(±)-Jasmonic Acid methyl ester

Cayman Chemical Item Number 9000059

(±)-Methyl Jasmonate (CAS 39924-52-2)

(±)-Jasmonic Acid methyl ester (CAS 39924-52-2)

Description

The jasmonates are a group of plant stress hormones that naturally occur in plants following exposure to certain types of stresses, including pathogen and herbivore attacks. (±)-Jasmonic acid methyl ester is a mixture of trans (3R/7R and 3S/7S) isomers. (±)-Jasmonic acid methyl ester induces the synthesis of proteinase inhibitors in plant leaves.¹ In cancer cells, it suppresses proliferation and induces apoptosis.² More specifically, methyl jasmonate inhibits hexokinase that is bound to mitochondria.³ As hexokinase is overexpressed in cancer cells and contributes to cancer cell growth and survival, methyl jasmonate’s disruption of mitochondrial hexokinase activity selectively targets, and kills, cancer cells. (±)-Jasmonic acid methyl ester derivatives also have potential as anti-inflammatory agents.⁴

1 Farmer, E.E., and Ryan, C.A. Interplant communication: Airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc Natl Acad Sci USA 87 7713-7716 (1990).

2 Fingrut, O., and Flescher, E. Plant stress hormones suppress the proliferation and induce apoptosis in human cancer cells. Leukemia 16 608-616 (2002).

3 Goldin, N., Arzoine, L., Heyfets, A., et al. Methyl jasmonate binds to and detaches mitochondria-bound hexokinase. Oncogene 27 4636-4643 (2008).

4 Dang, H.T., Lee, H.J., Yoo, E.S., et al. New jasmonate analogues as potential anti-inflammatory agents. Bioorg Med Chem 16 10228-10235 (2008).

Synonyms

(±)-Methyl Jasmonate

Formal Name

3-oxo-2-(2-penten-1-yl)-cyclopentaneacetic acid, methyl ester

CAS Number

39924-52-2

Molecular Formula

C₁₃H₂₀O₃

Formula Weight

224.3

Formulation

A neat oil

Purity

≥95% (mixture of isomers)

Stability

1 year

Storage

-20°C

Shipping

Room temperature in continental US; may vary elsewhere

SMILES

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O=C1[C@@](C/C=C\CC)([H])[C@](CC(OC)=O)([H])CC1

Background Reading

Fingrut, O., and Flescher, E. Plant stress hormones suppress the proliferation and induce apoptosis in human cancer cells. Leukemia 16 608-616 (2002).

Farmer, E.E., and Ryan, C.A. Interplant communication: Airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves. Proc Natl Acad Sci USA 87 7713-7716 (1990).

Goldin, N., Arzoine, L., Heyfets, A., et al. Methyl jasmonate binds to and detaches mitochondria-bound hexokinase. Oncogene 27 4636-4643 (2008).

Dang, H.T., Lee, H.J., Yoo, E.S., et al. New jasmonate analogues as potential anti-inflammatory agents. Bioorg Med Chem 16 10228-10235 (2008).

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Size

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