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Vernolic acid

HCID 5356421
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Grundinformationen

Standard-SMILES
CCCCCC1OC1C/C=C\CCCCCCCC(=O)O
InChIKey
CCPPLLJZDQAOHD-FLIBITNWSA-N
Summenformel
C18H32O3
Durchschnittliche Molmasse
296,4 g/mol
Monoisotopische Masse
296,23514488

Überblick

Vernolic acid is a monounsaturated epoxy fatty acid composed of cis-9-octadecenoic acid having a 12,13-epoxy group. It has a role as a plant metabolite. It is a long-chain fatty acid, a monounsaturated fatty acid, an epoxy fatty acid and an epoxyoctadecenoic acid. It is functionally related to an octadec-9-enoic acid. It is a conjugate acid of a vernolate.

Namen und Bezeichner

Bevorzugter Name
Vernolic acid
IUPAC
(Z)-11-(3-pentyloxiran-2-yl)undec-9-enoic acid

Namen und Synonyme

Vernolic acid(Z)-11-(3-pentyloxiran-2-yl)undec-9-enoic acid(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoic acid(9Z)-12,13-epoxyoctadecenoic acidCHEBI:3829912,13-cis-epoxyoctadecenoic acid503-07-1cis-12,13-epoxy-9-octadecenoic acidRefChem:933984cis-12-Epoxyoctadeca-cis-9-enoic acid12(13)-EpOMEisoleukotoxin
Weitere Namen anzeigen
(+/-)-12(13)-epoxy-9Z-octadecenoic acid12,13-epoxy-9(Z)-octadecenoic acidLEUKOTOXIN B (12,13-EODE)VernolsaeureVernolsaeuren(9Z)-11-(3-pentyloxiran-2-yl)undec-9-enoateNSC56858acide vernolique

Datenbank-Bezeichner

PubChem CID
5356421
DTXSID
DTXSID301017265
ChEMBL
CHEMBL2447889
ChEBI
CHEBI:38299
Nikkaji
J374.560K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
5,6
Polarare Oberfläche (TPSA)
49,8 Ų
H-Brücken-Donoren
1
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
14
Schwere Atome
21
Formalladung
0
Komplexität
299

Experimentelle und physikochemische Eigenschaften

LipidsFatty Acyls [FA] -> Octadecanoids [FA02] -> Other Octadecanoids [FA0200]
Physical DescriptionSolid
Collision Cross Section178.7 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Calculation: Single Field; Dataset: Oxylipins]

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Toxikologische Informationen

Treatment · 1 Eintrag

Treatment of carbamate poisoning is similar to that of organophosphate poisoning in that atropine sulfate injections readily reverse the effects. For acute exposures and first aid: EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1 Eintrag

Data concerning the effects of thiocarbamates on man are scarce. However, cases of irritation and sensitization have been observed among agricultural workers. Some thiocarbamates, e.g., molinate, have an effect on sperm morphology and, consequently, on reproduction. However, no teratogenic effects have been observed. The results of mutagenicity studies have shown that thiocarbamates containing dichloroallyl groups are highly mutagenic. Some thiocarbamates are acetylcholine esterase inhibitors. Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved.

Exposure RoutesInhalation (L793) ; oral (L793); dermal (L793)
Toxicity Summary · 1 Eintrag

Some thiocarbamates (EPTC, Molinate, Pebulate, and Cycloate) share a common mechanism of toxicity, i.e. the inhibition of acetylcholinesterase. An acetylcholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 2 Einträge

Isoleukotoxin is a known human metabolite of Linoleic acid.

As a general rule, thiocarbamates can be absorbed via the skin, mucous membranes, and the respiratory and gastrointestinal tracts. They are eliminated quite rapidly, mainly via expired air and urine. Two major pathways exist for the metabolism of thiocarbamates in mammals. One is via sulfoxidation and conjugation with glutathione. The conjugation product is then cleaved to a cysteine derivative, which is metabolized to a mercapturic acid compound. The second route is oxidation of the sulfur to a sulfoxide, which is then oxidized to a sulfone, or hydroxylation to compounds that enter the carbon metabolic pool.

Cellular LocationsExtracellular

Verwendung und Herstellung

UsesThiocarbamates are widely used throughout the world and are produced in great quantities, mainly as herbicides and fungicides.

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Signs and Symptoms · 1 Eintrag

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).