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Vernolic acid information


Vernolic acid
Names
Preferred IUPAC name
(9Z)-(12S,13R)-12,13-epoxyoctadecenoic acid
Other names
Racemic:
  • Linoleic acid 12:13-oxide
  • cis-12-Epoxyoctadeca-cis-9-enoic acid

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

  • (+)-(12S,13R)-epoxy-cis-9-octadecenoic acid
  • 12S,13R-EpOME
Identifiers
CAS Number
  • 503-07-1 (+)-isomer checkY
  • 32381-42-3 (−)-isomer checkY
  • 17966-13-1 (racemate) checkY
3D model (JSmol)
  • (−)-isomer: Interactive image
  • (+)-isomer: Interactive image
ChemSpider
  • 4444572 (−)-isomer ☒N
  • 4952464 (+)-isomer ☒N
PubChem CID
  • 5281128 (−)-isomer
  • 6449780 (+)-isomer
UNII
  • FR42854EPW (+)-isomer checkY
  • FF156V3318 (−)-isomer checkY
  • 4S5JF40ZOQ (racemate) checkY
CompTox Dashboard (EPA)
  • DTXSID001205124 Edit this at Wikidata
InChI
  • InChI=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 ☒N
    Key: CCPPLLJZDQAOHD-BEBBCNLGSA-N ☒N
  • (−)-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
    Key: CCPPLLJZDQAOHD-BEBBCNLGBK
  • (+)-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+/m1/s1
    Key: CCPPLLJZDQAOHD-GJGKEFFFBZ
  • (+)-isomer: InChI=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
    Key: CCPPLLJZDQAOHD-GJGKEFFFSA-N
SMILES
  • (−)-isomer: O=C(O)CCCCCCC/C=C\C[C@H]1O[C@H]1CCCCC
  • (+)-isomer: O=C(O)CCCCCCC/C=C\C[C@@H]1O[C@@H]1CCCCC
Properties
Chemical formula
C18H32O3
Molar mass 296.451 g·mol−1
Appearance Colorless oil
Melting point 23 to 25 °C (73 to 77 °F; 296 to 298 K)
Solubility in water
Insoluble
Solubility in other solvents organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
flammable
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Vernolic acid (leukotoxin B[1]) 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.[2] Vernolic acid was first definitively characterized in 1954.[3] 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.

  1. ^ National Center for Biotechnology Information. "PubChem Compound Summary for CID 6449780, Vernolic acid". PubChem. Retrieved 29 May 2023.
  2. ^ Metzger, J. O.; Bornscheuer, U. (2006). "Lipids as renewable resources: current state of chemical and biotechnological conversion and diversification". Applied Microbiology and Biotechnology. 71 (1): 13–22. doi:10.1007/s00253-006-0335-4. PMID 16604360. S2CID 28601501.
  3. ^ Gunstone FD (1954). "Fatty acids. Part II. The nature of the oxygenated acid present in Vernonia anthelmintica (Willd.) seed oil". Journal of the Chemical Society. 1954: 1611–1616. doi:10.1039/JR9540001611.

and 22 Related for: Vernolic acid information

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Vernolic acid

Last Update:

Vernolic acid (leukotoxin B) 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...

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Linoleic acid

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epoxide products viz., its 12,13-epoxide, vernolic acid, and its 9,10-epoxide, coronaric acid. These linoleic acid products are implicated in human physiology...

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Vernonia

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of Vernonia have the highest oil content, up to 41.9% with up to 80% vernolic acid, and is used in paint formulations, coatings plasticizers, and as a...

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Stokesia laevis

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a few other plants (such as some species of Vernonia), it contains vernolic acid, a vegetable oil with commercial applications. The genus is named after...

Word Count : 227

Coronaric acid

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acids. This (+) and (-) optical mixture is often termed vernolic acid when studied in plants and leukotoxin when studied in mammals. Coronaric acid is...

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Alchornea cordifolia

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acid, and ellagic acid (alizarine yellow). A C20 homolog of vernolic acid named alchornoic acid can be found in the seed oil. The plant is cultivated for...

Word Count : 254

CYP2C19

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epoxyeicosatrienoic acids (also termed EETs); linoleic acid to 9,10-epoxy octadecenoic acids (also termed vernolic acid, linoleic acid 9:10-oxide, or leukotoxin)...

Word Count : 3879

Epoxide hydrolase

Last Update:

sEH also metabolizes the epoxides of linoleic acid viz., Vernolic acid (leukotoxins) and Coronaric acids (isoleukotoxins) to their corresponding diols...

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Sesquiterpene lactone

Last Update:

3-oxo-5αH,8βH-eudesma-1,4(15),7(11)-trien-8,12-olide, can work with vernolic acid and other compounds in plants to reduce inflammation. Some plants containing...

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C18H32O3

Last Update:

refer to: Coronaric acid, or isoleukotoxin 9-Hydroxyoctadecadienoic acid 13-Hydroxyoctadecadienoic acid (13-HODE) Vernolic acid (leukotoxin) This set...

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CYP2C9

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fatty acids metabolites caused by dietary omega-3 fatty acids. CYP2C9 may also metabolize linoleic acid to the potentially very toxic products, vernolic acid...

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Epoxygenase

Last Update:

and 12R,13S-epoxy-9(Z)-octadecenoic acids; this set of optical isomers is also termed vernolic acid, linoleic acid 12:13-oxide, and leukotoxin. CYPC2C9...

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List of vegetable oils

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from the seeds of the Vernonia galamensis. It is composed of 73–80% vernolic acid, which can be used to make epoxies for manufacturing adhesives, varnishes...

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Vernonia galamensis

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source of vernonia oil, which is rich in a useful epoxy fatty acid called vernolic acid and is used to make plastics, rubbery coatings, and drying agents...

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Insect pheromones

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12-Hexadecadien-1-ol. Butenandt then synthesized bombycol from vernolic acid [(12R,13S)-Epoxy-9-cis-octadecenoic acid] in several steps via diol formation, its cleavage...

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Epoxide hydrolase 3

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epoxyeicosatrienoic acids. In its hydrolysis one isomer of vernolic acid (12S,13R-epoxy-cis-9-octadecenoic acid) 12S,13R-epoxy-cis-9-octadecenoic acid + H2O → 12S...

Word Count : 1141

CYP2C8

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epoxyeicosatrienoic acids (also termed EETs); 2) linoleic acid to 9,10-epoxy octadecenoic acids (also termed vernolic acid, linoleic acid 9:10-oxide, or leukotoxin)...

Word Count : 1464

Epoxyeicosatetraenoic acid

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9,10-epoxide isomers termed vernolic acids or leukotoxins and two different 12,13-epoxides isomers termed coronaric acids or isoleukotoxins. They metabolize...

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Bothriocline longipes

Last Update:

"Glyceride structure ofErlangea tomentosa seed oil, a new source of vernolic acid". Lipids. 4 (6): 473–477. doi:10.1007/BF02531027. ISSN 0024-4201. PMID 5367929...

Word Count : 353

CYP2C18

Last Update:

epoxyeicosatrienoic acids (also termed EETs); 2) linoleic acid to 9,10-epoxy octadecenoic acids (also termed vernolic acid, linoleic acid 9:10-oxide, or leukotoxin)...

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CYP2J2

Last Update:

CYP2J2 also metabolizes linoleic acid to 9,10-epoxy octadecenoic acids (also termed vernolic acid, linoleic acid 9:10-oxide, or leukotoxin) and 12...

Word Count : 1896

CYP2S1

Last Update:

epoxydocosapentaenoic acids (also termed EDPs); and 3) linoleic acid to its various epoxides, i.e. vernolic acid (also termed leukotoxin) and coronaric acid (also termed...

Word Count : 1322

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