Methyl dehydroabietate

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.

Methyl dehydroabietate

Skeletal formula
Names
Preferred IUPAC name Methyl (4β)-abieta-9(11),8(14),12-trien-18-oate
Identifiers
CAS Number	1235-74-1
3D model (JSmol)	Interactive image
ChEBI	CHEBI:228313
ChEMBL	ChEMBL12798
ChemSpider	13919
PubChem CID	14697
UNII	4P47O55S2W
CompTox Dashboard (EPA)	DTXSID10880714
InChI 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
SMILES COC(=O)C1(C)CCCC2(C)c3ccc(C(C)C)cc3CCC12
Properties
Chemical formula	C21H30O2
Molar mass	314.46 g/mol
Appearance	White to off-white solid
Density	1.017 g/cm3
Boiling point	390.2 °C (734.4 °F; 663.3 K) at 760 mmHg
Solubility in water	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:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P305+P351+P338
Flash point	184.3°C
Autoignition temperature	Not available
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N (what is YN ?) Infobox references

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:

• Antibacterial properties: It has shown activity against certain bacterial strains, suggesting potential as an antimicrobial agent.^[3]
• Antioxidant activity: Some studies suggest that methyl dehydroabietate may possess antioxidant properties, although further research is needed to confirm these findings.^[4]

Applications and safety

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

• Cosmetic industry: As an emollient and viscosity-controlling agent in skincare products.^[5]
• Pharmaceutical research: As a starting material for synthesizing derivatives with potential therapeutic applications.

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]