p-Anisic acid

p-Anisic acid^[1]
Names
	Preferred IUPAC name 4-Methoxybenzoic acid
	Other names Draconic acid
Identifiers
CAS Number	100-09-4;
3D model (JSmol)	Interactive image;
Beilstein Reference	508910
ChEBI	CHEBI:40813;
ChEMBL	ChEMBL21932; sodium salt: ChEMBL1762657;
ChemSpider	10181338;
ECHA InfoCard	100.002.562
EC Number	202-818-5;
Gmelin Reference	3499
KEGG	C02519;
PubChem CID	7478;
UNII	4SB6Y7DMM3 ;
CompTox Dashboard (EPA)	DTXSID4059205 ;
	InChI 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;
	SMILES O=C(O)C1=CC=C(OC)C=C1;
Properties
Chemical formula	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)
Solubility in water	1 part per 2500
Acidity (pKa)	4.47
Structure
Crystal structure	monoclinic
Space group	P21/a
Lattice constant	a = 16.98 Å, b = 10.95 Å, c = 3.98 Å α = 90°, β = 98.7°, γ = 90°
Formula units (Z)	4
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	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

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. 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

^ ^a ^b ^c Merck Index, 11th Edition, 696
^ Braude, E. A.; Nachod, F. C., eds. (1955). Determination of Organic Structure by Physical Methods. Academic Press. ISBN 9781483275727. {{cite book}}: ISBN / Date incompatibility (help)
^ 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-Methoxybenzoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 22 December 2021.
^ 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.
^ Crochard (París); Arago, François; Gay-Lussac, Joseph Louis (1841). Annales de chimie et de physique (in French). Chez Crochard.
^ 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.
^ 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.

[Merck-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. {{cite book}}: ISBN / Date incompatibility (help)

[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.

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