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.[1] It is a white crystalline solid which is insoluble in water, highly soluble in alcohols, and soluble in ether and ethyl acetate.[1]

Synthesis and occurrence

p-Anisic acid is found naturally in anise.[citation needed] It was first synthesized in 1841 by Auguste Cahours by oxidizing anethole that he had isolated from anise by recrystallization with diluted nitric acid:[5][6]

CH3CH=CHC6H4OCH3 + HNO3 → CH3OC6H4CHO + others
CH3OC6H4CHO + HNO3 → CH3OC6H4COOH + others

Oxidation of anisaldehyde, which was Cahours' intermediate product, is still used nowadays.[7] Anisic acid can also be obtained synthetically by the oxidation of p-methoxyacetophenone.

Uses

p-Anisic acid has antiseptic properties.[8] It is also used as an intermediate in the preparation of more complex organic compounds.

References

  1. ^ a b c 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: 1311–1316. doi:10.1039/j29670001311. ISSN 0045-6470.
  4. ^ "4-Methoxybenzoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 22 December 2021.
  5. ^ Wisniak, Jaime (2013-10-01). "Auguste André Thomas Cahours". Educación Química. 24 (4): 451–460. doi:10.1016/S0187-893X(13)72500-X. ISSN 0187-893X.
  6. ^ Crochard (París); Arago, François; Gay-Lussac, Joseph Louis (1841). Annales de chimie et de physique (in French). Chez Crochard.
  7. ^ Saha, Rumpa; Ghosh, Aniruddha; Saha, Bidyut (2013). "Kinetics of micellar catalysis on oxidation of p-anisaldehyde to p-anisic acid in aqueous medium at room temperature". Chemical Engineering Science. 99: 23–27. Bibcode:2013ChEnS..99...23S. doi:10.1016/j.ces.2013.05.043.
  8. ^ Herman, Anna (2019). "Antimicrobial Ingredients as Preservative Booster and Components of Self-Preserving Cosmetic Products". Current Microbiology. 76 (6): 744–754. doi:10.1007/s00284-018-1492-2. PMID 29651551.
Allikas: https://en.wikipedia.org/wiki/P-Anisic_acid
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