Basic information
- CAS
480-41-1- Standard SMILES
O=C1CC(c2ccc(O)cc2)Oc2cc(O)cc(O)c21- InChIKey
FTVWIRXFELQLPI-UHFFFAOYSA-N- Molecular formula
- C15H12O5
- Average molar mass
- 272.25 g/mol
- Monoisotopic mass
- 272.06847348
Overview
Naringenin is a trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4'. It is a member of 4'-hydroxyflavanones and a trihydroxyflavanone.
Names & identifiers
- Preferred name
- (+-)-Naringenin
- IUPAC
- 5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
- English name
- (±)-Naringenin
- Molecular formula
- C15H12O5
- Molecular weight
- 272.25
Names & synonyms
67604-48-25,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one(+-)-naringeninDTXSID50274239RefChem:528240DTXCID50196624266-769-1(+/-)-Naringenin4',5,7-Trihydroxyflavanonerac Naringenin( inverted exclamation markA)-Naringenin93602-28-9
Show more names
()-NaringeninD4-NaringeninBE-14348ANaringenin-RM(±)-NaringeninTIMTEC-BB SBB006461Naringenin Standard
(R,S)-NaringeninNaringenin (NAR)(-)-Naringenin5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-oneMFCD00006844NSC34875EINECS 266-769-14',7-Trihydroxyflavanone
Database identifiers
- CAS
480-41-1、67604-48-2- PubChem CID
- 932
- DTXSID
DTXSID50274239- ChEMBL
CHEMBL32571- ChEBI
CHEBI:50202
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 87 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 363
Experimental & physicochemical properties
Collision Cross Section
163.9 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID50274239]
160.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
158.98 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
167.96 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]
Physicochemical properties
- Melting point
- 247 · 247-250 °C (lit.)
- Boiling point
- 577.5 · 577.5±50.0 °C(Predicted)
- Density
- 1.485 · 1.485
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly)
- pka
- 7.52 · 7.52±0.40(Predicted)
- form
- Solid
- color
- Pale Yellow to Pale Brown
- biological source
- Citrus paradisi Macf.
- Water Solubility
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Regulation (EC) No 1331/2008
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesSkin Irrit. 2 (97.8%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- rtecs
- DJ2981530
- ridadr
- 3077
- hs_code
- 29329990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26-36
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
Metabolism/MetabolitesNarigenin has known human metabolites that include Narigenin 7-O-glucuronide.
Applications
UsesA PI 3-kinase inhibitor.
UsesThe aglucon of Naringin. Inhibitory mechanism of Naringenin against carcinogenic acrylamide formation and nonenzymic browning in Maillard model reactions.
General DescriptionNaringenin is a bioactive flavonoid found in citrus and grapefruit.
Preparation methods
PreparationNaringenin is derived from malonyl-CoA and 4-coumaryl-CoA. The latter is derived from phenylalanine. The resulting butenone is reacted with chalcone synthase to yield chalcone. Chalcone then undergoes ring closure to generate naringenin.
Suppliers147 total
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖南韵邦生物科技股份有限公司0731-88532326 13319508186 · [email protected]
西安祥源植化生物技术有限公司13991954170 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Related reactions
2 records
Compound notes
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