Vanillic acid
precursor
Showing entry for Vanillic acid
Identification
- PhytoHub ID
- PHUB000316
- Name
- Vanillic acid
- Systematic Name
- 4-hydroxy-3-methoxybenzoic acid
- Synonyms
- 3-Methoxy-4-hydroxybenzoic acid
- 4-Hydroxy-3-methoxybenzoic acid
- p-Vanillic acid
- CAS Number
- 121-34-6
- Average Mass
- 168.148
- Monoisotopic Mass
- 168.042258738
- Chemical Formula
- C8H8O4
- IUPAC Name
- 4-hydroxy-3-methoxybenzoic acid
- InChI Key
- WKOLLVMJNQIZCI-UHFFFAOYSA-N
- InChI Identifier
InChI=1S/C8H8O4/c1-12-7-4-5(8(10)11)2-3-6(7)9/h2-4,9H,1H3,(H,10,11)
- SMILES
COC1=CC(=CC=C1O)C(O)=O
- Structure
Structure for Vanillic acid
Calculated Properties
- Solubility (ALOGPS)
- 5.70e+00 g/l
- LogS (ALOGPS)
- -1.47
- LogP (ALOGPS)
- 1.70
- Hydrogen Acceptors
- 4
- Hydrogen Donors
- 2
- Rotatable Bond Count
- 2
- Polar Surface Area
- 66.76
- Refractivity
- 41.7583
- Polarizability
- 15.868081533318291
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -4.901377890748089
- pKa (strongest acidic)
- 4.155416072405769
- Number of Rings
- 1
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
- ChEBI
- 30816
- PubChem
- 8468
- Chemistry Dashboard
- DTXSID6059522
- KNApSAcK
- C00002682
- MetaboLights
- MTBLC30816
- Phenol-Explorer
- 414
- Exposome Explorer
- 1485
- FooDB (Compounds)
- FDB000846
- PeakForestCompound
- 000276
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 |
| Caffeic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
| Dihydrocaffeic acid | (Poly)phenol metabolites | Phenolic acid metabolites | Phenylpropanoic acids | Show Food Phytochemical |
| Ferulic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
| Orange flavanones | Polyphenols | Flavonoids | Flavanones | 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
- M-methoxybenzoic acids and derivatives
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "Alkyl aryl ethers", "Anisoles", "Benzoic acids", "Benzoyl derivatives", "Carboxylic acids", "Hydrocarbon derivatives", "Hydroxybenzoic acid derivatives", "Methoxybenzenes", "Methoxyphenols", "Monocarboxylic acids and derivatives", "Organic oxides", "Phenoxy compounds"]
- External Descriptor Annotations
- ["methoxybenzoic acid", "monohydroxybenzoic acid"]
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "Alkyl aryl ether", "Anisole", "Aromatic homomonocyclic compound", "Benzoic acid", "Benzoyl", "Carboxylic acid", "Carboxylic acid derivative", "Ether", "Hydrocarbon derivative", "Hydroxybenzoic acid", "M-methoxybenzoic acid or derivatives", "Methoxybenzene", "Methoxyphenol", "Monocarboxylic acid or derivatives", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Phenol ether", "Phenoxy compound"]
Spectra from Online Resources
| Record ID | Source | Description | View |
|---|---|---|---|
| JP008196 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
| KO001150 | MassBank | LC-ESI-QQ Spectrum - 10 V, unspecified | View Spectra |
| KO001151 | MassBank | LC-ESI-QQ Spectrum - 20 V, unspecified | View Spectra |
| KO001152 | MassBank | LC-ESI-QQ Spectrum - 30 V, unspecified | View Spectra |
| KO001153 | MassBank | LC-ESI-QQ Spectrum - 40 V, unspecified | View Spectra |
| KO001154 | MassBank | LC-ESI-QQ Spectrum - 50 V, unspecified | View Spectra |
| ML005851 | MassBank | LC-ESI-ITFT Spectrum - 50 % (nominal), unspecified | View Spectra |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| American cranberry | Fruit, Berries | Publications | Show | |
| Date | Fruit, Other fruits | Publications | Show | |
| Olive, black | Fruit, Drupes | Publications | Show | |
| Olive, green | Fruit, Drupes | Publications | Show | |
| Strawberry | Fruit, Berries | Publications | Show | |
| Vanilla | Herbs and Spices | Publications | Show | |
| Whisky | Beverages, Alcoholic | Publications | Show | |
| White wine | Beverages, Alcoholic | 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 | Vanillic acid | human | faeces, serum, urine | Not Available | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | Publications | |||
| Caffeic acid | Vanillic acid | human | urine | host metabolism | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | Publications | |||
| Dihydrocaffeic acid | Vanillic acid | rat | urine | Not Available | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | ||||
| Ferulic acid | Vanillic acid | human rat | urine | Not Available | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | Publications | |||
| Orange flavanones | Vanillic acid | human | urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | Detailed Intervention Studies |
Inter-Individual Variations Metabolism
No data on inter-individual variations available