Neurosporene

Base Information

• Chemical Name: Neurosporene
• CAS No.: 502-64-7
• Molecular Formula: C40H58
• Molecular Weight: 538.901
• UNII: FVN22YW634
• DSSTox Substance ID: DTXSID901045315
• Metabolomics Workbench ID: 28851
• Nikkaji Number: J12.234C,J367.189E,J367.190I,J367.192E,J367.193C,J367.194A,J367.195J,J367.196H
• Wikidata: Q15269719
• Wikipedia: Neurosporene
• Mol file: 502-64-7.mol

Synonyms:1,2-dihydroneurosporene;neurosporene;neurosporene, (cis)-isomer

Chemical Property of Neurosporene

Chemical Property:

• Boiling Point: 650.7°Cat760mmHg
• Flash Point: 346.3°C
• PSA: 0.00000
• Density: 0.882g/cm³
• LogP: 13.16200
• XLogP3: 15.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 17
• Exact Mass: 538.453851850
• Heavy Atom Count: 40
• Complexity: 1100

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C=C(\C)/CCC=C(C)C)/C)/C)/C)C
• Uses: Neurosporene is an antioxidant carotenoid compound found in human milk and serum.

Technology Process of Neurosporene

There total 20 articles about Neurosporene 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: 6.0%

(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal (103956-99-6,1071-52-9) + Triphenyl<(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl>phosphoniumbromid → all-trans-neurosporene (502-64-7)

Guidance literature:

With sodium methylate; In methanol; N,N-dimethyl-formamide; for 3h; Ambient temperature;

DOI:10.1002/hlca.19850680604

Reference yield:

phytofluene (13587-06-9,86087-06-1) → all-trans-neurosporene (502-64-7)

Guidance literature:

With tetrachloromethane; N-Bromosuccinimide; acetic acid; at 0 ℃;

DOI:10.1021/ja01640a020

Reference yield:

3-(5,5-Dimethyl-1,3-dioxan-2-yl)-2-butenal (51575-60-1) → all-trans-neurosporene (502-64-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 40 percent / KOH / tetrahydrofuran / 2 h / Ambient temperature

2: 76 percent / NaBH₄ / diethyl ether; methanol / 0.25 h

3: PBr₃ / diethyl ether / 2 h / 1.) Et₂O, 0 deg C; 2.) room temperature, 2 h

4: 2 h / 60 °C

5: 40 percent / KOH / tetrahydrofuran / 1 h / Ambient temperature

6: 1.) DIBAH; 2.) MnO₂ / 1.) THF, 0 deg C, 15 min; 2.) Et₂O, room temperature, 30 min

7: 43 percent / KOH / tetrahydrofuran / 1 h / 0 °C

8: 1.) DIBAH; 2.) MnO₂ / 1.) THF, 0 deg C, 15 min; 2.) Et₂O, room temperature, 30 min

9: 6 percent / NaOMe / methanol; dimethylformamide / 3 h / Ambient temperature

With manganese(IV) oxide; potassium hydroxide; sodium tetrahydroborate; sodium methylate; phosphorus tribromide; diisobutylaluminium hydride; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19850680604

upstream raw materials:

phytofluene

(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal

<(E,E)-3,7,11-trimethyl-2,6,10-dodecatrienyl>triphenylphosphoniumbromid

3-(5,5-Dimethyl-1,3-dioxan-2-yl)-2-butenal

Downstream raw materials:

lycopene

Refernces