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α-Eleostearic acid

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.

α-Eleostearic acid
Names
Preferred IUPAC name
(9Z,11E,13E)-Octadeca-9,11,13-trienoic acid
Identifiers
3D model (JSmol)
  • Interactive image
1726551
ChEBI
  • CHEBI:10275 Y
ChemSpider
  • 4444560 Y
ECHA InfoCard 100.007.300
EC Number
  • 208-029-2
KEGG
  • C08315
  • 5281115
UNII
  • 934U1Q8QHG
  • DTXSID00897457
  • InChI=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- Y
    Key: CUXYLFPMQMFGPL-WPOADVJFSA-N Y
  • 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-
  • O=C(O)CCCCCCC/C=C\C=C\C=C\CCCC
Properties
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).
N verify (what is YN ?)

Biochemical properties Edit

 
α-Eleostearic acid makes up about 60% of the fatty acids from bitter gourd oil.

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 Edit

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 Edit

Eleo- is a prefix derived from the Greek word for olive, ἔλαιον.[6]

See also Edit

References Edit

  1. ^ a b Burr, G.O.; Burr, M.M.; Miller, E. (1932). "On the nature and role of the fatty acids essential in nutrition" (PDF). J. Biol. Chem. 97 (1): 1–9. doi:10.1016/S0021-9258(18)76213-3. Retrieved 2007-01-17.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ Senning, Alexander (2006-10-30). Elsevier's Dictionary of Chemoetymology: The Whys and Whences of Chemical Nomenclature and Terminology. ISBN 9780080488813.

eleostearic, acid, octadeca, trienoic, acid, organic, compound, conjugated, fatty, acid, isomers, octadecatrienoic, acid, often, called, simply, eleostearic, acid, although, there, also, eleostearic, acid, trans, isomer, high, degree, unsaturation, gives, tung. a 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 b eleostearic acid the all trans or 9E 11E 13E isomer Its high degree of unsaturation gives tung oil its properties as a drying oil a Eleostearic acid NamesPreferred IUPAC name 9Z 11E 13E Octadeca 9 11 13 trienoic acidIdentifiersCAS Number 506 23 0 Y pubchem 3D model JSmol Interactive imageBeilstein Reference 1726551ChEBI CHEBI 10275 YChemSpider 4444560 YECHA InfoCard 100 007 300EC Number 208 029 2KEGG C08315PubChem CID 5281115UNII 934U1Q8QHGCompTox Dashboard EPA DTXSID00897457InChI InChI 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 YKey CUXYLFPMQMFGPL WPOADVJFSA N YInChI 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 SMILES O C O CCCCCCC C C C C C C CCCCPropertiesChemical formula C18H30O2Molar mass 278 43 g molMelting 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 N verify what is Y N Infobox references Contents 1 Biochemical properties 2 Sources 3 Etymology 4 See also 5 ReferencesBiochemical properties Edit a Eleostearic acid makes up about 60 of the fatty acids from bitter gourd oil In their pioneering work on essential fatty acids Burr Burr and Miller compared the nutritional properties of a eleostearic acid ELA to that of its isomer alpha linolenic acid ALA ALA relieved essential fatty acid deficiency ELA did not 1 In rats a 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 mM 4 Diets containing 0 01 bitter gourd seed oil 0 006 as a eleostearic acid were found to prevent azoxymethane induced colon carcinogenesis in rats 5 Sources Edita Eleostearic acid is found in the oils extracted from seeds Tung oil has 82 a eleostearic acid Bitter gourd seed oil has 60 a eleostearic acid Etymology EditEleo is a prefix derived from the Greek word for olive ἔlaion 6 See also Edit15 16 Dihydroxy alpha eleostearic acidReferences Edit a b Burr G O Burr M M Miller E 1932 On the nature and role of the fatty acids essential in nutrition PDF J Biol Chem 97 1 1 9 doi 10 1016 S0021 9258 18 76213 3 Retrieved 2007 01 17 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 a 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 g expression and alteration of lipid composition International Journal of Cancer 110 6 896 901 doi 10 1002 ijc 20179 PMID 15170673 S2CID 1817375 Senning Alexander 2006 10 30 Elsevier s Dictionary of Chemoetymology The Whys and Whences of Chemical Nomenclature and Terminology ISBN 9780080488813 Retrieved from https en wikipedia org w index php title A Eleostearic acid amp oldid 1158975219, wikipedia, wiki, book, books, library,

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