Naringenin Chemical Identity
Naringenin has the molecular formula C15H12O5 and a molecular weight of 272.3. It is a flavanone, a flavonoid with a saturated bond between positions 2 and 3, and it carries hydroxyl groups at positions 5, 7 and 4′. The saturated ring creates a stereocenter at C2, and the natural compound is the (2S) form. Because of the stereocenter and the absence of the C2–C3 double bond, naringenin is less flat than the related flavone apigenin, with which it shares the substitution pattern.
In citrus peel the compound is mostly glycosylated. Naringin carries the disaccharide neohesperidose at position 7 and is intensely bitter, while prunin carries a single glucose. The aglycone is obtained by hydrolysis of those glycosides, by acid or by the enzyme naringinase, and then purified. The natural source is the peel of Citrus paradisi Macfad., which GBIF lists as a synonym of Citrus aurantium, and the botanical identity here follows the master record. Related products are Naringin 98%, Prunin 98% and the 10:1 Grapefruit Extract Powder. The glycosides are the bitter, water-soluble forms, whereas naringenin here is the neutral, much less soluble aglycone.
Naringenin is also found in tomato skin and in other fruit, so the source belongs beside the name. The compound here comes from grapefruit peel, where the ratio of glycosides to aglycone depends on ripeness and variety, and the albedo holds more glycoside than the flavedo. A buyer who needs the single aglycone looks for the botanical source, the part and the CAS number together.












