Names | |
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IUPAC name
2-(4-Hydroxyphenyl)-2,3-dihydrochromen-4-one
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Other names
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Identifiers | |
3D model (
JSmol)
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384424 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
DrugBank | |
EC Number |
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KEGG | |
PubChem
CID
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UNII | |
CompTox Dashboard (
EPA)
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Properties | |
C15H12O3 | |
Molar mass | 240.258 g·mol−1 |
Hazards | |
GHS labelling: [1] | |
Warning | |
H315, H319, H335 | |
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).
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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).
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]
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]
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]
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]