lutein

CAS No. 127-40-2

Formula: C40H56O2
Basic Info

Lutein (from Latin luteus meaning "yellow") is a xanthophyll and one of 600 known naturally occurring carotenoids. Lutein is synthesized only by plants and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots. In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll (an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis. See xanthophyll cycle for this topic.
Lutein is obtained by animals directly or indirectly, from plants. Lutein is apparently employed by animals as an antioxidant and for blue light absorption. Lutein is found in egg yolks and animal fats. In addition to coloring yolks, lutein causes the yellow color of chicken skin and fat, and is used in chicken feed for this purpose. The human retina accumulates lutein and zeaxanthin. The latter predominates at the macula lutea while lutein predominates elsewhere in the retina. There, it may serve as a photoprotectant for the retina from the damaging effects of free radicals produced by blue light. Lutein is isomeric with zeaxanthin, differing only in the placement of one double bond.
The principal natural stereoisomer of lutein is (3R,3′R,6′R)-beta,epsilon-carotene-3,3′-diol. Lutein is a lipophilic molecule and is generally insoluble in water. The presence of the long chromophore of conjugated double bonds (polyene chain) provides the distinctive light-absorbing properties. The polyene chain is susceptible to oxidative degradation by light or heat and is chemically unstable in acids.
Lutein is present in plants as fatty-acid esters, with one or two fatty acids bound to the two hydroxyl-groups. For this reason, saponification (de-esterfication) of lutein esters to yield free lutein may yield lutein in any ratio from 1:1 to 1:2 molar ratio with the saponifying fatty acid.

Formula
C40H56O2
Molecular Weight
568.871
Exact Mass
568.428
LogP
10.4033
PSA
40.46
Synonyms

Lutein

β,-Carotene-3,3‘-diol, (3R,3‘R,6‘R)-

Xanthophyll

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Properties
Appearance & Physical State
Yellowish-brown, viscous liquid.
Density
1.004g/cm3
Boiling Point
702.3ºC at 760mmHg
Melting Point
183ºC
Flash Point
269.1ºC
Refractive Index
1.582
Storage Condition
-70ºC
Vapor Pressure
8.45E-23mmHg at 25°C
Safety Info
Safety Statements
S26; S37/39
WGK Germany
3
Risk Statements
R36/37/38
HS Code
2932999099
Hazard Codes
Spectrum
NMR Spectrum Predict 1H proton NMR
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