| Record Information |
|---|
| Version | 1.0 |
|---|
| Created at | 2020-03-19 00:33:55 UTC |
|---|
| Updated at | 2020-11-18 16:35:08 UTC |
|---|
| CannabisDB ID | CDB000379 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Cannabis Compound Identification |
|---|
| Common Name | Lignoceric acid |
|---|
| Description | Lignoceric acid or tetracosanoate, also known as lignocerat, with formula C23H47COOH, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Lignoceric acid is a fatty acid lipid molecule. Lignoceric acid is practically insoluble in water and a weakly acidic compound. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain 1.1% – 2.2% of lignoceric acid. This fatty acid is also a by product of lignin production. Lignoceric acid is one of the saturated fatty acids identified in the oil of cannabis seed (PMID: 6991645 ). In humans, Lignoceric acid, one of the very long chain fatty acids, is associate with the X-chromosome linked disease, adrenoleukodystrophy (ALD), marked by a deficiency in peroxisomal fatty acid beta oxidation. ALD is caused by mutations in ABCD1, a gene that encodes for ALD, a peroxisomal membrane transporter protein. Those with ALD build-up long chain fatty acids, affecting myelin in the central nervous system, the adrenal cortex, and the Leydig cells in the testes. Lignoceric acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. |
|---|
| Structure | |
|---|
| Synonyms | | Value | Source |
|---|
| CH3-[CH2]22-COO(-) | ChEBI | | Lignocerat | ChEBI | | Lignocerate | ChEBI | | N-Tetracosanoate | ChEBI | | Tetracosanate | ChEBI | | Tetracosanoat | ChEBI | | Tetracosoate | ChEBI | | Tetraeicosanoate | ChEBI | | Lignoceric acid | Generator | | N-Tetracosanoic acid | Generator | | Tetracosanic acid | Generator | | Tetracosoic acid | Generator | | Tetraeicosanoic acid | Generator | | Tetracosanoic acid | Generator | | Tetracosanoate | ChEBI |
|
|---|
| Chemical Formula | C24H47O2 |
|---|
| Average Molecular Weight | 367.63 |
|---|
| Monoisotopic Molecular Weight | 367.3576 |
|---|
| IUPAC Name | tetracosanoate |
|---|
| Traditional Name | lignocerate |
|---|
| CAS Registry Number | 46927-71-3 |
|---|
| SMILES | CCCCCCCCCCCCCCCCCCCCCCCC([O-])=O |
|---|
| InChI Identifier | InChI=1S/C24H48O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24(25)26/h2-23H2,1H3,(H,25,26)/p-1 |
|---|
| InChI Key | QZZGJDVWLFXDLK-UHFFFAOYSA-M |
|---|
| Chemical Taxonomy |
|---|
| Description | Belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Lipids and lipid-like molecules |
|---|
| Class | Fatty Acyls |
|---|
| Sub Class | Fatty acids and conjugates |
|---|
| Direct Parent | Very long-chain fatty acids |
|---|
| Alternative Parents | |
|---|
| Substituents | - Very long-chain fatty acid
- Straight chain fatty acid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Organic anion
- Aliphatic acyclic compound
|
|---|
| Molecular Framework | Aliphatic acyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
|
Not Available | | Physical Properties |
|---|
| State | Solid |
|---|
| Experimental Properties | | Property | Value | Reference |
|---|
| Melting Point | 84.2 °C | Wikipedia | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | logP | Not Available | Not Available |
|
|---|
| Predicted Properties | [] |
|---|
