Lutein
General
Synonyms	Luteine; Lutein ester; trans-lutein; beta, epsilon-Carotene-3,3'-diol
IUPAC Name	4-[18-(4-hydroxy-2,6,6-trimethyl-1-cyclohexenyl) -3,7,12,16-tetramethyl-octadeca -1,3,5,7,9,11,13,15,17-nonaenyl] -3,5,5-trimethyl-cyclohex-2-en-1-ol
CAS Number	127-40-2
Chemical formula	C40H56O2
Chemical properties
Molecular weight	568.871 g/mol
Color	Red-orange
Form	Crystalline
Solubility	Organic/fat soluble, aqueous insoluble
Molar absorption coefficient (EtOH)	255 ml/(mg*cm)
λmax	446 nm
Toxicity	GRAS
Deficiency symptoms
Eye damage Pale, dry skin
Excess symptoms
Carotenodermia
Common sources
Leafy vegetables Egg yolk Darkly colored fruits Marigold petals Vitamin Water Focus

Lutein (LOO-teen) (from Latin lutea meaning "yellow") is one of over 600 known naturally occurring carotenoids. Found in green leafy vegetables such as spinach and kale, lutein is employed by organisms as an antioxidant and for blue light absorption. Lutein is covalently bound to one or more fatty acids present in some fruits and flowers, notably marigolds (Tagetes). Saponification of lutein esters yields lutein in approximately a 2:1 weight-to-weight conversion. Image File history File links Lutein. ... The International Union of Pure and Applied Chemistry (IUPAC) is an international non-governmental organization devoted to the advancement of chemistry. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences and alloys. ... This article or section does not cite any references or sources. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... Solubility refers to the ability for a given substance, the solute, to dissolve in a solvent. ... In optics, the Beer-Lambert law, also known as Beers law or the Lambert-Beer law or the Beer-Lambert-Bouguer law is an empirical relationship that relates the absorption of light to the properties of the material through which the light is traveling. ... Generally Recognized as Safe (GRAS): Designation by the FDA that a chemical or substance (including certain pesticides) added to food is considered safe by experts, and so is exempted from the usual FFDCA food additive tolerance requirements. ... Carotenodermia (also carotenaemia, carotenemia or hypercarotenemia) is a yellowish/orange discoloration of the skin, most often occurring in the palms of the hands and soles of the feet as a result of high levels of carotene in the body. ... Latin is an ancient Indo-European language originally spoken in Latium, the region immediately surrounding Rome. ... The orange ring surrounding Grand Prismatic Spring is due to carotenoid molecules, produced by huge mats of algae and bacteria. ... Chinese cabbage Swiss chard Leaf vegetables, also called greens or leafy greens, are plant leaves eaten as a vegetable, sometimes accompanied by tender petioles and shoots. ... Binomial name Spinacia oleracea L. Percentages are relative to US recommendations for adults. ... Kale (also called Borecole) is a form of cabbage (Brassica oleracea Acephala Group), green in color, in which the central leaves do not form a head. ... Space-filling model of the antioxidant metabolite glutathione. ... Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms. ... In chemistry, especially biochemistry, a fatty acid is a carboxylic acid often with a long unbranched aliphatic tail (chain), which is either saturated or unsaturated. ... Marigold can mean: Flowering plants in the family Asteraceae in the following genera: Calendula (Marigold or Pot Marigold) Tagetes (Mexican marigold, African marigold or French marigold) Glebionis segetum (syn. ... Saponification of a lipid with potassium hydroxide. ... For the Biblical Ester, see Esther. ...

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. This article or section does not cite its references or sources. ... A chromophore is part (or moiety) of a molecule responsible for its color. ... Polyenes are poly-unsaturated organic compounds that contain one or more sequences of alternating double and single carbon-carbon bonds. ...

The principal natural stereoisomer of lutein is (3R,3'R,6'R)-beta, epsilon-Carotene-3,3'-diol. Stereoisomerism is the arrangement of atoms in molecules whose connectivity remains the same but their arrangement in space is different in each isomer. ...

As a pigment

This xanthophyll, like its sister compound zeaxanthin, has primarily been used as a natural colorant due to its orange-red color. Lutein absorbs blue light and therefore appears yellow at low concentrations and orange-red at high concentrations. This article or section does not cite its references or sources. ... Zeaxanthin is one of the two carotenoids contained within the retina. ... The colour orange occurs between red and yellow in the visible spectrum at a wavelength of about 585–620 nanometres. ... Color is an important part of the visual arts. ... YOU SUCK!!!!! ... A yellow Tulip. ...

Lutein was traditionally used in chicken feed to provide the yellow color of broiler chicken skin. Polled consumers viewed yellow chicken skin more favorably than white chicken skin. Such lutein fortification also results in a darker yellow egg yolk. Today the coloring of the egg yolk has become the primary reason for feed fortification. Lutein is not used as a colorant in other foods due to its limited stability, especially in the presence of other dyes. This article or section does not adequately cite its references or sources. ... A broiler is a chicken raised primarily for meat, as opposed to a one raised to produce eggs (called a Layer within the industry as it lays eggs). ... An egg yolk surrounded by the egg white An egg yolk is the part of an egg which serves as the food source for the developing embryo inside. ... A colourant is something added to something else to induce a change in colour. ...

Health benefits for eyes

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. Various research studies have shown that a direct relationship exists between lutein intake and pigmentation in the eye ^[1-7]. Several studies also show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD) ^[8-10]. Human eye cross-sectional view. ... Listen to this article · (info) · play in browser This audio file was created from an article revision dated 2005-07-19, and may not reflect subsequent edits to the article. ...

Lutein is a natural part of human diet when fruits and vegetables are consumed. For individuals lacking sufficient lutein intake, lutein-fortified foods are available, or in the case of elderly people with a poorly absorbing digestive system, fortification via a sublingual spray ensures maximum benefit to the eyes. As early as 1996, lutein has been incorporated into dietary supplements. While no recommended daily allowance currently exists for lutein as for other nutrients, positive effects have been seen at dietary intake levels of 6 mg/day ^[11]. The only definitive side effect of excess lutein consumption is the same observed for β-carotene overdose, namely bronzing of the skin (carotenodermia). The normal levels of Lutein found in a daily vitamin tablet can be as low as 0.25mg. It has been suggested that this article or section be merged with Daily values. ... Carotene is a terpene, an orange photosynthetic pigment, important for photosynthesis. ... Carotenodermia (also carotenaemia, carotenemia or hypercarotenemia) is a yellowish/orange discoloration of the skin, most often occurring in the palms of the hands and soles of the feet as a result of high levels of carotene in the body. ...

The functional difference between the benefits of lutein (free form) and lutein esters is not entirely known. It is suggested that the bioavailability is lower for lutein esters, but much debate continues. In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ...

As a food additive, lutein has the E number E161b. Food additives are substances added to food to preserve flavor or improve its taste and appearance. ... For the mathematical constant see: E (mathematical constant). ...

Commercial value

The Lutein market is segmented into Pharmaceutical, Nutraceutical, Food, Pet Foods and Animal Feed and Fish Feed. The Pharmaceutical market is estimated to be about US $ 190 Million, Nutraceutical and Food is estimated to be about US $ 110 Million. Pet foods and other applications are estimated at US $ 175 Million annually. Apart from the customary Age related Macular Degeneration applications , newer applications are emerging in Cosmetics, Skin Care and as an Antioxidant. It is one of the fastest growing areas of the $ 2 Billion carotenoid market ^[12]. There are several lutein ester suppliers, but few pure lutein (Free Form) suppliers due primarily to patent protections on obtaining purified Lutein from natural products, namely marigolds. Companies like Indus Biotech Pvt. Ltd, OmniActive Health Technologies and Kemin Industries have patents. The market size of lutein is anticipated to grow at an average annual growth rate of over 22%.

References

1. Malinow, M.R., et al., Diet-related macular anomalies in monkeys. Invest Ophthalmol Vis Sci, 1980. 19(8): p. 857-63.
2. Johnson, E.J., et al., Relation among serum and tissue concentrations of lutein and zeaxanthin and macular pigment density. Am J Clin Nutr. 2000 Jun; 71(6): 1555-62. PubMed Free text
3. Landrum, J., et al. Serum and macular pigment response to 2.4 mg dosage of lutein. in ARVO. 2000.
4. Berendschot, T.T., et al., Influence of lutein supplementation on macular pigment, assessed with two objective techniques. Invest Ophthalmol Vis Sci. 2000 Oct. 41(11): 3322-6; PubMed Free text
5. Aleman, T.S., et al., Macular pigment and lutein supplementation in retinitis pigmentosa and Usher syndrome. Invest Ophthalmol Vis Sci. 2001 Jul; 42(8): 1873-81. PubMed Free text
6. Duncan, J.L., et al., Macular pigment and lutein supplementation in choroideremia. Exp Eye Res, 2002. 74(3): p. 371-81. PubMed
7. Johnson, E.J., et al., Nutritional manipulation of primate retinas, III: Effects of lutein or zeaxanthin supplementation on adipose tissue and retina of xanthophyll-free monkeys. Invest Ophthalmol Vis Sci, 2005. 46(2): p. 692-702. PubMed Free text
8. Richer, S., ARMD--pilot (case series) environmental intervention data. J Am Optom Assoc, 1999. 70(1): p. 24-36. PubMed'
9. Richer, S., et al., Double-masked, placebo-controlled, randomized trial of lutein and antioxidant supplementation in the intervention of atrophic age-related macular degeneration: the Veterans LAST study (Lutein Antioxidant Supplementation Trial). Optometry, 2004. 75(4): p. 216-30. PubMed
10. A randomized, placebo-controlled, clinical trial of high-dose supplementation with vitamins C and E, beta carotene, and zinc for age- related macular degeneration and vision loss: AREDS report no. 8. Arch Ophthalmol, 2001. 119(10): p. 1417-36. PubMed
11. ^a  Seddon, J.M., et al., Dietary carotenoids, vitamins A, C, and E, and advanced age-related macular degeneration. Eye Disease Case-Control Study Group. JAMA, 1994. 272(18): p. 1413-20. PubMed
12. ^a  GA-110R The Global Market for Carotenoids, Business Communications Company, Inc.