Xanthophyll Chemical Properties

Melting point:

195 °C

alpha 

18Cd +165° (c = 0.7 in benzene)

Boiling point:

572.66°C (rough estimate)

Density 

0.9944 (rough estimate)

refractive index 

n20/D1.361-1.363

Flash point:

269.1±27.5 °C

storage temp. 

-20°C

solubility 

Chloroform (Slightly), Dichloromethane (Slightly), Methanol (Slightly, Heated, Sonicated)

pka

14.61±0.70(Predicted)

form 

Solid

color 

Red to Very Dark Red

optical activity

〔α〕656.3 +16220 (c 0.2, CHCl3)

λmax

λ: 441-451 nm Amax

Merck 

13,10120

BRN 

2068547

Stability:

Light Sensitive, Temperature Sensitive

InChIKey

KBPHJBAIARWVSC-RGZFRNHPSA-N

LogP

11.524 (est)

CAS DataBase Reference

127-40-2(CAS DataBase Reference)

EPA Substance Registry System

.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)- (127-40-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38-11

Safety Statements 

26-37/39-16-7-24/25

WGK Germany 

3

F 

1-8-10-16

HS Code 

29061990

MSDS

• Language:English Provider:alpha-Carotene-3,3'-diol
• Language:English Provider:SigmaAldrich

Xanthophyll Usage And Synthesis

Carotenoids

Xanthophyll is a type of carotenoid, which belongs to photosynthetic pigments and naturally widely presents in vegetables (such as spinach, kale, broccoli, etc.), flowers, fruits and other plants. It can absorb and transfer light energy to Chlorophyll a at a particular state to convert light energy. It plays a role in protecting chlorophyll.
Pure Xanthophyll is a rhombus yellow crystal with metallic luster, and it is unstable when exposed to light and hydrogen, insoluble in water and easily soluble in grease and fatty solvents. It shall be stored in a cool dry place, away from light and air.
Xanthophyll is the most important nutritive component in human retina. There is a high concentration of Xanthophyll in macula (central vision) and lens of the eye retina. The human body cannot synthesize Xanthophyll itself, and it must be taken up from food. After breaking through all difficulties, Xanthophyll goes into the lens and macular to perform antioxidant effects, and neutralize harmful free radicals, and filter out the blue light (which is harmful to the eye), and avoid oxidation damage to eyes caused by sunlight.
Natural Xanthophyll is an excellent antioxidant, which can prevent cell senescence and body organs aging when added to food with an appropriate amount. It can also prevent eyesight degeneration and blindness that caused by age-related retina macular degeneration, and can also be used as feed additives for staining of poultry meat and eggs, as well as a colorant and dietary supplements in food industry.
Carotenoids are the generic terms of an important kind of natural pigments, belonging to compounds. The yellow, orange or red pigments that commonly found in animals, higher plants, fungi, algae and bacteria are mainly β-carotene and a-carotene, hence the name. Since carotene was isolated in the early 19th century, there are more than 600 known carotenoids in nature, of which only about 20 kinds present in the human blood and tissues. Carotenoids that found in human body include d-carotene, P-carotene, cryptoxanthin, xanthophyll, lycopene and zeaxanthin, and they are insoluble in water and soluble in fats and fatty solvents.

Which food is Xanthophyll rich?

Xanthophyll is rich in some green vegetables and fruits such as cabbage, spinach, lettuce, green beans and rapes, but chlorophyll, β-carotene and other epoxy carotenoids and oxygen substituted derivatives of carotenoids are also rich in such plants, making is not easy to extract the pure xanthophyll. After long-term searching, people found very high levels of Xanthophyll and zeaxanthin and less impurities of other carotenoids in flowers of marigold, which makes separation and purification easy, thus marigold can be a good source for industrial production of Xanthophyll. In addition, this product and zeaxanthin are also rich in some yellow-orange fruits such as mango, papaya, peaches, and pumpkins.
The above information is edited by the Chemicalbook of Cheng Jingmin.

Function

Protection of eyesight
Xanthophyll plays an important role in protecting the macula of the retina. The absence of Xanthophyll can easily cause macular degeneration and blurred vision, and with the further symptoms of vision degeneration, myopia and so on. Xanthophyll is a precursor of NA, and it can be transformed into VA in the human body. The main physiological function for eyes of Xanthophyll is as antioxidants and light protectors. Optic nerves are non-renewable and highly vulnerable to harmful free radicals, and the antioxidant effects of Xanthophyll can inhibit the formation of harmful free radicals. Xanthophyll can absorb a large number of blue visible lights, which have the close wavelengths to ultraviolet lights and are a kind of harmful lights that can reach the retina and with the largest potential hazardous. Before reaching the sensitive cells of the retina, the light goes through the most heavily gathering area of Xanthophyll. If Xanthophyll is rich now, the damage can be lower to the minimum.
Reducing the incidence of cataract
Cataract is the major eye disease causing of blindness in the world. Recent studies showed that by increasing the intake of Xanthophyll, the incidence of cataracts can can be reduced. So far, the mechanism is that the lower density of macular pigment is closely related to the higher lens visual density in the elders, and the higher the lens visual density is considered to be a obvious feature of cataract.
The antioxidant effect
Xanthophyll has strong antioxidant effect, and it can inhibit the activity of reactive oxygen species and prevent its damage to normal cells. Related experiments showed that reactive oxygen species could react with DNA, proteins, lipids, and weaken their physiological functions, and thus cause diseases such as cancer, atherosclerosis, and age-related macular degenerative disorders. Xanthophyll can quench singlet oxygen physically or chemically, thereby protecting the body from injury and enhancing the body's immunity.
Retarding atherosclerosis
Recent research results showed that Xanthophyll has a retarding effect on early process of atherosclerosis. The main reason is the relationship between the intimal thickness of the main artery blood vessels and the content of Xanthophyll in blood. Low content of Xanthophyll in blood can easily cause thickening of arterial walls. With the increasing content of Xanthophyll, the trend of arterial wall thickening decreases significantly. Meanwhile, the Xanthophyll in arterial wall cells can reduce oxidation of LDL cholesterol.
Anticancer effects
Several studies have shown that Xanthophyll can inhibit a variety of cancers, such as breast cancer, prostate cancer, colorectal cancer, and skin cancer. According to a recent pharmaceutical research of New York University School, there is a very close relationship between reducing the incidence of breast cancer and the amount of Xanthophyll intake, and the survey found that the incidence of breast cancer in the group with a low intake of Xanthophyll was (2.08-2.21) times higher than the group with a high intake of Xanthophyll. This effect role may be related to indirect immunomodulatory of synergy with other organs and tissues. The study concluded that dietary intake of Xanthophyll can inhibit neoplasms and may even play a role in cancer prevention. It is recommended daily intake of 400 g~600 g fruits and vegetables per capita can make reduce the relative risk of cancer by 50%.

Identification test

Xanthophyll is not dissolve in water, but soluble in hexane.
Spectroscopy: The chloroform solution has the maximum absorption at about 445nm.
Chloroform solution turns to blue coloration when adding an excess of Cart-Price test solution.
Toxicity: not limited by ADII yet (FAO/WHO, 2001).

Who needs Xanthophyll supplements?

1. People who use computer for long time
2. People with dry eye syndrome
3. People whose eyes are easily fatigue with tears
4. People with retinal degeneration that caused by degradation of renal function
5. People with high myopia
6. People with degenerative macular area lesions
7. People who received Laser Surgery
8. People with diabetic retinopathy

Production methods

Xanthophyll is derived from the extraction of pasture or alfalfa, in which chlorophyll was removed through saponification. and then Xanthophyll was purified with a solvent and then desolventized. The solvent used is methanol, ethanol, isopropanol, hexane, acetone, methylene chloride and methyl ethyl ketone, according to the specified rules of FAO/WHO (1997).

Description

Lutein 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.

Characteristics

While it is one of the most widespread naturally occurring carotenoid alcohols, it does not possess any vitamin A activity. Xanthophyll is a yellow pigment, which can be isolated from certain natural products, and produced synthetically.
Xanthophyll is the major substance causing yolks to have a deeper yellow color. It has no nutritive value. Years ago when chickens ran freely on the farm they ate grass which contains xanthophyll. Modern production units put enough xanthophyll in the ration of chickens to produce a medium-yellow yolk.
Feeds that contain large amounts of xanthophylls produce a deep yellow color in the beak, skin, and shank of yellowskinned breeds of chickens. The consumer associates this pigmentation with quality and, in many cases, is willing to pay a premium price for a bird of this type. Also, processors of egg yolks are frequently interested in producing dark-colored yolks to maximize coloration of egg noodles and other food products. The latter can be accomplished by adding about 60 mg of xanthophyll per kilogram of diet. In recognition of these consumer preferences, many producers add ingredients that contain xanthophylls to poultry rations.

Uses

Xanthophyll 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.

Uses

Xanthophyll has been used:

• to quantify circulating lutein in birds
• to study its effect on the synthesis of factor D (FD) by adipocytes
• for the quantification of carotenoids from the leaves of Brassica oleracea

Definition

ChEBI: Lutein is a carotenol. It has a role as a food colouring and a plant metabolite. It derives from a hydride of a (6'R)-beta,epsilon-carotene.

Biotechnological Production

Petals of marigold flowers (Tagetes erecta and Tagetes patula) currently represent the main source of commercial Xanthophyll. More than 95 % of the Xanthophyll is esterified, and about half of this fraction is esterified with fatty acid. Therefore, saponification is a part of the downstream processing. Xanthophyll is supplemented to food and feed for aquaculture and poultry farming. Furthermore, Xanthophyll is suggested to be beneficial for health, for example, to prevent age-related macular degeneration [97] and progression of early atherosclerosis. In algae, Xanthophyll is accumulated in the nonesterified form. The alga Muriellopsis sp. is able to accumulate Xanthophyll up to high levels and is easy to cultivate photoautotrophically. The effects of critical growth and production parameters in outdoor continuous cultures have been investigated. Under optimized conditions, 40 g dry cell mass/m2 and 180 mg/m2 Xanthophyll were produced per day, respectively. Further optimization was performed by introduction of agitation with a paddlewheel in a semicontinuous cultivation system and by CO2 addition. Thus, the Xanthophyll content was increased to 0.4–0.6 % of the dry mass at a productivity level comparable to that in a closed tubular photobioreactor. Beneficial for Xanthophyll synthesis were high temperatures, high irradiance, an optimum pH value for biomass formation, and the addition of inducers such as H2O2 or NaClO in the presence of Fe2+ (for the generation of stress-inducing chemical species), especially under heterotrophic growth conditions where spontaneous oxidative stress is absent.

General Description

Lutein is a yellow dihydroxylated carotenoid which is found to be a common constituent in many dietary supplements.

Agricultural Uses

Xanthophyll is the yellow pigment in leaves containing oxygen and is derived from carotens, which is sometimes absorbed by insects. It is present, for instance, in the skin of caterpillar of cabbage and of white butterfly and in the cocoons of silkworms.

Biochem/physiol Actions

Dietary carotenoid with no vitamin A potency. Increases macular pigment concentration in the eye and may improve visual function.

target

ROS

Xanthophyll(127-40-2)Related Product Information

• Lycopene
• β-Carotene
• Carotene
• Procyanidin
• BISMERTHIAZOL
• Folic acid
• Sodium copper chlorophyllin
• Folitixorin (Mixture of DiastereoMers)
• Astaxanthin
• Chlorophyll b
• Chlorophyll A
• Chlorophyllin
• CHLOROPHYLL
• Organic silicon release agent
• LUTEIN EPOXIDE
• 9H-Xanthen-9-one, 2-[(2E)-3,7-dimethyl-2,6-octadien-1-yl]-1,3,6,7-tetrahydroxy-
• 2-Deoxy-D-xylose
• 7-ACETYLLYCOPSAMINE