α-Eleostearic acid
{{cs1 config|name-list-style=vanc}}
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{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477319043
| Name = α-Eleostearic acid
| ImageFile = Alpha-eleostearic acid.svg
| ImageSize =
| ImageName = α-Eleostearic acid
| PIN = (9Z,11E,13E)-Octadeca-9,11,13-trienoic acid
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444560
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 10275
| PubChem = 5281115
| EC_number = 208-029-2
| UNII = 934U1Q8QHG
| KEGG = C08315
| Beilstein = 1726551
| SMILES = O=C(O)CCCCCCC/C=C\C=C\C=C\CCCC
| CASNo_Ref = {{cascite|correct|pubchem}}
| CASNo =506-23-0
| InChI = 1/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7+,10-9-
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI =1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h5-10H,2-4,11-17H2,1H3,(H,19,20)/b6-5+,8-7+,10-9-
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CUXYLFPMQMFGPL-WPOADVJFSA-N
}}
|Section2={{Chembox Properties
| Formula = C18H30O2
| MolarMass = 278.43 g/mol
| MeltingPtC = 48
}}
}}
α-Eleostearic acid or (9Z,11E,13E)-octadeca-9,11,13-trienoic acid, is an organic compound, a conjugated fatty acid and one of the isomers of octadecatrienoic acid. It is often called simply eleostearic acid although there is also a β-eleostearic acid (the all-trans or (9E,11E,13E) isomer). Its high degree of unsaturation gives tung oil its properties as a drying oil.
Biochemical properties
In their pioneering work on essential fatty acids, George Burr, Mildred Burr and Elmer Miller compared the nutritional properties of α-eleostearic acid (ELA) to that of its isomer alpha-linolenic acid (ALA). ALA relieved essential fatty acid deficiency; ELA did not.
In rats, α-eleostearic acid is converted to a conjugated linoleic acid.{{cite journal
|pmid= 16857834
|journal= J Nutr|date=1 August 2006|volume=136|issue=8|pages=2153–9
|title= Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid
|vauthors =Tsuzuki T, Kawakami Y, Abe R|display-authors=etal|doi= 10.1093/jn/136.8.2153
|doi-access=free}}
The compound has been found to induce programmed cell death of fat cells,{{cite journal
|vauthors =Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K
|title=Regulation of apoptosis through arachidonate cascade in mammalian cells
|journal=Appl Biochem Biotechnol |volume=102–103 |issue=1–6 |pages=239–50
|year= 2002|pmid=12396127|doi=10.1385/ABAB:102-103:1-6:239|s2cid=25037285
}}
and of HL60 leukemia cells in vitro at a concentration of 20 μM.{{cite journal | vauthors = Kobori M, Ohnishi-Kameyama M, Akimoto Y, Yukizaki C, Yoshida M | year = 2008 | title = α-Eleostearic Acid and Its Dihydroxy Derivative Are Major Apoptosis-Inducing Components of Bitter Gourd | journal = Journal of Agricultural and Food Chemistry | volume = 56 | issue = 22| pages = 10515–10520 | doi = 10.1021/jf8020877 | pmid=18959405}} Diets containing 0.01% bitter gourd seed oil (0.006% as α-eleostearic acid) were found to prevent azoxymethane-induced colon carcinogenesis in rats.{{cite journal | vauthors = Kohno H, Yasui Y, Suzuki R, Hosokawa M, Miyashita K, Tanaka T | year = 2004 | title = Dietary seed oil rich in conjugated linolenic acid from bitter melon inhibits azoxymethane-induced rat colon carcinogenesis through elevation of colonic PPAR γ expression and alteration of lipid composition. | journal = International Journal of Cancer | volume = 110 | issue = 6| pages = 896–901 | doi=10.1002/ijc.20179 | pmid=15170673| s2cid = 1817375 | doi-access = free }}
Sources
α-Eleostearic acid is found in the oils extracted from seeds. Tung oil has 82% α-eleostearic acid. Bitter gourd seed oil has 60% α-eleostearic acid.
Etymology
Eleo- is a prefix derived from the Greek word for olive, ἔλαιον.{{Cite book | url=https://books.google.com/books?id=Fl4sdCYrq3cC&q=eleo |title = Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology|isbn = 978-0-08-048881-3|last1 = Senning|first1 = Alexander|date = 2006-10-30| publisher=Elsevier }}
See also
References
{{reflist}}
{{Fatty acids}}
{{DEFAULTSORT:Eleostearic Acid, alpha-}}