Record Information |
---|
Version | 1.0 |
---|
Creation date | 2010-04-08 22:05:26 UTC |
---|
Update date | 2019-11-26 02:57:38 UTC |
---|
Primary ID | FDB002571 |
---|
Secondary Accession Numbers | |
---|
Chemical Information |
---|
FooDB Name | Catechin |
---|
Description | Catechin, also known as (2R,3S)-catechin or cianidanol, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Catechin is a bitter tasting compound. Catechin is found, on average, in the highest concentration within a few different foods, such as blackcurrants (Ribes nigrum), evergreen blackberries (Rubus laciniatus), and blackberries (Rubus) and in a lower concentration in european plums (Prunus domestica), redcurrants (Ribes rubrum), and cocoa powder. Catechin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), pineapples (Ananas comosus), cloves (Syzygium aromaticum), lingonberries (Vaccinium vitis-idaea), and italian sweet red peppers (Capsicum annuum). This could make catechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Catechin. |
---|
CAS Number | 154-23-4 |
---|
Structure | |
---|
Synonyms | Synonym | Source |
---|
(+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol | ChEBI | (+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol | ChEBI | (+)-Catechol | ChEBI | (+)-Cyanidan-3-ol | ChEBI | (2R,3S)-(+)-Catechin | ChEBI | (2R,3S)-Catechin | ChEBI | (2R-trans)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol | ChEBI | Catechuic acid | ChEBI | Cianidanol | ChEBI | Cyanidanol | ChEBI | D-Catechin | ChEBI | Catechuate | Generator | (+)-Catechin | HMDB, MeSH | (+)-Catechin hydrate | HMDB | (+)-Cyanidanol | HMDB, MeSH | (+/-)-catechin | HMDB | (+/-)-catechin hydrate | HMDB | 3,3',4',5,7-Flavanpentol | HMDB, MeSH | Biocatechin | HMDB | Catechinate | HMDB | Catechinic acid | HMDB, MeSH | Catergen | HMDB, MeSH | Cianidanolum | HMDB | Cianidol | HMDB | D-(+)-Catechin | HMDB | trans3,3,4,5,7 Pentahydroxyflavane | HMDB | YK-85 light yellow powder 85 | HMDB | Acid, catechinic | MeSH, HMDB | KB-53 | MeSH, HMDB | Zyma | MeSH, HMDB | Cyanidanol 3 | MeSH, HMDB | Cyanidanol-3 | MeSH, HMDB | KB 53 | MeSH, HMDB | Acid, catechuic | MeSH, HMDB | (+)-Cyanidanol-3 | MeSH, HMDB | Epicatechin | MeSH, HMDB | Catechin | MeSH | (-)-Epicatechin | MeSH, HMDB | (+)-(2R:3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol | PhytoBank | (+)-(2R:3S)-5,7,3’,4’-Tetrahydroxyflavan-3-ol | PhytoBank | (+)-3’,4’,5,7-Tetrahydroxy-2,3-trans-flavan-3-ol | PhytoBank | (+)-Cianidanol | PhytoBank | 3-Cyanidanol, (+)- | PhytoBank | Cyanidol | PhytoBank | Dexcyanidanol | PhytoBank | trans-(+)-3,3',4',5,7-Flavanpentol | PhytoBank | trans-(+)-3,3’,4’,5,7-Flavanpentol | PhytoBank | (2R,3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol | biospider | (2R,3S)-3,3',4',5,7-Flavanpentol | biospider | 3,3',4',5,7-Pentahydroxyflavan; (+)-trans-form | db_source | Catechol (8CI) | manual | D-Catechol | biospider | Drenoliver | db_source |
|
---|
Predicted Properties | |
---|
Chemical Formula | C15H14O6 |
---|
IUPAC name | (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
---|
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 |
---|
InChI Key | PFTAWBLQPZVEMU-DZGCQCFKSA-N |
---|
Isomeric SMILES | O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC(O)=C(O)C=C1 |
---|
Average Molecular Weight | 290.2681 |
---|
Monoisotopic Molecular Weight | 290.07903818 |
---|
Classification |
---|
Description | Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Flavonoids |
---|
Sub Class | Flavans |
---|
Direct Parent | Catechins |
---|
Alternative Parents | |
---|
Substituents | - Catechin
- 3'-hydroxyflavonoid
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Chromane
- Benzopyran
- 1-benzopyran
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Secondary alcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Ether
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | |
---|
Ontology |
---|
|
Disposition | Route of exposure: Source: Biological location: |
---|
Foods | Cocoa and cocoa products Nuts and legumes: Fruits and vegetables: Beverages: |
---|
Physico-Chemical Properties - Experimental |
---|
Physico-Chemical Properties - Experimental | Property | Value | Reference |
---|
Physical state | Solid | |
---|
Physical Description | Not Available | |
---|
Mass Composition | C 62.07%; H 4.86%; O 33.07% | DFC |
---|
Melting Point | Mp 175-177° (anhyd.) | DFC |
---|
Boiling Point | Not Available | |
---|
Experimental Water Solubility | Not Available | |
---|
Experimental logP | 0.51 | PERRISSOUD,D & TESTA,B (1986) |
---|
Experimental pKa | Not Available | |
---|
Isoelectric point | Not Available | |
---|
Charge | Not Available | |
---|
Optical Rotation | [a]D +17 | DFC |
---|
Spectroscopic UV Data | Not Available | |
---|
Density | Not Available | |
---|
Refractive Index | Not Available | |
---|
|
---|
Spectra |
---|
Spectra | |
---|
EI-MS/GC-MS | Type | Description | Splash Key | View |
---|
GC-MS | Catechin, non-derivatized, GC-MS Spectrum | splash10-014i-0749000000-e5b0b7512526810c1758 | Spectrum | GC-MS | Catechin, non-derivatized, GC-MS Spectrum | splash10-014i-0749000000-e5b0b7512526810c1758 | Spectrum | GC-MS | Catechin, non-derivatized, GC-MS Spectrum | splash10-014i-0749000000-e5b0b7512526810c1758 | Spectrum | GC-MS | Catechin, non-derivatized, GC-MS Spectrum | splash10-014i-0749000000-e5b0b7512526810c1758 | Spectrum | Predicted GC-MS | Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-00di-0940000000-3790a10ce8b93dcb9236 | Spectrum | Predicted GC-MS | Catechin, 5 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-000i-3130069000-ca0968505fc89dd82640 | Spectrum | Predicted GC-MS | Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Catechin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
|
---|
MS/MS | Type | Description | Splash Key | View |
---|
MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-000i-0190000000-0b55363090666c3a1f0f | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-0ab9-0900000000-5dfb75ce17e0aea0642b | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-003r-9000000000-ae956114187e6320ae3a | 2012-07-25 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0079-0900000000-dd93ef481c2fea84d4a2 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-052r-0980000000-97f9a54412368150d277 | 2012-08-31 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-000i-0090010000-6ebf1de8cc1ea492a630 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-052k-0960000000-77945100b7a1f6311aea | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-052k-0960000000-77945100b7a1f6311aea | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 26V, Negative | splash10-05fr-0920000000-e829a07f24435afac743 | 2017-08-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 10V, Negative | splash10-000i-0090010000-6ebf1de8cc1ea492a630 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-052k-0960000000-77945100b7a1f6311aea | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-000i-0090000000-25414078e505f0193624 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - ESI-TOF 26V, Negative | splash10-05fr-0920000000-e829a07f24435afac743 | 2017-09-12 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-000i-0910000000-a98df14e459446ae6ae2 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Positive | splash10-00di-0090000000-142161e341ec3ee68a3a | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - DI-ESI-qTof , Negative | splash10-0fga-0980000000-3406dfb006e610eb6fce | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-000i-0090000000-466d29d8274d012f2ea3 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-0pds-0970000000-2631ce85b21e59412694 | 2017-09-14 | View Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-05fr-1900000000-3424d3d2af180d7eabd3 | 2017-09-14 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0590000000-aff1c3cc94786f87cacf | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0920000000-5e84c0d9207a0a018ab4 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05fr-4900000000-3e525d17e0b05647387a | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0290000000-52e8123f5ed55bc47962 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0940000000-cfcd9b4e416f64a26916 | 2016-09-12 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a6r-2910000000-be77474275eeee51824b | 2016-09-12 | View Spectrum |
|
---|
NMR | Type | Description | | View |
---|
1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | | Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, experimental) | | Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | | Spectrum |
|
---|
External Links |
---|
ChemSpider ID | 8711 |
---|
ChEMBL ID | CHEMBL311498 |
---|
KEGG Compound ID | C06562 |
---|
Pubchem Compound ID | 9064 |
---|
Pubchem Substance ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Phenol-Explorer ID | 124 |
---|
DrugBank ID | Not Available |
---|
HMDB ID | HMDB02780 |
---|
CRC / DFC (Dictionary of Food Compounds) ID | CML31-M:CML34-P |
---|
EAFUS ID | Not Available |
---|
Dr. Duke ID | D-CATECHIN|(+)-CATECHIN|CATECHIN |
---|
BIGG ID | Not Available |
---|
KNApSAcK ID | C00000947 |
---|
HET ID | KXN |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
Flavornet ID | Not Available |
---|
GoodScent ID | Not Available |
---|
SuperScent ID | Not Available |
---|
Wikipedia ID | Catechin |
---|
Phenol-Explorer Metabolite ID | 124 |
---|
Duplicate IDS | Not Available |
---|
Old DFC IDS | Not Available |
---|
Associated Foods |
---|
Food | Content Range | Average | Reference |
---|
Food | | | Reference |
---|
|
Biological Effects and Interactions |
---|
Health Effects / Bioactivities | Descriptor | ID | Definition | Reference |
---|
angiotensin converting enzyme inhibitor | 35457 | An EC 3.4.15.* (peptidyl-dipeptidase) inhibitor that interferes with the action of peptidyl-dipeptidase A (EC 3.4.15.1). | DUKE | allelochemic | | | DUKE | anti aggregant | | | DUKE | anti alcoholic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti arthritic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | anti cariogenic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti coagulant | 50249 | An agent that prevents blood clotting. | DUKE | anti complementary | | | DUKE | anti edemic | | | DUKE | anti endotoxic | 50247 | Any protective agent counteracting or neutralizing the action of poisons. | DUKE | anti feedant | | | DUKE | anti flu | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti hepatitic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | anti hepatotoxic | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti histaminic | 37956 | Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. | DUKE | anti HIV | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | anti hyperlipidemic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | anti lipoperoxidant | | | DUKE | anti mutagenic | | | DUKE | anti osteotic | | | DUKE | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | anti periodontal | | | DUKE | anti peroxidant | | | DUKE | anti plaque | | | DUKE | anti prostaglandin | 49020 | A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites. | DUKE | anti radicular | | | DUKE | anti sclerodermic | 50177 | A drug used to treat or prevent skin disorders or for the routine care of skin. | DUKE | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | astringent | 74783 | A compound that causes the contraction of body tissues, typically used to reduce bleeding from minor abrasions. | DUKE | beta-adrenergic receptor blocker | 37962 | Any agent that acts on an adrenergic receptor or affects the life cycle of an adrenergic transmitter. | DUKE | cAMP-phosphodiesterase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | cardiotonic | 38070 | A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres. | DUKE | catechol O-methyltransferase inhibitor | 48406 | An EC 2.1.1.* (methyltransferase) inhibitor that interferes with the action of catechol O-methyltransferase (EC 2.1.1.6). | DUKE | cyclooxygenase-1 inhibitor | 50630 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1. | DUKE | cyclooxygenase-2 inhibitor | 50629 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. | DUKE | cyclooxygenase inhibitor | 35544 | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. | DUKE | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | dermatitigenic | | | DUKE | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | hemostat | | | DUKE | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | hypocholesterolemic | | | DUKE | immunostimulant | 50847 | A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity. | DUKE | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | neuroprotective | 63726 | Any compound that can be used for the treatment of neurodegenerative disorders. | DUKE | nitric-oxide inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | phagocytotic | | | DUKE | propecic | | | DUKE | vasoconstrictor | 50514 | Drug used to cause constriction of the blood vessels. | DUKE | xanthine oxidase inhibitor | 35634 | An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2). | DUKE |
|
---|
Enzymes | Not Available |
---|
Pathways | Not Available |
---|
Metabolism | Not Available |
---|
Biosynthesis | Not Available |
---|
Organoleptic Properties |
---|
Flavours | Flavor | Citations |
---|
bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
|
|
---|
Files |
---|
MSDS | show |
---|
References |
---|
Synthesis Reference | Not Available |
---|
General Reference | Not Available |
---|
Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070. — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181. — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
|
---|