Mead acid

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Mead acid
Names
Preferred IUPAC name
(5Z,8Z,11Z)-Icosa-5,8,11-trienoic acid
Identifiers
3D model (
JSmol
)
ChEBI
ChemSpider
UNII
  • InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15- ☒N
    Key: UNSRRHDPHVZAHH-YOILPLPUSA-N ☒N
  • InChI=1/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h9-10,12-13,15-16H,2-8,11,14,17-19H2,1H3,(H,21,22)/b10-9-,13-12-,16-15-
    Key: UNSRRHDPHVZAHH-YOILPLPUBD
  • CCCCCCCC\C=C/C\C=C/C\C=C/CCCC(=O)O
Properties
C20H34O2
Molar mass 306.48276
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Mead acid is an

deficiency.[2] Mead acid is found in large quantities in cartilage
.

Chemistry

Mead acid, also referred to as eicosatrienoic acid, is chemically a

cytochrome p450, or cyclooxygenase, mead acid can form various hydroxyeicosatetraenoic acid (HETE) and hydroperoxy (HpETE) products.[3][4]

Physiology

Two fatty acids,

alpha-linolenic acid, are considered essential fatty acids (EFAs) in humans and other mammals. Both are 18 carbon fatty acids unlike mead acid, which has 20 carbons. Linoleic is an ω-6 fatty acid whereas linolenic is ω-3 and mead is ω-9. One study examined patients with intestinal fat malabsorption and suspected EFA deficiency; they were found to have blood-levels of mead acid about 13-fold higher than reference subjects.[5] Under severe conditions of essential fatty acid deprivation, mammals will elongate and desaturate oleic acid to make mead acid, (20:3, n−9).[6] This has been documented to a lesser extent in vegetarians and semi-vegetarians following an unbalanced diet.[7][8]

Mead acid has been found to decrease osteoblastic activity. This may be important in treating conditions where inhibition of bone formation is desired.[9]

Role in inflammation

allylic C-H bond when it encounters Mead acid instead.[3]

Mead acid is also converted to leukotrienes C3 and D3.[10]

Mead acid is metabolized by

5-hydroxyeicosanoid dehydrogenase to 5-oxoeicosatrienoic acid (5-oxo-ETrE).[12]
5-Oxo-ETrE is as potent as its arachidonic acid-derived analog,
5-oxo-eicosatetraenoic acid (5-oxo-ETE), in stimulating human blood eosinophils and neutrophils;[13]
it presumably does so by binding to the 5-oxo-ETE receptor (
OXER1) and therefore may be, like 5-oxo-ETE, a mediator of human allergic and inflammatory reactions.[12]

See also

References

  1. ISBN 9780080472072
    . One of these is 20:3ω9, termed 'Mead acid' after its discovery by James Mead....
  2. PMID 24184513
    .
  3. ^
    PMID 8373167
    .
  4. ^ Cyberlipid Center. "PROSTAGLANDINS AND RELATED COMPOUNDS". Archived from the original on April 13, 2018. Retrieved October 24, 2007.
  5. PMID 3665042. Archived from the original
    on September 27, 2011. Retrieved October 24, 2007.
  6. ISBN 9 78-0-19-876802-9
    .
  7. PMID 2106775
    .
  8. ^ Hornstra, Gerard (September 2007). "Essential Polyunsaturated Fatty Acids and Early Human Development". Fats of Life Newsletter. Archived from the original on June 7, 2008. Retrieved October 23, 2007.
  9. S2CID 4011759
    .
  10. PMID 6780563
    .
  11. PMID 2988021
    .
  12. ^
    PMID 24056189
    .
  13. S2CID 19936422
    .
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