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| Mead acid | |
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| IUPAC name | (5Z,8Z,11Z)-Eicosa-5,8,11-trienoic acid |
| Identifiers | |
| CAS number | [20590-32-3] |
| PubChem | |
| SMILES |
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| Properties | |
| Molecular formula | C20H34O2 |
| Molar mass | 306.48276 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references |
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Mead acid is an omega-9 fatty acid, first characterized by James F. Mead.[1] Mead acid is the only polyunsaturated fatty acid that the body can make de novo. Its elevated presence in the blood is an indication of essential fatty acid deficiency.
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Chemistry
Chemically, Mead acid is a carboxylic acid with a 20-carbon chain and three methylene-interrupted cis double bonds. The first double bond is located at the ninth carbon from the omega end. In physiological literature, it is given the name 20:3(n-9). In the presence of lipoxygenase, Mead acid can form various hydroxy products (HETE).[2]
Physiology
Humans and other mammals require essential fatty acids (EFA). During dietary EFA insufficiency—especially arachidonic acid deficiency—the body will make Mead acid by the elongation and desaturation of oleic acid.[3] [4] [5] Mead acid thus serves as an indicator of EFA deficiency. One study examined patients with intestinal fat malabsorption and suspected EFA deficiency. They were found to have blood-levels of Mead acid 1263% higher than reference subjects.[6]
Alternative views
The biologist Ray Peat suggests that the term essential fatty acid is a misnomer and that the human body can make eicosanoid-equivalents from Mead acid.[7] This view is disputed.[1]
References
- ^ a b Mary Enig (Spring, 2005). "A Reply to Ray Peat on Essential Fatty Acid Deficiency". Wise Traditions in Food, Farming and the Healing Arts. Retrieved on 2007-10-22.
- ^ Cyberlipid Center. "PROSTAGLANDINS AND RELATED COMPOUNDS". Retrieved on 2007-10-24.
- ^ Phinney, SD, RS Odin, SB Johnson and RT Holman (1990). "Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans". Retrieved on February 11, 2006. (reference is to 20:3n–9)
- ^ Lipomics. "Mead acid". Retrieved on February 14, 2006.
- ^ Gerard Hornstra (September 2007). "Essential Polyunsaturated Fatty Acids and Early Human Development". Fats of Life Newsletter. Retrieved on 2007-10-23.
- ^ EN Siguel, KM Chee, JX Gong and EJ Schaefer (1987). "Criteria for essential fatty acid deficiency in plasma as assessed by capillary column gas-liquid chromatography". Clinical Chemistry 33: 1869–1873. Retrieved on 2007-10-24.
- ^ Peat, Ray (2006). "Aspirin, brain, and cancer". Retrieved on 2007-10-22.
See also
- Polyunsaturated fatty acid – lists of ω-3, -6 and -9 fatty acids; some others.
Wikipedia content modification information:
- This page was last modified on 15 August 2008, at 16:35.
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