Chemistry:P-Anisic acid
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| Names | |||
|---|---|---|---|
| Preferred IUPAC name
4-Methoxybenzoic acid | |||
| Other names
Draconic acid
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| Identifiers | |||
3D model (JSmol)
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| 508910 | |||
| ChEBI | |||
| ChEMBL |
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| ChemSpider | |||
| EC Number |
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| 3499 | |||
| KEGG | |||
PubChem CID
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| UNII | |||
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| 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°
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Formula units (Z)
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4 | ||
| Hazards | |||
| GHS pictograms | 
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| GHS Signal word | Warning | ||
| H302, H315, H319, H335 | |||
| P261, P264, P270, P271, P280, P301+312, P302+352, P304+340, P305+351+338, P312, P330, P332+313, P337+313, P362, P403+233, 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.[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]
- CH
3CH=CHC
6H
4OCH
3 + HNO
3 → CH
3OC
6H
4CHO + others - CH
3OC
6H
4CHO + HNO
3 → CH
3OC
6H
4COOH + 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
- ↑ 1.0 1.1 1.2 Merck Index, 11th Edition, 696
- ↑ Braude, E. A.; Nachod, F. C., eds (1955). Determination of Organic Structure by Physical Methods. Academic Press. ISBN 9781483275727.
- ↑ Bryan, Robert F. (1967). "An X-ray study of the p-n-alkoxybenzoic acids. Part II. The crystal structure of anisic acid" (in en). Journal of the Chemical Society B: Physical Organic: 1311–1316. doi:10.1039/j29670001311. ISSN 0045-6470. http://xlink.rsc.org/?DOI=j29670001311.
- ↑ "4-Methoxybenzoic acid" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/7478#section=Safety-and-Hazards.
- ↑ 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. https://www.sciencedirect.com/science/article/pii/S0187893X1372500X.
- ↑ Crochard (París); Arago, François; Gay-Lussac, Joseph Louis (1841) (in fr). Annales de chimie et de physique. Chez Crochard. https://books.google.com/books?id=hChCAAAAcAAJ&pg=PA287.
- ↑ 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. doi:10.1016/j.ces.2013.05.043. Bibcode: 2013ChEnS..99...23S.
- ↑ 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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