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'''Elaidic acid''' is the [[organic compound]] with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CHCH(CH<sub>2</sub>)<sub>7</sub>CO<sub>2</sub>H. Classified as an [[Unsaturated fat|unsaturated]] [[trans fat|trans fatty acid]], it is a colorless oily solid. This compound has attracted attention because it is a major trans fat found in [[Hydrogenation|hydrogenated]] vegetable oils, and trans fats are implicated in heart disease.<ref>{{Cite journal | doi = 10.1017/S0954422411000011| pmid = 21320382| title = Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases| journal = Nutrition Research Reviews| volume = 24| issue = 1| pages = 111–7| year = 2011| last1 = Tardy| first1 = Anne-Laure| last2 = Morio| first2 = Béatrice| last3 = Chardigny| first3 = Jean-Michel| last4 = Malpuech-Brugère| first4 = Corinne}}</ref> The salts and esters of elaidic acid are called '''elaidates'''. |
'''Elaidic acid''' is the [[organic compound]] with the formula CH<sub>3</sub>(CH<sub>2</sub>)<sub>7</sub>CHCH(CH<sub>2</sub>)<sub>7</sub>CO<sub>2</sub>H. Classified as an [[Unsaturated fat|unsaturated]] [[trans fat|trans fatty acid]], it is a colorless oily solid. This compound has attracted attention because it is a major trans fat found in [[Hydrogenation|hydrogenated]] vegetable oils, and trans fats are implicated in heart disease.<ref>{{Cite journal | doi = 10.1017/S0954422411000011| pmid = 21320382| title = Ruminant and industrial sources of trans-fat and cardiovascular and diabetic diseases| journal = Nutrition Research Reviews| volume = 24| issue = 1| pages = 111–7| year = 2011| last1 = Tardy| first1 = Anne-Laure| last2 = Morio| first2 = Béatrice| last3 = Chardigny| first3 = Jean-Michel| last4 = Malpuech-Brugère| first4 = Corinne| doi-access = free}}</ref> The salts and esters of elaidic acid are called '''elaidates'''. |
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It is the [[Cis–trans isomerism|trans isomer]] of [[oleic acid]]. The name of the [[elaidinization]] reaction comes from elaidic acid. |
It is the [[Cis–trans isomerism|trans isomer]] of [[oleic acid]]. The name of the [[elaidinization]] reaction comes from elaidic acid. |
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==Occurrence and bioactivity== |
==Occurrence and bioactivity== |
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Elaidic acid occurs naturally in small amounts in [[Goat#Milk, butter and cheese|caprine]] and [[Milk|bovine milk]] (very roughly 0.1% of the fatty acids)<ref name=Alonso>{{cite journal |vauthors=Alonso L, Fontecha J, Lozada L, Fraga MJ, Juárez M |title=Fatty acid composition of caprine milk: major, branched-chain, and trans fatty acids |journal=J. Dairy Sci. |volume=82 |issue=5 |pages=878–84 |year=1999 |pmid=10342226 |doi=10.3168/jds.S0022-0302(99)75306-3|hdl=10261/113439 }}</ref> and in some meats.<ref>{{Cite book | title = Membranes and Human Health | author = William Stillwell | work = An Introduction to Biological Membranes | edition = Second | date = 2016}}</ref> It also comprises 2.50% of the fats from the fruit of the [[durian]] species ''[[Durio graveolens]]''.<ref name="Nasaruddin">{{cite journal|last1=Nasaruddin|first1=Mohd hanif|last2=Noor|first2=Noor Qhairul Izzreen Mohd|last3=Mamat|first3=Hasmadi|title=Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah|journal=Sains Malaysiana|date=2013|volume=42|issue=9|pages=1283–1288|url=http://www.ukm.my/jsm/pdf_files/SM-PDF-42-9-2013/11%20Mohd%20Hanif.pdf|accessdate=28 November 2017|trans-title=Proximate and Fatty Acid Composition of Sabah Yellow Durian (''Durio graveolens'')|language=Malay|format=PDF|issn=0126-6039|oclc=857479186}}</ref> |
Elaidic acid occurs naturally in small amounts in [[Goat#Milk, butter and cheese|caprine]] and [[Milk|bovine milk]] (very roughly 0.1% of the fatty acids)<ref name=Alonso>{{cite journal |vauthors=Alonso L, Fontecha J, Lozada L, Fraga MJ, Juárez M |title=Fatty acid composition of caprine milk: major, branched-chain, and trans fatty acids |journal=J. Dairy Sci. |volume=82 |issue=5 |pages=878–84 |year=1999 |pmid=10342226 |doi=10.3168/jds.S0022-0302(99)75306-3|hdl=10261/113439 |doi-access=free }}</ref> and in some meats.<ref>{{Cite book | title = Membranes and Human Health | author = William Stillwell | work = An Introduction to Biological Membranes | edition = Second | date = 2016}}</ref> It also comprises 2.50% of the fats from the fruit of the [[durian]] species ''[[Durio graveolens]]''.<ref name="Nasaruddin">{{cite journal|last1=Nasaruddin|first1=Mohd hanif|last2=Noor|first2=Noor Qhairul Izzreen Mohd|last3=Mamat|first3=Hasmadi|title=Komposisi Proksimat dan Komponen Asid Lemak Durian Kuning (Durio graveolens) Sabah|journal=Sains Malaysiana|date=2013|volume=42|issue=9|pages=1283–1288|url=http://www.ukm.my/jsm/pdf_files/SM-PDF-42-9-2013/11%20Mohd%20Hanif.pdf|accessdate=28 November 2017|trans-title=Proximate and Fatty Acid Composition of Sabah Yellow Durian (''Durio graveolens'')|language=Malay|format=PDF|issn=0126-6039|oclc=857479186}}</ref> |
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Elaidic acid increases plasma [[cholesterylester transfer protein]] (CETP) activity which lowers [[High-density lipoprotein|HDL]] cholesterol.<ref name="pmid8018112">{{cite journal |vauthors=Abbey M, Nestel PJ |title=Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet |journal=Atherosclerosis |volume=106 |issue=1 |pages=99–107 |year=1994 |pmid=8018112 |doi=10.1016/0021-9150(94)90086-8 }}</ref> |
Elaidic acid increases plasma [[cholesterylester transfer protein]] (CETP) activity which lowers [[High-density lipoprotein|HDL]] cholesterol.<ref name="pmid8018112">{{cite journal |vauthors=Abbey M, Nestel PJ |title=Plasma cholesteryl ester transfer protein activity is increased when trans-elaidic acid is substituted for cis-oleic acid in the diet |journal=Atherosclerosis |volume=106 |issue=1 |pages=99–107 |year=1994 |pmid=8018112 |doi=10.1016/0021-9150(94)90086-8 }}</ref> |
Names | |
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IUPAC name
(E)-octadec-9-enoic acid | |
Other names
(E)-9-Octadecenoic acid, | |
Identifiers | |
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3D model (JSmol) |
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ChEBI | |
ChEMBL | |
ChemSpider |
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DrugBank |
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ECHA InfoCard | 100.003.642 |
KEGG |
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PubChem CID |
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CompTox Dashboard (EPA) |
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Properties | |
C18H34O2 | |
Molar mass | 282.46 g/mol |
Appearance | colorless waxy solid |
Density | 0.8734 g/cm3 |
Melting point | 45 °C (113 °F) |
-204.8·10−6cm3/mol | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Elaidic acid is the organic compound with the formula CH3(CH2)7CHCH(CH2)7CO2H. Classified as an unsaturated trans fatty acid, it is a colorless oily solid. This compound has attracted attention because it is a major trans fat found in hydrogenated vegetable oils, and trans fats are implicated in heart disease.[1] The salts and esters of elaidic acid are called elaidates.
It is the trans isomerofoleic acid. The name of the elaidinization reaction comes from elaidic acid.
Elaidic acid occurs naturally in small amounts in caprine and bovine milk (very roughly 0.1% of the fatty acids)[2] and in some meats.[3] It also comprises 2.50% of the fats from the fruit of the durian species Durio graveolens.[4]
Elaidic acid increases plasma cholesterylester transfer protein (CETP) activity which lowers HDL cholesterol.[5]
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