Helenien

Base Information

• Chemical Name: Helenien
• CAS No.: 547-17-1
• Molecular Formula: C72H116O4
• Molecular Weight: 1045.71
• European Community (EC) Number: 208-916-4
• UNII: V2W1791D7V
• Metabolomics Workbench ID: 70184
• NCI Thesaurus Code: C66661
• Nikkaji Number: J2.067B
• Wikidata: Q27106836
• Mol file: 547-17-1.mol

Synonyms:helenien;heleniene;xanthophyll dipalmitate;xantofyle palmitate

Chemical Property of Helenien

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 82 °C
• Refractive Index: 1.523
• Boiling Point: 949.7°Cat760mmHg
• Flash Point: 457.9°C
• PSA: 52.60000
• Density: 0.96g/cm³
• LogP: 22.46770
• XLogP3: 26.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 42
• Exact Mass: 1044.88736218
• Heavy Atom Count: 76
• Complexity: 1980

Purity/Quality:

98%,99%, ^*data from raw suppliers

Helenien 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OC1CC(=C(C(C1)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2C(=CC(CC2(C)C)OC(=O)CCCCCCCCCCCCCCC)C)C)C)C
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)O[C@@H]1CC(=C(C(C1)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/[C@H]2C(=C[C@@H](CC2(C)C)OC(=O)CCCCCCCCCCCCCCC)C)/C)/C)C
• Uses: Lutein Dipalmitate is an antioxidant β-carotene (C184250) found in marigold flowers as well as human plasma.

Technology Process of Helenien

There total 2 articles about Helenien 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:

lutein (127-40-2) + 1-hexadecylcarboxylic acid (57-10-3) → all-trans-lutein 3'-O-palmitate + all-trans-lutein 3-O-palmitate + (3R,3'R,6'R)-lutein dipalmitate (547-17-1)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 4h; Title compound not separated from byproducts.;

DOI:10.1021/jf070357n

Reference yield:

all-trans lutein (7481-64-3) + n-hexadecanoyl chloride (112-67-4) → 3,7,12,16-Tetramethyl-1t-((1Ξ:4Ξ)-4-palmitoyloxy-2,2,6-trimethyl-cyclohexen-(5)-yl)-18t-((Ξ)-4-palmitoyloxy-2,2,6-trimethyl-cyclohexen-(6)-yl)-octadecanonaen-(1,3t,5t,7t,9t,11t,13t,15t,17) (547-17-1,115223-33-1,115223-34-2,117305-39-2)

Guidance literature:

With pyridine;

DOI:10.1002/hlca.19300130533

Reference yield:

propan-1-ol (71-23-8) + all-trans-lutein 3'-O-myristate-3-O-palmitate + zeaxanthin myristate palmitate (115095-08-4) + (3R,3'R)-zeaxanthin dipalmitate (637-05-8,143731-35-5,143789-35-9,144-67-2) + (3R,3'R,6'R)-lutein dipalmitate (547-17-1) + zeaxanthin dimyristic acid ester + (3R,3'R,6'R)-lutein dimyristate + all-trans-lutein 3'-O-palmitate-3-O-myristate → (3R,3'R,6'R)-lutein 3'-propyl ether (851854-29-0) + zeaxanthin (144-68-3,3309-19-1,24502-92-9,29472-68-2,31272-50-1,31272-53-4,57820-80-1,60046-54-0,60497-64-5,60497-65-6,72002-36-9,72580-10-0,100347-92-0,100347-97-5,136656-95-6,136733-98-7,136733-99-8,136734-01-5,136734-02-6)

Guidance literature:

propan-1-ol; all-trans-lutein 3'-O-myristate-3-O-palmitate; zeaxanthin myristate palmitate; (3R,3'R)-zeaxanthin dipalmitate; (3R,3'R,6'R)-lutein dipalmitate; zeaxanthin dimyristic acid ester; (3R,3'R,6'R)-lutein dimyristate; all-trans-lutein 3'-O-palmitate-3-O-myristate; With hydrogenchloride; In hexane; water; at 45 - 50 ℃; for 21h;

With potassium hydroxide; In methanol; hexane; water; Product distribution / selectivity;

upstream raw materials:

all-trans lutein

n-hexadecanoyl chloride

lutein

1-hexadecylcarboxylic acid

Downstream raw materials:

3,4-anhydrolutein

2',3'-anhydrolutein

2',3'-anhydrolutein palmitate

3,4-anhydrolutein palmitate

Refernces