α-Eleostearic acid or (9''Z'',11''E'',13''E'')-octadeca-9,11,13-trienoic acid, is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

, a conjugated fatty acid and one of the

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

s of

octadecatrienoic acid An octadecatrienoic acid is a chemical compound with formula , a polyunsaturated fatty acid whose molecule has an 18-carbon unbranched backbone with three double bonds. The name refers to many different structural and configurational isomers, tha ...

. It is often called simply eleostearic acid although there is also a

β-eleostearic acid β-Eleostearic acid, or (9''E'',11''E'',13''E'')-octadeca-9,11,13-trienoic acid, is an organic compound with formula or H3C(CH2)3(CH=CH)3(CH2)7COOH. It is an all-''trans'' isomer of octadecatrienoic acid. See also * α-Eleostearic acid, the ...

(the ''all-trans'' or (9''E'',11''E'',13''E'') isomer). Its high degree of unsaturation gives

tung oil Tung oil or China wood oil is a drying oil obtained by pressing the seed from the nut of the tung tree (''Vernicia fordii''). Tung oil hardens upon exposure to air (through polymerization), and the resulting coating is transparent and has a d ...

its properties as a

drying oil Drying is a mass transfer process consisting of the removal of water or another solvent by evaporation from a solid, semi-solid or liquid. This process is often used as a final production step before selling or packaging products. To be conside ...

Biochemical properties

In their pioneering work on

essential fatty acid Essential fatty acids, or EFAs, are fatty acids that are required by humans and other animals for normal physiological function that cannot be synthesized in the body.⁠ As they are not synthesized in the body, the essential fatty acids al ...

s, 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 Conjugated linoleic acids (CLA) are a family of isomers of linoleic acid. In principle, 28 isomers are possible. CLA is found mostly in the meat and dairy products derived from ruminants. The two C=C double bonds are conjugated (i.e., separated ...

. The compound has been found to induce

programmed cell death Programmed cell death (PCD) sometimes referred to as cell, or cellular suicide is the death of a cell (biology), cell as a result of events inside of a cell, such as apoptosis or autophagy. PCD is carried out in a biological process, which usual ...

fat cells Adipocytes, also known as lipocytes and fat cells, are the cell (biology), cells that primarily compose adipose tissue, specialized in storing energy as fat. Adipocytes are derived from mesenchymal stem cells which give rise to adipocytes through ...

, and of

HL60 The HL-60 cell line is a human leukemia cell line that has been used for laboratory research on blood cell formation and physiology. HL-60 proliferates continuously in suspension culture in nutrient and antibiotic chemicals. The doubling time is ...

leukemia Leukemia ( also spelled leukaemia; pronounced ) is a group of blood cancers that usually begin in the bone marrow and produce high numbers of abnormal blood cells. These blood cells are not fully developed and are called ''blasts'' or '' ...

cells

in vitro ''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...

at a concentration of 20

μM The micrometre (Commonwealth English as used by the International Bureau of Weights and Measures; SI symbol: μm) or micrometer (American English), also commonly known by the non-SI term micron, is a unit of length in the International System ...

. Diets containing 0.01% bitter gourd seed oil (0.006% as α-eleostearic acid) were found to prevent azoxymethane-induced colon

carcinogenesis Carcinogenesis, also called oncogenesis or tumorigenesis, is the formation of a cancer, whereby normal cell (biology), cells are malignant transformation, transformed into cancer cells. The process is characterized by changes at the cellular, G ...

rat Rats are various medium-sized, long-tailed rodents. Species of rats are found throughout the order Rodentia, but stereotypical rats are found in the genus ''Rattus''. Other rat genera include '' Neotoma'' (pack rats), '' Bandicota'' (bandicoo ...

Sources

α-Eleostearic acid is found in the oils extracted from seeds. Tung oil has 82% α-eleostearic acid.

Bitter gourd ''Momordica charantia'' (commonly called bitter melon, cerassee, goya, bitter apple, bitter gourd, bitter squash, balsam-pear, karela, karavila and many more names listed below) is a tropical and subtropical vine of the family Cucurbitaceae, w ...

seed oil has 60% α-eleostearic acid.

Etymology

Eleo- is a prefix derived from the Greek word for olive, ἔλαιον.

References

{{DEFAULTSORT:Eleostearic Acid, alpha- Fatty acids Alkenoic acids Polyenes