P-Anisic acid

Last updated
p-Anisic acid [1]
Kwas anyzowy.svg
P-Anisic-acid-3D-balls.png
Names
Preferred IUPAC name
4-Methoxybenzoic acid
Other names
Draconic acid
Identifiers
3D model (JSmol)
508910
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.562 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-818-5
3499
KEGG
PubChem CID
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]
GHS-pictogram-exclam.svg
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).

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]

Contents

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.

Related Research Articles

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Nitric acid is an inorganic compound with the formula HNO3. It is a highly corrosive mineral acid. The compound is colorless, but samples tend to acquire a yellow cast over time due to decomposition into oxides of nitrogen. Most commercially available nitric acid has a concentration of 68% in water. When the solution contains more than 86% HNO3, it is referred to as fuming nitric acid. Depending on the amount of nitrogen dioxide present, fuming nitric acid is further characterized as red fuming nitric acid at concentrations above 86%, or white fuming nitric acid at concentrations above 95%.

<span class="mw-page-title-main">Toluene</span> Chemical compound

Toluene, also known as toluol, is a substituted aromatic hydrocarbon with the chemical formula C6H5CH3, often abbreviated as PhCH3, where Ph stands for the phenyl group. It is a colorless, water-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

<span class="mw-page-title-main">Silver nitrate</span> Chemical compound

Silver nitrate is an inorganic compound with chemical formula AgNO
3
. It is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides. It was once called lunar caustic because silver was called luna by ancient alchemists who associated silver with the moon. In solid silver nitrate, the silver ions are three-coordinated in a trigonal planar arrangement.

<span class="mw-page-title-main">Anthracene</span> Chemical compound

Anthracene is a solid polycyclic aromatic hydrocarbon (PAH) of formula C14H10, consisting of three fused benzene rings. It is a component of coal tar. Anthracene is used in the production of the red dye alizarin and other dyes. Anthracene is colorless but exhibits a blue (400–500 nm peak) fluorescence under ultraviolet radiation.

<span class="mw-page-title-main">Phthalic acid</span> Aromatic organic compound with formula C6H4(COOH)2

In organic chemistry, phthalic acid is an aromatic dicarboxylic acid, with formula C6H4(CO2H)2 and structure HO(O)C−C6H4−C(O)OH. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large scale. Phthalic acid is one of three isomers of benzenedicarboxylic acid, the others being isophthalic acid and terephthalic acid.

<span class="mw-page-title-main">Dinitrogen pentoxide</span> Chemical compound

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<span class="mw-page-title-main">Allyl chloride</span> Chemical compound

Allyl chloride is the organic compound with the formula CH2=CHCH2Cl. This colorless liquid is insoluble in water but soluble in common organic solvents. It is mainly converted to epichlorohydrin, used in the production of plastics. It is a chlorinated derivative of propylene. It is an alkylating agent, which makes it both useful and hazardous to handle.

<span class="mw-page-title-main">Lead(II) chloride</span> Chemical compound

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Anisole, or methoxybenzene, is an organic compound with the formula CH3OC6H5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances. The compound is mainly made synthetically and is a precursor to other synthetic compounds. Structurally, it is an ether with a methyl and phenyl group attached. Anisole is a standard reagent of both practical and pedagogical value.

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Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of the aromatic compound allylbenzene and occurs widely in the essential oils of plants. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, which is abundant in tarragon (Asteraceae) and basil (Lamiaceae), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; this is called the ouzo effect.

<span class="mw-page-title-main">Gold(III) chloride</span> Chemical compound

Gold(III) chloride, traditionally called auric chloride, is an inorganic compound of gold and chlorine with the molecular formula Au2Cl6. The "III" in the name indicates that the gold has an oxidation state of +3, typical for many gold compounds. It has two forms, the monohydrate (AuCl3·H2O) and the anhydrous form, which are both hygroscopic and light-sensitive solids. This compound is a dimer of AuCl3. This compound has a few uses, such as an oxidizing agent and for catalyzing various organic reactions.

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Periodate is an anion composed of iodine and oxygen. It is one of a number of oxyanions of iodine and is the highest in the series, with iodine existing in oxidation state +7. Unlike other perhalogenates, such as perchlorate, it can exist in two forms: metaperiodateIO
4
and orthoperiodateIO5−
6
. In this regard it is comparable to the tellurate ion from the adjacent group. It can combine with a number of counter ions to form periodates, which may also be regarded as the salts of periodic acid.

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4-Anisaldehyde, or p-Anisaldehyde, is an organic compound with the formula CH3OC6H4CHO. The molecule consists of a benzene ring with a formyl and a methoxy group. It is a colorless liquid with a strong aroma. It provides sweet, floral and strong aniseed odor. Two isomers of 4-anisaldehyde are known, ortho-anisaldehyde and meta-anisaldehyde. They are less commonly encountered.

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<span class="mw-page-title-main">Neodymium(III) acetate</span> Compound of neodymium

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References

  1. 1 2 3 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.