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Add: s2cid, authors 1-1. Removed parameters. Some additions/deletions were parameter name changes. | Use this bot. Report bugs. | Suggested by Corvus florensis | #UCB_webform 1397/2499
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| ImageSize2=250 |
| ImageSize2=250 |
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| IUPACName=(''E'')-octadec-9-enoic acid |
| IUPACName=(''E'')-octadec-9-enoic acid |
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| SystematicName= |
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| OtherNames=(E)-9-Octadecenoic acid, |
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| 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 |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| StdInChIKey = ZQPPMHVWECSIRJ-MDZDMXLPSA-N |
| StdInChIKey = ZQPPMHVWECSIRJ-MDZDMXLPSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=112-79-8 |
| CASNo = 112-79-8 |
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| IUPHAR_ligand = |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 4837010H8C |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB04224 |
| DrugBank = DB04224 |
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|Section2={{Chembox Properties |
|Section2={{Chembox Properties |
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| Formula=C |
| Formula={{chem|C|18|H|34|O|2}} |
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| MolarMass=282.46 g/mol |
| MolarMass=282.46 g/mol |
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| Appearance= colorless waxy solid |
| Appearance= colorless waxy solid |
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| Density= 0.8734 g/cm<sup>3</sup> |
| Density= 0.8734 g/cm<sup>3</sup> |
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| MeltingPt={{convert|45|C|F}} |
| MeltingPt={{convert|45|C|F}} |
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| BoilingPt= |
| BoilingPt= |
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| Solubility= |
| Solubility= |
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'''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'''. |
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⚫ | 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> |
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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. |
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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. |
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Its name comes from the [[Ancient Greek]] word [[wikt:ἔλαιον|ἔλαιον]] (''elaion''), meaning oil. |
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==Occurrence and bioactivity== |
==Occurrence and bioactivity== |
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Elaidic acid occurs |
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> |
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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> |
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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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UNII | |
CompTox Dashboard (EPA) |
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Properties | |
C 18H 34O 2 | |
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 a chemical compound with the formula C
18H
34O
2, specifically the fatty acid with structural formula HOOC−(CH2)7−CH=CH−(CH2)7−CH3, with the double bond (between carbon atoms 9 and 10) in trans configuration. It is a colorless oily solid. Its salts and esters are called elaidates.
Elaidic acid is an unsaturated trans fatty acid, with code C18:1 trans-9. This compound has attracted attention because it is a major trans fat found in hydrogenated vegetable oils, and trans fats have been implicated in heart disease.[1]
It is the trans isomerofoleic acid. The name of the elaidinization reaction comes from elaidic acid.
Its name comes from the Ancient Greek word ἔλαιον (elaion), meaning oil.
Elaidic acid occurs mostly in industrial hydrogenation of polyunsaturated fatty acids.[2] It's also present in small amounts in caprine and bovine milk (very roughly 0.1% of the fatty acids)[3] and in some meats.[4]
Elaidic acid increases plasma cholesterylester transfer protein (CETP) activity which lowers HDL cholesterol.[5]