| Record Information |
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| Version | 1.0 |
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| Creation date | 2010-04-08 22:10:22 UTC |
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| Update date | 2019-11-26 03:07:38 UTC |
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| Primary ID | FDB012801 |
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| Secondary Accession Numbers | Not Available |
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| Chemical Information |
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| FooDB Name | Ferulic acid |
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| Description | Ferulic acid, also known as ferulate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Ferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Ferulic acid can be synthesized from cis-cinnamic acid. Ferulic acid is also a parent compound for other transformation products, including but not limited to, (2S,3S)-cis-fertaric acid, (2R,3R)-cis-fertaric acid, and (Z)-4-hydroxy-3-methoxycinnamoylagmatine. Ferulic acid can be found in a number of food items such as pineapple, pear, evergreen huckleberry, and silver linden, which makes ferulic acid a potential biomarker for the consumption of these food products. Ferulic acid is a hydroxycinnamic acid, a type of organic compound. It is an abundant phenolic phytochemical found in plant cell walls, covalently bonded as side chains to molecules such as arabinoxylans. As a component of lignin, ferulic acid is a precursor in the manufacture of other aromatic compounds. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis) . |
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| CAS Number | 1135-24-6 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Not Available | Not Available |
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| Predicted Properties | |
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| Chemical Formula | C10H10O4 |
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| IUPAC name | (2Z)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid |
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| InChI Identifier | InChI=1S/C10H10O4/c1-14-9-6-7(2-4-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3- |
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| InChI Key | KSEBMYQBYZTDHS-HYXAFXHYSA-N |
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| Isomeric SMILES | [H]\C(=C(/[H])C1=CC(OC)=C(O)C=C1)C(O)=O |
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| Average Molecular Weight | 194.184 |
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| Monoisotopic Molecular Weight | 194.057908808 |
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| Classification |
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| Description | Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Cinnamic acids and derivatives |
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| Sub Class | Hydroxycinnamic acids and derivatives |
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| Direct Parent | Hydroxycinnamic acids |
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| Alternative Parents | |
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| Substituents | - Cinnamic acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Styrene
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Ether
- Organic oxygen compound
- Carbonyl group
- Organic oxide
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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| Molecular Framework | Aromatic homomonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Ontology | No ontology term |
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| Physico-Chemical Properties - Experimental |
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| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
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| Physical state | Not Available | |
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| Physical Description | Not Available | |
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| Mass Composition | C 61.85%; H 5.19%; O 32.96% | DFC |
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| Melting Point | Not Available | |
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| Boiling Point | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Experimental logP | Not Available | |
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| Experimental pKa | Not Available | |
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| Isoelectric point | Not Available | |
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| Charge | Not Available | |
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| Optical Rotation | Not Available | |
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| Spectroscopic UV Data | Not Available | |
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| Density | Not Available | |
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| Refractive Index | Not Available | |
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| Spectra |
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| Spectra | |
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| EI-MS/GC-MS | | Type | Description | Splash Key | View |
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| GC-MS | Ferulic acid, 2 TMS, GC-MS Spectrum | splash10-000m-3975000000-b565cdbaaa5aa607842c | Spectrum | | Predicted GC-MS | Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002e-0900000000-364e88a08cf6d6286274 | Spectrum | | Predicted GC-MS | Ferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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| MS/MS | | Type | Description | Splash Key | View |
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| Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004j-0900000000-82a5db483030159be6c1 | 2018-04-05 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002k-0900000000-9adee713458d10117a2e | 2018-04-05 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05n1-5900000000-274ce6cbf728eecfdae9 | 2018-04-05 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-c3525a965490cdbb4dcf | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-002g-0900000000-88b5ab9b0b2e8101e049 | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a5d-3900000000-84ea72397fe862014d21 | 2018-04-06 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-0900000000-2cbbb17f31ea930e552f | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-1900000000-c60d5b5e427a10038367 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00os-5900000000-6816783e7c532ed0c682 | 2021-09-22 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0005-0900000000-39d7f6b12ceecc27ef82 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-001i-0900000000-d8f26b270bdd490ef7b7 | 2021-09-23 | View Spectrum | | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-1900000000-09a310572dc414e2f113 | 2021-09-23 | View Spectrum |
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| NMR | Not Available |
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| External Links |
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| ChemSpider ID | Not Available |
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| ChEMBL ID | Not Available |
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| KEGG Compound ID | Not Available |
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| Pubchem Compound ID | Not Available |
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| Pubchem Substance ID | Not Available |
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| ChEBI ID | Not Available |
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| Phenol-Explorer ID | 459 |
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| DrugBank ID | Not Available |
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| HMDB ID | Not Available |
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| CRC / DFC (Dictionary of Food Compounds) ID | HLG59-X:HLG59-X |
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| EAFUS ID | Not Available |
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| Dr. Duke ID | 4-HYDROXY-3-METHOXY-CINNAMIC-ACID|FERULIC-ACID |
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| BIGG ID | Not Available |
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| KNApSAcK ID | C00002743 |
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| HET ID | Not Available |
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| Food Biomarker Ontology | Not Available |
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| VMH ID | Not Available |
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| Flavornet ID | Not Available |
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| GoodScent ID | Not Available |
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| SuperScent ID | Not Available |
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| Wikipedia ID | Not Available |
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| Phenol-Explorer Metabolite ID | 459 |
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| Duplicate IDS | Not Available |
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| Old DFC IDS | Not Available |
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| Associated Foods |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Biological Effects and Interactions |
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| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
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| allelopathic | | | DUKE | | analgesic | 35480 | An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms. | DUKE | | anti aggregant | | | DUKE | | anti allergic | 50857 | A drug used to treat allergic reactions. | DUKE | | anti arrhythmic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti carcinogenic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti dysmenorrheic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti estrogenic | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti mitotic | | | DUKE | | anti mutagenic | | | DUKE | | anti neoplastic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti nitrosaminic | | | DUKE | | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | | anti radicular | | | DUKE | | anti serotonin | 48278 | | DUKE | | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti thrombic | 50248 | Drug that acts on blood and blood-forming organs and those that affect the hemostatic system. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | antitumor promoter | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | arteriodilator | | | DUKE | | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | candidicide | | | DUKE | | cardiac | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | | cholagogue | | | DUKE | | choleretic | | | DUKE | | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | | hepatotropic | | | DUKE | | herbicide | 24527 | A substance used to destroy plant pests. | DUKE | | hydrocholerectic | | | DUKE | | hypolipidemic | | | DUKE | | immunostimulant | 50847 | A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. | DUKE | | insectifuge | 24852 | Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. | DUKE | | metal chelator | 38161 | A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate. | DUKE | | ornithine-decarboxylase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | phagocytotic | | | DUKE | | preservative | 65255 | Substances which are added to food in order to prevent decomposition caused by microbial growth or by undesirable chemical changes. | DUKE | | prostaglandigenic | | | DUKE | | prostaglandin synthesis inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | sunscreen | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | uteros sedative | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE |
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| Enzymes | Not Available |
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| Pathways | Not Available |
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| Metabolism | Not Available |
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| Biosynthesis | Not Available |
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| Organoleptic Properties |
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| Flavours | Not Available |
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| Files |
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| MSDS | Not Available |
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| References |
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| Synthesis Reference | Not Available |
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| General Reference | Not Available |
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| Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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