Caffeic acid
precursor
Showing entry for Caffeic acid
Identification
- PhytoHub ID
- PHUB000574
- Name
- Caffeic acid
- Systematic Name
- 3',4'-dihydroxycinnamic acid
- Synonyms
- 3-(3,4-dihydroxyphenyl)acrylic acid
- 3,4-Dihydroxycinnamic acid
- 3,4-Dihydroxyphenylpropenic acid
- trans-caffeic acid
- CAS Number
- 331-39-5
- Average Mass
- 180.159
- Monoisotopic Mass
- 180.042258738
- Chemical Formula
- C9H8O4
- IUPAC Name
- (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
- InChI Key
- QAIPRVGONGVQAS-DUXPYHPUSA-N
- InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
- SMILES
OC(=O)\C=C\C1=CC(O)=C(O)C=C1
- Structure
Calculated Properties
- Solubility (ALOGPS)
- 1.61e+00 g/l
- LogS (ALOGPS)
- -2.05
- LogP (ALOGPS)
- 1.67
- Hydrogen Acceptors
- 4
- Hydrogen Donors
- 3
- Rotatable Bond Count
- 2
- Polar Surface Area
- 77.76
- Refractivity
- 47.021699999999996
- Polarizability
- 17.3100815082372
- Formal Charge
- 0
- Physiological Charge
- -1
- pKa (strongest basic)
- -6.283746523508148
- pKa (strongest acidic)
- 3.4517963199924626
- Number of Rings
- 1
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
External Links
- ChEBI
- 16433
- PubChem
- 689043
- KNApSAcK
- C00000615
- MetaboLights
- MTBLC16433
- Phenol-Explorer
- 457
- PeakForestCompound
- 000442
- HMDB
- HMDB0001964
Taxonomy as Food Phytochemical
- Family
- Polyphenols
- Class
- Phenolic acids
- Sub-class
- Hydroxycinnamic acids
Taxonomy as Metabolite
- Metabolite Family
- (Poly)phenol metabolites
- Metabolite Class
- Phenolic acid metabolites
- Metabolite Sub-class
- Cinnamic acids
Taxonomy of its Food Phytochemical Precursor(s)
Classyfire Taxonomy
- Kingdom Name
- Organic compounds
- Class
- Cinnamic acids and derivatives
- Super-class
- Phenylpropanoids and polyketides
- Sub-class
- Hydroxycinnamic acids and derivatives
- Direct Parent Name
- Hydroxycinnamic acids
- Alternative Parent Names
- ["1-hydroxy-2-unsubstituted benzenoids", "1-hydroxy-4-unsubstituted benzenoids", "Carbonyl compounds", "Carboxylic acids", "Catechols", "Cinnamic acids", "Coumaric acids and derivatives", "Hydrocarbon derivatives", "Monocarboxylic acids and derivatives", "Organic oxides", "Styrenes"]
- External Descriptor Annotations
- ["Caffeate derivatives", "caffeic acid"]
- Substituent Names
- ["1-hydroxy-2-unsubstituted benzenoid", "1-hydroxy-4-unsubstituted benzenoid", "Aromatic homomonocyclic compound", "Benzenoid", "Carbonyl group", "Carboxylic acid", "Carboxylic acid derivative", "Catechol", "Cinnamic acid", "Coumaric acid or derivatives", "Hydrocarbon derivative", "Hydroxycinnamic acid", "Monocarboxylic acid or derivatives", "Monocyclic benzene moiety", "Organic oxide", "Organic oxygen compound", "Organooxygen compound", "Phenol", "Styrene"]
Spectra from Online Resources
Record ID | Source | Description | View |
---|---|---|---|
BML00722 | MassBank | LC-ESI-QTOF Spectrum - 10 ev, unspecified | View Spectra |
BML00729 | MassBank | LC-ESI-QTOF Spectrum - 20 ev, unspecified | View Spectra |
BML80856 | MassBank | LC-ESI-QTOF Spectrum - -, unspecified | View Spectra |
JP004107 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
JP007237 | MassBank | EI-B Spectrum - -, [M]+* | View Spectra |
KO000510 | MassBank | LC-ESI-QQ Spectrum - 10 V, unspecified | View Spectra |
KO000511 | MassBank | LC-ESI-QQ Spectrum - 20 V, unspecified | View Spectra |
KO000512 | MassBank | LC-ESI-QQ Spectrum - 30 V, unspecified | View Spectra |
KO000513 | MassBank | LC-ESI-QQ Spectrum - 40 V, unspecified | View Spectra |
KO000514 | MassBank | LC-ESI-QQ Spectrum - 50 V, unspecified | View Spectra |
OUF00132 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
PR010139 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
PR010140 | MassBank | GC-EI-TOF Spectrum - -, unspecified | View Spectra |
PR040210 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, [M-H]- | View Spectra |
PR040211 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, [M-H-CO2]- | View Spectra |
PR040212 | MassBank | LC-ESI-QTOF Spectrum - 30 V, [M-H]- | View Spectra |
PR040213 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, [M+H]+ | View Spectra |
PR040214 | MassBank | LC-ESI-QTOF Spectrum - 30 V, [M+H]+ | View Spectra |
PR100110 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified | View Spectra |
PR100533 | MassBank | LC-ESI-QTOF Spectrum - Ramp 5-60 V, unspecified | View Spectra |
PS017701 | ReSpect | N/A Spectrum - 10, [M+H]+ | View Spectra |
PS017702 | ReSpect | N/A Spectrum - 20, [M+H]+ | View Spectra |
PS017707 | ReSpect | N/A Spectrum - 10, [M-H]- | View Spectra |
PS017708 | ReSpect | N/A Spectrum - 20, [M-H]- | View Spectra |
PS017709 | ReSpect | N/A Spectrum - 30, [M-H]- | View Spectra |
PS044601 | ReSpect | N/A Spectrum - 10, [M+H]+ | View Spectra |
PS044602 | ReSpect | N/A Spectrum - 20, [M+H]+ | View Spectra |
PS044607 | ReSpect | N/A Spectrum - 10, [M-H]- | View Spectra |
PS044608 | ReSpect | N/A Spectrum - 20, [M-H]- | View Spectra |
PS044609 | ReSpect | N/A Spectrum - 30, [M-H]- | View Spectra |
Food Sources
Name | Group | |||
---|---|---|---|---|
American cranberry | Fruit, Berries | Publications | Show | |
Apple | Fruit, Pomes | Publications | Show | |
Apple juice | Beverages, Non-alcoholic | Publications | Show | |
Beer | Beverages, Alcoholic | Publications | Show | |
Blackberry | Fruit, Berries | Publications | Show | |
Blueberry | Fruit, Berries | Publications | Show | |
Broccoli | Vegetables, Cabbages | Publications | Show | |
Carrot | Vegetables, Root vegetables | Publications | Show | |
Cider | Beverages, Alcoholic | Publications | Show | |
Coffee | Coffee and coffee products | Publications | Show | |
Common wheat | Cereals and cereal products | Publications | Show | |
Eggplant | Vegetables, Fruit vegetables | Publications | Show | |
European cranberry | Fruit, Berries | Publications | Show | |
European plum | Fruit, Drupes | Publications | Show | |
Mate | Teas and herbal teas | Publications | Show | |
Olive, black | Fruit, Drupes | Publications | Show | |
Olive, green | Fruit, Drupes | Publications | Show | |
Pear | Fruit, Pomes | Publications | Show | |
Strawberry | Fruit, Berries | Publications | Show | |
Sweet cherry | Fruit, Drupes | Publications | Show | |
Tomato | Vegetables, Fruit vegetables | Publications | Show | |
White wine grape | Fruit, Berries | 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 | ||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|
Caffeic acid | 3-Hydroxybenzoic acid | human in vitro (human) rat | feces, urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C7H6O3 | 138.031694053 | Publications | |||
Caffeic acid | p-Hydroxybenzoic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C7H6O3 | 138.031694053 | Publications | |||
Caffeic acid | Benzoic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C7H6O2 | 122.036779433 | Publications | |||
Caffeic acid | Protocatechuic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C7H6O4 | 154.026608673 | Publications | |||
Caffeic acid | Vanillic acid | human | urine | host metabolism | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | Publications | |||
Caffeic acid | 3',4'-Dihydroxyphenylacetic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | Publications | |||
Caffeic acid | 4'-Hydroxyphenylacetic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
Caffeic acid | Caffeic acid | human | plasma, urine | unchanged | 1h-3h | <20 nmol/L | <1% | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications | ||
Caffeic acid | Catechol | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C6H6O2 | 110.036779433 | Publications | |||
Caffeic acid | Coumaric acid (m-) | rat | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H8O3 | 164.047344118 | Publications | |||
Caffeic acid | Dihydrocaffeic acid | rat | urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Publications | |||
Caffeic acid | Phloretic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
Caffeic acid | Ferulic acid | human rat | plasma, urine | host metabolism | Not Available | Not Available | Not Available | C10H10O4 | 194.057908802 | Publications | |||
Caffeic acid | Isoferulic acid | human rat | feces, plasma, urine | host metabolism | Not Available | Not Available | Not Available | C10H10O4 | 194.057908802 | Publications | |||
Caffeic acid | 3-(3',4'-Dihydroxyphenyl)propionic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Publications | |||
Caffeic acid | 3-(3'-Hydroxyphenyl)propionic acid | rat | plasma, urine | gut microbiota metabolite | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
Caffeic acid | 3'-Hydroxyphenylacetic acid | human | Not Available | host metabolism | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
Caffeic acid | Phenylacetic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C8H8O2 | 136.052429498 | Publications | |||
Caffeic acid | 3-Phenylpropionic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C9H10O2 | 150.068079562 | Publications | |||
Caffeic acid | 3-Hydroxyhippuric acid | rat | urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C9H9NO4 | 195.053157774 | Publications | |||
Caffeic acid | Caffeic acid sulfoglucuronide | rat | plasma | Not Available | Not Available | Not Available | Not Available | C15H16O13S | 436.3485242 | Publications | |||
Caffeic acid | Dihydroferulic acid | human | urine | Not Available | Not Available | Not Available | Not Available | C10H12O4 | 196.073558866 | Publications | |||
Caffeic acid | Ferulic acid-4'-O-glucuronide | rat | plasma | Not Available | Not Available | Not Available | Not Available | C16H18O10 | 370.08999678 | Publications | |||
Caffeic acid | Ferulic acid-4'-sulfate | rat | plasma | Not Available | Not Available | Not Available | Not Available | C10H10O7S | 274.014723836 | Publications | |||
Caffeic acid | Ferulic acid sulfoglucuronide | rat | plasma | Not Available | Not Available | Not Available | Not Available | C16H18O13S | 450.375513 | Publications | |||
Caffeic acid | Feruloylglycine | human | urine | Not Available | Not Available | Not Available | Not Available | C12H13NO5 | 251.079372523 | Publications | |||
Caffeic acid | Hippuric acid | rat | plasma, urine | host-gut microbiota co-metabolite | Not Available | Not Available | Not Available | C9H9NO3 | 179.058243154 | Publications | |||
Caffeic acid | Hydroxybenzoic acid | rat | urine | Not Available | Not Available | Not Available | Not Available | C7H6O3 | 138.1230293 | Publications | |||
Caffeic acid | α-hydroxyhippuric acid | rat | urine | Not Available | Not Available | Not Available | Not Available | C9H9NO4 | 195.053157774 | Publications | |||
Caffeic acid | 4-Hydroxyphenylpropionic acid | rat | plasma, urine | Not Available | Not Available | Not Available | Not Available | C9H10O3 | 166.062994182 | Publications | |||
Caffeic acid | Vanilloyl-glycine | human | urine | Not Available | Not Available | Not Available | Not Available | C10H11NO5 | 225.063722458 | Publications | |||
Caffeic acid | Dihydrocaffeic acid-3'-O-glucuronide | human | plasma | host metabolism | Not Available | Not Available | Not Available | C15H18O10 | 358.08999678 | Publications | |||
Caffeic acid | Isoferulic acid-3'-sulfate | human | plasma | host metabolism | Not Available | Not Available | Not Available | C10H10O7S | 274.014723836 | Publications | |||
Caffeic acid | 4-Hydroxyhippuric acid | human | Not Available | host metabolism | Not Available | Not Available | Not Available | C9H9NO4 | 195.053157774 | Publications | |||
Caffeic acid | Isoferulic acid-3'-O-glucuronide | human | plasma | host metabolism | Not Available | Not Available | Not Available | C16H18O10 | 370.08999678 | Publications | |||
Caffeic acid | Dihydroisoferulic acid | human | plasma | host metabolism | Not Available | Not Available | Not Available | C10H12O4 | 196.073558866 | Publications | |||
Caffeic acid | Dihydroisoferulic acid-3'-glucuronide | human | plasma | host metabolism | Not Available | Not Available | Not Available | C16H18O10 | 370.08999678 | Publications | |||
Caffeic acid | Dihydroferulic acid-4'-O-glucuronide | human | plasma | host metabolism | Not Available | Not Available | Not Available | C16H20O10 | 372.105646844 | Publications | |||
Caffeic acid | Dihydroferulic acid-4'-sulfate | human | plasma | host metabolism | Not Available | Not Available | Not Available | C10H12O7S | 276.0303739 | Publications | |||
Caffeic acid | 4-Hydroxymandelic acid | human | Not Available | host metabolism | Not Available | Not Available | Not Available | C8H8O4 | 168.042258738 | Publications | |||
Caffeic acid | Dihydrocaffeic acid-3-sulfate | human | plasma | host metabolism | Not Available | Not Available | Not Available | C9H10O7S | 262.014723836 | Publications | |||
Caffeic acid | Caffeic acid 3'-sulfate | human | plasma | host metabolism | Not Available | Not Available | Not Available | C9H8O7S | 259.999073772 | Publications | |||
Caffeic acid | 4-Hydroxybenzoic acid -3-sulfate | human | Not Available | host metabolism | Not Available | Not Available | Not Available | C7H5O7S | 232.976147255 | Publications | |||
Caffeic acid | 3-(4'-Hydroxyphenyl)propionic acid-3'-sulfate | human | Not Available | host metabolism | Not Available | Not Available | Not Available | C9H9O7S | 261.007447384 | Publications | |||
Caffeic acid | caffeic acid-3'-O-glucuronide | rat | Not Available | Not Available | Not Available | Not Available | Not Available | C15H16O10 | 356.074346715 | Publications | |||
Caffeic acid | caffeic acid-4'-O-glucuronide | rat | Not Available | Not Available | Not Available | Not Available | Not Available | C15H16O10 | 356.074346715 | Publications | |||
Caffeic acid | caffeic acid-4-O-sulfate | human | plasma | host metabolism | Not Available | Not Available | Not Available | C9H8O7S | 259.999073772 | Publications | |||
Caffeic acid | 3'-Methoxy-4'-hydroxyphenylacetic acid | human | Not Available | Not Available | Not Available | Not Available | Not Available | C9H10O4 | 182.057908802 | Publications | |||
Caffeic acid | 3-Hydroxybenzoic acid-4-sulfate | human | Not Available | host metabolism | Not Available | Not Available | Not Available | C8H8O7S | 247.999073772 | Publications | |||
Caffeic acid | Caffeic acid sulfate | human | plasma | host metabolism | Not Available | 0.5-2µmol/L | Not Available | Detailed Intervention Studies | Publications | ||||
Cyanidin 3-O-glucoside | Caffeic acid | human | feces | Not Available | Not Available | Not Available | Not Available | C9H8O4 | 180.042258738 | Publications | |||
5-O-Caffeoylquinic acid | Caffeic acid | rat | urine | host metabolism | Not Available | Not Available | Not Available | C9H8O4 | 180.042258738 | Publications | |||
Rosmarinic acid | Caffeic acid | rat | urine | Not Available | Not Available | Not Available | Not Available | C9H8O4 | 180.042258738 | Publications | |||
Blueberry (Poly)phenols | Caffeic acid | human | plasma | gut microbiota metabolite | 5h-8h | <20 nmol/L | Not Available | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications | ||
Cranberry (Poly)phenols | Caffeic acid | human | plasma, urine | gut microbiota metabolite | 5h-8h | <20 nmol/L | <1% | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications | ||
Olive oil (Poly)phenols | Caffeic acid | human | plasma | gut microbiota metabolite | Not Available | 2-5µmol/L | Not Available | C9H8O4 | 180.042258738 | Detailed Intervention Studies | |||
Globe artichoke (Poly)phenols | Caffeic acid | human | plasma, urine | gut microbiota metabolite | 5h-8h | <20 nmol/L | <1% | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications | ||
Coffee Chlorogenic acids | Caffeic acid | human | plasma, urine | host metabolism | 1h-3h | <20 nmol/L | <1% | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications | ||
Rosemary tea (poly)phenols | Caffeic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | <1% | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications | ||
Tomato (Poly)phenols | Caffeic acid | human | urine | gut microbiota metabolite | Not Available | Not Available | 1-5% | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications | ||
Grape (Poly)phenols | Caffeic acid | human | plasma | host metabolism | <1h | 50-200 nmol/L | Not Available | C9H8O4 | 180.042258738 | Detailed Intervention Studies | Publications |
Inter-Individual Variations in Metabolism
Food Phytochemical | Metabolite | Effect | Value | |||
---|---|---|---|---|---|---|
Globe artichoke (Poly)phenols | Caffeic acid | Microbiota | Effect, clusters | Publications | ||
Coffee Chlorogenic acids | Caffeic acid | Microbiota | Effect, clusters | Publications |