Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Α-Eleostearic acid: Difference between pages

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| Watchedfields = changed

| verifiedrevid = 477319043

| Name = α-Eleostearic acid

| ImageFile = Alpha-eleostearic acid.svg

| ImageSize =

| ImageName = α-Eleostearic acid

| PIN = (9''Z'',11''E'',13''E'')-Octadeca-9,11,13-trienoic acid

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEBI_Ref = {{ebicite|correct|EBI}}

| PubChem = 5281115

| EC_number = 208-029-2

| UNII = 934U1Q8QHG

| KEGG = C08315

| Beilstein = 1726551

| 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-

|Section2={{Chembox Properties

| Formula = C₁₈H₃₀O₂

| MolarMass = 278.43 g/mol

| MeltingPtC = 48

| MeltingPt_ref = <ref name=Burr>{{cite journal | author=Burr, G.O. | author2=Burr, M.M. | author3=Miller, E. | year=1932 | title=On the nature and role of the fatty acids essential in nutrition | journal=J. Biol. Chem. | volume=97 | issue=1 | pages=1–9 | doi=10.1016/S0021-9258(18)76213-3 | doi-access=free }}</ref>

'''α-Eleostearic acid''' or '''(9''Z'',11''E'',13''E'')-octadeca-9,11,13-trienoic acid''', is an [[organic compound]], a [[conjugated fatty acids|conjugated fatty acid]] and one of the [[isomer]]s of [[octadecatrienoic acid]]. It is often called simply '''eleostearic acid''' although there is also a [[β-Eleostearic acid|β-eleostearic acid]] (the ''all-trans'' or (9''E'',11''E'',13''E'') isomer). Its high [[Polyunsaturated fatty acid|degree of unsaturation]] gives [[tung oil]] its properties as a [[drying oil]].

==Biochemical properties==

[[Image:bittermelonfruit.jpg|thumb|left|α-Eleostearic acid makes up about 60% of the fatty acids from bitter gourd oil.]]

In their pioneering work on [[essential fatty acid]]s, [[George O. Burr|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.<ref name=Burr/>

In rats, α-eleostearic acid is converted to a [[conjugated linoleic acid]].<ref name=Tsuzuki >{{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}}

</ref> The compound has been found to induce [[apoptosis|programmed cell death]] of [[adipose tissue|fat cells]],<ref name=Nishimura >{{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

}}<!--|accessdate=2007-01-29 -->

</ref> and of [[HL60]] [[leukemia]] cells [[in vitro]] at a concentration of 20 [[micromolar|μM]].<ref name="kob2008">{{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}}</ref> Diets containing 0.01% bitter gourd seed oil (0.006% as α-eleostearic acid) were found to prevent [[azoxymethane]]-induced colon [[carcinogenesis]] in [[rat]]s.<ref name="kohno2004">{{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 }}</ref>

==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.<ref>{{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 }}</ref>

==See also==

*[[15,16-Dihydroxy-alpha-eleostearic acid]]

==References==

{{reflist}}

{{Fatty acids}}

{{DEFAULTSORT:Eleostearic Acid, alpha-}}

[[Category:Fatty acids]]

[[Category:Alkenoic acids]]

[[Category:Polyenes]]