Dehydroabietic acid

Dehydroabietic acid

Skeletal formula
Names
Preferred IUPAC name Abieta-8,11,13-trien-18-oic acid
Other names DAA; DHA
Identifiers
CAS Number	1740-19-8
3D model (JSmol)	Interactive image
ChEBI	CHEBI:29571
ChEMBL	ChEMBL12850
ChemSpider	85184
ECHA InfoCard	100.015.548
EC Number	217-102-8
KEGG	C12078
PubChem CID	94391
UNII	0S5XP6S3AU
CompTox Dashboard (EPA)	DTXSID8022163
InChI InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1 Key: NFWKVWVWBFBAOV-MISYRCLQSA-N
SMILES CC(C)C1=CC2=C(C=C1)C3(CCCC(C3CC2)(C)C(=O)O)C
Properties
Chemical formula	C20H28O2
Molar mass	300.442 g·mol−1
Appearance	White to off-white solid
Density	1.03 g/cm3
Melting point	150–153 °C (302–307 °F; 423–426 K)
Boiling point	390 °C (734 °F; 663 K)
Solubility in water	Practically insoluble in water; soluble in organic solvents
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	Harmful if swallowed; causes skin and eye irritation
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301, H410
Precautionary statements	P273, P301+P310+P330
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

Dehydroabietic acid (DHA) is a naturally occurring abietane-type diterpenoid resin acid found predominantly in coniferous trees. It is a major component of rosin and is utilized in various industrial applications due to its chemical properties.

Chemical structure and properties

Dehydroabietic acid has the molecular formula C₂₀H₂₈O₂ and a molecular weight of 300.44 g/mol. It appears as a white to off-white solid with a melting point of 150–153 °C and a boiling point of approximately 390 °C. The compound is practically insoluble in water but soluble in organic solvents such as ethanol and acetone. ^[1]

Biological activity

It exhibits a range of biological activities, including:

• Anti-inflammatory: Acts as a dual activator of peroxisome proliferator-activated receptors alpha and gamma (PPAR α/γ), contributing to its anti-inflammatory effects. ^[2]

• Antimicrobial: Demonstrates antibacterial properties against multidrug-resistant strains. ^[3]

• Anticancer: Certain derivatives have shown cytotoxic activity against various cancer cell lines, indicating potential as anticancer agents. ^[4]

Applications and safety

Due to its bioactivity, dehydroabietic acid is used in:

• Pharmaceutical research: As a lead compound for developing anti-inflammatory and anticancer drugs.
• Industrial applications: In the synthesis of varnishes, adhesives, and as a component in the production of paper and other materials.

Dehydroabietic acid should be handled with care. It is harmful if swallowed and can cause skin and eye irritation. Appropriate personal protective equipment should be used when handling the compound. ^[5]

References

1. "Dehydroabietic Acid". PubChem. Retrieved 2025-05-25.
2. "Dehydroabietic acid - Sigma-Aldrich" . Retrieved 2025-05-25.
3. Lu, P.; Wei, X.; Zhang, R. (2010). "Synthesis and biological evaluation of dehydroabietic acid derivatives". European Journal of Medicinal Chemistry. 45 (7): 3144–3150. doi:10.1016/j.ejmech.2010.04.030. PMID   20488589.
4. Grigoropoulou, S.; Manou, D.; Antoniou, A. I.; Tsirogianni, A.; Siciliano, C.; Theocharis, A. D.; Athanassopoulos, C. M. (2022). "Synthesis and Biological Evaluation of Novel Dehydroabietic Acid Derivatives". Molecules. 27 (11): 3623. doi: 10.3390/molecules27113623 . PMC   9181926 . PMID   35684559.
5. "Dehydroabietic acid Safety Data Sheet" . Retrieved 2025-05-25.