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Elaidic acid: Difference between revisions

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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'DrugBank', 'ChEBI').
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{{chembox
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 407470582
| verifiedrevid = 443720273
|ImageFile=Elaidic-acid-2D-skeletal-reverse.png
| ImageFile=Elaidic-acid-2D-skeletal-reverse.png
|ImageSize=250
| ImageSize=250
|ImageFile1=Elaidic-acid-from-xtal-3D-balls.png
| ImageFile1=Elaidic-acid-from-xtal-3D-balls.png
|ImageSize1=250
| ImageSize1=250
|ImageFile2=Elaidic-acid-from-xtal-3D-vdW.png
| ImageFile2=Elaidic-acid-from-xtal-3D-vdW.png
|ImageSize2=250
| ImageSize2=250
|IUPACName=(''E'')-octadec-9-enoic acid
| IUPACName=(''E'')-octadec-9-enoic acid
| SystematicName=
|OtherNames=
| OtherNames=(''E'')-9-octadecenoic acid<br/>(9''E'')-octadecenoic acid<br/>''trans''-9-octadecenoic acid<br/>18:1 ''trans''-9<br/>C18:1 ''trans''-9
|Section1= {{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 553123
| ChemSpiderID = 553123
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01712
| KEGG = C01712
| InChI = 1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
| InChI = 1/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9+
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| StdInChIKey = ZQPPMHVWECSIRJ-MDZDMXLPSA-N
| StdInChIKey = ZQPPMHVWECSIRJ-MDZDMXLPSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo=112-79-8
| CASNo = 112-79-8
| IUPHAR_ligand =
⚫
| PubChem=637517
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| DrugBank = DB04224
| UNII = 4837010H8C
⚫
| PubChem = 637517
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
⚫
| DrugBank = DB04224
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 27997
| ChEBI = 27997
| SMILES = O=C(O)CCCCCCC/C=C/CCCCCCCC
| SMILES = O=C(O)CCCCCCC/C=C/CCCCCCCC
}}
}}
|Section2= {{Chembox Properties
|Section2={{Chembox Properties
| Formula=C<sub>18</sub>H<sub>34</sub>O<sub>2</sub>
| Formula={{chem|C|18|H|34|O|2}}
| MolarMass=282.46 g/mol
| MolarMass=282.46 g/mol
| Appearance=
| Appearance= colorless waxy solid
| Density=
| Density= 0.8734 g/cm<sup>3</sup>
| MeltingPt=
| MeltingPt={{convert|45|C|F}}
| BoilingPt=
| BoilingPt=
| Solubility=
| Solubility=
| MagSus = -204.8·10<sup>−6</sup> cm<sup>3</sup>/mol
}}
}}
|Section3= {{Chembox Hazards
|Section3={{Chembox Hazards
| MainHazards=
| MainHazards=
| FlashPt=
| FlashPt=
| AutoignitionPt =
| Autoignition=
}}
}}
}}
}}


'''Elaidic acid''' is a [[chemical compound]] with the formula {{chem|C|18|H|34|O|2}}, specifically the [[fatty acid]] with structural formula {{chem2|HOOC\s(CH2)7\sCH\dCH\s(CH2)7\sCH3}}, with the [[double bond]] (between [[carbon]] atoms 9 and 10) in [[cis-trans isomerism|''trans'']] configuration. It is a colorless oily solid. Its salts and esters are called '''elaidates'''.
'''Elaidic acid''' is the major [[trans fat]] found in [[Hydrogenation|hydrogenated]] vegetable oils and occurs in small amounts in caprine and bovine milk (very roughly 0.1 % of the fatty acids).<ref name=Alonso>{{cite journal |author=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}}</ref> It is the [[Geometric isomerism|trans isomer]] of [[oleic acid]]. The name of the [[elaidinization]] reaction comes from elaidic acid.


Elaidic acid is an [[unsaturated fat|unsaturated]] [[trans fat|trans fatty acid]], with code C18:1 ''trans''-9. This compound has attracted attention because it is a major trans fat found in [[Hydrogenation|hydrogenated]] vegetable oils, and trans fats have been 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>
⚫
Elaidic acid increases [[Cholesterylester transfer protein|CETP]] activity, which in turn raises [[Very low density lipoprotein|VLDL]] and lowers [[High density lipoprotein|HDL]] cholesterol.<ref name="pmid8018112">{{cite journal |author=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>

It is the [[Cis–trans isomerism|trans isomer]] of [[oleic acid]]. The name of the [[elaidinization]] reaction comes from elaidic acid.

Its name comes from the [[Ancient Greek]] word [[wikt:ἔλαιον|ἔλらむだαあるふぁιいおたοおみくろんνにゅー]] (''elaion''), meaning oil.

==Occurrence and bioactivity==
Elaidic acid occurs mostly in industrial hydrogenation of polyunsaturated fatty acids.<ref>{{Cite journal |last1=Wendeu-Foyet |first1=Gaëlle |last2=Bellicha |first2=Alice |last3=Chajès |first3=Véronique |last4=Huybrechts |first4=Inge |last5=Bard |first5=Jean-Marie |last6=Debras |first6=Charlotte |last7=Srour |first7=Bernard |last8=Sellem |first8=Laury |last9=Fezeu |first9=Léopold K. |last10=Julia |first10=Chantal |last11=Kesse-Guyot |first11=Emmanuelle |last12=Agaësse |first12=Cédric |last13=Druesne-Pecollo |first13=Nathalie |last14=Galan |first14=Pilar |last15=Hercberg |first15=Serge |date=2023 |title=Different Types of Industry-Produced and Ruminant Trans Fatty Acid Intake and Risk of Type 2 Diabetes: Findings From the NutriNet-Santé Prospective Cohort |journal=Diabetes Care |volume=46 |issue=2 |pages=321–330 |doi=10.2337/dc22-0900 |pmid=36542554|s2cid=255041911 }}</ref> It's also present 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 |last=Stillwell |first=William |date=2016 |title = An Introduction to Biological Membranes – Composition, Structure and Function |chapter=Chapter 23. Membranes and Human Health |publisher=Elsevier |edition=2 |doi=10.1016/B978-0-444-63772-7.00023-3}}</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>

==See also==
* [[Oleic acid]]


==References==
==References==
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[[Category:Fatty acids]]
[[Category:Fatty acids]]
[[Category:Alkenoic acids]]


{{organic-compound-stub}}

[[de:Elaidinsäure]]
[[fr:Acide élaïdique]]
[[it:Acido elaidinico]]
[[lv:Elaidīnskābe]]
[[nl:Elaïdinezuur]]
[[ja:エライジン酸さん]]
[[pl:Kwas elaidynowy]]
[[ru:Элаидиновая кислота]]
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