Protocatechuic acid
precursor
Showing entry for Protocatechuic acid
Identification
- PhytoHub ID
- PHUB000310
- Name
- Protocatechuic acid
- Systematic Name
- 3,4-dihydroxybenzoic acid
- Synonyms
- 3,4-Dihydroxybenzoic acid
- CAS Number
- 99-50-3
- Average Mass
- 154.121
- Monoisotopic Mass
- 154.026608673
- Chemical Formula
- C7H6O4
- IUPAC Name
- 3,4-dihydroxybenzoic acid
- InChI Key
- YQUVCSBJEUQKSH-UHFFFAOYSA-N
- InChI Identifier
InChI=1S/C7H6O4/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,8-9H,(H,10,11)
- SMILES
OC(=O)C1=CC(O)=C(O)C=C1
- Structure
Calculated Properties
- Solubility (ALOGPS)
- 1.24e+01 g/l
- LogS (ALOGPS)
- -1.10
- LogP (ALOGPS)
- 1.32
- Hydrogen Acceptors
- 4
- Hydrogen Donors
- 3
- Rotatable Bond Count
- 1
- Polar Surface Area
- 77.76
- Refractivity
- 37.275999999999996
- Polarizability
- 13.845510992306696
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -6.341303650784173
- pKa (strongest acidic)
- 4.160229176821464
- 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
- Hydroxybenzoic acids
Taxonomy as Metabolite
- Metabolite Family
- (Poly)phenol metabolites
- Metabolite Class
- Phenolic acid metabolites
- Metabolite Sub-class
- Benzoic and hippuric acids
Taxonomy of its Food Phytochemical Precursor(s)
Food Phytochemical | Family | Class | Sub-class | |
---|---|---|---|---|
Cyanidin 3-O-glucoside | Polyphenols | Flavonoids | Anthocyanins | Show Food Phytochemical |
Quercetin | Polyphenols | Flavonoids | Flavonols | Show Food Phytochemical |
Caffeic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
Ferulic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
Orange flavanones | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
Cocoa Flavan-3-ols | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
Black tea Flavan-3-ols | Polyphenols | Flavonoids | Flavan-3-ols | Show Food Phytochemical |
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Benzene and substituted derivatives
- Super-class
- Benzenoids
- Sub-class
- Benzoic acids and derivatives
- Direct Parent Name
- Hydroxybenzoic acid derivatives
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Benzoic acids", "Benzoyl derivatives", "Carboxylic acids", "Catechols", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Organooxygen compounds"]
- External Descriptor Annotations
- ["catechols", "dihydroxybenzoic acid"]
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Benzoic acid", "Benzoyl", "Carboxylic acid", "Carboxylic acid derivative", "Catechol", "Dihydroxybenzoic acid", "Hydrocarbon derivative", "Hydroxybenzoic acid", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol"]
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-MS | Not Available | Not Available | Not Available | View Spectrum | |
GC-MS | EI-B | instrument=HITACHI M-52 | 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)C1=CC=C(O[Si](C)(C)C)C(O[Si](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, energy0 | Ei | Not Available | View Spectrum | |
LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Positive | 10V | View Spectrum | |
LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Positive | 25V | View Spectrum | |
LC-MS/MS | Quattro_QQQ | delivery=Flow_Injection analyzer=Triple_Quad | Positive | 40V | View Spectrum | |
LC-MS/MS | EI-B (HITACHI M-52) | Not Available | Positive | V | View Spectrum | |
LC-MS/MS | LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) | Not Available | Negative | V | View Spectrum | |
LC-MS/MS | LC-ESI-QTOF | instrument=UPLC Q-Tof Premier, Waters | negative | V | View Spectrum | |
LC-MS/MS | Not Available | instrument=Q-Exactive Plus | negative | V | View Spectrum | |
LC-MS/MS | Not Available | instrument=qTof | positive | V | View Spectrum | |
LC-MS/MS | Not Available | Not Available | Negative | 40V | View Spectrum | |
LC-MS/MS | Not Available | Not Available | Negative | 35V | View Spectrum | |
LC-MS/MS | Not Available | Not Available | Negative | 35V | View Spectrum | |
LC-MS/MS | Not Available | Not Available | Negative | 20V | View Spectrum | |
LC-MS/MS | Not Available | Not Available | Negative | 10V | 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 | 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 | |
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 | |||
---|---|---|---|---|
Apple juice | Beverages, Non-alcoholic | Publications | Show | |
Apricot | Fruit, Drupes | Publications | Show | |
Beer | Beverages, Alcoholic | Publications | Show | |
Cocoa | Cocoa and cocoa products | Publications | Show | |
Date | Fruit, Other fruits | Publications | Show | |
Olive, black | Fruit, Drupes | Publications | Show | |
Olive, green | Fruit, Drupes | Publications | Show | |
Onion | Vegetables, Onion-family | 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 | Protocatechuic acid | human | feces, serum, urine | Not Available | Not Available | Not Available | Not Available | C7H6O4 | 154.026608673 | Publications | |||
Quercetin | Protocatechuic acid | in vitro (human) | duodenal juice | gut microbiota metabolite | Not Available | Not Available | Not Available | C7H6O4 | 154.026608673 | Publications | |||
Caffeic acid | Protocatechuic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C7H6O4 | 154.026608673 | Publications | |||
Ferulic acid | Protocatechuic acid | human | plasma, urine | Not Available | Not Available | Not Available | Not Available | C7H6O4 | 154.026608673 | Publications | |||
Orange flavanones | Protocatechuic acid | human | plasma, urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C7H6O4 | 154.026608673 | Detailed Intervention Studies | Publications | ||
Cocoa Flavan-3-ols | Protocatechuic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | <1% | C7H6O4 | 154.026608673 | Detailed Intervention Studies | Publications | ||
Black tea Flavan-3-ols | Protocatechuic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | <1% | C7H6O4 | 154.026608673 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value | |||
---|---|---|---|---|---|---|
Cocoa Flavan-3-ols | Protocatechuic acid | Microbiota | Effect, clusters | Publications |