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Encyclopedia > Lycopene
Lycopene
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 Image File history File links Chemical structure of lycopene (generated at Wikisophia. ... Image File history File links Size of this preview: 800 × 235 pixelsFull resolution (997 × 293 pixel, file size: 96 KB, MIME type: image/png) 3D representation of lycopene. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ...

Identifiers
CAS number 502-65-8
PubChem 446925
EINECS number 207-949-1
SMILES CC(=CCC/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(C)

/C=C/C=C(C)/C=C/C=C(C)/CCC=C(C)C)/C)/C)/C)C CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... The EINECS number (for European Inventory of Existing Chemical Substances) is a registry number given to each chemical substance commercially available in the European Union between 1 January 1971 and 18 September 1981. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ...

Properties
Molecular formula C40H56
Molar mass 536.873 g/mol
Appearance Deep red solid
Melting point

172–173 °C This article or section does not cite any references or sources. ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... This article does not cite any references or sources. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ...

Solubility in water Insoluble
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Lycopene is a bright red carotenoid pigment, a phytochemical found in tomatoes and other red fruits. Lycopene is the most common carotenoid in the human body and is one of the most potent carotenoid antioxidants. Its name is derived from the tomato's species classification, Solanum lycopersicum (formerly Lycopersicon esculentum). Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ... For other uses, see Red (disambiguation). ... The orange ring surrounding Grand Prismatic Spring is due to carotenoid molecules, produced by huge mats of algae and bacteria. ... Natural Ultramarine pigment in powdered form. ... Phytochemicals are sometimes referred to as phytonutrients; these terms are often used interchangeably. ... For other uses, see Tomato (disambiguation). ... For other uses, see Fruit (disambiguation). ... This article is about modern humans. ... Space-filling model of the antioxidant metabolite glutathione. ... For other uses, see Tomato (disambiguation). ...

Contents

Structure and chemistry

Lycopene is a terpene assembled from 8 isoprene units. Many terpenes are derived from conifer resins, here a pine. ... Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. ...


The color of lycopene is due to its many conjugated carbon double bonds. Each double bond reduces the energy required for electrons to transition to higher energy states, allowing the molecule to absorb visible light of progressively longer wavelengths. Lycopene absorbs most of the visible spectrum, so it appears red. Color is an important part of the visual arts. ... A chemically conjugated system, is a system of atoms covalently bonded with alternating single and double bonds (e. ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... Covalent bonding is a form of chemical bonding that is characterized by the sharing of pairs of electrons between atoms, or sometimes between atoms and other covalent bonds. ... A chemical bond is the physical process responsible for the attractive interactions between atoms and molecules, and that which confers stability to diatomic and polyatomic chemical compounds. ... For other uses, see Electron (disambiguation). ... An energy level is a quantified stable energy, which a physical system can have; the term is most commonly used in reference to the electron configuration of electrons, in atoms or molecules. ... 3D (left and center) and 2D (right) representations of the terpenoid molecule atisane. ... The optical spectrum (light or visible spectrum) is the portion of the electromagnetic spectrum that is visible to the human eye. ... The wavelength is the distance between repeating units of a wave pattern. ... Legend γ = Gamma rays HX = Hard X-rays SX = Soft X-Rays EUV = Extreme ultraviolet NUV = Near ultraviolet Visible light NIR = Near infrared MIR = Moderate infrared FIR = Far infrared Radio waves EHF = Extremely high frequency (Microwaves) SHF = Super high frequency (Microwaves) UHF = Ultra high frequency VHF = Very high frequency HF = High...


If lycopene is oxidized (for example, by reacting with bleaches or acids), the double bonds between carbon atoms will be broken, cleaving the molecule into smaller molecules each double-bonded to an oxygen atom. Although C=O bonds are also chromophoric, the much shorter molecules are unable to absorb enough light to appear colorful. A similar effect occurs if lycopene is reduced; reduction may saturate (convert the double bonds to single bonds) the lycopene molecule, diminishing its ability to absorb light. The most fundamental reactions in chemistry are the redox processes. ... For other uses, see Atom (disambiguation). ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... A reducing agent (also called a reductant or reducer) is the element or a compound in a redox (reduction-oxidation) reaction (see electrochemistry) that reduces another species. ... Chemical structure of methane, the simplest alkane Alkanes are chemical compounds that consist only of the elements carbon (C) and hydrogen (H) (i. ...


Dietary sources

Fruits and vegetables that are high in lycopene include tomatoes, watermelon, pink grapefruit, pink guava, papaya, gac, and rosehip. For other uses, see Fruit (disambiguation). ... A plate of vegetables Vegetable is a culinary term which generally refers to an edible part of a plant. ... For the political designation, see Eco-socialism. ... Binomial name Macfad. ... Species About 100 species, see text. ... Binomial name Carica papaya L. The papaya (from Carib via Spanish), is the fruit of the tree Carica papaya, in the genus Carica. ... Binomial name (Lour. ... Dog Rose showing the bright red hips Rosehips, also called rose haws are the fruit of the rose plant, particularly wild roses that form at the base of the flower, typically red to orange but dark purple to black in some species. ...


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. Lycopene in tomato paste is four times more bioavailable than in fresh tomatoes. This is because lycopene is so insoluble in water and is so tightly bound to vegetable fiber. Thus processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain the highest concentrations of bioavailable lycopene. 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. This article is about the nutrient. ... Food processing is the set of methods and techniques used to transform raw ingredients into food for consumption by humans or animals. ... 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. ... This article does not cite any references or sources. ... Cooked spaghetti in a bowl. ... For other uses, see Pizza (disambiguation). ...


Production

Lycopene may be obtained from vegetables such as tomato, but another source of lycopene is the fungus Blakeslea trispora. Binomial name Thaxt. ...


Nutritional benefits

Lycopene is the most powerful carotenoid quencher of singlet oxygen[1], being 100 times more efficient in the singlet-oxygen quenching action than Vitamin E, which in turn has 125 times the quenching action of glutathione (water soluble). Singlet oxygen produced during exposure to ultraviolet light is a primary cause of skin aging.[2] Molecular orbital diagram for singlet oxygen. ... Tocopherol, or Vitamin E, is a fat-soluble vitamin in eight forms that is an important antioxidant. ... Glutathione (GSH) is a tripeptide. ... For other uses, see Ultraviolet (disambiguation). ... Beyond overall skin structure, refer below to: See-also. ... Ageing or aging is the process of getting older. ...


Given its antioxidant properties, some scientific research has investigated the correlation between lycopene consumption and general health. Early research suggested some amelioration of cardiovascular disease, cancer, diabetes, osteoporosis, and even male infertility.[3] [4][5]. The most recent study, however, has cast significant doubt on these benefits, showing no link between lycopene and cancer prevention. In fact, a related antioxidant, beta-carotene, was shown to increase the number of prostate cancer cases[6]. Cardiovascular disease refers to the class of diseases that involve the heart and/or blood vessels (arteries and veins). ... Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... This article is about the disease that features high blood sugar. ... Osteoporosis is a disease of bone in which the bone mineral density (BMD) is reduced, bone microarchitecture is disrupted, and the amount and variety of non-collagenous proteins in bone is altered. ... Infertility primarily refers to the biological inability of a man or a woman to contribute to conception. ... Carotene is a terpene, an orange photosynthetic pigment, important for photosynthesis. ... Prostate cancer is a disease in which cancer develops in the prostate, a gland in the male reproductive system. ...


Food coloring

Due to its ubiquity, lycopene has been licensed for use as a food coloring. Food coloring spreading on a thin water film. ...


Lycopene is not water-soluble and instantly stains any sufficiently porous material, including most plastics. While a tomato stain can be fairly easily removed from fabric (provided the stain is fresh), lycopene diffuses into plastic, making it impossible to remove with hot water, soap, or detergent. (Bleach will destroy lycopene, however.) Plastics are especially susceptible to staining if heated, scratched, oiled, or pitted, for example by acids. Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... It has been suggested that this article or section be merged with Solution. ... A stain is a discoloration that distinguishes itself from the material on which it is found. ... Porosity is a measure of the void spaces in a material, and is measured as a fraction, between 0–1, or as a percentage between 0–100%. The term porosity is used in multiple fields including manufacturing, earth sciences and construction. ... This article or section does not cite any references or sources. ... It has been suggested that Textile be merged into this article or section. ... This article does not cite any references or sources. ... This article is about the computer protocol. ... Laundry detergents are just one of many possible uses for detergents Detergent is a compound, or a mixture of compounds, intended to assist cleaning. ... This article is about the chemical substance. ... For other uses, see Heat (disambiguation) In physics, heat, symbolized by Q, is energy transferred from one body or system to another due to a difference in temperature. ... Synthetic motor oil An oil is any substance that is in a viscous liquid state (oily) at ambient temperatures or slightly warmer, and is both hydrophobic (immiscible with water, literally water fearing) and lipophilic (miscible with other oils, literally fat loving). This general definition includes compound classes with otherwise unrelated... For other uses, see Acid (disambiguation). ...


Formulations Available

Lycopene is available in the market as mix formulation with some other carotinoids and antioxidants. It is marketted by a number of pharma companies under different brand names. Some commonly avialable formulations are LYCORED, LYNET, LYCORICH etc.


References

  1. ^ Di Mascio P, Kaiser S, Sies H (1989). "Lycopene as the most efficient biological carotenoid singlet oxygen quencher". Archives of Biochemistry and Biophysics 274 (2): 532–538. PMID 2802626. 
  2. ^ Berneburg M, Grether-Beck S, Kurten V, Ruzicka T, Briviba K, Sies H, Krutmann J (1999). "Singlet oxygen mediates the UVA-induced generation of the photoaging-associated mitochondrial common deletion". The Journal of Biological Chemistry 274 (22): 15345–15349. PMID 10336420. 
  3. ^ Giovannucci, E. et al (1995). "Intake of Carotenoids and Retinol in Relation to Risk of Prostrate Cancer". Journal of the National Cancer Institute. 
  4. ^ Bowen P, Chen L, Stacewicz-Sapuntzakis M, Duncan C, Sharifi R, Ghosh L, Kim HS, Christov-Tzelkov K, van Breemen R (2002). "Tomato sauce supplementation and prostate cancer: lycopene accumulation and modulation of biomarkers of carcinogenesis". Experimental Biology and Medicine 227 (10): 886–893. PMID 12424330. 
  5. ^ "http://news.bbc.co.uk/2/3086013.stm" BBC News - 22 July 2003
  6. ^ American Association for Cancer Research. "No Magic Tomato? Study Breaks Link between Lycopene and Prostate Cancer Prevention", Science Daily, May 17, 2007. 
  • Gerster, H. The potential role of lycopene for human health. J. Amer. Coll. Nutr. 16: 109–126, 1997
  • Stahl, W. and Sies, H. lycopene: a biologically important carotenoid for humans? Arch. Biochem. Biophys. 336: 1–9, 1996

is the 203rd day of the year (204th in leap years) in the Gregorian calendar. ... Year 2003 (MMIII) was a common year starting on Wednesday of the Gregorian calendar. ...

External links

  • [1]
  • [2]
  • A website promoting a lycopene rich diet

  Results from FactBites:
 
Lycopene.org (482 words)
Lycopene is an open-chain unsaturated carotenoid that imparts red colour to tomatoes, guava, rosehip, watermelon and pink grapefruit.
The chemical form of lycopene found in tomatoes is converted by the temperature changes involved in processing to make it more easily absorbed by the body.
Ongoing preliminary research suggests that lycopene is associated with reduced risk of macular degenerative disease, serum lipid oxidation and cancers of the lung, bladder, cervix and skin.
ACS :: Lycopene (1849 words)
Lycopene is the compound that gives tomatoes and certain other fruits and vegetables their color.
Lycopene is considered one of the more effective antioxidants because it is not converted to vitamin A after it is eaten.
Lycopene obtained from eating fruits and vegetables has no known side effects and is thought to be safe for humans who are not allergic to the foods.
  More results at FactBites »


 

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