β,ε-Carotin-3,3'-diol

Lutein A

HCID 5281243CAS 127-40-2

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

Lutein127-40-2all-trans-LuteinLutein AVegetable luteinVegetable luteolXantofyltrans-Luteinall-trans-XanthophyllFloraGLOFloraGLO LuteinE 161b
Weitere Namen anzeigen
DimerMARIGOLD EXTRACTLutein 5%DaucolluteochromeXANTHOPHYLL FROM CORNxanthophyllfromalfalfabeta,
Oro Glo 7beta,epsilon-Carotene-3,3'-diol, (3R,3'R,6'R)-LeuteinDTXSID8046749(3R,3'R,6'R)-beta,epsilon-carotene-3,3'-diolOS 24INS NO.161B(I)X72A60C9MT

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

Experimentelle und physikochemische Eigenschaften

LogP7.9
SolubilityInsoluble
Melting Point · 2 Einträge

196

196 °C

Physical Description · 2 Einträge

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

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 3 Einträge

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 · 3 Einträge

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.

Hazard Classes and CategoriesNot Classified

Regulatorische Informationen

Regulatory Information · 3 Einträge

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

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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 · 1 Eintrag

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.

Tissue LocationsAdipose Tissue;Adrenal Gland;Epidermis;Eye Lens;Fibroblasts;Intestine;Neuron;Ovary;Placenta;Retina;Spleen;Testis
Cellular LocationsExtracellular;Membrane

Verwendung und Herstellung

Use Classification · 4 Einträge

Food additives

Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes

Food Additives -> COLOUR -> JECFA Functional Classes

Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes

General Manufacturing Information.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: ACTIVE
Anwendungen · 2 Einträge

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.

Vor- und nachgelagerte Produkte

Anbieter50 Anbieter

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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