(+)-Catechin
precursor
Showing entry for (+)-Catechin
Identification
- PhytoHub ID
- PHUB000261
- Name
- (+)-Catechin
- Systematic Name
- (+)-Catechin
- Synonyms
- (2R,3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol
- 3,5,7,3',4'-Pentahydroxyflavane
- catechuic acid
- Cianidanol
- CAS Number
- 154-23-4
- Average Mass
- 290.271
- Monoisotopic Mass
- 290.079038171
- Chemical Formula
- C15H14O6
- IUPAC Name
- (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
- InChI Key
- PFTAWBLQPZVEMU-DZGCQCFKSA-N
- InChI Identifier
InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15+/m0/s1
- SMILES
O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1
- Structure
Structure for (+)-Catechin
Calculated Properties
- Solubility (ALOGPS)
- 6.45e-01 g/l
- LogS (ALOGPS)
- -2.65
- LogP (ALOGPS)
- 1.02
- Hydrogen Acceptors
- 6
- Hydrogen Donors
- 5
- Rotatable Bond Count
- 1
- Polar Surface Area
- 110.38000000000001
- Refractivity
- 73.99969999999999
- Polarizability
- 28.523855267889235
- Formal Charge
- 0
- Physiological Charge
- 0
- pKa (strongest basic)
- -3.2897193322428566
- pKa (strongest acidic)
- 9.004573813837975
- Number of Rings
- 3
- Rule of Five
- Yes
- Bioavailability
- Yes
- Ghose Filter
- Yes
- Veber's Rule
- No
- MDDR-like Rule
- No
Taxonomy as Food Phytochemical
- Family
- Polyphenols
- Class
- Flavonoids
- Sub-class
- Flavan-3-ols
Spectra from Phytohub
| Spectrum Type | Instrument Type | Ion Mode | Collision Energy Level | View | Peaks | |
|---|---|---|---|---|---|---|
| LC-MS/MS | ESI- LC-Q-TOF/MS | Positive | low | View Spectrum | (123.045,0.793);(139.0397,0.999);(147.0451,0.241);(161.0609,0.099);(165.0558,0.148);(291.0868,0.155) | |
| LC-MS/MS | ESI- LC-Q-TOF/MS | Negative | low | View Spectrum | (81.0353,0.055);(83.015,0.072);(93.0355,0.05);(95.051,0.073);(97.0299,0.126);(109.0298,0.447);(121.0298,0.108);(122.0374,0.078);(123.0455,0.403);(125.0248,0.261);(135.0451,0.051);(137.0248,0.16);(149.0249,0.085);(151.0403,0.167);(159.0451,0.07);(161.0612,0.087);(164.0119,0.059);(165.0196,0.07);(179.0356,0.106);(187.041,0.094);(188.0487,0.071);(203.0721,0.25);(205.052,0.189);(221.0833,0.079);(245.0828,0.364);(289.0712,0.999) |
Food Sources
| Name | Group | |||
|---|---|---|---|---|
| Apple | Fruit, Pomes | Publications | Show | |
| Apple cider | Beverages, Alcoholic | Publications | Show | |
| Apple juice | Beverages, Non-alcoholic | Publications | Show | |
| Apricot | Fruit, Drupes | Publications | Show | |
| Banana | Fruit, Tropical fruits | Publications | Show | |
| Beer | Beverages, Alcoholic | Publications | Show | |
| Black tea | Teas and herbal teas | Publications | Show | |
| Blackberry | Fruit, Berries | Publications | Show | |
| Broad bean | Pulses and beans | Publications | Show | |
| Chocolate | Cocoa and cocoa products | Publications | Show | |
| Cocoa | Cocoa and cocoa products | Publications | Show | |
| Cocoa bean | Cocoa and cocoa products | Publications | Show | |
| European plum | Fruit, Drupes | Publications | Show | |
| Green tea | Teas and herbal teas | Publications | Show | |
| Peach | Fruit, Drupes | Publications | Show | |
| Pear | Fruit, Pomes | Publications | Show | |
| Pecan nut | Nuts | Publications | Show | |
| Red wine | Beverages, Alcoholic | Publications | Show | |
| Strawberry | Fruit, Berries | Publications | Show | |
| Sweet cherry | Fruit, Drupes | Publications | Show |
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 | ||||
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| (+)-Catechin | (+)-Catechin | human | plasma, urine | unchanged | Not Available | <20 nmol/L | <1% | C15H14O6 | 290.079038171 | Detailed Intervention Studies | Publications | ||
| (+)-Catechin | 4'-Hydroxyphenylacetic acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C8H8O3 | 152.047344118 | Publications | |||
| (+)-Catechin | (Epi)catechin O-glucuronide | human | plasma, urine | host metabolism | Not Available | <20 nmol/L | 1-5% | C21H22O12 | 466.3989068 | Publications | |||
| (+)-Catechin | (Epi)catechin O-sulfate | human | plasma, urine | host metabolism | Not Available | 50-200 nmol/L | 30-50% | C15H14O9S | 370.335352 | Publications | |||
| (+)-Catechin | 5-(3',4'-dihydroxyphenyl)-gamma-valerolactone | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C11H12O4 | 208.073558866 | Publications | |||
| (+)-Catechin | 5-(3',4'-dihydroxyphenyl)valeric acid | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C11H14O4 | 210.089208931 | Publications | |||
| (+)-Catechin | 5-(4’-hydroxyphenyl)-gamma-valerolactone | human | Not Available | gut microbiota metabolite | Not Available | Not Available | Not Available | C11H12O3 | 192.078644246 | Publications | |||
| (+)-Catechin | Methoxy-(epi)catechin-sulfate | human | plasma, urine | host metabolism | Not Available | <20 nmol/L | 5-10% | Publications | |||||
| (+)-Catechin | Methoxy-(epi)catechin-glucuronide | human | plasma, urine | host metabolism | Not Available | 20-50 nmol/L | 1-5% | Publications | |||||
| (+)-Catechin | 3'-Methoxy-(+)-catechin | Not Available | Not Available | Not Available | Not Available | Not Available | Not Available | C16H16O6 | 304.094688235 | Detailed Intervention Studies |
Inter-Individual Variations in Metabolism
| Food Phytochemical | Metabolite | Effect | Value |
|---|