Vernolic acid: Difference between revisions

| Verifiedfields = changed

| verifiedrevid = 446486701

| Name = Vernolic acid

| ImageFile = Vernolic Acid.png

| ImageSize =

| PIN = (9''Z'')-(12''S'',13''R'')-12,13-epoxyoctadecenoic acid

| OtherNames =

* Linoleic acid 12:13-oxide

* ''cis''-12-Epoxyoctadeca-''cis''-9-enoic acid

Single-enantiomer (corresponding to IUPAC-name isomer):

* (+)-(12''S'',13''R'')-epoxy-''cis''-9-octadecenoic acid

* 12''S'',13''R''-EpOME

|Section1={{Chembox Identifiers

| CASNo = 503-07-1

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo_Comment = (+)-isomer

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo2 = 32381-42-3

| CASNo2_Comment = (−)-isomer

| CASNo3_Ref = {{cascite|correct|CAS}}

| CASNo3 = 17966-13-1

| CASNo3_Comment = (racemate)

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = FR42854EPW

| UNII_Comment = (+)-isomer

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII2 = FF156V3318

| UNII2_Comment = (−)-isomer

| UNII3_Ref = {{fdacite|correct|FDA}}

| UNII3 = 4S5JF40ZOQ

| UNII3_Comment = (racemate)

| RTECS =

| PubChem = 5281128

| PubChem_Comment = (−)-isomer

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444572

| ChemSpiderID_Comment = (−)-isomer

| SMILES = O=C(O)CCCCCCC/C=C\C[C@H]1O[C@H]1CCCCC

| SMILES_Comment = (−)-isomer

| InChI = 1/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m0/s1

| InChI_Comment = (−)-isomer

| InChIKey = CCPPLLJZDQAOHD-BEBBCNLGBK

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m0/s1

| StdInChI_Comment = (−)-isomer

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = CCPPLLJZDQAOHD-BEBBCNLGSA-N

| PubChem1 = 6449780

| PubChem1_Comment = (+)-isomer

| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID1 = 4952464

| ChemSpiderID1_Comment = (+)-isomer

| SMILES1 = O=C(O)CCCCCCC/C=C\C[C@@H]1O[C@@H]1CCCCC

| SMILES1_Comment = (+)-isomer

| InChI1 = 1/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1

| InChI1_Comment = (+)-isomer

| InChIKey1 = CCPPLLJZDQAOHD-GJGKEFFFBZ

| InChI3 = 1S/C18H32O3/c1-2-3-10-13-16-17(21-16)14-11-8-6-4-5-7-9-12-15-18(19)20/h8,11,16-17H,2-7,9-10,12-15H2,1H3,(H,19,20)/b11-8-/t16-,17+/m1/s1

| InChI3_Comment = (+)-isomer

| InChIKey3 = CCPPLLJZDQAOHD-GJGKEFFFSA-N

}}

|Section2={{Chembox Properties

| C=18 | H=32 | O=3

| Appearance = Colorless oil

| Density =

| Solubility = Insoluble

| Solvent = other solvents

| SolubleOther = organic solvents

| MeltingPtC = 23 to 25

| MeltingPt_notes =

| BoilingPt =

| pKa =

| Viscosity =

}}

|Section3={{Chembox Structure

| MolShape =

| Dipole =

}}

|Section7={{Chembox Hazards

| MainHazards = flammable

| HPhrases =

| PPhrases =

| GHS_ref =

|Section8={{Chembox Related

| OtherFunction_label = compounds

| OtherFunction =

}}

}}

'''Vernolic acid''' ('''leukotoxin B'''<ref>{{cite web|title=PubChem Compound Summary for CID 6449780, Vernolic acid|url=https://pubchem.ncbi.nlm.nih.gov/compound/Vernolic-acid|website=PubChem|author=National Center for Biotechnology Information|access-date=29 May 2023}}</ref>) is a [[long chain fatty acid]] that is [[monounsaturated]] and contains an [[epoxide]]. It is the R,R-''cis'' epoxide derived from the C12–C13 alkene of [[linoleic acid]].<ref>{{cite journal |title=Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification|last1=Metzger|first1=J. O.|last2=Bornscheuer|first2=U.|journal=Applied Microbiology and Biotechnology|year=2006|volume=71|issue=1|pages=13–22|doi=10.1007/s00253-006-0335-4|pmid=16604360|s2cid=28601501}}</ref> Vernolic acid was first definitively characterized in 1954.<ref>{{cite journal | vauthors = Gunstone FD | year = 1954| title = Fatty acids. Part II. The nature of the oxygenated acid present in ''Vernonia anthelmintica'' (Willd.) seed oil | journal = Journal of the Chemical Society | volume = 1954 | pages = 1611–1616 | doi = 10.1039/JR9540001611 }}</ref> It is a major component in vernonia oil, which is produced in abundance by the genera ''[[Vernonia]]'' and ''[[Euphorbia]]'' and is a potentially useful biofeedstock.

==Occurrence==

Vernonia oil is extracted from the seeds of the ''[[Vernonia galamensis]]'' (ironweed), a plant native to eastern [[Africa]]. The seeds contain about 40 to 42% oil of which 73 to 80% is vernolic acid. The best varieties of ''V. anthelmintica'' contain about 30% less vernolic acid.

Vernolic acid is not commonly found in plants in significant quantities, but some plants which do contain it are ''[[Vernonia]]'', ''[[Stokesia (plant)|Stokesia]]'', ''[[Crepis]]'' (from the [[Asteraceae|daisy family]]), and ''[[Euphorbia lagascae]]'' and ''[[Bernardia pulchella]]'' from the [[Euphorbiaceae]].<ref>{{cite journal | vauthors = Cahoon EB, Ripp KG, Hall SE, McGonigle B | title = Transgenic production of epoxy fatty acids by expression of a cytochrome P450 enzyme from Euphorbia lagascae seed | journal = Plant Physiology | volume = 128 | issue = 2 | pages = 615–24 | date = February 2002 | pmid = 11842164 | pmc = 148923 | doi = 10.1104/pp.010768 }}</ref>

==Potential applications==

Vernonia oil has been proposed as a precursor to [[adhesive]]s, [[varnish]]es and [[paint]]s, and industrial coatings. Its low [[viscosity]] recommends its use as a nonvolatile [[solvent]] in [[oil-based paint]]s since it will become incorporated in the dry paint rather than evaporating into the air.''<ref>{{cite book | url = http://www.hort.purdue.edu/newcrop/afcm/vernonia.html | title = Alternative Field Crops Manual | chapter = Vernonia | vauthors = Teynor TM, Putnam DJ, Oplinger ES, Oelke EA, Kelling KA, Doll JD | access-date = 2006-09-10 | date = February 1992 }}</ref>

In its application as an [[epoxy]] oil,<ref>{{cite journal | url = http://www.hort.purdue.edu/newcrop/proceedings1999/v4-272.html | vauthors = Mohamed AI, Mebrahtu T, Andebrhan T | year = 1999 | title = Variability in oil and vernolic acid contents in the new Vernonia galamensis collection from East Africa | pages = 272–274 | veditors = Janick J | journal = Perspectives on New Crops and New Uses | access-date = 2006-09-10 }}</ref> vernonia oil competes with [[soybean oil|soybean]] or [[linseed oil]], which supply most of the market for these applications. Its low [[viscosity]] makes it more desirable than fully [[epoxidation|epoxidized]] linseed or soybean oils. It is comparable to partially epoxidized linseed or soybean oil.<ref>{{cite journal | last1 = Muturi | first1 = Patrick | last2 = Wang | first2 = Danqing | last3 = Dirlikov | first3 = Stoil | name-list-style = vanc | title = Epoxidized vegetable oils as reactive diluents I. Comparison of vernonia, epoxidized soybean and epoxidized linseed oils | journal = Progress in Organic Coatings | volume = 25 | pages = 85–94 | year = 1994 | doi = 10.1016/0300-9440(94)00504-4 }}</ref>

==Toxicity==

In a variety of mammalian species, vernolic acid is made by the metabolism of [[linoleic acid]] by [[cytochrome P450]] [[epoxygenase]] enzymes; under these circumstances it is termed leukotoxin because of its toxic effects on [[leukocytes]] and other cell types and of its ability to produce multiple organ failure and respiratory distress when injected into rodent animal models of the [[acute respiratory distress syndrome]].<ref>{{cite journal | vauthors = Linhartová I, Bumba L, Mašín J, Basler M, Osička R, Kamanová J, Procházková K, Adkins I, Hejnová-Holubová J, Sadílková L, Morová J, Sebo P | title = RTX proteins: a highly diverse family secreted by a common mechanism | journal = FEMS Microbiology Reviews | volume = 34 | issue = 6 | pages = 1076–112 | date = November 2010 | pmid = 20528947 | pmc = 3034196 | doi = 10.1111/j.1574-6976.2010.00231.x }}</ref><ref name = "Spector_2015">{{cite journal | vauthors = Spector AA, Kim HY | title = Cytochrome P450 epoxygenase pathway of polyunsaturated fatty acid metabolism | journal = Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids | volume = 1851 | issue = 4 | pages = 356–65 | date = April 2015 | pmid = 25093613 | pmc = 4314516 | doi = 10.1016/j.bbalip.2014.07.020 }}</ref> These effects appear due to the conversion of vernolic acid to its dihydroxy counterparts, 12''S'',13''R''- and 12''R'',13''S''-dihydroxy-''cis''-9-octadecenoic acids by [[soluble epoxide hydrolase]] (this dihydroxy mixture has been termed leukotoxin diol).<ref>{{cite journal | vauthors = Greene JF, Newman JW, Williamson KC, Hammock BD | title = Toxicity of epoxy fatty acids and related compounds to cells expressing human soluble epoxide hydrolase | journal = Chemical Research in Toxicology | volume = 13 | issue = 4 | pages = 217–26 | date = April 2000 | pmid = 10775319 | doi = 10.1021/tx990162c }}</ref><ref name = "Spector_2015" /> Some studies suggest but have not yet proven that vernolic acid is responsible for or contributes to multiple organ failure, respiratory distress, and certain other cataclysmic diseases in humans (see [[epoxygenase]] subsection on linoleic acid).

==Related compounds==

* [[coronaric acid]], C9-C10 epoxide of linoleic acid.

== References ==

{{reflist|33em}}

[[Category:Alkenoic acids]]