Dihydrocaffeic acid
precursor
Showing entry for Dihydrocaffeic acid
Identification
- PhytoHub ID
- PHUB000604
- Name
- Dihydrocaffeic acid
- Systematic Name
- 3-(3',4'-dihydroxyphenyl)propanoic acid
- Synonyms
- 2,3-Dihydrocaffeic acid
- 3-(3,4-dihydroxyphenyl)propanoic acid
- 3-(3,4-dihydroxyphenyl)propionic acid
- 3-(3',4'-Dihydroxyphenyl)propionic acid
- 3,4-dihydroxy-dihydrocinnamic acid
- 3,4-dihydroxybenzenepropanoic acid
- hydrocaffeic acid
- CAS Number
- 1078-61-1
- Average Mass
- 182.175
- Monoisotopic Mass
- 182.057908802
- Chemical Formula
- C9H10O4
- IUPAC Name
- 3-(3,4-dihydroxyphenyl)propanoic acid
- InChI Key
- DZAUWHJDUNRCTF-UHFFFAOYSA-N
- InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
- SMILES
OC(=O)CCC1=CC(O)=C(O)C=C1
- Structure
Structure for Dihydrocaffeic acid
Calculated Properties
- Solubility (ALOGPS)
- 2.62e+00 g/l
- LogS (ALOGPS)
- -1.84
- LogP (ALOGPS)
- 1.04
- Hydrogen Acceptors
- 4
- Hydrogen Donors
- 3
- Rotatable Bond Count
- 3
- Polar Surface Area
- 77.76
- Refractivity
- 45.9284
- Polarizability
- 17.84878987605153
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -6.289086658260411
- pKa (strongest acidic)
- 3.8379150142223004
- Number of Rings
- 1
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- Yes
- 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
- Phenylpropanoic acids
Taxonomy of its Food Phytochemical Precursor(s)
| Food Phytochemical | Family | Class | Sub-class | |
|---|---|---|---|---|
| Eriocitrin | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
| Eriodictyol | Polyphenols | Flavonoids | Flavanones | Show Food Phytochemical |
| Caffeic acid | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
| 5-O-Caffeoylquinic 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 |
| Coffee Chlorogenic acids | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
| Yerba mate Chlorogenic acids | Polyphenols | Phenolic acids | Hydroxycinnamic acids | Show Food Phytochemical |
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Phenylpropanoic acids
- Super-class
- Phenylpropanoids and polyketides
- Sub-class
- Not Available
- Direct Parent Name
- Phenylpropanoic acids
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Benzene and substituted derivatives", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides"]
- External Descriptor Annotations
- ["catechols", "monocarboxylic acid"]
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "3-phenylpropanoic-acid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Catechol", "Hydrocarbon derivative", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol"]
Spectra from Phytohub
| Spectrum Type | Instrument Type | Technology | Ion Mode | Collision Energy | View | |
|---|---|---|---|---|---|---|
| GC-MS | GC-MS | Not Available | Not Available | Not Available | View Spectrum | |
| GC-MS | GC-MS | Not Available | Not Available | 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)CCC1=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, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC(=O)CCC1=CC=C(O)C(O)=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(CCC(=O)O)=CC=C1O) | 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(CCC(=O)O)C=C1O) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC(=O)CCC1=CC=C(O[Si](C)(C)C)C(O)=C1) | Positive | Not Available | View Spectrum | |
| Predicted GC-MS | GC-MS | Predicted by CFMID-EI, 70eV, fully TMS-derivatized (structure: C[Si](C)(C)OC(=O)CCC1=CC=C(O)C(O[Si](C)(C)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(CCC(=O)O)C=C1O[Si](C)(C)C) | 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)CCC1=CC=C(O)C(O)=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(CCC(=O)O)=CC=C1O) | 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(CCC(=O)O)C=C1O) | 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)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=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)CCC1=CC=C(O)C(O[Si](C)(C)C(C)(C)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(CCC(=O)O)C=C1O[Si](C)(C)C(C)(C)C) | 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)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1) | Positive | 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 | 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 | |
| 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 4.0 | Negative | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID 4.0 | Negative | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID 4.0 | Negative | 40V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID 4.0 | Positive | 10V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID 4.0 | Positive | 20V | View Spectrum | |
| Predicted LC-MS/MS | Not Available | Predicted by CFM-ID 4.0 | Positive | 40V | View Spectrum |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Blueberry | Fruit, Berries | Show | ||
| Broccoli | Vegetables, Cabbages | Show | ||
| Cider | Beverages, Alcoholic | Show | ||
| Coffee | Coffee and coffee products | Show | ||
| Common wheat | Cereals and cereal products | Show | ||
| Corn | Cereals and cereal products | Show | ||
| Grapes | Fruit, Berries | Show | ||
| Lemon | Fruit, Citrus | Show | ||
| Lettuce | Vegetables, Leaf vegetables | Show | ||
| Lime | Fruit, Citrus | Show | ||
| Olive, black | Fruit, Drupes | Publications | Show | |
| Olive, green | Fruit, Drupes | Publications | Show | |
| Spinach | Vegetables, Leaf vegetables | Show | ||
| Wheat bread | Cereals and cereal products | 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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Dihydrocaffeic acid | Vanillic acid | rat | urine | Not Available | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | ||||
| Dihydrocaffeic acid | 3-(3'-Hydroxyphenyl)propionic acid | rat | urine | Not Available | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
| Dihydrocaffeic acid | Dihydroferulic acid | rat | urine | Not Available | Not Available | Not Available | Not Available | C10H12O4 | 196.073558866 | Publications | |||
| Dihydrocaffeic acid | Dihydrocaffeic acid-3'-O-glucuronide | rat | urine | Not Available | Not Available | Not Available | Not Available | C15H18O10 | 358.08999678 | Publications | |||
| Dihydrocaffeic acid | Dihydrocaffeic acid-4'-O-glucuronide | rat | urine | Not Available | Not Available | Not Available | Not Available | C15H18O10 | 358.08999678 | Publications | |||
| Dihydrocaffeic acid | Dihydrocaffeic acid-4'-sulfate | rat | urine | Not Available | Not Available | Not Available | Not Available | C9H10O7S | 262.014723836 | Publications | |||
| Eriocitrin | Dihydrocaffeic acid | in vitro (human) rat | plasma (major), urine (major) | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Publications | |||
| Eriodictyol | Dihydrocaffeic acid | in vitro (human) rat | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Publications | |||
| Caffeic acid | Dihydrocaffeic acid | rat | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Publications | |||
| 5-O-Caffeoylquinic acid | Dihydrocaffeic acid | rat | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Publications | |||
| Ferulic acid | Dihydrocaffeic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | ||||
| Orange flavanones | Dihydrocaffeic acid | human | plasma, urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Detailed Intervention Studies | Publications | ||
| Cocoa Flavan-3-ols | Dihydrocaffeic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | <1% | C9H10O4 | 182.057908802 | Detailed Intervention Studies | Publications | ||
| Black tea Flavan-3-ols | Dihydrocaffeic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | <1% | C9H10O4 | 182.057908802 | Detailed Intervention Studies | Publications | ||
| Coffee Chlorogenic acids | Dihydrocaffeic acid | human | plasma, urine | gut microbiota metabolite | 5h-8h | 50-200 nmol/L | <1% | C9H10O4 | 182.057908802 | Detailed Intervention Studies | Publications | ||
| Yerba mate Chlorogenic acids | Dihydrocaffeic acid | human | plasma, urine | gut microbiota metabolite | 5h-8h | 20-50 nmol/L | <1% | C9H10O4 | 182.057908802 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value | |||
|---|---|---|---|---|---|---|
| Cocoa Flavan-3-ols | Dihydrocaffeic acid | Microbiota | Effect, clusters | Publications | ||
| Coffee Chlorogenic acids | Dihydrocaffeic acid | Microbiota | Effect, clusters | Publications |