Methyl jasmonate

From Wikipedia, the free encyclopedia

Methyl jasmonate

IUPAC name	Methyl (1R,2R)-3-Oxo-2-(2Z)-2- pentenyl-cyclopentaneacetate
Other names	Methyl jasmonate
Identifiers
CAS number	[39924-52-2]
SMILES	O=C1[C@H](C/C=C\CC) [C@@H](CC(OC)=O)CC1
Properties
Molecular formula	C₁₃H₂₀O₃
Molar mass	224.3 g/mol
Appearance	Colorless liquid
Melting point	<25 °C
Boiling point	88-90 °C at 0.1 mmHg
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Methyl jasmonate (MeJA) is a substance used in plant defense [1]and also under early research for cancer treatment in humans.^[1] Plants produce jasmonic acid and methyl jasmonate in response to many biotic and abiotic stresses (particularly herbivory and wounding), which build up in the damaged parts of the plant. Jasmonates act as signaling compounds for the production of phytoalexins. MeJa has been used to stimulate traumatic resin duct production in lodgepole pine trees. This can be used as a defense against many insect attackers as a type of vaccine. Phytoalexins, once ingested by the attacker (e.g., insect), can be toxic or interfere with its digestion and may deter the attacker from further feeding. The jasmonate signal often spreads systemically throughout the plant and is a major component of systemic acquired resistance.

MeJA is also a plant hormone involved in tendril (root) coiling and seed maturation.

[edit] See also

Jasmonate

[edit] References

^ Flescher E (2005). "Jasmonates--a new family of anti-cancer agents". Anticancer Drugs 16 (9): 911–6. doi:10.1097/01.cad.0000176501.63680.80. PMID 16162967.