Showing Compound Catechin (FDB002571)

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

FDB004453
FDB017125

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

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol	ChEBI
(+)-(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	ChEBI
(+)-3’,4’,5,7-Tetrahydroxy-2,3-trans-flavan-3-ol	PhytoBank
(+)-Catechin	HMDB, MeSH
(+)-Catechin hydrate	HMDB
(+)-Catechol	ChEBI
(+)-Cianidanol	PhytoBank
(+)-Cyanidan-3-ol	ChEBI

Showing 1 to 10 of 53 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.64 g/L	ALOGPS
logP	1.02	ALOGPS
logP	1.8	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	9	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.38 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74 m³·mol⁻¹	ChemAxon
Polarizability	27.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

catechin (CHEBI:15600 )
Flavans, Flavanols and Leucoanthocyanidins (C06562 )
Flavan 3-ols (C06562 )
Condensed tannins (Proanthocyanidins) (C06562 )
Flavans, Flavanols and Leucoanthocyanidins (LMPK12020001 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Biological location:

Organ and components:

Cell and elements:

Cell:

Fibroblast

Element:

Platelet

Biofluid and excreta:

Foods

Cocoa and cocoa products

Nuts and legumes:

Nuts

Fruits and vegetables:

Fruits:

Berries

Pomes:

Apple

Red wine

Infusions:

Tea products

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	0.51	PERRISSOUD,D & TESTA,B (1986)
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 62.07%; H 4.86%; O 33.07%	DFC
Melting Point	Mp 175-177° (anhyd.)	DFC
Optical Rotation	[a]D +17	DFC

Showing 1 to 10 of 14 entries

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

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

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

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allelochemic			DUKE
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
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