4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[4-(hexadecanoyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl hexadecanoate

Base Information

• Chemical Name: 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[4-(hexadecanoyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl hexadecanoate
• CAS No.: 144-67-2
• Molecular Formula: C₇₂H₁₁₆O₄
• Molecular Weight: 1045.71
• Nikkaji Number: J2.980.513J
• Metabolomics Workbench ID: 47019
• ChEMBL ID: CHEMBL2105817
• Mol file: 144-67-2.mol

Synonyms:Physalin;CHEMBL2105817;beta,beta-Carotene-3,3'-diol dipalmitate;4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[4-(hexadecanoyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl hexadecanoate

Chemical Property of 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[4-(hexadecanoyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl hexadecanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 98～100℃
• Boiling Point: 956.4°C at 760 mmHg
• Flash Point: 462.1°C
• PSA: 52.60000
• Density: 0.96g/cm³
• LogP: 22.61180
• XLogP3: 26.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 42
• Exact Mass: 1044.88736218
• Heavy Atom Count: 76
• Complexity: 1850

Purity/Quality:

97% ^*data from raw suppliers

Zeaxanthin dipalmitate ^*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=CC2=C(CC(CC2(C)C)OC(=O)CCCCCCCCCCCCCCC)C)C)C)C
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC1CC(C(=C(C1)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C2=C(CC(CC2(C)C)OC(=O)CCCCCCCCCCCCCCC)C)\C)\C)/C)/C)(C)C
• Uses: Zeaxanthin dipalmitate is an antioxidant carotenoid compound, and is the main carotenoid in Lycium barbarum and Lycium chinense fruits. Zeaxanthin dipalmitate from Lycium chinense has been shown to reduce experimentally induced hepatic fibrosis in rats.

Technology Process of 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[4-(hexadecanoyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl hexadecanoate

There total 2 articles about 4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[4-(hexadecanoyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl hexadecanoate 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:

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) + n-hexadecanoyl chloride (112-67-4) → (3R,3'R)-zeaxanthin dipalmitate (637-05-8,143731-35-5,143789-35-9,144-67-2)

Guidance literature:

With pyridine; chloroform; at 50 ℃;

DOI:10.1080/13583883.2002.9967066

Reference yield:

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) + n-hexadecanoyl chloride (112-67-4) → (3R,3'R)-zeaxanthin palmitate (87891-75-6,143731-36-6) + (3R,3'R)-zeaxanthin dipalmitate (637-05-8,143731-35-5,143789-35-9,144-67-2)

Guidance literature:

With pyridine;

DOI:10.1021/jf034803s

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:

zeaxanthin

n-hexadecanoyl chloride

Downstream raw materials:

(3R,3'R)-zeaxanthin palmitate

3,3'-bis-palmitoyloxy-6,6'-didehydro-ε,ε-carotene

zeaxanthin

(9Z)-zeaxanthin