| Revision as of 13:34, 24 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validation|← Previous edit |
Latest revision as of 09:51, 13 October 2024 edit undo109.241.162.167 (talk) →Toxicity: stereodescriptors correction: the dihydroxy counterparts of 12,13-EpOME are (12R,13R) and (12S,13S) diHOME due to inversion during enzymic hydrolysis, +ref |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 391138095 |
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| verifiedrevid = 446486701 |
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| Name = Vernolic acid |
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| Name = Vernolic acid |
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| ImageFile = Vernolic Acid.png |
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| ImageFile = Vernolic Acid.png |
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| ImageCaption = (−)-(12''R'',13''S'')-EpOME |
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| ImageSize = 200px |
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| IUPACName = (+)-(12S,13R)-Epoxy-cis-9-octadecenoic acid |
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| PIN = (9''Z'')-(12''S'',13''R'')-12,13-epoxyoctadecenoic acid |
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| OtherNames = Linoleic acid 12:13-oxide |
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| OtherNames = |
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Racemic: |
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* Linoleic acid 12,13-oxide |
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* ''cis''-12-Epoxyoctadeca-''cis''-9-enoic acid |
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| Section1 = {{Chembox Identifiers |
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Single-enantiomer (corresponding to IUPAC-name isomer): |
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| SMILES = |
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* (+)-(12''S'',13''R'')-epoxy-''cis''-9-octadecenoic acid |
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| CASNo = 503-07-1 |
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* 12''S'',13''R''-EpOME |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|Section1={{Chembox Identifiers |
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| RTECS = |
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| CASNo = 503-07-1 |
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}} |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| Section2 = {{Chembox Properties |
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| CASNo_Comment = (+)-isomer |
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| C=18|H=32|O=3 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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| Appearance = Colorless oil |
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| Density = |
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| CASNo2 = 32381-42-3 |
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| CASNo2_Comment = (−)-isomer |
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| Solubility = Insoluble |
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| CASNo3_Ref = {{cascite|correct|CAS}} |
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| Solvent = other solvents |
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| CASNo3 = 17966-13-1 |
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| SolubleOther = organic solvents |
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| CASNo3_Comment = (racemate) |
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| MeltingPt = 23-25 °C |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| BoilingPt = |
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| pKa = |
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| UNII = FR42854EPW |
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| UNII_Comment = (+)-isomer |
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| Viscosity = |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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}} |
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| UNII2 = FF156V3318 |
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| Section3 = {{Chembox Structure |
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| UNII2_Comment = (−)-isomer |
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| MolShape = |
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| UNII3_Ref = {{fdacite|correct|FDA}} |
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| Dipole = |
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| UNII3 = 4S5JF40ZOQ |
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}} |
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| UNII3_Comment = (racemate) |
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| Section7 = {{Chembox Hazards |
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| ChEBI = 38300 |
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| MainHazards = flammable |
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| ChEBI_Comment = (−)-isomer |
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| RPhrases = |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SPhrases = |
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| ChEBI1 = 27706 |
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}} |
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| ChEBI1_Comment = (+)-isomer |
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| Section8 = {{Chembox Related |
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| ChEBI1_Ref = {{ebicite|correct|EBI}} |
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| Function = compounds |
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| PubChem = 5281128 |
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| OtherFunctn = |
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| PubChem_Comment = (−)-isomer |
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}} |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID = 4444572 |
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| ChemSpiderID_Comment = (−)-isomer |
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| SMILES = O=C(O)CCCCCCC/C=C\C1O1CCCCC |
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| SMILES_Comment = (−)-isomer |
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| 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 |
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| InChI_Comment = (−)-isomer |
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| InChIKey = CCPPLLJZDQAOHD-BEBBCNLGBK |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| 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 |
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| StdInChI_Comment = (−)-isomer |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = CCPPLLJZDQAOHD-BEBBCNLGSA-N |
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| PubChem1 = 6449780 |
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| PubChem1_Comment = (+)-isomer |
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| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID1 = 4952464 |
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| ChemSpiderID1_Comment = (+)-isomer |
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| SMILES1 = O=C(O)CCCCCCC/C=C\C1O1CCCCC |
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| SMILES1_Comment = (+)-isomer |
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| 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 |
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| InChI1_Comment = (+)-isomer |
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| InChIKey1 = CCPPLLJZDQAOHD-GJGKEFFFBZ |
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| 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 |
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| InChI3_Comment = (+)-isomer |
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| InChIKey3 = CCPPLLJZDQAOHD-GJGKEFFFSA-N |
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}} |
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|Section2={{Chembox Properties |
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| C=18 | H=32 | O=3 |
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| Appearance = Colorless oil |
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| Density = |
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| Solubility = Insoluble |
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| Solvent = other solvents |
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| SolubleOther = organic solvents |
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| MeltingPtC = 23 to 25 |
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| MeltingPt_notes = |
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| BoilingPt = |
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| pKa = |
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| Viscosity = |
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}} |
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|Section3={{Chembox Structure |
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| MolShape = |
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| Dipole = |
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}} |
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|Section7={{Chembox Hazards |
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| MainHazards = flammable |
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| HPhrases = |
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| PPhrases = |
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| GHS_ref = |
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}} |
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}} |
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|Section8={{Chembox Related |
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| OtherFunction_label = compounds |
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| OtherFunction = |
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}} |
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}} |
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'''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> or '''isoleukotoxin'''<ref name= Quaranta >{{cite journal |title=The octadecanoids: an emerging class of lipid mediators |vauthors=Quaranta A, Revol-Cavalier J, Wheelock CE |date=December 2022 |journal=Biochem Soc Trans |volume=50 |issue=6 |pages=1569–1582 |doi=10.1042/BST20210644 |pmc=9788390 |pmid=36454542}}</ref>) is a ] that is ] and contains an ]. It is a ''cis'' epoxide derived from the C12–C13 alkene of ].<ref name= Hildreth >{{cite journal |title=Cytochrome P450-derived Linoleic Acid Metabolites EpOMEs and DiHOMEs: A Review of Recent Studies |date=December 2020 |vauthors=Hildreth K, Kodani SD, Hammock BD, Zhao L |journal=The Journal of Nutritional Biochemistry |volume=86 |issue=article 108484 |doi=10.1016/j.jnutbio.2020.108484 |pmc=7606796 |pmid=32827665 }}</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> and its ] determined in 1966.<ref name= Morris>{{cite journal | title=Naturally occurring epoxy acids. IV. The absolute optical configuration of vernolic acid |date=January 1966 |last1=Morris |first1=L.J. |last2=Wharry |first2=D.M. |journal=Lipids |volume=1 |issue=1 |pages=41–46 |publisher=] |doi=10.1007/BF02668123 }}</ref> It is a major component in vernonia oil, which is produced in abundance by the genera '']'' and '']'' and is a potentially useful biofeedstock. |
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==Occurrence== |
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Vernonia oil is extracted from the seeds of the '']'' (ironweed), a plant native to eastern ]. 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. |
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Vernolic acid is not commonly found in plants in significant quantities, but some plants which do contain it are '']'', '']'', '']'' (from the ]), and '']'' and '']'' from the ].<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> |
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'''Vernolic acid''' is an ] and a ]. This monounsaturated long chain ] contains an ]. This isomer of coronaric acid was first definitively characterized in 1954.<ref>{{cite journal | author = Gunstone F. D. | year = 1954| title = Fatty acids. Part II. The nature of the oxygenated acid present in ''Vernonia anthelmintica'' (Willd.) seed oil | url = | journal = Journal of the Chemical Society | volume = 1954 | issue = | pages = 1611–1616 | doi = 10.1039/JR9540001611 }}</ref> It is the key component in vernonia oil, which is produced in abundance by the genuses Vernonia and Euphorbia and is a potentially useful biofeedstock. |
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==Potential applications== |
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==Vernonia oil== |
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Vernonia oil is extracted from the seeds of the '']'' (or ironweed), a plant native to eastern ]. 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. Products that can be made from vernonia oil include epoxies for manufacturing ]s, ]es and ]s, and industrial coatings. Its low ] recommends its use as a nonvolatile ] in ]s since it will become incorporated in the dry paint rather than evaporating into the air.''<ref>{{cite book |
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Vernonia oil has been proposed as a precursor to ]s, ]es and ]s, and industrial coatings. Its low ] recommends its use as a nonvolatile ] in ]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> |
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| url=http://www.hort.purdue.edu/newcrop/afcm/vernonia.html |
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| title=Alternative Field Crops Manual |
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| chapter=Vernonia |
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| author=T.M. Teynor ''et al.'' |
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| accessdate=2006-09-10 |
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}}</ref> |
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In its application as an ] 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 ] or ], which supply most of the market for these applications. Its low ] makes it more desirable than fully ] 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> |
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This use of vernonia oil offers potential ] benefits, since its use could reduce emissions associated with man-made chemicals. |
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==Toxicity== |
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In its application as an ] oil,<ref>{{cite journal |
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In a variety of mammalian species, vernolic acid is made by the metabolism of ] by ] ] enzymes; under these circumstances it is termed leukotoxin because of its toxic effects on ] and other cell types and of its ability to produce multiple organ failure and respiratory distress when injected into rodent animal models of the ].<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><ref name= Edwards >{{cite journal | pmid = 22715155 | pmc = 3413237 | year = 2012 | last1 = Edwards | first1 = L. M. | title = Metabolomics reveals increased isoleukotoxin diol (12,13-DHOME) in human plasma after acute Intralipid infusion | journal = The Journal of Lipid Research | volume = 53 | issue = 9 | pages = 1979–86 | last2 = Lawler | first2 = N. G. | last3 = Nikolic | first3 = S. B. | last4 = Peters | first4 = J. M. | last5 = Horne | first5 = J | last6 = Wilson | first6 = R | last7 = Davies | first7 = N. W. | last8 = Sharman | first8 = J. E. | doi = 10.1194/jlr.P027706 |doi-access=free }}</ref> These effects appear due to the conversion of vernolic acid to its dihydroxy counterparts. For instance, (12''S'',13''R'')-EpOME is converted by ] (sEH) to (12''R'',13''R'')-dihydroxy-9''Z''-octadecenoic acid due to inversion at C12 carbon atom during hydrolysis. A mixture of this dihydroxy acid with its 12''S'',13''S'' enantiomer has been termed isoleukotoxin 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" /><ref name= Moghaddam >{{cite journal |title=Bioactivation of leukotoxins to their toxic diols by epoxide hydrolase |vauthors=Moghaddam MF, Grant DF, Cheek JM, Greene JF, Williamson KC, Hammock BD |date=May 1997 |journal=Nature Medicine |volume=3 |number=5 |publisher=Nature Publishing Group |pages=562–566 |doi=10.1038/nm0597-562 |pmc=7095900 |pmid=9142128 }}</ref>{{rp|at=Fig. 1|q=threo means ''R'',''R'' and/or ''S'',''S'' enantiomers}} 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 {{slink|Epoxygenase|Linoleic acid}}). |
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| url=http://www.hort.purdue.edu/newcrop/proceedings1999/v4-272.html |
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| author=A.I Mohamed, T. Mebrahtu, and T. Andebrhan |
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| year=1999 |
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| title=Variability in oil and vernolic acid contents in the new Vernonia galamensis collection from East Africa |
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| pages=272–274 |
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| editor=J. Janick |
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| journal=Perspectives on new crops and new uses |
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| accessdate=2006-09-10 |
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}}</ref> vernonia oil competes with ] or ], which supply most of the market for these applications. Its low ] makes it more desirable than fully ] linseed or soybean oils. It is more comparable to partially epoxidized linseed or soybean oil.<ref>{{cite journal | last1 = Muturi | first1 = Patrick | last2 = Wang | first2 = Danqing | last3 = Dirlikov | first3 = Stoil | 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 | year = 1994 | doi = 10.1016/0300-9440(94)00504-4 }}</ref> |
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==Related compounds== |
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==Other plant sources== |
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* ], C9-C10 epoxide of linoleic acid. |
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Vernolic acid is not commonly found in plants in significant quantities, but some plants which do contain it are '']'', '']'', '']'' (from the ]), and ''] ]'' and ''] ]'' from the ].<ref>{{Cite journal | journal = Plant Physiol. | year = 2002 | month = February | volume = 128 | issue = 2 | pages = 615–624 | doi = 10.1104/pp.010768 | pmc = 148923 | title = Transgenic Production of Epoxy Fatty Acids by Expression of a Cytochrome P450 Enzyme from Euphorbia lagascae Seed | author = Edgar B. Cahoon, Kevin G. Ripp, Sarah E. Hall, and Brian McGonigle | pmid = 11842164 }}</ref> |
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==References== |
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== References == |
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{{reflist}} |
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