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EC / List no.: 204-840-0
CAS no.: 127-40-2
Mol. formula: C40H56O2
E161b (Lutein) (/ˈljuːtiɪn, -tiːn/; from Latin luteus meaning "yellow") is a xanthophyll and one of 600 known naturally occurring carotenoids.
E161b (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.
Animals obtain lutein by ingesting plants.
In the human retina, lutein is absorbed from blood specifically into the macula lutea, although its precise role in the body is unknown.
E161b (Lutein) is also found in egg yolks and animal fats.
E161b (Lutein) is isomeric with zeaxanthin, differing only in the placement of one double bond. E161b (Lutein) can be interconverted in the body through an intermediate called meso-zeaxanthin.
The principal natural stereoisomer of lutein is (3R,3′R,6′R)-beta,epsilon-carotene-3,3′-diol.
E161b (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.
E161b (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-esterification) 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.
As a pigment
This xanthophyll, like its sister compound zeaxanthin, has primarily been used in food and supplement manufacturing as a colorant due to its yellow-red color.
E161b (Lutein) absorbs blue light and therefore appears yellow at low concentrations and orange-red at high concentrations.
Many songbirds (like golden oriole, evening grosbeak, yellow warbler, common yellowthroat and Javan green magpie, but not American goldfinch or yellow canaries) deposit lutein obtained from the diet into growing tissues to color their feathers.
E161b (Lutein) is a type of organic pigment called a carotenoid.
E161b (Lutein) is related to beta-carotene and vitamin A. Many people think of lutein as "the eye vitamin."
E161b (Lutein) is one of two major carotenoids found in the human eye (macula and retina).
E161b (Lutein) is thought to function as a light filter, protecting the eye tissues from sunlight damage.
Foods rich in lutein include egg yolks, spinach, kale, corn, orange pepper, kiwi fruit, grapes, zucchini, and squash.
E161b (Lutein) is commonly taken by mouth to prevent eye diseases, including cataracts and a disease that leads to vision loss in older adults (age-related macular degeneration or AMD).
E161b (Lutein) is used for many other conditions, but there is no good scientific evidence to support these other uses.
Description
E161b (Lutein) is a hormone released by luteal cells in the ovaries which contains 21 Carbon Atoms.
E161b (Lutein) is also a crucial metabolic intermediate in the production of other endogenous steroids.
There are two crystal forms of E161b (Lutein), that are type-α and type-β, the two types have similar physiological activity.
Type-α is precipitated from dilute ethanol as orthorhombic white prismatic crystal, while type-β is orthorhombic white needle crystal, they are both insoluble in water, but soluble in ethanol, ethyl ether, chloroform, acetone, dioxane and concentrated sulfuric acid.
E161b (Lutein) can be released by the ovary, placenta and adrenal cortex.
E161b (Lutein)s physiological function mainly manifests in promoting estrogen treated over thicken lining of the uterus to continue the development, proliferation and thickening and hypertrophy, soften and secretion of mucus in order to make good condition for implantation of the fertilized egg.
After the implantation, early stage survival and development of fertilized egg is also under the control of the high E161b (Lutein) release.
As a result, E161b (Lutein) is a very important hormone in the female reproductive system, and E161b (Lutein) is also an important intermediate in the biosynthesis of steroid hormones.
All steroid hormone releasable glands can produce E161b (Lutein), but only ovarian and placenta can release E161b (Lutein) as the main hormone.
Ovarian will release large amount of E161b (Lutein) in the luteal phase after ovulation by granulose luteal cells, so E161b (Lutein) is also named as progestin.
E161b (Lutein) will decrease in result of corpus luteum atrophy.
For normal women, placenta will becomes the main organ maintain E161b (Lutein) after 8 to 9 weeks of pregnancy, accompany with the ovary releasing until the end of pregnancy.
Uses:
The main physiological effects of E161b (Lutein):
1. E161b (Lutein) can maintain the female animal pregnancy, and cause a series of physiological changes, such as inhibition of female estrus.
2. E161b (Lutein) has the power to promote the thickening of the lining of the uterus, promote the bending of the gland and to increase secretion function.
3. E161b (Lutein) can inhibit the peristalsis of the uterus, and contribute to the cervix contraction, secretion of mucus, etc.. These physiological changes provide suitable environment for the operation, growth and development of early embryos, as well as the continued growth of the fetus.
4. Small amount of E161b (Lutein) is also used in combination with the hormone estrogen to promote female estrus.
The synergy between E161b (Lutein) and prolactin can promote the development of mammary glands.
5. E161b (Lutein) is involved in the feedback regulation of the hypothalamus and anterior pituitary, which makes the balance of the animal reproductive hormones.
In vivo, E161b (Lutein) content of all sorts of livestock follicular phase is below 1 ng/ml, while in bovine corpus luteum period is approximately 4 ng/ml, pregnancy period is about 18 ng/ml.
6. Formerly biochemical study shows that E161b (Lutein) modulates action as progestogens, clinical for the treatment of habitual abortion, dysmenorrhea, amenorrhea and other symptoms.
One of E161b (Lutein)'s most important functions is as hormone drugs, to promote and maintain the uterine changes in the early stage of pregnancy, used in habitual abortion, irregular menstruation, etc.. In addition, E161b (Lutein) also behaves as steroid hormone drug as well as progestogens, which is used in treatment of threatened abortion.
Preparation
E161b (Lutein) can be obtained by oxidation of the pregnenolone.
Dry toluene was added to a oven dried reaction kettle, and then cyclohexanone and pregnenolone were added in order with vigorous stirring to dissolve.
Side product H2O was removed by Soxhlet extraction with toluene steam, aluminium isopropoxidequickly was added flowingly, the oxidation reaction was hold on at 115 oC for 2h, cooling to 80 oC, add 5% dilute sulfuric acid under stirring then stand by until water and toluene separated, the toluene layer was extracted with water to neutrality and then distillation off toluene and cyclohexanone.
Cooling, filtering, filter cake was beated with petroleum, filtering, washing with petroleum, dried as crude E161b (Lutein).
The crude product was dissolved in ethanol, decolorized by activated carbon, recrystallized to get the final product, yield 80%.
Another way to produce E161b (Lutein) is choosing the 16-Dehydropregnenolone acetate as start material, treated consecutively by catalytic hydrogenation, alkali hydrolysis, oxidation by aluminum isopropoxide, to get the E161b (Lutein) as final product.
Description
E161b (Lutein), along with pregnenolone, is the biosynthetic precursor of all other steroid hormones.
E161b (Lutein) is synthesized from cholesterol by the sequential action of desmolase in the mitochondria, which produces pregnenolone, followed by Δ4,5-isomerase in the outer mitochondrial membrane and smooth endoplasmic reticulum of steroid-secreting cells.
E161b (Lutein) activates the human E161b (Lutein) receptor with an EC50 value of 0.5 nM.
Chemical Properties
White powder. Melting point 121°C. Stable in air. Insoluble in water. A female sex hormone. Low toxicity.
Occurrence
Colchicum luteum also yields this alkaloid.
Uses
E161b (Lutein) is used as a contraceptive, for amenorrhea, for premenopausal syndrome, infertility, incomplete pregnancies, and anovulatory uterine bleeding.
Steroid hormone produced by the corpus luteum.
Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation.
E161b (Lutein) is implicated in the etiology of breast cancer.
This compound is a contaminant of emerging concern (CECs).
Sterid hormone produced by the corpus luteum.
Induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. E161b (Lutein) is implicated in the etiology of breast cancer
General Description
E161b (Lutein), pregn-4-en-3,20-dione, is so rapidly metabolized that it is not particularlyeffective orally, being only one twelfth as active as intramuscularly.
An oral formulation of micronized E161b (Lutein)(Prometrium) is available.
E161b (Lutein) given intramuscularlycan be very irritating.
A vaginal gel containing 4% or8% E161b (Lutein) offers an alternative dosage form.
E161b (Lutein) was originally obtained from animal ovariesbut is now prepared synthetically from plant sterol precursors.
The discovery of 19-nortestosterones with E161b (Lutein)activity made synthetically modified progestins of tremendoustherapeutic importance.
E161b (Lutein) (and all other steroid 4-ene-3-ones) is lightsensitive and should be protected from light.
Chemical Synthesis
E161b (Lutein), pregn-4-en-3,20-dione (28.3.1), is made by oxidizing pregnenolon with aluminum isopropylate in the presence of cyclohexanone as a proton acceptor (Oppenauer oxidation).
Pregnenolon itself is made by subsequent oxidation and further cleavage of the side chain of stigmasterin, a sterin of plant origin that is isolated from soybeans.
E161b (Lutein) are powerful antioxidants that defend your body against unstable molecules called free radicals.
In excess, free radicals can damage your cells, contribute to aging and lead to the progression of diseases like heart disease, cancer, type 2 diabetes and Alzheimer’s disease.
E161b (Lutein) protect your body’s proteins, fats and DNA from stressors and can even help recycle glutathione, another key antioxidant in your body.
Additionally, their antioxidant properties may reduce the effects of “bad” LDL cholesterol, thus decreasing plaque build-up in your arteries and reducing your risk of heart disease.
E161b (Lutein) also work to protect your eyes from free radical damage.
Your eyes are exposed to both oxygen and light, which in turn promote the production of harmful oxygen free radicals.
E161b (Lutein) cancel out these free radicals, so they’re no longer able to damage your eye cells.
These carotenoids seem to work better together and can combat free radicals more effectively when combined, even at the same concentration.
E161b (Lutein) are the only dietary carotenoids that accumulate in the retina, particularly the macula region, which is located at the back of your eye.
Because they’re found in concentrated amounts in the macula, they’re known as macular pigments.
The macula is essential for vision.
E161b (Lutein) work as important antioxidants in this area by protecting your eyes from harmful free radicals.
E161b (Lutein)’s thought that a reduction of these antioxidants over time can impair eye health.
E161b (Lutein) also act as a natural sunblock by absorbing excess light energy.
They’re thought to especially protect your eyes from harmful blue light.
Only in recent years have the beneficial effects of E161b (Lutein) on skin been discovered.
Their antioxidant effects allow them to protect your skin from the sun’s damaging ultraviolet (UV) rays .
A two-week animal study showed that rats who received 0.4% lutein- and zeaxanthin-enriched diets had less UVB-induced skin inflammation than those who received only 0.04% of these carotenoids.
Another study in 46 people with mild-to-moderate dry skin found that those who received 10 mg of lutein and 2 mg of zeaxanthin had significantly improved skin tone, compared to the control group.
Furthermore, E161b (Lutein) may protect your skin cells from premature aging and UVB-induced tumors.
E161b (Lutein) is part of the carotenoid family of antioxidants. Carotenoids are a type of phytonutrient, or plant chemical, found in the cells of many types of plants.
Carotenoids are responsible for the vibrant colors seen in many plants, such as the bright red, orange, and yellow hues of various fruits and vegetables.
While these pigments play an important role in plant health, they also provide health benefits for people who eat foods that are a good source of this phytonutrient.
Along with lutein, zeaxanthin is another important carotenoid that offers eye health benefits.
E161b (Lutein)’s structurally similar to lutein, with just a small difference in the arrangement of its atoms.
E161b (Lutein) and zeaxanthin are the only dietary carotenoids found in your retina. They’re concentrated mostly in the macula region, located at the back of your eye, which is essential for your vision. Because of where they’re concentrated, these two carotenoids are known as macular pigments.
What’s known about the eye health benefits of lutein?
As powerful antioxidants, lutein and zeaxanthin may protect your body and especially your eyes in numerous ways. With regards to your eye health, research suggests that these nutrients may help:
suppress inflammation
defend against free radicals and oxidative stress
enhance the sharpness of your vision
improve your visual contrast sensitivity
reduce glare impairment
protect eye tissue from sunlight damage
reduce cell loss and death related to eye disease
protect your eyes from harmful blue light
convert light signals into electrical signals in your retina and aid in the transmission of those signals to the visual cortex in your brain
protect against nearsightedness (myopia) and protect pre-term infants against the effects of retinopathy of prematurity (ROP)
E161b (Lutein) and eye conditions
Aside from the benefits listed above, there’s also evidence that lutein and zeaxanthin may provide benefits related to the following eye conditions:
Age-related macular degeneration (AMD).
In developed countries, AMD is the leading cause of blindness and permanent visual impairment.
According to a 2011 study, lutein and zeaxanthin may be protective against the progression of late-stage AMD to blindness.
Diabetic retinopathy.
Diabetic retinopathy impacts about one-third of people with diabetes.
Although research is limited, an animal study has shown that lutein and zeaxanthin may help reduce oxidative stress markers that can lead to eye damage and vision loss.
Cataracts.
Cataracts are cloudy patches that develop in the lens of your eye.
According to a 2006 study, people who consume a diet that’s low in lutein and zeaxanthin may be at a higher risk for developing cataracts.
Dry eye disease.
With dry eye disease, also known as dry eye syndrome, your eyes don’t make enough lubrication to coat your eyes.
This can cause red, itchy, burning, eyes, temporary blurriness, and a feeling as if there’s sand in your eye.
According to a 2016 study, lutein may help reduce these symptoms.
E161b (Lutein) is a carotenoid that’s synthesized by plants.
High concentrations of lutein and a similar phytonutrient, zeaxanthin, are found in the macula region of your eye.
This part of your eye is essential for your vision.
Due to its powerful antioxidant properties, lutein may help reduce inflammation in your eyes, fight off free radicals, reduce oxidative stress, and boost the sharpness of your vision.
Research has shown that it may also have benefits related to various eye diseases and conditions, including age-related macular degeneration.
E161b (Lutein) is naturally found in a number of fruits and vegetables, especially those with deep green, orange, and yellow coloring.
E161b (Lutein) is a type of xanthophyll often used in treatment or prevention of eye diseases.
E161b (Lutein) supplements contain a natural substance classified as a carotenoid—a group of plant pigments with antioxidant effects.
E161b (Lutein) supplements provide a more concentrated supply of this antioxidant.
Health Benefits
E161b (Lutein) supplements are typically used in alternative medicine for eye diseases, such as cataracts and macular degeneration.
Known to build up in the retina and lens of the eye, lutein is thought to protect the eye from injury induced by free radicals, chemical byproducts shown to damage cells and contribute to the development of certain diseases.
Some alternative medicine proponents claim that lutein supplements can also help prevent colon cancer, breast cancer, diabetes, and heart disease.
To date, most of the studies on lutein's health benefits have focused on dietary intake of lutein.
Those studies suggest that dietary intake of lutein may help protect against atherosclerosis, age-related macular degeneration, and cataracts.
While few studies have examined the health effects of lutein supplements, there's some evidence that lutein supplements may improve eye health.
Here's a look at two study findings:
Age-Related Macular Degeneration
E161b (Lutein) supplements may improve visual function in people with age-related macular degeneration, a leading cause of blindness.
One study that looked at more than 100,000 people from 1984 to 2010 found that a higher intake of bioavailable lutein and zeaxanthin was associated with a lower long-term risk of developing advanced age-related macular degeneration.2
Visual Function
In a 2009 study of 37 healthy adults, researchers found that subjects who took lutein supplements for 12 weeks experienced improvements in visual function.
The study's findings also suggest that lutein supplements may help treat vision problems brought on by long-term exposure to light from computer screens.3
Eye Health Benefits
A 2018 review of research concluded that there are many studies supporting lutein beneficial effects on eye health.
The researchers suggested that not only should a diet rich in fruits and vegetables containing lutein be encouraged, they also suggested that supplementation could be beneficial, particularly in populations at high risk of certain conditions such as the elderly.
E161b (Lutein) is a yellow-to-orange pigment that's related to vitamin A.
E161b (Lutein) is concentrated in the retinas of your eyes, so it's a necessary component of healthy vision.
E161b (Lutein) also works as an antioxidant to reduce the damage done by free radicals and may support healthy blood vessels.
Several dark leafy green and yellow/orange vegetables are high in lutein.
Your body can't synthesize its own lutein, so you need to consume it in your diet.
These 15 lutein-rich foods also offer other nutritious vitamins, minerals, antioxidants, and, in most cases, fiber.
Benefits of E161b (Lutein)
E161b (Lutein) is particularly beneficial for eye health.
Research shows that lutein can help prevent cataracts and macular degeneration, which is the leading cause of age-related vision decline.
E161b (Lutein) contains anti-inflammatory properties and may also improve cognitive functioning, lower cancer risks, and improve cardiovascular health.
High E161b (Lutein) Foods
Several foods are high in lutein, including many fruits and vegetables.
Foods that are dark green, yellow, or orange are typically highest in lutein.
Kale has a reputation as a health food for a reason.
E161b (Lutein) contains 6447 mcg of lutein per cooked cup.
Besides lutein, kale is rich in calcium, vitamin C, beta-carotene, vitamin A, vitamin K, and fiber.
E161b (Lutein)'s also low in calories—one cup of raw kale has only 8 calories.4
Winter squash, which includes butternut, Hubbard, and acorn squash, is very high in lutein and zeaxanthin (3170 mcg) and vitamin A.
These squashes are also rich in potassium and contain substantial amounts of several other vitamins and minerals.
One cup of cooked butternut squash has 6.3 grams of fiber and about 80 calories.
Collards are rich in vitamins and minerals, including 11774 mcg of lutein per cooked cup.
Besides lutein, beta-carotene, and vitamin A, collards are particularly high in calcium and magnesium. They're also super-rich in vitamin K and have plenty of vitamin C.6
Yellow sweet corn is high in lutein (934 mcg per cup) and potassium, plus it has some fiber and B vitamins.
Popcorn is also high in lutein and fiber and is a whole grain—making it a nutritious snack, as long as it's not soaked in butter or topped with too much salt.
Spinach is another green leafy vegetable that's super good for you.
E161b (Lutein)'s rich in lutein with 20354 mcg per cooked cup and iron, calcium, potassium, vitamin A, vitamin C, vitamin K, and fiber.
E161b (Lutein)'s also low in calories—only 7 calories per cup of raw spinach leaves.
Swiss chard is yet another leafy green vegetable rich in lutein, containing 19276 mcg per cup.
A 1-cup serving of chopped cooked chard has just 35 calories, but it's a good source of calcium, iron, potassium, vitamin A, vitamin C, and vitamin K.
Peas aren't the most exciting of vegetables, but they are nutrient-dense.
Not only are they high in lutein, with 4149 per cup, they also offer magnesium, iron, potassium, zinc, B-complex vitamins, and vitamin A.
Arugula, also known as "rocket," is another green leafy vegetable that's high in lutein (containing 711 per cup) and just about every other vitamin and mineral.
Arugula is super low in calories and is perfect for a salad base or wilted in a little bit of olive oil and garlic.
Brussels sprouts are a good source of lutein, with 2012 mcg per cup, and they also contain many other vitamins and several minerals.
They're also high in dietary fiber and have only 56 calories per cup.
Broccoli rabe (also called broccoli raab or rapini) is high in lutein, with 1431 mcg per cup, vitamin A, folate, potassium, calcium, magnesium, and vitamin K.
E161b (Lutein)'s also a good source of fiber and very low in calories—about 9 calories per cup, raw.
Pumpkin's rich orange flesh is super high in lutein, containing 2484 mcg per cooked cup.
E161b (Lutein)'s also high in potassium. Pumpkin also isn't high in calories unless you add a lot of sugar.
One cup of plain mashed pumpkin provides about 50 calories.
Eggs are a fantastic source of lutein, with 251.5 mcg each.
E161b (Lutein) gives the yolk its yellow color.
Eggs are also a good source of protein.
Sweet potatoes are rich in lutein, with 1053 mcg per 100 grams.
They also offer vitamin A, beta-carotene, potassium, manganese, vitamin C, and fiber.
Carrots have been rumored to help you see better, with good reason.
They are high in lutein, beta-carotene, vitamin A, and vitamin C, plus they're a good source of several B vitamins, potassium, and manganese.
A 1-cup serving of sliced carrots has about 50 calories.
Asparagus is high in lutein, with 1388 mcg per cooked cup, and provides many other nutrients, including calcium and magnesium.
E161b (Lutein)'s also an excellent source of vitamins A, K, and C. Asparagus is low in calories too—1 cup of cooked asparagus has about 40 calories.
IUPAC NAMES:
(1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-Hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-2-en-1-ol
(1R,4R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4S)-4-hydroxy-2,6,6-trimethylcyclohexen-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-2-en-1-ol
.beta.,.epsilon.-Carotene-3,3'-diol
4,5-didehydro-5,6-dihydro-beta,beta-carotene-3,3'-diol
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
β,ε-Carotene-3,3'-diol
β,ε-carotene-3,3'-diol
SYNONYMS:
E161b (Lutein)-WATER SOLUBLE
progestin
PROGESTERONE
PRIMOLUT
Glanducorpin
Gynlutin
gynoluton
Gynolutone
Hormoflaveine
Hormoluton
Lingusorbs
Lipo-lutin
Lucorteum
Lucorteum sol
lucorteumsol
Lugesteron
E161b (Lutein)e
E161b (Lutein)ique
Luteocrin normale
luteocrinnormale
Luteodyn
Luteogan
Luteol
Luteopur
Luteosan
Luteostab
Luteovis
E161b (Lutein) Prog
progesterone(INN)
Progesteronum
Progestogel
Progestol
Progeston
Progestone
Progestosol
Progestron
Progestronol
Progstin
projestaject
Prolets
Prolidon
Prolutin
Proluton
Prolutone
Protormone
Syngesterone
synGestrets
Synovex S
synovexs
synTolutan
Thiuram E
Thiuranide
Utrogestan
PROGESTERONE GAMMA-IRRADIATED*CELL CULTU RE TESTED
PROGESTERONE VETRANAL, 250 MG
ProgesteroneAndProgesteroneMicronize
10%Beadlet
CIDR
