CAS 480-41-1 Naringenin (HCID 439246)

Overview

(S)-naringenin is the (S)-enantiomer of naringenin. It has a role as a plant metabolite and an expectorant. It is a (2S)-flavan-4-one and a naringenin. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin.

Names & identifiers

Preferred name: Naringenin
IUPAC: (2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
English name: Naringenin
Molecular formula: C15H12O5
Molecular weight: 272.25

Names & synonyms

naringenin480-41-1(S)-Naringeninsalipurpol(2S)-NaringeninNaringenineSalipurolnaringetolpelargidanon5,7,4'-Trihydroxyflavanone(-)-(2S)-NaringeninHN5425SBF2

Show more names

NARIGENIN5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)CHROMAN-4-ONE(S)-5,7-Dihydroxy-2-(4-hydroxyphenyl)chroMan-4-one5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-oneringenin(2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one

(S)-2,3-Dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneDTXSID1022392CHEBI:17846(2S)-5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneNSC-11855NSC-34875CHEBI:50202BE-14348A

Database identifiers

CAS: 480-41-1
PubChem CID: 439246
DTXSID: DTXSID1022392
ChEMBL: CHEMBL9352
ChEBI: CHEBI:17846
UNII: HN5425SBF2
EC Number: 207-550-2
Nikkaji: J325.849A

Properties

Computed structural properties

XLogP: 2.4
Topological polar surface area: 87 Å²
Hydrogen bond donors: 3
Hydrogen bond acceptors: 5
Rotatable bonds: 1
Heavy atoms: 20
Formal charge: 0
Complexity: 363

Experimental & physicochemical properties

Chemical ClassesAntioxidant

DrugsPharmaceuticals -> Listed in ZINC15

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]

SpringerMaterials PropertiesCrystal structure

LogP2.52

Endocrine DisruptorsPotential endocrine disrupting compound

Physicochemical properties

Melting point: 247 · 247-250 °C(lit.)
Boiling point: 335.31 °C · 335.31°C (rough estimate)
Density: 1.2066 · 1.2066 (rough estimate)
refractive index: 1.6 · 1.6000 (estimate)
FEMA: 4797 · 4797 | (+/-)-NARINGENIN
storage temp.: Inert atmosphere,Room Temperature
solubility: DMSO (Slightly), Methanol (Slightly, Sonicated)
form: Powder
pka: 7.52 · 7.52±0.40(Predicted)
color: Beige-brown
Cosmetics Ingredients Functions: SKIN CONDITIONING
InChI: 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
InChIKey: FTVWIRXFELQLPI-ZDUSSCGKSA-N
SMILES: [C@H]1(C2=CC=C(O)C=C2)OC2=CC(O)=CC(O)=C2C(=O)C1
LogP: 2.52 · 2.520
CAS DataBase Reference: 480 · 480-41-1(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 5425 SBF2 · HN5425SBF2
EPA Substance Registry System: 4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (2S)- (480-41-1)
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
Hazard Codes: Xi,Xn
Risk Statements: 36 · 36/37/38-22
Safety Statements: 26 · 26-36-37/39
WGK Germany: 3 · 3
HazardClass: IRRITANT
HS Code: 29329990 · 29329990

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (99.3%): Causes skin irritation [Warning Skin corrosion/irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 305 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (99.3%)

Toxicology

Toxicity Summary · 1 item

A 2022 review notes that Naringenin has protective effects against toxicities produced by various natural toxins, pharmaceuticals, heavy metals, and environmental chemicals, and that the effects are mainly mediated via suppression of lipid peroxidation, oxidative stress (one example is lead), and inflammatory factors (one example is daunorubicin), and the activation of PI3K/Akt and MAPK survival signaling pathways.

Safety data

wgk: 3
hs_code: 29329990
risk_code: 36/37/38-22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi,Xn
safety_code: 26-36-37/39
hazard_class: IRRITANT
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

A 2021 review notes that the anti-inflammatory and antioxidant activities are via mechanisms such as enhancement of glutathione S-transferase, superoxide dismutase, glutathione peroxidase, and catalase activity, while reducing serum levels of alanine aminotransferase, aspartate aminotransferase, lactate dehydrogenase, and malondialdehyde. The review also notes that the anti-apoptotic potential was mediated by regulating B-cell leukemia/lymphoma 2 (Bcl-2), Bcl-2-associated X protein, and caspase-3/9.

MeSH Pharmacological Classification · 2 items

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.

Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds.

Tissue LocationsFibroblasts

Cellular LocationsMembrane

Applications · 3 items

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

Usesantiulcer, antioxidant, immunomodulator, cholesterol lowering

Uses(S)-Naringenin, an active flavanone, maintains antioxidative, anti-inflammatory and antitumorigenic activities. Used in the treatment of praquat (PQ)-induced oxidative stress.

Upstream & downstream products

Upstream raw materials

Downstream products

2,3-Dihydro-5-hydroxy-2-(4-hydroxyphenyl)-7-(phenylmethoxy)-4H-1-benzopyran-4-one

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

上海纯优生物科技有限公司18302135232 18302135232 · [email protected]

T&W GROUP021-61551611 13296011611 · [email protected]

上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]

Additional notes · 1 item

DefinitionChEBI: (S)-naringenin is the (S)-enantiomer of naringenin. It has a role as an expectorant and a plant metabolite. It is a naringenin and a (2S)-flavan-4-one. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin.