Names | |
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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 |
EC Number |
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E number | E160d (colours) |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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Properties | |
C40H56 | |
Molar mass | 536.888 g·mol−1 |
Appearance | deep 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) | |
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). |
Lycopene is an organic compound classified as a tetraterpene and a carotene. [3] Lycopene (from the Neo-Latin Lycopersicon , the name of a former tomato genus) is a bright red carotenoid hydrocarbon found in tomatoes and other red fruits and vegetables.
Aside from tomatoes or tomato products like ketchup, it is found in watermelons, grapefruits, red guavas, and baked beans. [4] It has no vitamin A activity. [4]
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. [4]
Like all carotenoids, lycopene is a tetraterpene. [4] It is soluble in fat, but insoluble in water. [4] Eleven conjugated double bonds give lycopene its deep red color. [4]
Owing to the strong color, lycopene is used as a food coloring (registered as E160d) and is approved for use in the US, [5] Australia and New Zealand (registered as 160d), [6] and the European Union (E160d). [7]
Lycopene is a symmetrical tetraterpene because it consists entirely of carbon and hydrogen and is derived from eight isoprene subunits. [4] 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. [4]
Plants and photosynthetic bacteria produce all-trans lycopene. [4] 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. [8] [9] 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. [10]
Carotenoids like lycopene are found in photosynthetic pigment-protein complexes in plants, photosynthetic bacteria, fungi, and algae. [4] 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. [11]
Dispersed lycopene molecules can be encapsulated into carbon nanotubes enhancing their optical properties. [12] 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. [13]
The unconditioned biosynthesis of lycopene in eukaryotic plants and in prokaryotic cyanobacteria is similar, as are the enzymes involved. [4] 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. [4]
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. [14] The bleach oxidizes the lycopene, thus rendering it colourless.
Absorption of lycopene requires that it be combined with bile salts and fat to form micelles. [4] Intestinal absorption of lycopene is enhanced by the presence of fat and by cooking. [4] Lycopene dietary supplements (in oil) may be more efficiently absorbed than lycopene from food. [4]
Lycopene is not an essential nutrient for humans, but is commonly found in the diet mainly from dishes prepared from tomatoes. [4] The median and 99th percentile of dietary lycopene intake have been estimated to be 5.2 and 123 mg/d, respectively. [15]
Source | mg wet weight |
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Gac aril | 2~6 per gram [16] [17] |
Raw tomato | 4.6 per cup |
Tomato juice | 22 per cup |
Tomato paste | 75 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. [4] Ketchup is a common dietary source of lycopene. [4] Although gac (Momordica cochinchinensis Spreng) has the highest content of lycopene of any known fruit or vegetable (multiple times more than tomatoes), [18] [19] tomatoes and tomato-based sauces, juices, and ketchup account for more than 85% of the dietary intake of lycopene for most people. [4] The lycopene content of tomatoes depends on variety and increases as the fruit ripens. [20]
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. [4] [21] Lycopene in tomato paste is up to four times more bioavailable than in fresh tomatoes. [22] Processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain a higher concentration of bioavailable lycopene compared to raw tomatoes. [4] [23]
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. [24] Cara cara navel, and other citrus fruit, such as pink grapefruit, also contain lycopene. [4] [25] Some foods that do not appear red also contain lycopene, e.g., baked beans. [4] When lycopene is used as a food additive (E160d), it is usually obtained from tomatoes. [4] [26]
Lycopene is non-toxic and commonly found in the diet, mainly from tomato products. [4] 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. [27] Lycopene may increase the risk of bleeding when taken with anticoagulant drugs. [27] 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. [27]
Lycopenemia is an orange discoloration of the skin that is observed with high intakes of lycopene. [15] The discoloration is expected to fade after discontinuing excessive lycopene intake. [15]
A 2020 review of randomized controlled trials found conflicting evidence for lycopene having an effect on cardiovascular risk factors, [28] whereas a 2017 review concluded that tomato products and lycopene supplementation reduced blood lipids and blood pressure. [29]
A 2015 review found that dietary lycopene was associated with reduced risk of prostate cancer, [30] whereas a 2021 meta-analysis found that dietary lycopene did not affect prostate cancer risk. [31] Other reviews concluded that research has been insufficient to establish whether lycopene consumption affects human health. [32]
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. [33]
Although lycopene from tomatoes has been tested in humans for cardiovascular diseases and prostate cancer, no effect on any disease was found. [34] 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 2015 [update] :
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. [34]
In a review of research through 2024, the US National Cancer Institute concluded that the FDA has not approved the use of lycopene as effective for treating any medical condition, including various types of cancer. [35]
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.
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.
Vitamin A is a fat-soluble vitamin that is an essential nutrient. The term "vitamin A" encompasses a group of chemically related organic compounds that includes retinol, retinyl esters, and several provitamin (precursor) carotenoids, most notably β-carotene (beta-carotene). Vitamin A has multiple functions: growth during embryo development, maintaining the immune system, and healthy vision. For aiding vision specifically, it combines with the protein opsin to form rhodopsin, the light-absorbing molecule necessary for both low-light and color vision.
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.
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.
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 (beta-carotene) is an organic, strongly colored 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.
Astaxanthin is a keto-carotenoid within a group of chemical compounds known as carotenones or terpenes. Astaxanthin is a metabolite of zeaxanthin and canthaxanthin, containing both hydroxyl and ketone functional groups.
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.
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.
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.
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.
Gac, from the Vietnamese gấc, scientific name Momordica cochinchinensis, is a species of plant in the melon and cucumber family Cucurbitaceae which is native to countries throughout Southeast Asia and to Queensland, Australia. It is notable for its vivid orange-reddish color resulting from a mix 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.
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.
A health claim found on a food labels and in food marketing is a claim by a food manufacturer that their product will reduce the risk of developing a disease or condition.
α-Zeacarotene (alpha-zeacarotene) is a form of carotene with a β-ionone ring at one end and a ζ-ionone ring at the opposite end. It is an intermediate in the biosynthesis of various carotenoids and plays a crucial role in the metabolic pathway leading to the production of lycopene and other important carotenoids.
Carotenoids are a class of natural pigments synthesized by various organisms, including plants, algae, and photosynthetic bacteria. They are characterized by their vibrant yellow, orange, and red colors, which contribute significantly to the coloration of fruits and vegetables. Carotenoids play essential roles in photosynthesis and offer various health benefits, such as antioxidant properties and serving as precursors to vitamin A.
Lycopenemia, characterized by an orange discoloration of the skin, has been observed with high intakes of lycopene-containing foods. One case study reported the incidence of lycopenemia in a 61-y-old woman who had consumed ~2 L of tomato juice daily for several years (10). Although there was evidence of lycopene and fatty deposits in the liver, there was an absence of measurable hepatic dysfunction. After 3 wk of consuming a diet free of tomato juice, the orange discoloration faded.