p-Anisic acid

p-Anisic acid, also known as 4-methoxybenzoic acid or draconic acid, is one of the isomers of anisic acid. The term "anisic acid" often refers to this form specifically. It is a white crystalline solid which is insoluble in water, highly soluble in alcohols and soluble in ether, and ethyl acetate.

p-Anisic acid[1]
Skeletal formula of p-anisic acid
Ball-and-stick model of the p-anisic acid molecule
Names
Preferred IUPAC name
4-Methoxybenzoic acid
Other names
Draconic acid
Identifiers
3D model (JSmol)
508910
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.562
EC Number
  • 202-818-5
3499
KEGG
UNII
  • InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
    Key: ZEYHEAKUIGZSGI-UHFFFAOYSA-N
  • O=C(O)C1=CC=C(OC)C=C1
Properties
C8H8O3
Molar mass 152.149 g·mol−1
Density 1.385 g/cm3
Melting point 184 °C (363 °F; 457 K) (sublimation)
Boiling point 275 to 280 °C (527 to 536 °F; 548 to 553 K)
1 part per 2500
Acidity (pKa) 4.47[2]
Structure[3]
monoclinic
P21/a
a = 16.98 Å, b = 10.95 Å, c = 3.98 Å
α = 90°, β = 98.7°, γ = 90°
4
Hazards
GHS labelling:[4]
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P330, P332+P313, P337+P313, P362, P403+P233, P405
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Synthesis and occurrence

p-Anisic acid is found naturally in anise. It is generally obtained by the oxidation of anethole or p-methoxyacetophenone.

Uses

p-Anisic acid has antiseptic properties. It is also used as an intermediate in the preparation of more complex organic compounds.

References
  1. Merck Index, 11th Edition, 696
  2. Braude, E. A.; Nachod, F. C., eds. (1955). Determination of Organic Structure by Physical Methods. Academic Press. ISBN 9781483275727.
  3. Bryan, Robert F. (1967). "An X-ray study of the p-n-alkoxybenzoic acids. Part II. The crystal structure of anisic acid". Journal of the Chemical Society B: Physical Organic: 1311. doi:10.1039/j29670001311. ISSN 0045-6470.
  4. "4-Methoxybenzoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 22 December 2021.
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