Lycopene

Last updated
Lycopene
Lycopene powder.jpg
Lycopene.svg
Lycopene-3D-balls-(rotated).png
Names
IUPAC name
ψ,ψ-Carotene
Systematic IUPAC name
(6E,8E,10E,12E,14E,16E,18E,20E,22E,24E,26E)-2,6,10,14,19,23,27,31-Octamethyldotriaconta-2,6,8,10,12,14,16,18,20,22,24,26,30-tridecaene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.227 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-949-1
E number E160d (colours)
PubChem CID
UNII
  • InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+ Yes check.svgY
    Key: OAIJSZIZWZSQBC-GYZMGTAESA-N Yes check.svgY
  • InChI=1/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+
    Key: OAIJSZIZWZSQBC-GYZMGTAEBZ
  • C(\C=C\C=C(\CC/C=C(\C)C)C)(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(\C)CC\C=C(/C)C)C)C)C)C
Properties
C40H56
Molar mass 536.888 g·mol−1
Appearancedeep red solid
Density 0.889 g/cm3
Melting point 177 °C (351 °F; 450 K) [1]
Boiling point 660.9 °C (1,221.6 °F; 934.0 K)
at 760 mmHg [2]
insoluble
Solubility soluble in CS2, CHCl3, THF, ether, C6H14, vegetable oil
insoluble in CH3OH, C2H5OH [2]
Solubility in hexane 1 g/L (14 °C) [2]
Vapor pressure 1.33·10−16 mmHg (25 °C) [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Combustible
NFPA 704 (fire diamond)
NFPA 704.svgHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Flash point 350.7 °C (663.3 °F; 623.8 K) [2]
Supplementary data page
Lycopene (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Lycopene is an organic compound classified as a tetraterpene and a carotene. [3] Lycopene (from the Neo-Latin Lycopersicon , the tomato species) is a bright red carotenoid hydrocarbon found in tomatoes and other red fruits and vegetables.

Contents

Occurrence

Aside from tomatoes, it is found in red carrots, watermelons, grapefruits, and papayas. It is not present in strawberries or cherries. [4] It has no vitamin A activity. [5]

In plants, algae, and other photosynthetic organisms, lycopene is an intermediate in the biosynthesis of many carotenoids, including beta-carotene, which is responsible for yellow, orange, or red pigmentation, photosynthesis, and photoprotection. [5] Like all carotenoids, lycopene is a tetraterpene. [5] It is insoluble in water. Eleven conjugated double bonds give lycopene its deep red color. Owing to the strong color, lycopene is useful as a food coloring (registered as E160d) and is approved for use in the US, [6] Australia and New Zealand (registered as 160d) [7] and the European Union. [8]

Structure and physical properties

Lycopene is a symmetrical tetraterpene because it consists entirely of carbon and hydrogen and is derived from eight isoprene subunits. [5] Isolation procedures for lycopene were first reported in 1910, and the structure of the molecule was determined by 1931. In its natural, all-trans form, the molecule is long and somewhat flat, constrained by its system of 11 conjugated double bonds. The extended conjugation is responsible for its deep red color. [5]

Plants and photosynthetic bacteria produce all-trans lycopene. [5] When exposed to light or heat, lycopene can undergo isomerization to any of a number of cis-isomers, which have a less linear shape. Isomers distinct stabilities, with highest stability: 5-cis ≥ all-trans ≥ 9-cis ≥ 13-cis > 15-cis > 7-cis > 11-cis: lowest. [9] [10] In human blood, various cis-isomers constitute more than 60% of the total lycopene concentration, but the biological effects of individual isomers have not been investigated. [11]

Lycopene is a key intermediate in the biosynthesis of many carotenoids. Carotenoid synthetic pathway.svg
Lycopene is a key intermediate in the biosynthesis of many carotenoids.

Carotenoids like lycopene are found in photosynthetic pigment-protein complexes in plants, photosynthetic bacteria, fungi, and algae. [5] They are responsible for the bright orange–red colors of fruits and vegetables, perform various functions in photosynthesis, and protect photosynthetic organisms from excessive light damage. Lycopene is a key intermediate in the biosynthesis of carotenoids, such as beta-carotene, and xanthophylls. [12]

Dispersed lycopene molecules can be encapsulated into carbon nanotubes enhancing their optical properties. [13] Efficient energy transfer occurs between the encapsulated dye and nanotube—light is absorbed by the dye and without significant loss is transferred to the nanotube. Encapsulation increases chemical and thermal stability of lycopene molecules; it also allows their isolation and individual characterization. [14]

Biosynthesis

The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved. [5] Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. This is then condensed with three molecules of isopentenyl pyrophosphate (an isomer of dimethylallyl pyrophosphate), to give the 20-carbon geranylgeranyl pyrophosphate. Two molecules of this product are then condensed in a tail-to-tail configuration to give the 40-carbon phytoene, the first committed step in carotenoid biosynthesis. Through several desaturation steps, phytoene is converted into lycopene. The two terminal isoprene groups of lycopene can be cyclized to produce beta-carotene, which can then be transformed into a wide variety of xanthophylls. [5]

Staining and removal

Lycopene is the pigment in tomato sauces that turns plastic cookware orange. It is insoluble in plain water, but it can be dissolved in organic solvents and oils. Because of its non-polarity, lycopene in food preparations will stain any sufficiently porous material, including most plastics. To remove this staining, the plastics may be soaked in a solution containing a small amount of chlorine bleach. [15] The bleach oxidizes the lycopene, thus allowing the product to dissolve.

Diet

Consumption by humans

Absorption of lycopene requires that it be combined with bile salts and fat to form micelles. [5] Intestinal absorption of lycopene is enhanced by the presence of fat and by cooking. [5] Lycopene dietary supplements (in oil) may be more efficiently absorbed than lycopene from food. [5]

Lycopene is not an essential nutrient for humans, but is commonly found in the diet mainly from dishes prepared from tomatoes. [4] [5] The median and 99th percentile of dietary lycopene intake have been estimated to be 5.2 and 123 mg/d, respectively. [16]

Sources

Dietary sources of lycopene [5]
Sourcemg wet weight
Gac aril2~6 per gram [17] [18]
Raw tomato 4.6 per cup
Tomato juice22 per cup
Tomato paste75 per cup
Tomato ketchup 2.5 per tablespoon
Watermelon 13 per wedge
Pink grapefruit 2 per half grapefruit

Fruits and vegetables that are high in lycopene include autumn olive, gac, tomatoes, watermelon, pink grapefruit, pink guava, papaya, seabuckthorn, wolfberry (goji, a berry relative of tomato), and rosehip. [5] Ketchup is a common dietary source of lycopene. [5] Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable (multiple times more than tomatoes), [19] [20] tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people. [5] The lycopene content of tomatoes depends on variety and increases as the fruit ripens. [21]

Unlike other fruits and vegetables, where nutritional content such as vitamin C is diminished upon cooking, processing of tomatoes increases the concentration of bioavailable lycopene. [5] [22] Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes. [23] Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain a higher concentration of bioavailable lycopene compared to raw tomatoes. [5] [24]

Cooking and crushing tomatoes (as in the canning process) and serving in oil-rich dishes (such as spaghetti sauce or pizza) greatly increases assimilation from the digestive tract into the bloodstream. Lycopene is fat-soluble, so the oil is said to help absorption. Gac has high lycopene content derived mainly from its seed coats. [25] Cara cara navel, and other citrus fruit, such as pink grapefruit, also contain lycopene. [4] [26] Some foods that do not appear red also contain lycopene, e.g., asparagus, which contains about 30 μg of lycopene per 100-g serving [4] (0.3 μg/g) and dried parsley and basil, which contain around 3.5–7.0 μg/g of lycopene. [4] When lycopene is used as a food additive (E160d), it is usually obtained from tomatoes. [27]

Adverse effects

Test tube containing a dichloromethane solution of lycopene Lycopene in DCM.jpg
Test tube containing a dichloromethane solution of lycopene

Lycopene is non-toxic and commonly found in the diet, mainly from tomato products. There are cases of intolerance or allergic reaction to dietary lycopene, which may cause diarrhea, nausea, stomach pain or cramps, gas, and loss of appetite. [28] Lycopene may increase the risk of bleeding when taken with anticoagulant drugs. [28] Because lycopene may cause low blood pressure, interactions with drugs that affect blood pressure may occur. Lycopene may affect the immune system, the nervous system, sensitivity to sunlight, or drugs used for stomach ailments. [28]

Lycopenemia is an orange discoloration of the skin that is observed with high intakes of lycopene. [16] The discoloration is expected to fade after discontinuing excessive lycopene intake. [16]

Research and potential health effects

A 2020 review of randomized controlled trials found conflicting evidence for lycopene having an effect on cardiovascular risk factors, [29] whereas a 2017 review concluded that tomato products and lycopene supplementation reduced blood lipids and blood pressure. [30]

A 2015 review found that dietary lycopene was associated with reduced risk of prostate cancer, [31] whereas a 2021 meta-analysis found that dietary lycopene did not affect prostate cancer risk. [32] Other reviews concluded that research has been insufficient to establish whether lycopene consumption affects human health. [33]

Regulatory status in Europe and the United States

In a review of literature on lycopene and its potential benefit in the diet, the European Food Safety Authority concluded there was insufficient evidence for lycopene having antioxidant effects in humans, particularly in skin, heart function, or vision protection from ultraviolet light. [34]

Although lycopene from tomatoes has been tested in humans for cardiovascular diseases and prostate cancer, no effect on any disease was found. [35] The US Food and Drug Administration, in rejecting manufacturers' requests in 2005 to allow "qualified labeling" for lycopene and the reduction of various cancer risks, provided a conclusion that remains in effect as of 2017:

...no studies provided information about whether lycopene intake may reduce the risk of any of the specific forms of cancer. Based on the above, FDA concludes that there is no credible evidence supporting a relationship between lycopene consumption, either as a food ingredient, a component of food, or as a dietary supplement, and any of these cancers.

See also

Related Research Articles

<span class="mw-page-title-main">Carotene</span> Class of compounds

The term carotene (also carotin, from the Latin carota, "carrot") is used for many related unsaturated hydrocarbon substances having the formula C40Hx, which are synthesized by plants but in general cannot be made by animals (with the exception of some aphids and spider mites which acquired the synthesizing genes from fungi). Carotenes are photosynthetic pigments important for photosynthesis. Carotenes contain no oxygen atoms. They absorb ultraviolet, violet, and blue light and scatter orange or red light, and (in low concentrations) yellow light.

Tocopherols are a class of organic compounds comprising various methylated phenols, many of which have vitamin E activity. Because the vitamin activity was first identified in 1936 from a dietary fertility factor in rats, it was named tocopherol, from Greek τόκοςtókos 'birth' and φέρεινphérein 'to bear or carry', that is 'to carry a pregnancy', with the ending -ol signifying its status as a chemical alcohol.

<span class="mw-page-title-main">Vitamin A</span> Essential nutrient

Vitamin A is a fat-soluble vitamin and an essential nutrient for animals. The term "vitamin A" encompasses a group of chemically related organic compounds that includes retinol, retinal, retinoic acid, and several provitamin (precursor) carotenoids, most notably beta-carotene. Vitamin A has multiple functions: it is essential for embryo development and growth, for maintenance of the immune system, and for vision, where it combines with the protein opsin to form rhodopsin – the light-absorbing molecule necessary for both low-light and color vision.

<span class="mw-page-title-main">Retinol</span> Chemical compound

Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family that is found in food and used as a dietary supplement. Retinol or other forms of vitamin A are needed for vision, cellular development, maintenance of skin and mucous membranes, immune function and reproductive development. Dietary sources include fish, dairy products, and meat. As a supplement it is used to treat and prevent vitamin A deficiency, especially that which results in xerophthalmia. It is taken by mouth or by injection into a muscle. As an ingredient in skin-care products, it is used to reduce wrinkles and other effects of skin aging.

<span class="mw-page-title-main">Carotenoid</span> Class of chemical compounds; yellow, orange or red plant pigments

Carotenoids are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, archaea, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, corn, tomatoes, canaries, flamingos, salmon, lobster, shrimp, and daffodils. Over 1,100 identified carotenoids can be further categorized into two classes – xanthophylls and carotenes.

<span class="mw-page-title-main">Phytochemical</span> Chemical compounds produced by plants

Phytochemicals are chemical compounds produced by plants, generally to help them resist fungi, bacteria and plant virus infections, and also consumption by insects and other animals. The name comes from Greek φυτόν (phyton) 'plant'. Some phytochemicals have been used as poisons and others as traditional medicine.

β-Carotene Red-orange pigment of the terpenoids class

β-Carotene (beta-carotene) is an organic, strongly coloured red-orange pigment abundant in fungi, plants, and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons. Among the carotenes, β-carotene is distinguished by having beta-rings at both ends of the molecule. β-Carotene is biosynthesized from geranylgeranyl pyrophosphate.

<span class="mw-page-title-main">Astaxanthin</span> Chemical compound

Astaxanthin is a keto-carotenoid within a group of chemical compounds known as terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups. It is a lipid-soluble pigment with red coloring properties, which result from the extended chain of conjugated double bonds at the center of the compound. The presence of the hydroxyl functional groups and the hydrophobic hydrocarbons render the molecule amphiphilic.

<span class="mw-page-title-main">Lutein</span> Yellow organic pigment created by plants

Lutein 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.

<span class="mw-page-title-main">Zeaxanthin</span> Chemical compound

Zeaxanthin is one of the most common carotenoids in nature, and is used in the xanthophyll cycle. Synthesized in plants and some micro-organisms, it is the pigment that gives paprika, corn, saffron, goji (wolfberries), and many other plants and microbes their characteristic color.

<span class="mw-page-title-main">Carotenoid oxygenase</span>

Carotenoid oxygenases are a family of enzymes involved in the cleavage of carotenoids to produce, for example, retinol, commonly known as vitamin A. This family includes an enzyme known as RPE65 which is abundantly expressed in the retinal pigment epithelium where it catalyzed the formation of 11-cis-retinol from all-trans-retinyl esters.

<span class="mw-page-title-main">Carotenosis</span> Skin discoloration caused by carotenoids

Carotenosis is a benign and reversible medical condition where an excess of dietary carotenoids results in orange discoloration of the outermost skin layer. The discoloration is most easily observed in light-skinned people and may be mistaken for jaundice. Carotenoids are lipid-soluble compounds that include alpha- and beta-carotene, beta-cryptoxanthin, lycopene, lutein, and zeaxanthin. The primary serum carotenoids are beta-carotene, lycopene, and lutein. Serum levels of carotenoids vary between region, ethnicity, and sex in the healthy population. All are absorbed by passive diffusion from the gastrointestinal tract and are then partially metabolized in the intestinal mucosa and liver to vitamin A. From there they are transported in the plasma into the peripheral tissues. Carotenoids are eliminated via sweat, sebum, urine, and gastrointestinal secretions. Carotenoids contribute to normal-appearing human skin color, and are a significant component of physiologic ultraviolet photoprotection.

<span class="mw-page-title-main">Gac</span> Species of melon

Gấc [IPA ɣək̚˧˦] is a type of perennial melon grown throughout Southeast Asian countries and Northeastern Australia. Gấc is notable for its vivid orange-reddish color resulting from its rich content of beta-carotene and lycopene.

Vitamins occur in a variety of related forms known as vitamers. A vitamer of a particular vitamin is one of several related compounds that performs the functions of said vitamin and prevents the symptoms of deficiency of said vitamin.

A co-carcinogen is a chemical that promotes the effects of a carcinogen in the production of cancer. Usually, the term is used to refer to chemicals that are not carcinogenic on their own, such that an equivalent amount of the chemical is insufficient to initiate carcinogenesis. A chemical can be co-carcinogenic with other chemicals or with nonchemical carcinogens, such as UV radiation.

<span class="mw-page-title-main">Phytoene</span> Chemical compound

Phytoene is a 40-carbon intermediate in the biosynthesis of carotenoids. The synthesis of phytoene is the first committed step in the synthesis of carotenoids in plants. Phytoene is produced from two molecules of geranylgeranyl pyrophosphate (GGPP) by the action of the enzyme phytoene synthase. The two GGPP molecules are condensed together followed by removal of diphosphate and proton shift leading to the formation of phytoene.

Canadian health claims by Health Canada, the department of the Government of Canada responsible for national health, has allowed five scientifically verified disease risk reduction claims to be used on food labels and on food advertising. Other countries, including the United States and Great Britain, have approved similar health claims on food labels.

<small>D</small>-Fructose-<small>L</small>-histidine Chemical compound

d-Fructose-l-histidine (FruHis) is a ketosamine combining the d-isomer of fructose and the l-isomer of histidine into a functional group. FruHis is present in dried fruits. In interaction with lycopene, FruHis is a potential food related antioxidant and chemopreventive agent, found abundantly in dried tomatoes.

Carotenoid complexes are physical associations of carotenoids with other molecules.

References

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