Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:05:29 UTC |
---|
Update date | 2019-11-26 02:57:50 UTC |
---|
Primary ID | FDB002700 |
---|
Secondary Accession Numbers | Not Available |
---|
Chemical Information |
---|
FooDB Name | Isoferulic acid |
---|
Description | It is used as a food additive; listed in the EAFUS Food Additive Database (Jan 2001)
Isoferulic acid is a chlorogenic acid (CGA). CGAs are formed by the esterification of hydroxycinnamic acids, such as caffeic, ferulic, and {rho}-coumaric, with quinic acid. CGA are abundant phenolic compounds in coffee, with caffeoylquinic (CQA), feruloylquinic (FQA), and dicaffeoylquinic (diCQA) acids being the major subclasses, and coffee is the most consumed food product in the world. Isoferulic acid is present in normal human urine in concentrations of 0.05-2.07 umol/mmol creatinine at baseline, and reaches 0.2 - 9.6 umol/mmol creatinine in four hours after a cup of coffee, with a large inter-individual variation. (PMID: 17884997). Isoferulic acid is found in many foods, some of which are sunflower, peanut, common wheat, and vinegar. |
---|
CAS Number | 537-73-5 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
3-Hydroxy-4-methoxycinnamic acid | ChEBI | Hesperetic acid | ChEBI | 3-Hydroxy-4-methoxycinnamate | Generator | Isoferulate | Generator | 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoate | HMDB | 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid | HMDB | 3-Hydroxy-4-methoxy-cinnamate | HMDB | 3-Hydroxy-4-methoxy-cinnamic acid | HMDB | (2E)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid | HMDB | (e)-3-Hydroxy-4-methoxycinnamic acid | HMDB | (e)-4-Methoxycaffeic acid | HMDB | (e)-4-O-Methylcaffeic acid | HMDB | (e)-Hesperetic acid | HMDB | (e)-Isoferulic acid | HMDB | 4-Methoxycaffeic acid | HMDB | 4-O-Methylcaffeic acid | HMDB | trans-3-Hydroxy-4-methoxycinnamic acid | HMDB | trans-4-Methoxycaffeic acid | HMDB | trans-4-O-Methylcaffeic acid | HMDB | trans-Hesperetic acid | HMDB | trans-Isoferulic acid | HMDB | (2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoate | HMDB | 3'-Hydroxy-4'-methoxycinnamic acid | HMDB | (e)-3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid | HMDB | (2E)-3-(3-Hydroxy-4-methoxyphenyl)prop-2-enoic acid | HMDB | 3-(3-Hydroxy-4-methoxyphenyl)-2-propenoic acid, 9CI | db_source | Hesperetate | biospider | Hesperetinic acid | db_source | Isoferulic acid | db_source |
|
---|
Predicted Properties | |
---|
Chemical Formula | C10H10O4 |
---|
IUPAC name | (2E)-3-(3-hydroxy-4-methoxyphenyl)prop-2-enoic acid |
---|
InChI Identifier | InChI=1S/C10H10O4/c1-14-9-4-2-7(6-8(9)11)3-5-10(12)13/h2-6,11H,1H3,(H,12,13)/b5-3+ |
---|
InChI Key | QURCVMIEKCOAJU-HWKANZROSA-N |
---|
Isomeric SMILES | COC1=C(O)C=C(\C=C\C(O)=O)C=C1 |
---|
Average Molecular Weight | 194.184 |
---|
Monoisotopic Molecular Weight | 194.057908808 |
---|
Classification |
---|
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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Cinnamic acids and derivatives |
---|
Sub Class | Hydroxycinnamic acids and derivatives |
---|
Direct Parent | Hydroxycinnamic acids |
---|
Alternative Parents | |
---|
Substituents | - Cinnamic acid
- Coumaric acid or derivatives
- Hydroxycinnamic acid
- Methoxyphenol
- Phenoxy compound
- Anisole
- Methoxybenzene
- Styrene
- Phenol ether
- 1-hydroxy-4-unsubstituted benzenoid
- 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
|
---|
Molecular Framework | Aromatic homomonocyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Role | Industrial application: |
---|
Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 61.85%; H 5.19%; O 32.96% | DFC |
---|
Melting Point | 228 - 233 oC | |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | Not Available | |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | Not Available | |
---|
Spectroscopic UV Data | 322 (e 27500) (MeOH) (Derep) | DFC |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
EI-MS | Mass Spectrum (Electron Ionization) | splash10-0006-5900000000-db5f99d89dd9e349c86c | 2015-03-01 | View Spectrum | Predicted GC-MS | Isoferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-002e-0900000000-b51b390a0727d3838cab | Spectrum | Predicted GC-MS | Isoferulic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-7094000000-6021a908fd1b4eec8f00 | Spectrum | Predicted GC-MS | Isoferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isoferulic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isoferulic acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isoferulic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isoferulic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isoferulic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Isoferulic acid, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-004l-0900000000-ab3320c9d0dfcba00b6e | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-001i-0900000000-2b9775043a4af5fdc064 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-001i-0900000000-29fd32eacfaa52704559 | 2012-07-24 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0006-0900000000-d26e8f9f43c25710a04d | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-003r-0900000000-25d10f2b53d467937524 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-001i-0900000000-b2f1dd5274585c5f6b0b | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-001i-3900000000-2e21dbcbb598dba64525 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-001i-2900000000-7a28000b74f8c4f5b27f | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-01p9-0920000000-7aaa9640d85177e2e6b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-01p9-0920000000-7aaa9640d85177e2e6b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-01p9-0920000000-7aaa9640d85177e2e6b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-01p9-0920000000-7aaa9640d85177e2e6b5 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-005l-0902100000-6fc8730bd28daa779b66 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-005l-0902100000-6fc8730bd28daa779b66 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-001i-0900000000-623ecba5385a03e0406b | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-004i-0900000000-205ebeb435685d894bcf | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 30V, Negative | splash10-001i-0900000000-97eb2cfc1a86c4933f76 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-001i-0900000000-49f1d1fd82311df29713 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-005l-0902100000-6fc8730bd28daa779b66 | 2017-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-002b-0900000000-eaa8fbddbddb5c585ea4 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-002b-1900000000-c2fa54dcd41f9ab16b8e | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00fs-5900000000-a969ea13d0a4ad63b2a6 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-0900000000-6b2f8b891907a56146d6 | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0006-0900000000-6139186c0691cc7b95bb | 2017-06-28 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00o0-2900000000-8d4f500b0c438df01f41 | 2017-06-28 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental) | | Spectrum | 1D NMR | 13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | 643318 |
---|
ChEMBL ID | CHEMBL233295 |
---|
KEGG Compound ID | C10470 |
---|
Pubchem Compound ID | 736186 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | 485 |
---|
DrugBank ID | DB07109 |
---|
HMDB ID | HMDB00955 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | CMK09-G:CND07-C |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | ISOFERULIC-ACID |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00002752 |
---|
HET ID | 4FE |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Not Available |
---|
Phenol-Explorer Metabolite ID | 485 |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | |
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Not Available |
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — 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.
|
---|