(2Z,4E,6Z,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal

Base Information

• Chemical Name: (2Z,4E,6Z,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal
• CAS No.: 6890-91-1
• Molecular Formula: C20H28O2
• Molecular Weight: 300.441
• Mol file: 6890-91-1.mol

Synonyms:3-hydroxyretinal;all-trans-3-hydroxyretinal

Chemical Property of (2Z,4E,6Z,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal

Chemical Property:

• Vapor Pressure: 1.73E-10mmHg at 25°C
• Refractive Index: 1.558
• Boiling Point: 462.3°C at 760 mmHg
• Flash Point: 196.7°C
• PSA: 37.30000
• Density: 1.012g/cm³
• LogP: 4.68770
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate, Methanol (Slightly)
• 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% ^*data from raw suppliers

rac-all-trans3-HydroxyRetinal(80%) ^*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: This item is provided at a purity of approximately 80%.

Technology Process of (2Z,4E,6Z,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal

There total 35 articles about (2Z,4E,6Z,8E)-9-(4-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7-dimethylnona-2,4,6,8-tetraenal 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,3E,5E,7E)-9-Hydroxy-3,7-dimethyl-nona-1,3,5,7-tetraenyl)-3,5,5-trimethyl-cyclohex-3-enol

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

methyl (E)-3-formylcrotonate

triethyl 3-methyl-4-phosphonocrotonate

Downstream raw materials:

all trans, 13-cis 3-hydroxyretinal

C₂₉H₃₆N₂O₅S

3-diazoacetoxy-9-cis-retinal

Refernces

• 1、 Scherzinger, Daniel,Scheffer, Erdmann,Baer, Cornelia,Ernst, Hansgeorg,Al-Babili, Salim. "The Mycobacterium tuberculosis ORF Rv0654 encodes a carotenoid oxygenase mediating central and excentric cleavage of conventional and aromatic carotenoids". experimental part. p. 4662 - 4673. Retrieved 2011/12/04.
• 2、 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.