4'-Hydroxyphenylacetic acid
precursor
Showing entry for 4'-Hydroxyphenylacetic acid
Identification
- PhytoHub ID
- PHUB000543
- Name
- 4'-Hydroxyphenylacetic acid
- Systematic Name
- 4'-Hydroxyphenylacetic acid
- Synonyms
- (4-Hydroxyphenyl)acetic acid
- 2-(4'-Hydroxyphenyl)acetic acid
- 4-Hydroxyphenylacetic acid
- 4-hydroxyphenylethanoic acid
- CAS Number
- 156-38-7
- Average Mass
- 152.149
- Monoisotopic Mass
- 152.047344118
- Chemical Formula
- C8H8O3
- IUPAC Name
- 2-(4-hydroxyphenyl)acetic acid
- InChI Key
- XQXPVVBIMDBYFF-UHFFFAOYSA-N
- InChI Identifier
InChI=1S/C8H8O3/c9-7-3-1-6(2-4-7)5-8(10)11/h1-4,9H,5H2,(H,10,11)
- SMILES
OC(=O)CC1=CC=C(O)C=C1
- Structure
Structure for 4'-Hydroxyphenylacetic acid
Calculated Properties
- Solubility (ALOGPS)
- 7.12e+00 g/l
- LogS (ALOGPS)
- -1.33
- LogP (ALOGPS)
- 0.93
- Hydrogen Acceptors
- 3
- Hydrogen Donors
- 2
- Rotatable Bond Count
- 2
- Polar Surface Area
- 57.53
- Refractivity
- 39.3465
- Polarizability
- 14.826780263933822
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -5.958556388425476
- pKa (strongest acidic)
- 3.9984367127077793
- Number of Rings
- 1
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- No
- Veber's Rule
- No
- MDDR-like Rule
- No
Taxonomy as Food Phytochemical
- Family
- Polyphenols
- Class
- Phenolic acids
- Sub-class
- Phenolic acids subclass not specified
Taxonomy as Metabolite
- Metabolite Family
- (Poly)phenol metabolites
- Metabolite Class
- Phenolic acid metabolites
- Metabolite Sub-class
- Phenylacetic acids
Taxonomy of its Food Phytochemical Precursor(s)
| Food Phytochemical | Family | Class | Sub-class | |
|---|---|---|---|---|
| Cyanidin 3-O-glucoside | Polyphenols | Flavonoids | Anthocyanins | Show Food Phytochemical |
| Procyanidin dimer A2 | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
| Orange flavanones | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
| (-)-Epicatechin | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
| (+)-Catechin | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
| Quercetin | Polyphenols | Flavonoids | Flavonols | Show Food Phytochemical |
| Caffeic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
| Black tea Flavan-3-ols | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
| Green tea Flavan-3-ols | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
| Hydroxytyrosol | Polyphenols | Miscellaneous polyphenols | Not Available | Show Food Phytochemical |
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Phenols
- Super-class
- Benzenoids
- Sub-class
- 1-hydroxy-2-unsubstituted benzenoids
- Direct Parent Name
- 1-hydroxy-2-unsubstituted benzenoids
- Alternative Parent Names
- ["Benzene and substituted derivatives", "Carbonyl compounds", "Carboxylic acids", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides"]
- External Descriptor Annotations
- ["monocarboxylic acid", "phenols"]
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound"]
Spectra from Phytohub
| Spectrum Type | Instrument Type | Technology | Ion Mode | Collision Energy | View | |
|---|---|---|---|---|---|---|
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) | Not Available | Positive | Not Available | View Spectrum | |
| GC-MS | GC-MS | Not Available | Not Available | Not Available | View Spectrum | |
| GC-MS | EI-B | instrument=HITACHI M-68 | positive | Not Available | View Spectrum | |
| GC-MS | EI-B | instrument=HITACHI M-52 | positive | Not Available | View Spectrum | |
| GC-MS | EI-B | instrument=GCMS-2010 Plus, Shimadzu | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies | positive | Not Available | View Spectrum | |
| GC-MS | GC-MS | Not Available | Not Available | Not Available | View Spectrum | |
| GC-MS | GC-EI-TOF | instrument=Leco Pegasus IV | positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, energy0 | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, Ionization energy 70 eV fully TMS-derivatized (structure: C[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C)C=C1) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, energy0 | Ei | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC(=O)CC1=CC=C(O)C=C1) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O)C=C1) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: CC(C)(C)[Si](C)(C)OC1=CC=C(CC(=O)O)C=C1) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: CC(C)(C)[Si](C)(C)OC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1) | Positive | Not Available | View Spectrum | |
| LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Negative | 10V | View Spectrum | |
| LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Negative | 25V | View Spectrum | |
| LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Negative | 40V | View Spectrum | |
| LC-MS/MS | EI-B (HITACHI M-68) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | EI-B (HITACHI M-52) | Not Available | Positive | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Negative | 10V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Negative | 20V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Negative | 30V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Negative | 40V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ (API3000, Applied Biosystems) | Not Available | Negative | 50V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ | instrument=API3000, Applied Biosystems | negative | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ | instrument=API3000, Applied Biosystems | negative | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ | instrument=API3000, Applied Biosystems | negative | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ | instrument=API3000, Applied Biosystems | negative | V | View Spectrum | |
| LC-MS/MS | LC-ESI-QQ | instrument=API3000, Applied Biosystems | negative | V | View Spectrum | |
| LC-MS/MS | Linear Ion Trap | instrument=Thermo Finnigan LTQ | negative | V | View Spectrum | |
| LC-MS/MS | Linear Ion Trap | instrument=Thermo Finnigan LTQ | negative | V | View Spectrum | |
| LC-MS/MS | Linear Ion Trap | instrument=Thermo Finnigan LTQ | positive | V | View Spectrum | |
| LC-MS/MS | Linear Ion Trap | instrument=Thermo Finnigan LTQ | positive | V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Positive | 40V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID | Negative | 40V | View Spectrum |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Olive, black | Fruit, Drupes | Publications | Show | |
| Olive, green | Fruit, Drupes | Publications | Show |
Food Sources of its Food Phytochemical(s)
Role as Biomarker of intake
No roles as Biomarker of intake found
Metabolism
| Food Phytochemical | Metabolite | Species | Biofluids | Origin | TMax | CMax | Urinary Excretion | Formula | Monoisotopic mass | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Cyanidin 3-O-glucoside | 4'-Hydroxyphenylacetic acid | human | feces, urine | Not Available | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
| Procyanidin dimer A2 | 4'-Hydroxyphenylacetic acid | in vitro (human) | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
| Orange flavanones | 4'-Hydroxyphenylacetic acid | human | plasma, urine, urine (major) | gut microbiota metabolite | 5h-8h | 50-200 nmol/L | 10-30% | C8H8O3 | 152.047344118 | Detailed Intervention Studies | Publications | ||
| (-)-Epicatechin | 4'-Hydroxyphenylacetic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
| (+)-Catechin | 4'-Hydroxyphenylacetic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
| Quercetin | 4'-Hydroxyphenylacetic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
| Caffeic acid | 4'-Hydroxyphenylacetic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
| Black tea Flavan-3-ols | 4'-Hydroxyphenylacetic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | <1% | C8H8O3 | 152.047344118 | Detailed Intervention Studies | Publications | ||
| Green tea Flavan-3-ols | 4'-Hydroxyphenylacetic acid | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Detailed Intervention Studies | |||
| Hydroxytyrosol | 4'-Hydroxyphenylacetic acid | human | plasma | gut microbiota metabolite | Not Available | 5-20µmol/L | Not Available | C8H8O3 | 152.047344118 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value |
|---|