Aldehydde, Retinyl;Aldehyde, Vitamin A;all trans Retinal;all-trans-Retinal;Axerophthal;Retinal;Retinaldehyde;Retinene;Retinyl Aldehydde;Vitamin A Aldehyde

Chemical Property of 11-cis-Retinal

Chemical Property:

• Vapor Pressure: 2.61E-07mmHg at 25°C
• Refractive Index: 1.54
• Boiling Point: 421.4°Cat760mmHg
• Flash Point: 205.4°C
• PSA: 17.07000
• Density: 0.948g/cm³
• LogP: 5.71690
• Storage Temp.: Amber Vial, -86°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Ethyl Acetate (Slightly), Methanol (S
• 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:

99%, ^*data from raw suppliers

11-cis-Retinal(>65%),inBenzene(0.5mg/mL) ^*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(=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: A natural chromophore 11-cis-Retinal (>65%), in Benzene (0.5mg/mL) is an isomer of all-trans-Retinal (R240000).

Technology Process of 11-cis-Retinal

There total 83 articles about 11-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:

11-cis-retinol (22737-96-8) + benzaldehyde (100-52-7) → (11Z)-retinal (564-87-4) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

With carp cone membrane suspension; In ethanol; at 25 ℃; Kinetics; Mechanism; Enzymatic reaction;

DOI:10.1074/jbc.M113.521153

upstream raw materials:

all-trans-Retinal

11-cis-retinol

(2X,4E)-3-methyl-5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-2,4-dienal

<(2E)-4-hydroxy-2-methyl-2-butenyl>triphenylphosphonium bromide

Downstream raw materials:

11-cis-retinol

11-cis-retinal piperidine perchlorate Schiff base

9-cis vitamin A aldehyde

13-cis-vitamin A aldehyde

Refernces

• 1、 Wada, Akimori,Tanaka, Yukiko,Fujioka, Naoko,Ito, Masayoshi. "Stereoselective synthesis of 11Z-retinal by use of tricarbonyliron complex". . p. 2049 - 2052. Retrieved 1996.
• 2、 Brien,Muellenberg. "". . p. 1695,1696. Retrieved 1975.
• 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.