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5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one

PubChem CID
932
Structure
5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one_small.png
5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one_3D_Structure.png
Molecular Formula
Synonyms
  • naringenin
  • 67604-48-2
  • 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
  • (+/-)-Naringenin
  • 4',5,7-Trihydroxyflavanone
Molecular Weight
272.25 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-25
Description
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.
5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one has been reported in Trichoderma virens, Cadophora gregata, and other organisms with data available.
See also: Naringenin (annotation moved to) ... View More ...

1 Structures

1.1 2D Structure

Chemical Structure Depiction
5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

FTVWIRXFELQLPI-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C1C(OC2=CC(=CC(=C2C1=O)O)O)C3=CC=C(C=C3)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H12O5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

480-41-1

2.3.2 European Community (EC) Number

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 FEMA Number

2.3.7 HMDB ID

2.3.8 Metabolomics Workbench ID

2.3.9 Nikkaji Number

2.3.10 NSC Number

2.3.11 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (2S)-naringenin
  • 4',5,7-trihydroxyflavanone
  • BE 14348A
  • BE-14348A
  • naringenin
  • naringenin-7-sulfate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
272.25 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
2.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
272.06847348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
272.06847348 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
87 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
363
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Collision Cross Section

160.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

150.98 Ų [M+H-H2O]+ [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]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

167.33 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

167.96 Ų [M+H]+ [CCS Type: DT; Method: stepped-field]

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
T66001
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 8
View All
Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

473.0 1

296.0 0.71

179.0 0.60

474.0 0.45

177.0 0.31

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2 of 8
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Spectra ID
Instrument Type
GC-MS
Top 5 Peaks

209.0 1

545.0 0.75

486.0 0.37

89.0 0.29

210.0 0.27

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4.2.2 MS-MS

1 of 9
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

119.05054 100

271.05429 66.67

177.01141 25.81

93.03358 25.81

151.00171 22.58

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2 of 9
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Spectra ID
Ionization Mode
Negative
Top 5 Peaks

119.05 100

65.004 45.92

63.025 29.82

93.035 10.03

117.035 9.69

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4.2.3 LC-MS

1 of 51
View All
Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
30
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
9.18 min
Precursor m/z
271.0612
Precursor Adduct
[M-H]-
Top 5 Peaks

151.0045 999

119.051 787

271.0605 320

107.0141 273

177.0196 134

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License
dl-de/by-2-0
2 of 51
View All
Authors
Kevin S. Jewell; Björn Ehlig; Arne Wick
Instrument
TripleTOF 5600 SCIEX
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
90
Fragmentation Mode
CID
Column Name
Zorbax Eclipse Plus C18 2.1 mm x 150 mm, 3.5 um, Agilent
Retention Time
9.18 min
Precursor m/z
271.0612
Precursor Adduct
[M-H]-
Top 5 Peaks

65.003 999

41.0033 613

93.0345 499

119.0509 411

117.0345 254

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License
dl-de/by-2-0

4.2.4 Other MS

1 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M-H]-
Precursor m/z
271.0
Instrument
Ion Trap
Ionization Mode
negative
Top 5 Peaks

150.914993 100

270.988007 25.97

176.929993 23.87

164.940002 4.53

106.967003 4.25

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2 of 3
View All
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
273.0
Instrument
Ion Trap
Ionization Mode
positive
Top 5 Peaks

152.977005 100

147.011993 76.59

147.014008 76.59

273.027008 22.82

231.044006 6.29

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4.3 UV Spectra

4.3.1 UV-VIS Spectra

1 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4 IR Spectra

4.4.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
T. Seshadri, University of Delhi, Delhi, India
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
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2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
KBr1
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L09834
Lot Number
10114473
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.4.2 ATR-IR Spectra

1 of 2
Instrument Name
Bio-Rad FTS
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Indofine Chemical Company, Inc.
Catalog Number
N-101
Lot Number
406219
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Bruker Tensor 27 FT-IR
Technique
ATR-Neat (DuraSamplIR II)
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L09834
Lot Number
10114473
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.5 Raman Spectra

Instrument Name
Bruker MultiRAM Stand Alone FT-Raman Spectrometer
Technique
FT-Raman
Source of Spectrum
Bio-Rad Laboratories, Inc.
Source of Sample
Alfa Aesar, Thermo Fisher Scientific
Catalog Number
L09834
Lot Number
10114473
Copyright
Copyright © 2016-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Clinical Trials

7.1.1 ClinicalTrials.gov

8 Food Additives and Ingredients

8.1 FEMA Flavor Profile

Can help to reduce the bitter character of certain flavor formulations

8.2 Associated Foods

9 Pharmacology and Biochemistry

9.1 MeSH Pharmacological Classification

Estrogen Antagonists
Compounds which inhibit or antagonize the action or biosynthesis of estrogenic compounds. (See all compounds classified as Estrogen Antagonists.)
Anti-Ulcer Agents
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.)

9.2 Metabolism / Metabolites

Narigenin has known human metabolites that include Narigenin 7-O-glucuronide.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

9.3 Transformations

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

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

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Skin Irrit. 2 (100%)

Eye Irrit. 2A (100%)

STOT SE 3 (100%)

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Wiley References

11.6 Nature Journal References

11.7 Chemical Co-Occurrences in Literature

11.8 Chemical-Gene Co-Occurrences in Literature

11.9 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Interactions and Pathways

13.1 Chemical-Target Interactions

13.2 Pathways

14 Biological Test Results

14.1 BioAssay Results

15 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

16 Classification

16.1 MeSH Tree

16.2 ChEBI Ontology

16.3 ChemIDplus

16.4 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

16.5 ChEMBL Target Tree

16.6 UN GHS Classification

16.7 NORMAN Suspect List Exchange Classification

16.8 CCSBase Classification

16.9 EPA DSSTox Classification

16.10 LOTUS Tree

16.11 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  2. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  3. Therapeutic Target Database (TTD)
  4. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  5. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  6. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  7. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  8. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    5,7-dihydroxy-2-(4-hydroxyphenyl)chroman-4-one (EC: 266-769-1)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/30434
  9. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  10. ChEBI
  11. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
    5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one
    https://www.wikidata.org/wiki/Q57826857
  12. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  13. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  14. Flavor and Extract Manufacturers Association (FEMA)
  15. FooDB
    LICENSE
    FooDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (FooDB) and the original publication.
    https://foodb.ca/about
  16. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    (2R)-5,7-Dihydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-4H-chromen-4-one
    http://www.hmdb.ca/metabolites/HMDB0242579
  17. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  18. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  19. SpectraBase
    4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(4-hydroxyphenyl)-, (S)-
    https://spectrabase.com/spectrum/DCRewlMU9Lc
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. Natural Product Activity and Species Source (NPASS)
    5,7-Dihydroxy-2-(4-Hydroxyphenyl)-2,3-Dihydrochromen-4-One
    https://bidd.group/NPASS/compound.php?compoundID=NPC79943
  22. MassBank Europe
  23. Metabolomics Workbench
    5,7-Dihydroxy-2-(4-Hydroxyphenyl)-2,3-Dihydrochromen-4-One
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=130884
  24. Nature Chemistry
  25. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    Narigenin
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  26. Springer Nature
  27. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  28. Wikidata
  29. Wiley
  30. PubChem
  31. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  32. GHS Classification (UNECE)
  33. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  34. PATENTSCOPE (WIPO)
CONTENTS