Α-Eleostearic acid
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Preferred IUPAC name (9Z,11E,13E)-Octadeca-9,11,13-trienoic acid | |
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Beilstein Reference | 1726551 |
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ECHA InfoCard | 100.007.300 ![]() |
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InChI
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Properties | |
Chemical formula | C18H30O2 |
Molar mass | 278.43 g/mol |
Melting point | 48 °C (118 °F; 321 K)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ![]() ![]() ![]() Infobox references |
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
![](http://upload.wikimedia.org/wikipedia/commons/thumb/9/94/Bittermelonfruit.jpg/220px-Bittermelonfruit.jpg)
In their pioneering work on essential fatty acids, Burr, Burr and 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.[1]
In rats, α-eleostearic acid is converted to a conjugated linoleic acid.[2] The compound has been found to induce programmed cell death of fat cells,[3] and of HL60 leukemia cells in vitro at a concentration of 20 μM.[4] Diets containing 0.01% bitter gourd seed oil (0.006% as α-eleostearic acid) were found to prevent azoxymethane-induced colon carcinogenesis in rats.[5]
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.[6]
See also
References
- ^ a b Burr, G.O., Burr, M.M., Miller, E. (1932). "On the nature and role of the fatty acids essential in nutrition". J. Biol. Chem. 97 (1): 1–9. doi:10.1016/S0021-9258(18)76213-3.
- ^ Tsuzuki T, Kawakami Y, Abe R, et al. (1 August 2006). "Conjugated linolenic acid is slowly absorbed in rat intestine, but quickly converted to conjugated linoleic acid". J Nutr. 136 (8): 2153–9. doi:10.1093/jn/136.8.2153. PMID 16857834.
- ^ Nishimura K, Tsumagari H, Morioka A, Yamauchi Y, Miyashita K, Lu S, Jisaka M, Nagaya T, Yokota K (2002). "Regulation of apoptosis through arachidonate cascade in mammalian cells". Appl Biochem Biotechnol. 102–103 (1–6): 239–50. doi:10.1385/ABAB:102-103:1-6:239. PMID 12396127. S2CID 25037285.
- ^ Kobori M, Ohnishi-Kameyama M, Akimoto Y, Yukizaki C, Yoshida M (2008). "α-Eleostearic Acid and Its Dihydroxy Derivative Are Major Apoptosis-Inducing Components of Bitter Gourd". Journal of Agricultural and Food Chemistry. 56 (22): 10515–10520. doi:10.1021/jf8020877. PMID 18959405.
- ^ Kohno H, Yasui Y, Suzuki R, Hosokawa M, Miyashita K, Tanaka T (2004). "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". International Journal of Cancer. 110 (6): 896–901. doi:10.1002/ijc.20179. PMID 15170673. S2CID 1817375.
- ^ Senning A (2006-10-30). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. Elsevier. ISBN 978-0-08-048881-3.
- v
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- Propionic (C3)
- Butyric (C4)
- Valeric (C5)
- Caproic (C6)
- Enanthic (C7)
- Caprylic (C8)
- Pelargonic (C9)
- Capric (C10)
- Undecylic (C11)
- Lauric (C12)
- Tridecylic (C13)
- Myristic (C14)
- Pentadecylic (C15)
- Palmitic (C16)
- Margaric (C17)
- Stearic (C18)
- Nonadecylic (C19)
- Arachidic (C20)
- Heneicosylic (C21)
- Behenic (C22)
- Tricosylic (C23)
- Lignoceric (C24)
- Pentacosylic (C25)
- Cerotic (C26)
- Carboceric (C27)
- Montanic (C28)
- Nonacosylic (C29)
- Melissic (C30)
- Hentriacontylic (C31)
- Lacceroic (C32)
- Psyllic (C33)
- Geddic (C34)
- Ceroplastic (C35)
- Hexatriacontylic (C36)
- Heptatriacontanoic (C37)
- Octatriacontanoic (C38)
- Nonatriacontanoic (C39)
- Tetracontanoic (C40)
- Octenoic (8:1)
- Decenoic (10:1)
- Decadienoic (10:2)
- Lauroleic (12:1)
- Laurolinoleic (12:2)
- Myristovaccenic (14:1)
- Myristolinoleic (14:2)
- Myristolinolenic (14:3)
- Palmitolinolenic (16:3)
- Palmitidonic (16:4)
- α-Linolenic (18:3)
- Stearidonic (18:4)
- α-Parinaric (18:4)
- Dihomo-α-linolenic (20:3)
- Eicosatetraenoic (20:4)
- Eicosapentaenoic (20:5)
- Clupanodonic (22:5)
- Docosahexaenoic (22:6)
- 9,12,15,18,21-Tetracosapentaenoic (24:5)
- 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
- Myristoleic (14:1)
- Palmitovaccenic (16:1)
- α-Eleostearic (18:3)
- β-Eleostearic (trans-18:3)
- Punicic (18:3)
- 7,10,13-Octadecatrienoic (18:3)
- 9,12,15-Eicosatrienoic (20:3)
- β-Eicosatetraenoic (20:4)
- 8-Tetradecenoic (14:1)
- 12-Octadecenoic (18:1)
- Linoleic (18:2)
- Linolelaidic (trans-18:2)
- γ-Linolenic (18:3)
- Calendic (18:3)
- Pinolenic (18:3)
- Dihomo-linoleic (20:2)
- Dihomo-γ-linolenic (20:3)
- Sciadonic (20:3)
- Arachidonic (20:4)
- Adrenic (22:4)
- Osbond (22:5)
- Palmitoleic (16:1)
- Vaccenic (18:1)
- Rumenic (18:2)
- Paullinic (20:1)
- 7,10,13-Eicosatrienoic (20:3)
- Sapienic (16:1)
- Gadoleic (20:1)
- 4-Hexadecenoic (16:1)
- Petroselinic (18:1)
- 8-Eicosenoic (20:1)