4'-Hydroxyflavanone
Chemical compound
From Wikipedia, the free encyclopedia
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).
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| Names | |
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| IUPAC name
4′-Hydroxyflavan-4-one | |
| Systematic IUPAC name
2-(4-Hydroxyphenyl)-2,3-dihydro-4H-1-benzopyran-4-one | |
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] | |
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| 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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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]