4'-Hydroxyflavanone

4'-Hydroxyflavanone
Names
	IUPAC name 2-(4-Hydroxyphenyl)-2,3-dihydrochromen-4-one
	Other names 2-(4-Hydroxyphenyl)chroman-4-one; 4-Hydroxyflavanone; 2,3-Dihydro-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one;
Identifiers
CAS Number	6515-37-3;
3D model (JSmol)	Interactive image;
Beilstein Reference	384424
ChEBI	CHEBI:34361;
ChEMBL	ChEMBL73933;
ChemSpider	145054;
DrugBank	DB04429;
EC Number	676-790-1;
KEGG	C14241;
PubChem CID	165506;
UNII	5K6L8O868Y;
CompTox Dashboard (EPA)	DTXSID5022487 ;
	InChI InChI=1S/C15H12O3/c16-11-7-5-10(6-8-11)15-9-13(17)12-3-1-2-4-14(12)18-15/h1-8,15-16H,9H2 Key: ZLHVIYHWWQYJID-UHFFFAOYSA-N;
	SMILES C1C(OC2=CC=CC=C2C1=O)C3=CC=C(C=C3)O;
Properties
Chemical formula	C15H12O3
Molar mass	240.258 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4'-Hydroxyflavanone is a naturally occurring monohydroxybenzoic acid and a member of the 4'-hydroxyflavanones family. It is white to pale orange in color and generally soluble in organic solvents such as chloroform and ethanol, but insoluble with water.^[2] 4'-Hydroxyflavanone is a naturally occurring product with cosmetic and potential clinical applications that is found in plants such as carnations (Dianthus caryophyllus).

Natural occurrence

As part of the flavanone family, 4'-hydroxyflavanone can be found naturally in celery, red peppers, citrus fruits, parsley (Petroselinum crispum), berries, tea, and onions (Allium cepa L.).^[3]

Applications

Cosmetic

Flavanone, with its orange-like color, has been used in natural dyes for cotton fabrics.^[4] Additionally, flavanone is used in various anti-wrinkle cosmetics and skin care products to treat psoriasis, melanogenesis, and photo-aging.^[5]

Clinical research

4'-Hydroxyflavanone is an inhibitor of SREBP, transcription factors that control the expression of a range of enzymes that regulate lipid homeostasis.^[6]

Research also suggests that 4'-hydroxyflavanones have potential pharmaceutic applications against fatty liver disease, hepatic steatosis, and dyslipidemia.^[6]

Flavanones are widely considered to be beneficial to human health as a result of their ability to control free radicals in the body. Flavanones deriving from citrus fruits in particular exhibit antioxidant, anti-inflammatory, blood lipid-lowering and cholesterol-lowering agents.^[3]

In general, flavonoids have been used extensively as anticancer, antimicrobial, antiviral, antiangiogenic, antimalarial, antioxidant, neuroprotective, antitumor, and anti-proliferative agents.^[4] Extracts that were rich in flavonoids have also been demonstrated to be ACE inhibitors in vitro, therefore acting as effective antihypertensive agents. They also have been shown to prevent cardio-metabolic disorders and preserve cognitive performance with aging.^[4]

Toxicity

4'-Hydroxyflavanone is classified as an irritant due to its ability to cause skin corrosion, eye damage, and respiratory tract irritation if unprotected exposure occurs.^[7]

References

^ "4'-Hydroxyflavanone". pubchem.ncbi.nlm.nih.gov.
^ Miao L, Zhang H, Yang L, Chen L, Xie Y, Xiao J (2020). "Flavonoids". In Nabavi SM, Silva AS (eds.). Antioxidants effects in health: the bright and the dark side. Amsterdam: Elsevier. pp. 353–374. doi:10.1016/B978-0-12-819096-8.00048-3. ISBN 978-0-12-819096-8.
^ ^a ^b Panche AN, Diwan AD, Chandra SR (2016). "Flavonoids: an overview". Journal of Nutritional Science. 5: e47. doi:10.1017/jns.2016.41. PMC 5465813. PMID 28620474.
^ ^a ^b ^c Ullah A, Munir S, Badshah SL, Khan N, Ghani L, Poulson BG, et al. (November 2020). "Important Flavonoids and Their Role as a Therapeutic Agent". Molecules. 25 (22): 5243. doi:10.3390/molecules25225243. PMC 7697716. PMID 33187049.
^ Alalaiwe A, Lin CF, Hsiao CY, Chen EL, Lin CY, Lien WC, et al. (May 2020). "Development of flavanone and its derivatives as topical agents against psoriasis: The prediction of therapeutic efficiency through skin permeation evaluation and cell-based assay". International Journal of Pharmaceutics. 581: 119256. doi:10.1016/j.ijpharm.2020.119256. PMID 32220586.
^ ^a ^b "4'-Hydroxyflavanone". NCATS Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. Food and Drug Administration. Retrieved 2024-04-10.
^ "4'-Hydroxyflavanone". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. Retrieved 2024-04-10.

[1] "4'-Hydroxyflavanone". pubchem.ncbi.nlm.nih.gov.

[2] Miao L, Zhang H, Yang L, Chen L, Xie Y, Xiao J (2020). "Flavonoids". In Nabavi SM, Silva AS (eds.). Antioxidants effects in health: the bright and the dark side. Amsterdam: Elsevier. pp. 353–374. doi:10.1016/B978-0-12-819096-8.00048-3. ISBN 978-0-12-819096-8.

[Panche_2016-3] Panche AN, Diwan AD, Chandra SR (2016). "Flavonoids: an overview". Journal of Nutritional Science. 5: e47. doi:10.1017/jns.2016.41. PMC 5465813. PMID 28620474.

[Ullah_2020-4] Ullah A, Munir S, Badshah SL, Khan N, Ghani L, Poulson BG, et al. (November 2020). "Important Flavonoids and Their Role as a Therapeutic Agent". Molecules. 25 (22): 5243. doi:10.3390/molecules25225243. PMC 7697716. PMID 33187049.

[5] Alalaiwe A, Lin CF, Hsiao CY, Chen EL, Lin CY, Lien WC, et al. (May 2020). "Development of flavanone and its derivatives as topical agents against psoriasis: The prediction of therapeutic efficiency through skin permeation evaluation and cell-based assay". International Journal of Pharmaceutics. 581: 119256. doi:10.1016/j.ijpharm.2020.119256. PMID 32220586.

[Inxight-6] "4'-Hydroxyflavanone". NCATS Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. Food and Drug Administration. Retrieved 2024-04-10.

[7] "4'-Hydroxyflavanone". PubChem. National Center for Biotechnology Information (NCBI), U.S. National Library of Medicine. Retrieved 2024-04-10.

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Names

IUPAC name 2-(4-Hydroxyphenyl)-2,3-dihydrochromen-4-one
Other names 2-(4-Hydroxyphenyl)chroman-4-one 4-Hydroxyflavanone 2,3-Dihydro-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Identifiers
CAS Number	6515-37-3
3D model (JSmol)	Interactive image
Beilstein Reference	384424
ChEBI	CHEBI:34361
ChEMBL	ChEMBL73933
ChemSpider	145054
DrugBank	DB04429
EC Number	676-790-1
KEGG	C14241
PubChem CID	165506
UNII	5K6L8O868Y
CompTox Dashboard (EPA)	DTXSID5022487
InChI InChI=1S/C15H12O3/c16-11-7-5-10(6-8-11)15-9-13(17)12-3-1-2-4-14(12)18-15/h1-8,15-16H,9H2 Key: ZLHVIYHWWQYJID-UHFFFAOYSA-N
SMILES C1C(OC2=CC=CC=C2C1=O)C3=CC=C(C=C3)O
Properties
Chemical formula	C₁₅H₁₂O₃
Molar mass	240.258 g·mol⁻¹
Hazards
GHS labelling:^[1]
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references