NARINGENIN

PRODUCT IDENTIFICATION

CAS NO. 67604-48-2 (Isomer mixture)
480-41-1 (S-form)

NARINGENIN

EINECS NO.

207-550-2

FORMULA C15H12O5
MOL WT. 272.26

H.S. CODE

2932.99.6100

TOXICITY

 
SYNONYMS 2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-benzopyrone;
(S)-Naringenin; 4,5,7-Trihydroxyflavanone; 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; (S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; 5,7,4'-Trihydroxyflavanone; Naringenin; Naringenine; Naringetol; 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one; Salipurol; Salipurpol; Other RN: 13308-00-4, 15912-71-7, 67604-48-2 (Isomer mixture)
SMILES

c12c(O[C@@H](c3ccc(O)cc3)CC1=O)cc(O)cc2O

CLASSIFICATION

Anti-ulcer, Estrogen antagonist, Gastrointestinal agent, Resorcinol

EXTRA NOTES

Naringenin is a flavanone, a type of flavonoid, that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, anti-inflammatory, carbohydrate metabolism promoter, and immune system modulator. It is the predominant flavanone in grapefruit. wikipedia

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE white crystalline powder
MELTING POINT

247 - 250 C

BOILING POINT

 

SPECIFIC GRAVITY

 

SOLUBILITY IN WATER 475 mg/l
pH  
VAPOR DENSITY

 

REFRACTIVE INDEX

 

NFPA RATINGS

Health: 2, Flammability: 0, Instability: 0

AUTOIGNITION

 

FLASH POINT

 

STABILITY Stable under normal conditions

EXTERNAL LINKS & GENERAL DESCRIPTION

Wikipedia Linking - Naringenin

Google Scholar Search - Naringenin

Drug Information Portal (U.S. National Library of Medicine) - Naringenin

PubChem Compound Summary - Naringenin

Drug Bank -  Naringenin

KEGG (Kyoto Encyclopedia of Genes and Genomes)Naringenin

http://www.ebi.ac.uk/Naringenin

http://www.ncbi.nlm.nih.gov/Naringenin

Human Metabolome Database - Naringenin

http://toxnet.nlm.nih.gov/
Hazardous Substances Data Bank -
Naringenin

http://ajpgi.physiology.org/
Naringenin, the predominant flavanone in grapefruit, mainly occurs as glycosides such as naringenin-7- rhamnoglucoside or naringenin-7-glucoside. This study compared kinetics of absorption of naringenin and its glycosides in rats either after a single flavanone-containing meal or after adaptation to a diet for 14 days. Regardless of the diet, circulating metabolites were glucurono- and sulfoconjugated derivatives of naringenin. The kinetics of absorption of naringenin and naringenin-7-glucoside were similar, whereas naringenin-7-rhamnoglucoside exhibited a delay in its intestinal absorption, resulting in decreased bioavailability. After naringenin-7-glucoside feeding, no glucoside was found in the cecum. However, after feeding naringenin-7-rhamnoglucoside,

Local:
Naringenin is a flavonone that is considered to have a bioactive effect on human health as antioxidant, radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater.  It works as an anti-ulcer agent and estrogen antagonist which inhibit the action or biosynthesis of estrogenic compounds. Naringin is the aglycones of naringenin. Naringin is known as an antioxidant in the body. in biology, antioxidants act to protect cells against free radicals. Free radicals play an important role in a number of biological processes such as the intracellular killing of bacteria by neutrophil granulocytes and certain cell signaling processes. However, because of their reactivity, free radicals can cause side reactions resulting in cell damage, which may contribute to the development of cardiovascular disease and cancer. Lipids, protein and nucleic acids are weak to free radicals. Free radicals may be involved in the mechanisms of aging itself also. The body has a number of mechanisms to minimize free radical induced damage and to repair damage.  Antioxidant enzymes produced in the body play a key role in these defense mechanisms, such as glutathione peroxidase, glutathione reductase, catalase, thioredoxin reductase and superoxide dismutase. Additionally, chemical antioxidants neutralize free radicals by accepting or donating an electron to eliminate the unpaired condition. These antioxidants include three vitamins (vitamin A, vitamin C and vitamin E), polyphenols, bilirubin and uric acid. Synthetic or natural antioxidants are widely used in nutrition and medicine and prepared foods for the effect to slow down the natural aging process and to prevent or delay certain diseases that result from cellular damage. But there should be considerable researches whether antioxidant supplementation provide beneficial effect, and if so, which and what amount of antioxidants are optimal. There are hundreds of different types of nutritional antioxidants include vitamins, coenzymes, selenium, minerals, hormones, carotenoids, non-carotenoid terpenoids, flavonoids (flavonols, flavones isoflavones, flavanols,, anthocyanidins), nonflavonoid phenolics, polyphenolics and their esters (ellagic acids, citric acids, uric acids, gallic acids, salicylic acids, rosmarinic acids, cinnamic acids, chlorogenic acids, chicoric acids). Some naringenin molecules include:

Product

CAS RN

Phlorhizin

60-81-1

Phloretin 60-82-2
Carthamidin 479-54-9
Naringenin 480-41-1
4'-Methylnaringenin 480-43-3
Pectolinarigenin 520-12-7

Prunin

529-55-5

Sakuranetin

2957-21-3

Naringenin-6-C-glucoside 3682-03-9
Naringin 10236-47-2
Narirutin 14259-46-2

Didymin

14259-47-3

Poncirin

14941-08-3

Naringin dihydrochalcone

18916-17-1

Naringenin 4',7-dimethyl ether

29424-96-2

Naringenin chalcone 73692-50-9
3'-Prenylnaringenin119240-82-3

Flavonoid is any member of a class of widely distributed biological natural products containing aromatic heterocyclic skeleton of flavan (2-Phenylbenzopyran) but no nitrogen in plants. Generally, flavonoids are biological pigments providing colours from red to blue in flowers, fruit and leaves. Besides their coloring in plants, flavonoids have important roles in the growth and development of plants; protection against UV-B radiation; forming antifungal barriers; antimicrobial, insecticidal and oestrogenic activities; plant reproduction. Flavonoids also exhibit a wide range of biological properties including anti-microbial, insecticidal and oestrogenic activities. Flavonoids are usually classified into main 6 subgroups as below plus flavans, neoflavonoids, flavonols, aurons, catechins according to the structural patterns.

  • Flavonols (Hydroxy derivatives of flavone): Fisetin, Galangin, Kaempferide, Kaempferol, Morin, Myricetin, Myricitrin, Quercetin, Quercetrin, Rhamnetin, Robinin, Rutin, Spirenoside
  • Flavones (skeleton: 2-phenylchromen-4-one): Apigenin, Baicalein, Chrysin, Diosmetin, Diosmin, Flavone, Luteolin, Rpoifolin,Tangeretin, Techtochrysin, Rhamnazin, Nobiletin, Natsudaidain.
  • Isoflavones (skeleton: 3-phenylchromen-4-one): Daidzin, Genistein, Irilone, Luteone, Prunetin, Pratensein,
  • Flavonones (derivation by reduction of the 2(3) C=C bond): Eriodictyol, Hesperidin, Hesperetin, Likvirtin, Naringin; Naringenin; Pinocembrin
  • Flavanols (derivation by reduction of the keto group):(+)-Catechin, (+)-Gallocatechin, (-)-Epicatechin (EC), (-)-Epigallocatechin (EGC), (-)-Epicatechin 3-gallate (ECG), (-)-Epigallocatechin 3-gallate (EGCG), Theaflavin, Theaflavin 3-gallate, Theaflavin 3'-gallate, Theaflavin 3,3' digallate, Thearubigins
  • Anthocyanidins (aglycones of the glycoside anthocyanins): Apigeninidin, Cyanidin, Delphinidin, Diosmetinidin, Guibourtinidin, Fisetinidin, Luteolinidin, Malvidin, Pelargonidin, Peonidin, Robinetinidin, Tricetinidin, Capensinidin, Petunidin, Europinidin, Aurentinidin, Columnidin, 5-Desoxy-malvidin, 5-Desoxy-peonidin, Hirsutinidin, Rosinidin
SALES SPECIFICATION

APPEARANCE

white crystalline powder

ASSAY

98.0% min

LOSS ON DRYING

5% max

ASH

5% max

HEAVY METALS

10ppm max

ARSENIC (As)

2ppm max

MERCURY(Hg)

ippm max

LEAD (Pb)

2ppm max

PESTICIDE RESIDUES

2ppm max

MICROBIOLOGICAL TEST

Total Plate Count:10000cfu/g max
Yeast & Mold:1000cfu/g max
E.Coli:Negative
Salmonella:Negative
Staph Aureus:Negative
Pseudomonas aeruginosa:Negative

PARTICLE SIZE

100 mesh

GMO STATUS

GMO Free

TRANSPORTATION
PACKING
 
HAZARD CLASS 9 (Packing Group: III)
UN NO. 3077
SAFETY INFORMATION

HAZARD OVERVIEW

Causes eye, skin, and respiratory tract irritation. Target Organs: Respiratory system, eyes, skin.

GHS

 

SIGNAL WORD Warning

PICTOGRAMS

 

HAZARD STATEMENTS

H315-H319-H335

P STATEMENTS

P261-P305 + P351 + P338

EC DIRECTIVES

 

HAZARD CODES

RISK PHRASES

36/37/38

SAFETY PHRASES

26-36

PRICE INFORMATION