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Jasmonic acid information


Jasmonic acid
Jasmonic acid
Ball-and-stick model of jasmonic acid
Names
Preferred IUPAC name
{(1R,2R)-3-Oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetic acid
Other names
Jasmonic acid
(−)-Jasmonic acid
JA
(1R,2R)-3-Oxo-2-(2Z)-2-pentenylcyclopentylethanoic acid
{(1R,2R)-3-Oxo-2-[(2Z)-2-penten-1-yl]cyclopentyl}acetic acid
Identifiers
CAS Number
  • 6894-38-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18292 ☒N
ChemSpider
  • 4444606 ☒N
PubChem CID
  • 5281166
UNII
  • 6RI5N05OWW checkY
CompTox Dashboard (EPA)
  • DTXSID4037665 Edit this at Wikidata
InChI
  • InChI=1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1 ☒N
    Key: ZNJFBWYDHIGLCU-HWKXXFMVSA-N ☒N
  • InChI=1/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
    Key: ZNJFBWYDHIGLCU-HWKXXFMVBZ
SMILES
  • CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)O
Properties
Chemical formula
C12H18O3
Molar mass 210.27 g/mol
Density 1.1 g/cm3
Boiling point 160 °C (320 °F; 433 K) at 0.7 mmHg
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

Jasmonic acid (JA) is an organic compound found in several plants including jasmine. The molecule is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway. It was first isolated in 1957 as the methyl ester of jasmonic acid by the Swiss chemist Édouard Demole and his colleagues.[1]

  1. ^ Demole, E.; Lederer, E.; Mercier, D. (1962). "Isolement et determination de la structure du jasmonate de methyle, constituent odorant characteristique de l'essence de jasmin" [Isolation and determination of the structure of methyl jasmonate, the aromatic constituent characteristic of jasmine essential oil]. Helvetica Chimica Acta (in French). 45 (2): 675–685. doi:10.1002/hlca.19620450233.
    • Chapuis, Christian (December 2011). "The chemistry and creative legacy of methyl jasmonate and hedione". Perfumer & Flavorist. 36: 36–48.

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Jasmonic acid

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Jasmonic acid (JA) is an organic compound found in several plants including jasmine. The molecule is a member of the jasmonate class of plant hormones...

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Jasmonate

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12-oxo-phytodienoic acid (OPDA), which then undergoes a reduction and three rounds of oxidation to form (+)-7-iso-JA, jasmonic acid. Only the conversion...

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Plant hormone

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and necrotrophic pathogens. The most active JA in plants is jasmonic acid. Jasmonic acid can be further metabolized into methyl jasmonate (MeJA), which...

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Wound response in plants

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others are systemic, which involve a variety of hormones like jasmonic acid and abscisic acid. There are many forms of defense that plants use to respond...

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Rhizome

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for replanting and greater yields. The plant hormones ethylene and jasmonic acid have been found to help induce and regulate the growth of rhizomes,...

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Lima bean

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hosts. The main induced defense of the lima bean is the Jasmonic acid pathway. Jasmonic acid induces production of extrafloral nectar flow or induces...

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Biotic stress

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activated. These genes when activated, play a role in the jasmonic acid pathway. The jasmonic acid pathway is also referred to as the Octadecanoid pathway...

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Octadecanoid pathway

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the phytohormone jasmonic acid (JA), an important hormone for induction of defense genes. JA is synthesized from alpha-linolenic acid, which can be released...

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Brassinolide

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provides a decrease in BZR1 binding affinity to DNA. Brassinolide inhibits jasmonic acid (JA) induced pathogen defensive for an ideal trade-off between growth...

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Methyl jasmonate

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from jasmonic acid and the reaction is catalyzed by S-adenosyl-L-methionine:jasmonic acid carboxyl methyltransferase. Plants produce jasmonic acid and...

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Coronatine

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salicylic acid after the infection has begun. It consists of coronafacic acid (CFA), which is an analog of methyl jasmonic acid (MeJA), and coronamic acid (CMA)...

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Jasmone

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Lavoslav Ružička. Jasmone is produced by some plants by the metabolism of jasmonic acid, via a decarboxylation. It can act as either an attractant or a repellent...

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Innate immune system

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involves the production of chemical messengers, such as salicylic acid or jasmonic acid. Some of these travel through the plant and signal other cells to...

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Cytochrome P450

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Cytochromes P450 are largely responsible for the synthesis of the jasmonic acid (JA), a common hormonal defenses against abiotic and biotic stresses...

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Soil microbiology

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hormones, salicylic acid, jasmonic acid and ethylene are key regulators of innate immunity in plant leaves. Mutants impaired in salicylic acid synthesis and...

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Plant senescence

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influenced by plant hormones. The hormones abscisic acid, ethylene, jasmonic acid and salicylic acid are accepted by most scientists as promoters of senescence...

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Jasmolone

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then a decarboxylation. 12-Oxophytodienoic acid is also used in the production of jasmonic acid. Jasmonic acid is used in the production of secondary metabolites...

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JA

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Carabidae Chrysler JA platform, a series of vehicles made by Chrysler Jasmonic acid, a plant hormone British Rail Class 73/0 electro-diesel locomotives...

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Alternaria alternata

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AAL. Salicylic acid promotes resistance to AAL and antagonizes the ethylene response. Ethylene controls the synthesis of jasmonic acid, which is a necessary...

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Venus flytrap

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occurs. Release of the digestive enzymes is controlled by the hormone jasmonic acid, the same hormone that triggers the release of toxins as an anti-herbivore...

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Ripening

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process in non-climacteric fruits. This class of hormones includes jasmonic acid and methyl jasmonate. Studies showed that the expression of genes involved...

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Systemin

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acquired resistance, now it is thought that it increases the production of jasmonic acid causing the same result. The main function of systemins is to coordinate...

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Magnaporthe grisea

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plants. The rice plant responds to the blast pathogen by releasing jasmonic acid, which cascades into the activation of further downstream metabolic...

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Solanum quitoense

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Cristina; Ochoa, José; Proaño, Karina; Martínez, M. Carmen (April 2019). "Jasmonic acid and nitric oxide protects naranjilla (Solanum quitoense) against infection...

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Nicotiana attenuata

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herbivory-induced plant volatiles (HIPVs) that N. attenuata emits via jasmonic acid signaling. When GLVs come into contact with saliva from the hornworm...

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Phospholipid

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prostaglandin precursors. In plants they serve as the raw material to produce jasmonic acid, a plant hormone similar in structure to prostaglandins that mediates...

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Tuber

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stolon must be a certain age. The enzyme lipoxygenase makes a hormone, jasmonic acid, which is involved in the control of potato tuber development.[citation...

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Tritrophic interactions in plant defense

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profile. This plasticity is controlled by either the jasmonic acid pathway or the salicylic acid pathway, depending largely on the herbivore; these substances...

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