Isozeaxanthin

Base Information

• Chemical Name: Isozeaxanthin
• CAS No.: 29065-03-0
• Deprecated CAS: 21940-25-0
• Molecular Formula: C₄₀H₅₆O₂
• Molecular Weight: 568.883
• UNII: 9D87Z858YJ
• Metabolomics Workbench ID: 157342
• Nikkaji Number: J375.027B
• Wikidata: Q27272388
• Mol file: 29065-03-0.mol

Synonyms:isozeaxanthin;29065-03-0;beta,beta-Carotene-4,4'-diol;Isozeaxanthin, all-trans-;9D87Z858YJ;beta-Carotene-4,4'-diol;UNII-9D87Z858YJ;3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(3-hydroxy-2,6,6-trimethylcyclohexen-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,4,4-trimethylcyclohex-2-en-1-ol;isoseaxanthin;Aphanicol;b,b-Carotene-4,4'-diol;|A,|A-Carotene-4,4'-diol;SCHEMBL1498298;4,4'-dihydro-beta,beta-carotene;CHEBI:176095;GYZWNQLEQAGWGD-DKLMTRRASA-N;.BETA.-CAROTENE-4,4'-DIOL;.BETA.,.BETA.-CAROTENE-4,4'-DIOL;Q27272388;3-[(1E, 3E, 5E, 7E, 9E, 11E, 13E, 15E, 17E)-18-(3-hydroxy-2, 6, 6-trimethylcyclohexen-1-yl)-3, 7, 12, 16-tetramethyloctadeca-1, 3, 5, 7, 9, 11, 13, 15, 17-nonaenyl]-2, 4, 4-trimethylcyclohex-2-en-1-ol

Chemical Property of Isozeaxanthin

Chemical Property:

• Boiling Point: 713.735oC at 760 mmHg
• Flash Point: 274.461oC
• PSA: 40.46000
• Density: 1.008g/cm3
• LogP: 10.54740
• Storage Temp.: Amber Vial, -86°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 10.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 568.42803102
• Heavy Atom Count: 42
• Complexity: 1190

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2=C(C(CCC2(C)C)O)C)C)C
• Isomeric SMILES: CC1=C(C(CCC1O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(C(CCC2(C)C)O)C)\C)\C)/C)/C
• Uses: Isozeaxanthin is an antioxidant β-carotene (C184250) derivative with anti-cancer properties found in soybean oil.

Technology Process of Isozeaxanthin

There total 25 articles about Isozeaxanthin 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:

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) + [(1E,3E)?3?methyl?5?(3?hydroxyl?2,6,6?trimethylcyclohex?2?en?2?yl)penta?1,3?dien?1?yl]phosphonate → isozeaxanthin (29065-03-0,68538-97-6,84142-78-9,84518-15-0,106037-10-9,125472-26-6,21940-25-0)

Guidance literature:

[(1E,3E)?3?methyl?5?(3?hydroxyl?2,6,6?trimethylcyclohex?2?en?2?yl)penta?1,3?dien?1?yl]phosphonate; With potassium tert-butylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; for 5.5h; Inert atmosphere;

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -25 - 25 ℃; for 2.58333h; Inert atmosphere;

DOI:10.1007/s13738-019-01784-2

Reference yield:

canthaxanthin (514-78-3) → isozeaxanthin (29065-03-0,68538-97-6,84142-78-9,84518-15-0,106037-10-9,125472-26-6,21940-25-0)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1021/ja01588a044 DOI:10.1021/j100384a026

Reference yield:

4'-hydroxy-β,β-caroten-4-one (106356-06-3,125377-14-2,125472-27-7,2213-17-4) → isozeaxanthin (29065-03-0,68538-97-6,84142-78-9,84518-15-0,106037-10-9,125472-26-6,21940-25-0)

Guidance literature:

With lithium aluminium tetrahydride;

DOI:10.1021/ja01588a044

upstream raw materials:

canthaxanthin

4'-hydroxy-β,β-caroten-4-one

4'-acetylthio-β,β-carotene

4,4'-diacetoxy-β,β-carotene

Downstream raw materials:

Thioacetic acid S-{2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxo-cyclohex-1-enyl)-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-cyclohex-2-enyl} ester

4,4'-diacetylthio-β,β-carotene

4'-acetylthio-β,β-carotene

canthaxanthin

Refernces

• 1、 Fontan, Noelia,Dominguez, Marta,Ulvarez, Rosana,De Lera, Ungel R.. "Synthesis of C40-symmetrical fully conjugated carotenoids by olefin metathesis". . p. 6704 - 6712. Retrieved 2012/01/03.
• 2、 Sliwka, Hans-Richard,Liaaen-Jensen, Synnove. "Selective hydrogenation of carotenones II.? Reduction of rhodoxanthin to lutein and zeaxanthin, and of canthaxanthin to a dihydro-retro-carotenediol by tellurium hydride". . p. 637 - 639. Retrieved 2007/10/03.