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(±)-Naringenin

(±)-Naringenin structure

CAS No:
67604-48-2
Formula:
C15H12O5
Chemical Name:
(±)-Naringenin
Synonyms:
4H-1-Benzopyran-4-one,2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-;2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;4′,5,7-Trihydroxyflavanone;5,7,4′-Trihydroxyflavanone;(R,S)-Naringenin;(±)-Naringenin;(RS)-Naringenin;(±)-5,7,4′-Trihydroxyflavanone;ST 057236;5,7-Dihydroxy-2-(4-hydroxyphenyl)-4H-chroman-4-one;5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one;TCI-CA 03;93602-28-9
Categories:
Biochemical Engineering > Plant Extracts

Description

(±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1].

Naringenin is a trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4'. It is a trihydroxyflavanone and a member of 4'-hydroxyflavanones.

(±)-Naringenin Basic Attributes

Molecular Weight：

272.25

Exact Mass：

272.25

EC Number：

266-769-1

NSC Number：

34875|11855

DSSTox ID：

DTXSID1022392|DTXSID50274239

HScode：

29329990

Characteristics

PSA：

XLogP3：

2.4

Density：

1.485g/cm3

Melting Point：

248 °C

Boiling Point：

577.5°C at 760 mmHg

Water Solubility：

soluble in ethanol (50 mg/ml), DMSO, methanol, and ammonium hydroxide (50 mg/ml). Insoluble in water (almost)

Storage Conditions：

0-6°C

Collision Cross Section：

167.96 Å² [M+H]+ [CCS Type: DT, Method: stepped-field]|167.33 Å² [M-H]- [CCS Type: DT, Method: stepped-field]|160.6 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

3077

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

RTECS Number：

DJ2981530

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 200 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)|Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

Metabolism/Metabolites：

Narigenin has known human metabolites that include Narigenin 7-O-glucuronide.

MeSH Entry Terms：

4',5,7-trihydroxyflavanone

(±)-Naringenin Use and Manufacturing

The aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions

Computed Properties

Molecular Weight:272.25
XLogP3:2.4
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:272.06847348
Monoisotopic Mass:272.06847348
Topological Polar Surface Area:87
Heavy Atom Count:20
Complexity:363
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Guide of (±)-Naringenin

Description
Basic Attributes
Characteristics
Safety Information
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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(±)-Naringenin

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