| Record Information |
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| Version | 1.0 |
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| Created at | 2005-11-16 15:48:42 UTC |
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| Updated at | 2020-09-11 01:33:22 UTC |
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| NP-MRD ID | NP0000019 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | p-Anisic acid |
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| Description | P-Anisic acid, also known as 4-anisate or draconic acid, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. P-Anisic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). P-Anisic acid exists in all eukaryotes, ranging from yeast to humans. P-Anisic acid is a faint, sweet, and cadaverous tasting compound. Outside of the human body, p-Anisic acid has been detected, but not quantified in, several different foods, such as anises, cocoa beans, fennels, and german camomiles. This could make p-anisic acid a potential biomarker for the consumption of these foods. A methoxybenzoic acid substituted with a methoxy group at position C-4. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 4-Anisic acid | ChEBI | | Anisic acid | ChEBI | | Draconic acid | ChEBI | | p-Methoxybenzoic acid | ChEBI | | 4-Methoxybenzoic acid | Kegg | | 4-Anisate | Generator | | Anisate | Generator | | Draconate | Generator | | p-Methoxybenzoate | Generator | | 4-Methoxybenzoate | Generator | | p-Anisate | Generator | | 4-Anisic acid, copper (+2) salt | HMDB | | 4-Anisic acid, 14C-carboxy | HMDB | | 4-Anisic acid, potassium salt | HMDB | | 4-Anisic acid, sodium salt | HMDB | | Para-anisic acid | HMDB | | p-Anisic acid | ChEBI |
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| Chemical Formula | C8H8O3 |
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| Average Molecular Weight | 152.1473 |
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| Monoisotopic Molecular Weight | 152.047344122 |
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| IUPAC Name | 4-methoxybenzoic acid |
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| Traditional Name | P-anisic acid |
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| CAS Registry Number | 100-09-4 |
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| SMILES | COC1=CC=C(C=C1)C(O)=O |
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| InChI Identifier | InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10) |
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| InChI Key | ZEYHEAKUIGZSGI-UHFFFAOYSA-N |
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| Spectra |
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| | | Species of Origin |
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| Species | Animalia; Plantae |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. |
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| Kingdom | Organic compounds |
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| Super Class | Benzenoids |
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| Class | Benzene and substituted derivatives |
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| Sub Class | Benzoic acids and derivatives |
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| Direct Parent | P-methoxybenzoic acids and derivatives |
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| Alternative Parents | |
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| Substituents | - P-methoxybenzoic acid or derivatives
- Benzoic acid
- Anisole
- Phenoxy compound
- Benzoyl
- Phenol ether
- Methoxybenzene
- Alkyl aryl ether
- Monocarboxylic acid or derivatives
- Ether
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Physical Properties |
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| State | Solid |
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| Experimental Properties | | Property | Value | Reference |
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| Melting Point | 185 °C | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | 0.53 mg/mL at 37 °C | Not Available | | LogP | 1.96 | HANSCH,C ET AL. (1995) |
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| Predicted Properties | |
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| General References | - Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]
- Thoma H, Reiner J, Spiteller G: Profiles of strongly polar and less polar acids obtained from human blood, plasma and serum by two-step ultrafiltration. J Chromatogr. 1984 Jul 13;309(1):17-32. [PubMed:6480763 ]
- Kubo I, Chen QX, Nihei K, Calderon JS, Cespedes CL: Tyrosinase inhibition kinetics of anisic acid. Z Naturforsch C. 2003 Sep-Oct;58(9-10):713-8. [PubMed:14577637 ]
- Shirane M, Nakamura K: Aniracetam enhances cortical dopamine and serotonin release via cholinergic and glutamatergic mechanisms in SHRSP. Brain Res. 2001 Oct 19;916(1-2):211-21. [PubMed:11597608 ]
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