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2,4-Dihydroxybenzophenone

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2,4-Dihydroxybenzophenone Basic information
pollution
Product Name:2,4-Dihydroxybenzophenone
Synonyms:(2,4-dihydroxyphenyl)phenyl-methanon;(2,4-Dihydroxyphenyl)-phenylmethanon (2,4-dihydroxybenzophenon);2,4-DHBP;2,4-Dihydroxtbenzophenone;2,4-Dihydroxybenzofenon;2,4-dihydroxy-benzophenon;2,4-dihydroxydiphenylketone;Advastab 48
CAS:131-56-6
MF:C13H10O3
MW:214.22
EINECS:205-029-4
Product Categories:proteins;Industrial/Fine Chemicals;Additives for Plastic
Mol File:131-56-6.mol
2,4-Dihydroxybenzophenone Structure
2,4-Dihydroxybenzophenone Chemical Properties
Melting point 144.5-147 °C(lit.)
Boiling point 194 °C (1 mmHg)
density 1,32 g/cm3
bulk density750kg/m3
vapor pressure 0Pa at 25℃
refractive index 1.5090 (estimate)
Fp 125 °C
storage temp. Store below +30°C.
solubility Chloroform (Slightly, Heated), Ethanol (Slightly, Heated)
pka7.72±0.35(Predicted)
form Crystalline Powder
color Yellow
PH5 (10g/l, H2O, 20℃)(slurry)
biological sourcehuman
Water Solubility insoluble
Merck 14,1106
BRN 1311566
Henry's Law Constant4.6×105 mol/(m3Pa) at 25℃, Abraham and Jr. (2019)
Cosmetics Ingredients FunctionsLIGHT STABILIZER
UV ABSORBER
Cosmetic Ingredient Review (CIR)2,4-Dihydroxybenzophenone (131-56-6)
InChI1S/C13H10O3/c14-10-6-7-11(12(15)8-10)13(16)9-4-2-1-3-5-9/h1-8,14-15H
InChIKeyZXDDPOHVAMWLBH-UHFFFAOYSA-N
SMILESOc1ccc(c(O)c1)C(=O)c2ccccc2
LogP2.964 at 25℃
CAS DataBase Reference131-56-6(CAS DataBase Reference)
NIST Chemistry ReferenceMethanone, (2,4-dihydroxyphenyl)phenyl-(131-56-6)
EPA Substance Registry SystemMethanone, (2,4-dihydroxyphenyl)phenyl- (131-56-6)
Safety Information
Hazard Codes Xi,T
Risk Statements 36-36/37/38-61
Safety Statements 26-37/39-45-53
WGK Germany 2
RTECS DJ0700000
Hazard Note Irritant
TSCA TSCA listed
HS Code 29145000
Storage Class11 - Combustible Solids
Hazard ClassificationsAquatic Chronic 2
Eye Irrit. 2
Repr. 2
Hazardous Substances Data131-56-6(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: > 5000 mg/kg
MSDS Information
ProviderLanguage
(2,4-dihydroxyphenyl)phenyl-methanone English
SigmaAldrich English
ACROS English
ALFA English
2,4-Dihydroxybenzophenone Usage And Synthesis
pollutionBenzophenones (BPs), as UV filters, are widely utilized in personal care products such as sunscreen, body lotion and plastic products. 2,4-Dihydroxybenzophenone (BP-1) is a representative type of BP that has attracted wide attention owing to the high residues in the aquatic environment. According to previous studies, this compound can enter the aquatic environment through recreational water activities or incomplete removal in wastewater treatment plants (WWTPs). For example, BP-1 has been widely detected in seawater, groundwater, river water and WWTP effluents in Spain at concentrations ranging from 4.2 ng/L to 722.0 ng/L. More seriously, because of extensive human exposure through plastic products and sunscreen cosmetics, BP-1 has been detected in human urine, blood and milk[1].
Description2,4-Dihydroxybenzophenone (DHP) is an organic compound derived from Garcinia xanthochymus, but there have been no reports on its biochemical functions and bioavailability. 2,4-dihydroxybenzophenone has been prepared by reacting resorcinol with benzoyl chloride or benzoic acid under anhydrous conditions in the presence of Friedel-Crafts catalysts such as AlCl3 or ZnCl2[1].
Chemical Propertiesyellow crystalline powder
Uses2,4-Dihydroxybenzophenone is an metabolite of Benzophenone (B204980), an compound used in the manufacturing of antihistamines, hypnotics and insecticides.
UsesUltraviolet light absorber, especially in paints and plastics.
UsesNovel mordent and disperse azo dyes were prepared by the coupling of various diazo solutions of aromatic amines with 2, 4-dihydroxybenzophenone. The ultraviolet absorbing monomers were synthesized by reaction of 2, 4-dihydroxybenzophenone with glycidyl acrylate and glycidyl methacrylate. Two new polymerizable stabilizers, 4-benzoyl-2-(α-piperidino-2-chlorobenzyl)-3-hydroxyphenyl acrylate (BPBHA) and corresponding methacrylate (BPBHMA), were synthesized and characterized from 2,4-Dihydroxybenzophenone. a polymerizable UV-stabilizer, 2-hydroxy-4-(3-methacryloxy-2-hydroxylpropoxy) benzophenone (BPMA), was synthesized using 2, 4-dihydroxybenzophenone (UV-0) and glycidyl methacrylate (GMA).
DefinitionChEBI: 2,4-Dihydroxybenzophenone is a member of benzophenones.
PreparationObtained by condensation of benzanilide with resorcinol in the presence of zinc chloride and phosphorous oxychloride at 130–140° for 1 h (25%).
Biological Activity2,4-Dihydroxybenzophenone has potential effects on the stimulation of osteoblast differentiation and mitigate PDS-induced osteoporosisthrough the activation of the β-catenin pathway. Moreover, 2,4-Dihydroxybenzophenone demonstrated a capacity to enhance the expression of crucial osteogenic markers, including RUNX2, OSX, and ALP[2].
Contact allergensBZP-1 is used, for example, in paints, plastics, and nail varnishes.
Safety ProfilePoison by intravenous and intraperitoneal routes. Mildly toxic by ingestion. An eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.
ToxicologyAs a persistent and bioaccumulative compound, 2,4-Dihydroxybenzophenone (BP-1) exhibits estrogenic activity or anti-androgenic activity in vitro, which could pose potential risks to the ecological environment and human health. At present, there are a large amount of reports that concentrated on the biotoxicity of BP-1, mainly focusing on its endocrine disrupting effects and genetic toxicity. Endocrine-toxicological studies have shown that the toxicity of BP-1 is five times that of bisphenol A (BPA)[2].
Purification MethodsRecrystallise it from MeOH. [Beilstein 8 IV 2442.]
References [1] Mengting Zou . “Effective degradation of 2,4-dihydroxybenzophenone by zero–valent iron powder (Fe0)-activated persulfate in aqueous solution: Kinetic study, product identification and theoretical calculations.” Science of the Total Environment 771 (2021): Article 144743.
[2] Mirissa Hewage Dumindu Kavinda and & Gi-Young Kim*. “2,4′-Dihydroxybenzophenone Exerts Bone Formation and Antiosteoporotic Activity by Stimulating the β-Catenin Signaling Pathway.” ACS Pharmacology and Translational Science 7 2 (2024): 395–405.
Tag:2,4-Dihydroxybenzophenone(131-56-6) Related Product Information
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