PhytoHub: Showing entry for 5-(3',4'-dihydroxyphenyl)-gamma-valerolactone

5-(3',4'-dihydroxyphenyl)-gamma-valerolactone

Identification

PhytoHub ID

PHUB001060

Name

5-(3',4'-dihydroxyphenyl)-gamma-valerolactone

Systematic Name

5-(3',4'-dihydroxyphenyl)-γ-valerolactone

Synonyms

[M6]
5-(3,4-dihydroxyphenyl)-gamma-valerolactone
5-(3,4-dihydroxyphenyl)-γ-valerolactone
5-(dihydroxyphenyl)-valerolactone
5-(dihydroxyphenyl)-γ-valerolactone
δ-(3,4-dihydroxyphenyl)-γ-valerolactone

CAS Number

21618-92-8

Average Mass

208.213

Monoisotopic Mass

208.073558866

Chemical Formula

C₁₁H₁₂O₄

IUPAC Name

5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one

InChI Key

KTDWBJGUMIZRHU-UHFFFAOYSA-N

InChI Identifier

InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2

SMILES

OC1=C(O)C=C(CC2CCC(=O)O2)C=C1

Structure

Similar Structures

Calculated Properties

Solubility (ALOGPS): 1.38e+00 g/l
LogS (ALOGPS): -2.18
LogP (ALOGPS): 1.47
Hydrogen Acceptors: 3
Hydrogen Donors: 2
Rotatable Bond Count: 2
Polar Surface Area: 66.76
Refractivity: 53.30770000000001
Polarizability: 20.789901850517715
Formal Charge: 0
Physiological Charge: 0
pKa (strongest basic): -6.289147264805463
pKa (strongest acidic): 9.284113130939318
Number of Rings: 2
Rule of Five: Yes
Bioavailability: Yes
Ghose Filter: Yes
Veber's Rule: No
MDDR-like Rule: No

External Links

ChEBI: 89285
PubChem: 152432
Phenol-Explorer: 983
FooDB (Compounds): FDB029853
PeakForestCompound: 000767

Taxonomy as Metabolite

Family: (Poly)phenol metabolites
Class: Flavonoid metabolites
Sub-class: Phenylvalerolactones and phenylvaleric acids

Taxonomy of its Food Phytochemical Precursor(s)

Food Phytochemical	Family	Class	Sub-class
(-)-Epicatechin	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Procyanidin dimer B2	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
(+)-Catechin	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Cocoa Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Red Grape pomace Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Green tea Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Cranberry Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Apple Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical
Red Wine Flavan-3-ols	Polyphenols	Flavonoids	Flavan-3-ols	Show Food Phytochemical

Spectra from Phytohub

	Spectrum Type	Instrument Type	Ion Mode	Collision Energy Level	View	Peaks

Food Sources

No food source information available

Food Sources of its Food Phytochemical(s)

Food Phytochemical	Food Source	Food Source Group
(-)-Epicatechin	Almond	Nuts	Publications	Show
(-)-Epicatechin	Apple	Fruit, Pomes	Publications	Show
Procyanidin dimer B2	Apple	Fruit, Pomes	Publications	Show
(+)-Catechin	Apple	Fruit, Pomes	Publications	Show
(-)-Epicatechin	Apple cider	Beverages, Alcoholic	Publications	Show
Procyanidin dimer B2	Apple cider	Beverages, Alcoholic	Publications	Show
(+)-Catechin	Apple cider	Beverages, Alcoholic	Publications	Show
(-)-Epicatechin	Apple juice	Beverages, Non-alcoholic	Publications	Show
Procyanidin dimer B2	Apple juice	Beverages, Non-alcoholic	Publications	Show
(+)-Catechin	Apple juice	Beverages, Non-alcoholic	Publications	Show
(-)-Epicatechin	Apricot	Fruit, Drupes	Publications	Show
Procyanidin dimer B2	Apricot	Fruit, Drupes	Publications	Show
(+)-Catechin	Apricot	Fruit, Drupes	Publications	Show
(+)-Catechin	Banana	Fruit, Tropical fruits	Publications	Show
(-)-Epicatechin	Beer	Beverages, Alcoholic	Publications	Show
(+)-Catechin	Beer	Beverages, Alcoholic	Publications	Show
(-)-Epicatechin	Black tea	Teas and herbal teas	Publications	Show
Procyanidin dimer B2	Black tea	Teas and herbal teas	Publications	Show
(+)-Catechin	Black tea	Teas and herbal teas	Publications	Show
(-)-Epicatechin	Blackberry	Fruit, Berries	Publications	Show
Procyanidin dimer B2	Blackberry	Fruit, Berries	Publications	Show
(+)-Catechin	Blackberry	Fruit, Berries	Publications	Show
(-)-Epicatechin	Broad bean	Pulses and beans	Publications	Show
(+)-Catechin	Broad bean	Pulses and beans	Publications	Show
(-)-Epicatechin	Chocolate	Cocoa and cocoa products	Publications	Show
(+)-Catechin	Chocolate	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Cider	Beverages, Alcoholic	Publications	Show
(-)-Epicatechin	Cocoa	Cocoa and cocoa products	Publications	Show
Procyanidin dimer B2	Cocoa	Cocoa and cocoa products	Publications	Show
(+)-Catechin	Cocoa	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Cocoa bean	Cocoa and cocoa products	Publications	Show
Procyanidin dimer B2	Cocoa bean	Cocoa and cocoa products	Publications	Show
(+)-Catechin	Cocoa bean	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Cocoa powder	Cocoa and cocoa products	Publications	Show
(-)-Epicatechin	Common chokecherry	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Common walnut	Nuts	Publications	Show
(-)-Epicatechin	European cranberry	Fruit, Berries	Publications	Show
(-)-Epicatechin	European plum	Fruit, Drupes	Publications	Show
(+)-Catechin	European plum	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Grape	Fruit, Berries	Publications	Show
(-)-Epicatechin	Green tea	Teas and herbal teas		Show
Procyanidin dimer B2	Green tea	Teas and herbal teas	Publications	Show
(+)-Catechin	Green tea	Teas and herbal teas	Publications	Show
(-)-Epicatechin	Peach	Fruit, Drupes	Publications	Show
(+)-Catechin	Peach	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Pear	Fruit, Pomes	Publications	Show
(+)-Catechin	Pear	Fruit, Pomes	Publications	Show
(+)-Catechin	Pecan nut	Nuts	Publications	Show
(-)-Epicatechin	Pomegranate	Fruit, Tropical fruits	Publications	Show
(+)-Catechin	Red wine	Beverages, Alcoholic	Publications	Show
(-)-Epicatechin	Strawberry	Fruit, Berries	Publications	Show
(+)-Catechin	Strawberry	Fruit, Berries	Publications	Show
(-)-Epicatechin	Sweet cherry	Fruit, Drupes	Publications	Show
(+)-Catechin	Sweet cherry	Fruit, Drupes	Publications	Show
(-)-Epicatechin	Tea	Teas and herbal teas	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
(-)-Epicatechin	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human in vitro (human) rat	plasma, urine	gut microbiota metabolite	5h-8h	Not Available	Not Available	C₁₁H₁₂O₄	208.073558866	Publications
Procyanidin dimer B2	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	in vitro (human)	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₂O₄	208.073558866	Publications
(+)-Catechin	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human	Not Available	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₂O₄	208.073558866	Publications
Cocoa Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human	plasma, urine	gut microbiota metabolite	3h-5h	20-50 nmol/L	<1%	C₁₁H₁₂O₄	208.073558866	Publications
Red Grape pomace Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human	plasma, urine	gut microbiota metabolite	5h-8h	<20 nmol/L	<1%	C₁₁H₁₂O₄	208.073558866	Publications
Green tea Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human	plasma, urine	gut microbiota metabolite	Not Available	<20 nmol/L	<1%	C₁₁H₁₂O₄	208.073558866	Publications
Cranberry Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human	urine	gut microbiota metabolite	Not Available	Not Available	<1%	C₁₁H₁₂O₄	208.073558866	Publications
Apple Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human	urine	gut microbiota metabolite	Not Available	Not Available	<1%	C₁₁H₁₂O₄	208.073558866	Publications
Red Wine Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	human	urine	gut microbiota metabolite	Not Available	Not Available	Not Available	C₁₁H₁₂O₄	208.073558866	Publications

Inter-Individual Variations in Metabolism

Food Phytochemical	Metabolite	Effect	Value
Cocoa Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	Microbiota	Effect, clusters	Publications
Red Grape pomace Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	Microbiota	Effect, clusters	Publications
Green tea Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	Genotype	Discordant	Publications
Green tea Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	Microbiota	Effect, clusters	Publications
Green tea Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	Smoking	Effect, clusters	Publications
Cranberry Flavan-3-ols	5-(3',4'-dihydroxyphenyl)-gamma-valerolactone	Microbiota	Effect, clusters	Publications

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Showing entry for 5-(3',4'-dihydroxyphenyl)-gamma-valerolactone