Mead's acid
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| General | ||||||||||
| Surname | Mead's acid | |||||||||
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| Molecular formula | C 20 H 34 O 2 | |||||||||
| Brief description |
oil |
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| properties | ||||||||||
| Molar mass | 306.48 g · mol -1 | |||||||||
| Physical state |
liquid |
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| boiling point |
78-80 ° C |
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| solubility |
soluble in acetone , ethanol , ethyl acetate and hexane |
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| As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . | ||||||||||
The mead acid is a carboxylic acid having a linear chain of 20 carbon atoms and three cis double bonds. The first double bond begins on the ninth carbon atom from the omega end. In the physiological literature, the acid is therefore referred to by the lipid name 20: 3 (ω-9).
history
Mead's acid is one of the omega-9 fatty acids and was first described by the biochemist James F. Mead .
Occurrence
Mead's acid is the only polyunsaturated fatty acid that the human body can produce de novo . An increased occurrence of this fatty acid in the blood indicates a deficiency in essential fatty acids . The fatty acid is particularly concentrated in the connective tissue and other tissues with little blood supply.
physiology
Mead's acid is converted into various hydroxylated products (HETE) by lipoxygenase . However, these cannot serve as precursors to prostaglandins .
Humans and other mammals need essential fatty acids. If insufficient essential fatty acids are absorbed by the food, particularly in a shortage of arachidonic acid , mead acid produced by the body extension and dehydrogenation of oleic acid .
Mead's acid thus serves as an indicator of the lack of essential fatty acids. One study examined patients with intestinal fat malabsorption and a suspected lack of essential fatty acids. Her blood levels of Mead's acid were 1263% higher than the control group.
The accumulation of Mead's acid leads to decreased expression of E- cadherin and desmoglein , two cell-cell adhesion proteins , in cells . As a result, metastasis is facilitated by cancer cells.
Individual evidence
- ↑ a b c Enzolifesciences: Mead Acid data sheet (20: 3, n-9). Retrieved September 23, 2017.
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Cyberlipid Center: PROSTAGLANDINS AND RELATED COMPOUNDS . Archived from the original on June 14, 2018. Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. Retrieved September 16, 2008.
- ↑ WJ Elliott, AR Morrison, H. Sprecher, P. Needleman: Calcium-dependent oxidation of 5,8,11-icosatrienoic acid by the cyclooxygenase enzyme system . In: Journal of Biological Chemistry . tape 261 , 1986, pp. 6719-6724 , PMID 3084488 (free full text).
- ↑ SD Phinney, RS Odin, SB Johnson, RT Holman: Reduced arachidonate in serum phospholipids and cholesteryl esters associated with vegetarian diets in humans . In: American Journal of Clinical Nutrition . tape 51 , 1990, ISSN 0002-9165 , pp. 385-392 (source for 20: 3n-9).
- ↑ Lipomics: acid Mead . Archived from the original on March 19, 2006. Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. Retrieved September 16, 2008.
- ↑ Siguel, Edward N .; Chee, Kew M .; Gong, Junxian; Schaefer, Ernst J .: Criteria for Essential Fatty Acid Deficiency in Plasma as Assessed by Capillary Column Gas-Liquid Chromatography . In: Clinical Chemistry . tape 33 , 1987, ISSN 0009-9147 , pp. 1869-1878 .
- ↑ AR Eynard, WG Jiang, RE Mansel: Eicosatrienoic acid (20: 3 n-9) inhibits the expression of E-cadherin and desmoglein in human squamous cell carcinoma in vitro . In: Prostaglandins, Leukotrienes and Essential Fatty Acids . tape 59 , 1998, ISSN 0952-3278 , p. 371-377 , doi : 10.1016 / S0952-3278 (98) 90098-9 .
