Luteine

Base Information

• Chemical Name: Luteine
• CAS No.: 127-40-2
• Deprecated CAS: 50894-29-6
• Molecular Formula: C40H56O2
• Molecular Weight: 568.883
• Hs Code.: 29061990
• European Community (EC) Number: 204-840-0
• NSC Number: 59193
• Wikipedia: Lutein
• Metabolomics Workbench ID: 42578
• ChEMBL ID: CHEMBL1979448
• Mol file: 127-40-2.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:

• Appearance/Colour: Orange powder
• Vapor Pressure: 8.45E-23mmHg at 25°C
• Melting Point: 183 °C
• Refractive Index: 1.582
• Boiling Point: 702.266 °C at 760 mmHg
• PKA: 14.61±0.70(Predicted)
• Flash Point: 269.068 °C
• PSA: 40.46000
• Density: 1.004 g/cm³
• LogP: 10.40330
• Storage Temp.: −70°C
• Solubility.: Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly, Heated, S
• 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:

80% ^*data from raw suppliers

beta- ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,F
• Statements: 36/37/38-11
• Safety Statements: 26-37/39-16-7-24/25

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
• Description: Lutein is a dietary carotenoid that has been found in eggs and yellow-colored fruits and vegetables and has diverse biological activities. It reduces hyperglycemia-induced mitochondrial DNA damage and production of reactive oxygen species (ROS) and promotes mitochondrial biogenesis in ARPE-19 cells when used at a concentration of 10 μM. Lutein (20 mg/kg) increases nitric oxide (NO) production and decreases serum levels of endothelin-1 in a rat model of hyperhomocysteinemia. Dietary administration of lutein (0.2%) decreases monocyte migration and lesion size in an ApoE-/- and Ldlr-/- mouse models of atherosclerosis. Lutein reduces infarct size and cardiac malondialdehyde (MDA), lactate dehydrogenase (LDH), and troponin T levels, and increases cardiac levels of catalase (CAT), superoxide dismutase (SOD), heme oxygenase-1 (HO-1), and Nrf2 in a rat model of heart failure induced by isoproterenol . It forms a retinal pigment in human eyes, and high dietary intake of lutein is positively correlated with reduced risk of age-related macular degeneration and cataracts in humans.
• Uses: Xanthophyll is one of the most widespread carotenoid alcohols in nature. Originally isolated from egg yolk, also isolated by chromatography from nettles, algae, and petals of many yellow flowers. One of the most widespread carotenoid alcohols in nature. Originally isolated from egg yolk, also isolated by chromatography from nettles, algae, and petals of many yellow flowers. Xanthophyll has been used: to quantify circulating lutein in birds to study its effect on the synthesis of factor D (FD) by adipocytes for the quantification of carotenoids from the leaves of Brassica oleracea

Technology Process of Luteine

There total 28 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: 94.0%

marigold oleoresin → lutein (127-40-2)

Guidance literature:

marigold oleoresin; With INDION 860; In butan-1-ol; at 50 ℃; for 2h;

With sodium hydroxide; tetrabutylammomium bromide; In butan-1-ol; at 50 ℃; for 1h; Product distribution / selectivity;

Reference yield: 25.0%

[(2E,4E)-5-((1R,4R)-4-Acetoxy-2,6,6-trimethyl-cyclohex-2-enyl)-3-methyl-penta-2,4-dienyl]-triphenyl-phosphonium; chloride + (3R)-3-hydroxy-12′-apo-β-caroten-12'-al → lutein (127-40-2)

Guidance literature:

With potassium hydroxide; In dichloromethane; water; isopropyl alcohol; Ambient temperature;

DOI:10.1002/hlca.19800630614

Reference yield:

marigold oleoresin → cis-luteins + beta-carotene (7235-40-7) + 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) + lutein (127-40-2) + (3R)-cryptoxanthin (472-70-8)

Guidance literature:

With potassium hydroxide; water; In ethanol; at 73 - 75 ℃; for 0.5h; Product distribution / selectivity;

upstream raw materials:

(3R,6'R)-3-hydroxy-β,ε-caroten-3'-one

4',5'-didehydro-4,5'-retro-β,β-carotene-3,3'-dione

3,3'-dioxo-trans-α-carotene

Downstream raw materials:

3'-epilutein

lutein

(3'S,6'R)-2,3-didehydro-β,ε-caroten-3'-ol

(3S,3'S,6'R)-lutein

Refernces

• 1、 -. "NANOEMULSIONS HAVING REVERSIBLE CONTINUOUS AND DISPERSED PHASES". . . Retrieved 2017/08/01.
• 2、 -. "NUTRITIONAL FORMULATION". . . Retrieved 2009/09/08.