Lycopene
From Wikipedia, the free encyclopedia
| Lycopene | |
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| 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 | |
| CAS number | [] |
| PubChem | |
| EINECS number | |
| 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 |
| Properties | |
| Molecular formula | C40H56 |
| Molar mass | 536.873 g/mol |
| Appearance | Deep red solid |
| Melting point |
172-173 °C |
| 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 |
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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).
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[edit] Structure and Chemistry
Lycopene is a terpene assembled from 8 isoprene units.
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.
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.
[edit] Dietary sources
Fruits and vegetables that are high in lycopene include tomatoes, watermelon, pink grapefruit, pink guava, papaya, gac, and rosehip.
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. Thus processed tomato products such as pasteurized tomato juice, soup, sauce, and ketchup contain the highest concentrations of bioavailable lycopene. Because lycopene is so insoluble in water and is so tightly bound to vegetable fiber, the bioavailability of lycopene is increased by food processing. 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.
[edit] Production
Lycopene may be obtained from vegetables such as tomato, but another source of lycopene is Blakeslea trispora, a natural occurring bacteria.
[edit] Nutritional benefits
Lycopene is the most powerful carotenoid quencher of singlet oxygen.[1] Singlet oxygen from ultraviolet light is a primary cause of skin aging.[2]
There is evidence that frequent intake of such products is associated with reduced risk of cardiovascular disease, cancer (especially prostate cancer), diabetes, osteoporosis, and even male infertility.[3] Lycopene may also be related to a reduced risk of oesophageal, colorectal, and oral cancer.[4]
[edit] Food Coloring
Due to its ubiquity, lycopene has been licensed for use as a food coloring.
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.
[edit] References
- ^ 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.
- ^ 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.
- ^ 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.
- ^ "http://news.bbc.co.uk/2/3086013.stm" BBC News - 22 July 2003
- 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
