2,4-Dihydroxybenzophenone Property

Melting point:

144.5-147 °C(lit.)

Boiling point:

194 °C (1 mmHg)

Density 

1,32 g/cm³

vapor pressure 

0Pa at 25℃

refractive index 

1.5090 (estimate)

Flash point:

125 °C

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly, Heated), Ethanol (Slightly, Heated)

pka

7.72±0.35(Predicted)

form 

Crystalline Powder

color 

Yellow

PH

5 (10g/l, H2O, 20℃)(slurry)

Water Solubility 

insoluble

Merck 

14,1106

BRN 

1311566

InChIKey

ZXDDPOHVAMWLBH-UHFFFAOYSA-N

LogP

2.964 at 25℃

CAS DataBase Reference

131-56-6(CAS DataBase Reference)

NIST Chemistry Reference

Methanone, (2,4-dihydroxyphenyl)phenyl-(131-56-6)

EPA Substance Registry System

Methanone, (2,4-dihydroxyphenyl)phenyl- (131-56-6)

Safety

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 

Yes

HS Code 

29145000

Hazardous Substances Data

131-56-6(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: > 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

2,4-Dihydroxybenzophenone Chemical Properties,Usage,Production

pollution

Benzophenones (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].

Description

2,4-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 Properties

yellow crystalline powder

Uses

Novel 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).

Uses

2,4-Dihydroxybenzophenone is an metabolite of Benzophenone (B204980), an compound used in the manufacturing of antihistamines, hypnotics and insecticides.

Uses

Ultraviolet light absorber, especially in paints and plastics.

Definition

ChEBI: 2,4-Dihydroxybenzophenone is a member of benzophenones.

Preparation

Obtained by condensation of benzanilide with resorcinol in the presence of zinc chloride and phosphorous oxychloride at 130–140° for 1 h (25%).

Biological Activity

2,4-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 allergens

BZP-1 is used, for example, in paints, plastics, and nail varnishes.

Safety Profile

Poison by intravenous and intraperitoneal routes. Mildly toxic by ingestion. An eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Toxicology

As 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 Methods

Recrystallise 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.