Jasmonic Acid

HCID 5281166CAS 59366-47-1

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Grundinformationen

Standard-SMILES: CC/C=C\C[C@H]1C(=O)CC[C@@H]1CC(=O)O
InChIKey: ZNJFBWYDHIGLCU-HWKXXFMVSA-N
Summenformel: C12H18O3
Durchschnittliche Molmasse: 210,27 g/mol
Monoisotopische Masse: 210,12559444

Überblick

Jasmonic acid is an oxo monocarboxylic acid. It has a role as a member of jasmonates and a plant metabolite. It is a conjugate acid of a jasmonate(1-). It is an enantiomer of a (+)-jasmonic acid.

Namen und Bezeichner

Bevorzugter Name: Jasmonic Acid
IUPAC: 2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetic acid
Englischer Name: (-)-Jasmonic acid
Summenformel: C12H18O3
Molmasse: 210.27

Namen und Synonyme

Jasmonic acid6894-38-83-Oxo-2-(2-pentenyl)cyclopentaneacetic acid2-[(1R,2R)-3-oxo-2-[(Z)-pent-2-enyl]cyclopentyl]acetic acid6RI5N05OWW(1R,2R)-3-oxo-2-(pent-2Z-enyl)-cyclopentaneacetic acidDTXSID4037665CHEBI:182922-((1R,2R)-3-oxo-2-((Z)-pent-2-enyl)cyclopentyl)acetic acidRefChem:150366DTXCID2017665(-)-Jasmonic acid

Weitere Namen anzeigen

JAjasmonicaciJA6894-38-8 C12H18O3 (-)-JASMONIC ACID(+-)-jasmonic acid plant cell*culture tested(Z)-2-(2-(But-2-en-1-yl)-4-oxocyclopentyl)-acetic acid(1R)-2β-[(Z)-2-Pentenyl]-3-oxocyclopentane-1α-acetic acid(1R,2R)-2-[(Z)-2-Pentenyl]-3-oxocyclopentane-1-acetic acid

Jasmonate(+/-)-Jasmonic acid77026-92-7trans-Jasmonic Acid (1 g/ 10 mL Ethanol){(1R,2R)-3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetic acidCHEMBL449572( inverted exclamation markA)-Jasmonic acidCyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, (1R,2R)-

Datenbank-Bezeichner

CAS: 59366-47-1、6894-38-8
PubChem CID: 5281166
DTXSID: DTXSID4037665
ChEMBL: CHEMBL2139332、CHEMBL449572
ChEBI: CHEBI:18292
UNII: 6RI5N05OWW
Nikkaji: J15.678G

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 1,6
Polarare Oberfläche (TPSA): 54,4 Å²
H-Brücken-Donoren: 1
H-Brücken-Akzeptoren: 3
Frei drehbare Bindungen: 5
Schwere Atome: 15
Formalladung: 0
Komplexität: 268

Experimentelle und physikochemische Eigenschaften

Chemical ClassesBiological Agents -> Plant Oils and Extracts

LipidsFatty Acyls [FA] -> Octadecanoids [FA02] -> Jasmonic acids [FA0202]

Pesticides · 2 Einträge

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Physical DescriptionColorless liquid; [Merck Index]

Physikochemische Eigenschaften

Siedepunkt: 160 °C · 160 °C(Press: 0.7 Torr)
Dichte: 1.061 · 1.061±0.06 g/cm3(Predicted)
Brechungsindex: 23 · nD23 1.486
storage temp.: 2 · 2-8°C
Löslichkeit: Benzene (Slightly), Chloroform (Slightly), Methanol (Slightly)
Aggregatzustand: liquid
pka: 4.52 · 4.52±0.10(Predicted)
Farbe: Clear Colourless

Sicherheit und Regulatorisches

Gefahrenhinweise

Regulatory Information · 2 Einträge

2007/442

Cyclopentaneacetic acid, 3-oxo-2-(2Z)-2-pentenyl-, (1R,2R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazards SummaryMay cause irritation; [Sigma-Aldrich MSDS] See Methyl jasmonate.

Sicherheitsdaten

wgk: 3

Chemie und Industrie

Pharmakologische Informationen

MeSH Pharmacological ClassificationAny of the hormones produced naturally in plants and active in controlling growth and other functions. There are three primary classes: auxins, cytokinins, and gibberellins.

Cellular LocationsCytoplasm

Verwendung und Herstellung

UsesA natural plant growth inhibitor; [Merck Index]

Anwendungen · 1 Eintrag

VerwendenJasmonic acid (JA) is an important hormonelike signaling molecule that is apparently distributed throughout the plant kingdom. It functions as an intermediate in defense response pathways against both pathogens and insects. JA is derived from the oxygenation of the octadecanoid α-linolenic acid by the enzyme lipoxygenase. The synthetic pathway includes a cyclization step yielding a cyclopentanone that has overall structural similarity with the prostaglandin class of animal hormones. Several but not all of the enzymes for JA biosynthesis are located in the chloroplast (1).