Luteine

Base Information

• Chemical Name: Luteine
• CAS No.: 38327-39-8
• Deprecated CAS: 50894-29-6
• Molecular Formula: C₄₀H₅₆O₂
• Molecular Weight: 568.883
• European Community (EC) Number: 204-840-0
• NSC Number: 59193
• Wikipedia: Lutein
• Metabolomics Workbench ID: 42578
• ChEMBL ID: CHEMBL1979448
• Mol file: 38327-39-8.mol

Synonyms:cis-Lutein;(Z)-xanthophyll;Luteine;127-40-2;NSC59193;38327-39-8;beta,?-carotene-3,3'-diol;C40H56O2;Beta, e- carotene- 3, 3'- diol;C40-H56-O2;xanthophyll from alfalfa;4',5'-Didehydro-5',6'-dihydro-beta,beta-carotene-3,3'-diol;SCHEMBL822798;3,3'-Dihydroxy-alpha-Carotin;CHEMBL1979448;NCGC00482960-01;LS-15429;.beta.,3'-diol, (3R,3'R,6'R)-;Q-100115;(1R)-4-[18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol;4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-2,6,6-trimethyl-cyclohex-2-en-1-yl)-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-cyclohex-3-en-1-ol;4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-(4-hydroxy-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-2-en-1-ol

Chemical Property of Luteine

Chemical Property:

• Boiling Point: 702.3 °C at 760 mmHg
• Flash Point: 269 °C
• PSA: 40.46000
• Density: 1.004 g/cm³
• LogP: 10.40330
• XLogP3: 11
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 10
• Exact Mass: 568.42803102
• Heavy Atom Count: 42
• Complexity: 1270

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(CC(C1)O)(C)C)C=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC2C(=CC(CC2(C)C)O)C)C)C
• Isomeric SMILES: CC1=C(C(CC(C1)O)(C)C)/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/C=C/C2C(=CC(CC2(C)C)O)C)/C)/C

Technology Process of Luteine

There total 15 articles about Luteine 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:

(3R,6'R)-3-hydroxy-β,ε-caroten-3'-one (23984-55-6) → 3'-epilutein (127-40-2,7481-64-3,13836-72-1,14596-49-7,15904-92-4,24502-86-1,29414-89-9,32449-88-0,38327-39-8,52842-48-5,70267-39-9,79464-33-8,79516-56-6,82915-91-1,83023-36-3,89615-89-4,89673-72-3,97169-07-8,105452-20-8,116947-92-3,116947-93-4,144068-66-6,144068-67-7) + lutein (127-40-2)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; water; at 0 ℃;

DOI:10.1021/ac00042a016

Reference yield:

lutein (127-40-2) → 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) + 3'-epilutein (127-40-2,7481-64-3,13836-72-1,14596-49-7,15904-92-4,24502-86-1,29414-89-9,32449-88-0,38327-39-8,52842-48-5,70267-39-9,79464-33-8,79516-56-6,82915-91-1,83023-36-3,89615-89-4,89673-72-3,97169-07-8,105452-20-8,116947-92-3,116947-93-4,144068-66-6,144068-67-7) + (3R,6'R)-3-hydroxy-3',4'-didehydro-β,γ-carotene (92760-20-8) + (3R,3'S,6'R,9Z)-4',5'-didehydro-5',6'-dihydro-β,β-carotene-3,3'-diol

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃; for 43h; Further byproducts given;

DOI:10.1002/hlca.200490195

Reference yield:

lutein (127-40-2) → 3'-epilutein (127-40-2,7481-64-3,13836-72-1,14596-49-7,15904-92-4,24502-86-1,29414-89-9,32449-88-0,38327-39-8,52842-48-5,70267-39-9,79464-33-8,79516-56-6,82915-91-1,83023-36-3,89615-89-4,89673-72-3,97169-07-8,105452-20-8,116947-92-3,116947-93-4,144068-66-6,144068-67-7)

Guidance literature:

With sulfuric acid; In tetrahydrofuran; at 25 - 30 ℃; Inert atmosphere;

upstream raw materials:

lutein

(3R,6'R)-3-hydroxy-β,ε-caroten-3'-one

Downstream raw materials:

(3R,6'R)-3-hydroxy-β,ε-caroten-3'-one

Refernces

• 1、 -. "Process for Synthesis of (3R,3'R,6'R)-Lutein and its Stereoisomers". Page/Page column 10-11; 25. . Retrieved 2009/10/30.
• 2、 Molnar, Peter,Deli, Jozsef,Osz, Erzsebet,Zsila, Ferenc,Simonyi, Miklos,Toth, Gyula. "Confirmation of the absolute (3R,3′S,6′R)-configuration of (all-E)-3′-epilutein". . p. 2159 - 2168. Retrieved 2007/10/03.