11-cis-3-Hydroxyretinal

Base Information

• Chemical Name: 11-cis-3-Hydroxyretinal
• CAS No.: 102918-00-3
• Molecular Formula: C₂₀H₂₈O₂
• Molecular Weight: 300.441
• DSSTox Substance ID: DTXSID10554347
• Wikidata: Q27155470
• Mol file: 102918-00-3.mol

Synonyms:11-cis-3-Hydroxyretinal;102918-00-3;rac 11-cis-3-Hydroxy Retinal;(2E,4Z,6E,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal;(11cis)-3-Hydroxyretinal;3-Hydroxy-11-cis-retinal;3-hydroxy-11-cis-retinaldehyde;SCHEMBL20561154;CHEBI:81574;DTXSID10554347;Q27155470;(2E,4Z,6E,8E)-9-(4-HYDROXY-2,6,6-TRIMETHYLCYCLOHEX-1-EN-1-YL)-3,7-DIMETHYLNONA-2,4,6,8-TETRAENAL

Chemical Property of 11-cis-3-Hydroxyretinal

Chemical Property:

• PSA: 37.30000
• LogP: 4.68770
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 300.208930132
• Heavy Atom Count: 22
• Complexity: 554

Purity/Quality:

99.90% ^*data from raw suppliers

rac11-cis-3-HydroxyRetinal ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=O)C)C
• Isomeric SMILES: CC1=C(C(CC(C1)O)(C)C)/C=C/C(=C/C=C\C(=C\C=O)\C)/C
• Uses: 11-cis-3-Hydroxyretinal is a hydroxylated 11-cis-Retinal (R239860) derivative. 11-cis-3-Hydroxyretinal is formed in the cytosol of butterfly eye and that of other insects via a light dependant metaboli pathway.

Technology Process of 11-cis-3-Hydroxyretinal

There total 16 articles about 11-cis-3-Hydroxyretinal 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:

4-((1E,3Z,5E,7E)-9-Hydroxy-3,7-dimethyl-nona-1,3,5,7-tetraenyl)-3,5,5-trimethyl-cyclohex-3-enol (6890-93-3,60046-52-8,106623-46-5,106623-47-6,120674-70-6,120674-71-7,120674-72-8,120674-73-9,120674-87-5,120674-88-6) → 3-hydroxy-9-cis-retinal (6890-91-1,60046-53-9,81600-86-4,81600-87-5,102918-00-3,115075-58-6,120657-98-9,120674-41-1,120674-42-2,120674-45-5,121521-19-5,145681-21-6,7584-74-9)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; Yield given; Ambient temperature;

DOI:10.1021/ja00375a048

Reference yield:

(3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one (14398-35-7) → 3-hydroxy-9-cis-retinal (6890-91-1,60046-53-9,81600-86-4,81600-87-5,102918-00-3,115075-58-6,120657-98-9,120674-41-1,120674-42-2,120674-45-5,121521-19-5,145681-21-6,7584-74-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / p-TsOH / benzene / Heating

2: 1.) 9-BBN, 2.) NaOH, H₂O₂ / 1.) 55-60 deg C

3: 90 percent / Im*DMF / Ambient temperature

4: 90 percent / HCl / acetone

5: 1.) LDA, 2.) HCO₂H / 1.) THF, -78 deg C, 2.) room temperature

6: 85 percent / NaH / tetrahydrofuran / -10 °C

7: n-Bu₄N(+)F(-) / tetrahydrofuran / Ambient temperature

8: Dibal / diethyl ether / -78 °C

9: MnO₂ / CH₂Cl₂ / Ambient temperature

With hydrogenchloride; manganese(IV) oxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; formic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; benzene;

DOI:10.1021/ja00375a048

Reference yield:

triethyl 3-methyl-4-phosphonocrotonate (39760-56-0,3917-43-9,41891-54-7) → 3-hydroxy-9-cis-retinal (6890-91-1,60046-53-9,81600-86-4,81600-87-5,102918-00-3,115075-58-6,120657-98-9,120674-41-1,120674-42-2,120674-45-5,121521-19-5,145681-21-6,7584-74-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / NaH / tetrahydrofuran / -10 °C

2: n-Bu₄N(+)F(-) / tetrahydrofuran / Ambient temperature

3: Dibal / diethyl ether / -78 °C

4: MnO₂ / CH₂Cl₂ / Ambient temperature

With manganese(IV) oxide; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja00375a048

upstream raw materials:

4-((1E,3Z,5E,7E)-9-Hydroxy-3,7-dimethyl-nona-1,3,5,7-tetraenyl)-3,5,5-trimethyl-cyclohex-3-enol

(3E)-4-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-3-en-2-one

triethyl 3-methyl-4-phosphonocrotonate

2-Methyl-2-[(E)-2-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-vinyl]-[1,3]dioxolane

Downstream raw materials:

C₂₉H₃₆N₂O₅S

3-diazoacetoxy-9-cis-retinal

Refernces

• 1、 Sen, Ranjan,Carriker, John D.,Balogh-Nair, Valeria,Nakanishi, Koji. "Synthesis and Binding Studies of a Photoaffinity Label for Bovine Rhodopsin". . p. 3214 - 3216. Retrieved 2007/10/02.