14'-apo-beta-Carotenal

Base Information

• Chemical Name: 14'-apo-beta-Carotenal
• CAS No.: 6985-27-9
• Molecular Formula: C22H30 O
• Molecular Weight: 310.48
• ChEMBL ID: CHEMBL1952258
• DSSTox Substance ID: DTXSID901315740
• Metabolomics Workbench ID: 29016
• Nikkaji Number: J575.850E
• Wikidata: Q27102407
• Mol file: 6985-27-9.mol

Synonyms:beta-apo-14'-carotenal

Chemical Property of 14'-apo-beta-Carotenal

Chemical Property:

• Vapor Pressure: 1.47E-08mmHg at 25°C
• Boiling Point: 457.6°C at 760 mmHg
• Flash Point: 224.5°C
• PSA: 17.07000
• Density: 0.95g/cm³
• LogP: 6.27310
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 6
• Exact Mass: 310.229665576
• Heavy Atom Count: 23
• Complexity: 590

Purity/Quality:

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=CC=O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=O)/C)/C

Technology Process of 14'-apo-beta-Carotenal

There total 28 articles about 14'-apo-beta-Carotenal 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: 88.0%

(2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohex-1-en-1-yl)undeca-2,4,6,8,10-pentaene-1-ol (6985-26-8,24109-36-2,90819-75-3) → β-apo-14'-carotenal (6985-27-9)

Guidance literature:

With manganese(IV) oxide; sodium carbonate; In dichloromethane; at 0 - 25 ℃; for 5h;

DOI:10.1016/j.tet.2018.03.050

Reference yield: 12.4%

Retinyliden-acetonitril → β-apo-14'-carotenal (6985-27-9)

Guidance literature:

With diisobutylaluminium hydride; In toluene; at -5 - 0 ℃; for 1h; Inert atmosphere;

DOI:10.1124/mol.114.096560

Reference yield:

trans-β-apo-8'-carotenal (1107-26-2,4172-46-7) → 12'-apo-β-caroten-12'-al (1638-05-7) + (E)-β-ionone (79-77-6,14901-07-6) + all-trans-Retinal (116-31-4) + β-apo-14'-carotenal (6985-27-9)

Guidance literature:

With oxygen; In benzene; at 30 ℃; for 24h; Yield given. Further byproducts given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)80333-1

upstream raw materials:

(2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethylcyclohex-1-en-1-yl)undeca-2,4,6,8,10-pentaene-1-ol

beta-carotene

trans-β-apo-8'-carotenal

13-cis-retinylideneacetaldehyde

Downstream raw materials:

9-cis-retinylideneacetaldehyde

13-cis-retinylideneacetaldehyde

(E)-2,5-Bis-[(2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethyl-cyclohex-1-enyl)-undeca-2,4,6,8,10-pentaen-(Z)-ylidene]-hex-3-enedinitrile

Butyl-[(2E,4E,6E,8E,10E)-5,9-dimethyl-11-(2,6,6-trimethyl-cyclohex-1-enyl)-undeca-2,4,6,8,10-pentaen-(E)-ylidene]-amine

Refernces

• 1、 Domínguez, Marta,Pequerul, Raquel,Alvarez, Rosana,Giménez-Dejoz, Joan,Birta, Eszter,Porté, Sergio,Rühl, Ralph,Parés, Xavier,Farrés, Jaume,de Lera, Angel R.. "Synthesis of apocarotenoids by acyclic cross metathesis and characterization as substrates for human retinaldehyde dehydrogenases". . p. 2567 - 2574. Retrieved 2018/04/19.
• 2、 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.