Grundinformationen
- Standard-SMILES
CC1=C[C@H](O)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C- InChIKey
KBPHJBAIARWVSC-RGZFRNHPSA-N- Summenformel
- C40H56O2
- Durchschnittliche Molmasse
- 568,9 g/mol
- Monoisotopische Masse
- 568,42803102
Namen und Bezeichner
- Bevorzugter Name
- Lutein A
- IUPAC
- (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-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
- Lokaler Name
- β,ε-Carotin-3,3'-diol
- Englischer Name
- Xanthophyll
- Summenformel
- C40H56O2
- Molmasse
- 568.87
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
127-40-2- PubChem CID
- 5281243
- DTXSID
DTXSID8046749- ChEMBL
CHEMBL173929- ChEBI
CHEBI:28838- UNII
- X72A60C9MT
- EC Number
- 204-840-0
- Nikkaji
- J5.394E
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 11
- Polarare Oberfläche (TPSA)
- 40,5 Ų
- H-Brücken-Donoren
- 2
- H-Brücken-Akzeptoren
- 2
- Frei drehbare Bindungen
- 10
- Schwere Atome
- 42
- Formalladung
- 0
- Komplexität
- 1.270
Experimentelle und physikochemische Eigenschaften
Melting Point
196
196 °C
Physical Description
Dark, yellowish brown liquid
Solid
Physikochemische Eigenschaften
- Schmelzpunkt
- 195 °C · 195 °C
- Siedepunkt
- 572.66 °C · 572.66°C (rough estimate)
- Dichte
- 0.9944 · 0.9944 (rough estimate)
- Brechungsindex
- 20 · n20/D1.361-1.363
- Flammpunkt
- 269.1 · 269.1±27.5 °C
- storage temp.
- -20 °C · -20°C
- Löslichkeit
- Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly, Heated, Sonicated)
- pka
- 14.61 · 14.61±0.70(Predicted)
- Aggregatzustand
- Solid
- Farbe
- Red to Very Dark Red
- Biologische Quelle
- rabbit
- Merck
- 13 · 13,10120
- BRN
- 2068547 · 2068547
- Stabilität
- Light Sensitive, Temperature Sensitive
- Kosmetik-Inhaltsstoffe Funktionen
- SKIN CONDITIONING
- InChIKey
- KBPHJBAIARWVSC-RGZFRNHPSA-N
- SMILES
- CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C)\C=C\C=C(C)\C=C\[C@H]2C(C)=C[C@H](O)CC2(C)C
- LogP
- 11.524 · 11.524 (est)
- CAS Datenbank
- 127 · 127-40-2(CAS DataBase Reference)
- EPA chemische Informationen
- -3 · .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)- (127-40-2)
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
This chemical does not meet GHS hazard criteria for 95.6% (151 of 158) of all reports.
Not Classified;Reported as not meeting GHS hazard criteria by 151 of 158 companies (only 4.4% companies provided GHS information). For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 158 reports by companies from 4 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 151 of 158 reports by companies.;There are 2 notifications provided by 7 of 158 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Gefahrenhinweise
Regulatory Information
Chemical: .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
Regulation (EC) No 1333/2008 (amended)
.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Regulatorische Informationen
Regulatory Information
Chemical: .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
Regulation (EC) No 1333/2008 (amended)
.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Sicherheitsdaten
- F
- 1-8-10-16
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29061990
- risk_code
- 36/37/38-11
- hazard_code
- Xi
- safety_code
- 26-37/39-16-7-24/25
- Speicherklasse
- 11 - Combustible Solids
Chemie und Industrie
Pharmakologische Informationen
Pharmacodynamics
Lutein was found to be present in a concentrated area of the macula, a small area of the retina responsible for central vision. The hypothesis for the natural concentration is that lutein helps protect from oxidative stress and high-energy light. Several studies show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD).
Mechanism of Action
Xanthophylls have antioxidant activity and react with active oxygen species, producing biologically active degradation products. They also can inhibit peroxidation of membrane phospholipids and reduce lipofuscin formation, both of which contribute to their antioxidant properties. Lutein is naturally present in the macula of the human retina. It filters out potentially phototoxic blue light and near-ultraviolet radiation from the macula. The protective effect is due in part, to the reactive oxygen species quenching ability of these carotenoids. Lutein is more stable to decomposition by pro-oxidants than are other carotenoids such as beta-carotene and lycopene. Lutein is abundant in the region surrounding the fovea, and lutein is the predominant pigment at the outermost periphery of the macula. Zeaxanthin, which is fully conjugated (lutein is not), may offer somewhat better protection than lutein against phototoxic damage caused by blue and near-ultraviolet light radiation. Lutein is one of only two carotenoids that have been identified in the human lens, may be protective against age-related increases in lens density and cataract formation. Again, the possible protection afforded by lutein may be accounted for, in part, by its reactive oxygen species scavenging abilities. Carotenoids also provide protection from cancer. One of the mechanisms of this is by increasing the expression of the protein connexin-43, thereby stimulating gap junctional communication and preventing unrestrained cell proliferation.
Verwendung und Herstellung
Use Classification
Food additives
Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes
Food Additives -> COLOUR -> JECFA Functional Classes
Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes
Anwendungen
BeschreibungLutein 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.
VerwendenXanthophyll 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.
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