Methyl dehydroabietate

Last updated
Methyl dehydroabietate
Skeletal formula Methyl dehydroabietate.svg
Skeletal formula
Names
Preferred IUPAC name
Methyl (4β)-abieta-9(11),8(14),12-trien-18-oate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C21H30O2/c1-14(2)15-7-9-17-16(13-15)8-10-18-20(17,3)11-6-12-21(18,4)19(22)23-5/h7,9,13-14,18H,6,8,10-12H2,1-5H3/t18-,20-,21-/m1/s1
    Key: PGZCJOPTDHWYES-HMXCVIKNSA-N
  • COC(=O)C1(C)CCCC2(C)c3ccc(C(C)C)cc3CCC12
Properties
C21H30O2
Molar mass 314.46 g/mol
AppearanceWhite to off-white solid
Density 1.017 g/cm3
Boiling point 390.2 °C (734.4 °F; 663.3 K) at 760 mmHg
Practically insoluble in water; soluble in organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Not extensively studied; handle with care
GHS labelling:
GHS-pictogram-exclam.svg
Warning
H302, H315, H319, H335
P261, P305+P351+P338
Flash point 184.3°C
Not available
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl dehydroabietate is a methyl ester derivative of dehydroabietic acid, a naturally occurring resin acid found in coniferous trees. It is characterized by a tricyclic diterpenoid structure and is commonly used in the synthesis of various chemical derivatives.

Contents

Chemical structure and properties

Methyl dehydroabietate has the molecular formula C21H30O2 and a molecular weight of 314.46 g/mol. It appears as a white to off-white solid with a boiling point of 390.2 °C at 760 mmHg and a flash point of 184.3 °C. The compound is practically insoluble in water but soluble in organic solvents such as ethanol and DMSO. [1]

Synthesis and derivatives

It can be synthesized through the esterification of dehydroabietic acid. Various derivatives have been developed for research purposes. For instance, chalcone and pyrazole derivatives have been synthesized and characterized using NMR, MS, and X-ray crystallography. These studies help in understanding the steric and electronic effects of substituents on the compound's biological activity. [2]

Biological activity

Research indicates that methyl dehydroabietate exhibits several biological activities:

Applications and safety

Due to its chemical properties, methyl dehydroabietate is utilized in:

While specific toxicological data is limited, methyl dehydroabietate should be handled with standard laboratory precautions. It is classified under GHS as causing skin and eye irritation and may cause respiratory irritation. Appropriate personal protective equipment should be used when handling the compound. [6]

References

  1. ↑ "Methyl Dehydroabietate". PubChem. Retrieved 2025-05-25.
  2. ↑ Silvestre, Armando J. D.; Monteiro, Sílvia M. C.; Silva, Artur M. S.; Cavaleiro, José A. S.; Félix, Vítor M. S.; Ferreira, Paula; Drew, Michael G. B. (2000). "New Methyl Dehydroabietate Derivatives: Synthesis and Structural Characterization". Chemistry of Natural Compounds. 36 (6): 560–563. doi:10.1007/PL00010130.
  3. ↑ Burčová, Z. (2018). "Antibacterial and antifungal activity of phytosterols and methyl dehydroabietate of Norway spruce bark extracts". Journal of Biotechnology. 282: 18–24. doi: 10.1016/j.jbiotec.2018.07.034 .
  4. ↑ "Methyl dehydroabietate". Smolecule. Retrieved 2025-05-25.
  5. ↑ "Methyl dehydroabietate". The Good Scents Company. Retrieved 2025-05-25.
  6. ↑ "Methyl dehydroabietate Safety Data Sheet" (PDF). MedChemExpress. Retrieved 2025-05-25.
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