| Record Information |
|---|
| Version | 1.0 |
|---|
| Created at | 2005-11-16 15:48:42 UTC |
|---|
| Updated at | 2020-11-24 22:12:10 UTC |
|---|
| NP-MRD ID | NP0000019 |
|---|
| Secondary Accession Numbers | None |
|---|
| Natural Product Identification |
|---|
| Common Name | p-Anisic acid |
|---|
| 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. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| 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 |
|
|---|
| Chemical Formula | C8H8O3 |
|---|
| Average Molecular Weight | 152.1473 |
|---|
| Monoisotopic Molecular Weight | 152.047344122 |
|---|
| IUPAC Name | 4-methoxybenzoic acid |
|---|
| Traditional Name | P-anisic acid |
|---|
| CAS Registry Number | 100-09-4 |
|---|
| SMILES | COC1=CC=C(C=C1)C(O)=O |
|---|
| InChI Identifier | InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10) |
|---|
| InChI Key | ZEYHEAKUIGZSGI-UHFFFAOYSA-N |
|---|
| Spectra |
|---|
|
| | | Species of Origin |
|---|
| Species | Animalia; Plantae |
|---|
| Chemical Taxonomy |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Benzenoids |
|---|
| Class | Benzene and substituted derivatives |
|---|
| Sub Class | Benzoic acids and derivatives |
|---|
| Direct Parent | P-methoxybenzoic acids and derivatives |
|---|
| Alternative Parents | |
|---|
| 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
|
|---|
| Molecular Framework | Aromatic homomonocyclic compounds |
|---|
| External Descriptors | |
|---|
| Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| 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) |
|
|---|
| Predicted Properties | |
|---|
| 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 ]
|
|---|
