β-Apocarotenal

Base Information

• Chemical Name: β-Apocarotenal
• CAS No.: 640-49-3
• Deprecated CAS: 16699-51-7
• Molecular Formula: C27H36 O
• Molecular Weight: 376.582
• UNII: D8AT287SHE
• DSSTox Substance ID: DTXSID701315499
• Nikkaji Number: J17.020H
• Wikidata: Q27123983
• Metabolomics Workbench ID: 58566
• Mol file: 640-49-3.mol

Synonyms:10'-Apo-b,y-carotenal; 10'-Apo-b-carotenal (6CI,7CI); 10'-Apo-b-carotenal, all-trans- (8CI);10'-Apo-b-caroten-10'-al;2,4,6,8,10,12,14-Pentadecaheptaenal,4,9,13-trimethyl-15-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)-; b-Apo-10'-carotenal; b-apo-10'-Carotenal

Chemical Property of β-Apocarotenal

Chemical Property:

• Vapor Pressure: 1.67E-11mmHg at 25°C
• Boiling Point: 534.6°C at 760 mmHg
• Flash Point: 258.4°C
• PSA: 17.07000
• Density: 0.95g/cm³
• LogP: 7.77560
• XLogP3: 8.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 376.276615768
• Heavy Atom Count: 28
• Complexity: 771

Purity/Quality:

99%, ^*data from raw 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=CC=C(C)C=CC=O)C)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=O)/C)/C
• Uses: 10’-Apo-β-carotenal is an antioxidant β-carotene (C184250) derivative that facilitates embryogenesis as a substrate for BCO1-catalyzed retinoid formation.

Technology Process of β-Apocarotenal

There total 21 articles about β-Apocarotenal 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: 80.0%

C31H48O3 → (2E,4E,6Z,8E,10E,12E,14E)-4,9,13-Trimethyl-15-(2,6,6-trimethyl-cyclohex-1-enyl)-pentadeca-2,4,6,8,10,12,14-heptaenal (640-49-3)

Guidance literature:

With water; trifluoroacetic acid; In dichloromethane; for 3h; Reagent/catalyst; Solvent; Reflux;

Reference yield: 68.0%

(2E,4E,6E,8E,10E,12E,14E)-4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-en-1-yl)pentadeca-2,4,6,8,10,12,14-heptaen-1-ol (6541-42-0) → 4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-enyl)pentadeca-2,4,6,8,10,12,14-heptaenal (640-49-3)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 0 ℃; for 5h;

DOI:10.1002/jlcr.536

Reference yield:

beta-carotene (7235-40-7) → (E)-β-ionone (79-77-6,14901-07-6) + 4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-enyl)pentadeca-2,4,6,8,10,12,14-heptaenal (640-49-3) + 2,6,6-trimethylcyclohex-1-enecarbaldehyde (432-25-7) + trans-β-apo-8'-carotenal (1107-26-2,4172-46-7) + 5,6-epoxy-trans-β-ionone (36340-49-5)

Guidance literature:

With tert.-butylhydroperoxide; μ-carbido-bis[(5,10,15,20-tetraphenyl-21H,23H-porphyrinato)iron(IV)]; In benzene; at 24.84 ℃; Reagent/catalyst; Kinetics;

DOI:10.1134/S0036024418110390

upstream raw materials:

β-carotene

beta-carotene

(2E,4E,6E,8E,10E,12E,14E)-4,9,13-trimethyl-15-(2,6,6-trimethylcyclohex-1-en-1-yl)pentadeca-2,4,6,8,10,12,14-heptaen-1-ol

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

Downstream raw materials:

(3E,5E,7E)-6-methyl-8-(2,6,6-trimethyl-1-cyclohexenyl)-3,5,7-octatriene-2-one

C₃₂H₄₃⁽³⁾HO₂

C₂₇H₃₅⁽³⁾HO

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、 Reddy, Pulgam Veera,Rabago-Smith, Monsterrat,Borhan, Babak. "Synthesis of all-trans-[10′-3H]-8′-apo-β-carotenoic acid". . p. 79 - 89. Retrieved 2007/10/03.