FComEx: (S)-Naringenin (PC000705)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:02 UTC

Update date

2017-01-19 02:36:33 UTC

FoodComEx ID

PC000705

FoodDB Record

FDB000678

Chemical Information

Name

(S)-Naringenin

Description

Naringenin, also known as (2S)-naringenin or naringetol, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, naringenin is considered to be a flavonoid lipid molecule. The (S)-enantiomer of naringenin. Naringenin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Naringenin exists in all living organisms, ranging from bacteria to humans. Naringenin is a bitter tasting compound. Outside of the human body, Naringenin is found, on average, in the highest concentration within a few different foods, such as sweet oranges, common oregano, and mexican oregano and in a lower concentration in sorghums, grape wines, and mandarin orange (clementine, tangerine). Naringenin has also been detected, but not quantified in, several different foods, such as saffrons, white lupines, alpine sweetvetchs, dates, and elderberries. This could make naringenin a potential biomarker for the consumption of these foods.

CAS Number

480-41-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(-)-(2S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one	biospider
(-)-(2S)-Naringenin	biospider
(-)-Naringenin	biospider
(2S)-4',5,7-Trihydroxy-flavanone	manual
(2S)-Naringenin	manual
(S)-2,3-Dihydo-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	ChEBI
(S)-Naringenin	biospider
4',5,7-Trihydroxyflavanone	ChEBI
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)-	manual
Asahina	HMDB
Naringenin	biospider
Naringenine	HMDB
Naringetol	biospider
Pelargidanon	ChEBI
S-Dihydrogenistein	manual
Salipurol	biospider
Salipurpol	biospider

Chemical Formula

C15H12O5

IUPAC name

(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one

InChI Identifier

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)13-7-12(19)15-11(18)5-10(17)6-14(15)20-13/h1-6,13,16-18H,7H2/t13-/m0/s1

InChI Key

FTVWIRXFELQLPI-ZDUSSCGKSA-N

Isomeric SMILES

[H][C@]1(CC(=O)C2=C(O1)C=C(O)C=C2O)C1=CC=C(O)C=C1

Average Molecular Weight

272.2528

Monoisotopic Molecular Weight

272.068473494

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanones

Alternative Parents