2-Hydroxy-4-methoxybenzophenone
Product Information
Molecular Formula
C14H12O3
Molecular Weight
228.24
Description
2-Hydroxy-4-methoxybenzophenone (benzophenone-3) is commonly employed as broad-band UV-filter in sunscreen cosmetic products. It protects skin from the deleterious effects of the sun. It is one of the sunscreen constituent and its trace determination in water samples by solid-phase microextraction (SPME) and gas chromatography with flame ionization and mass spectrometric detection has been reported.
Synonyms
(2-hydroxy-4-methoxyphenyl)-phenylmethanone
IUPAC Name
(2-hydroxy-4-methoxyphenyl)-phenylmethanone
SMILES
COC1=CC(=C(C=C1)C(=O)C2=CC=CC=C2)O
InChI
InChI=1S/C14H12O3/c1-17-11-7-8-12(13(15)9-11)14(16)10-5-3-2-4-6-10/h2-9,15H,1H3
InChI Key
DXGLGDHPHMLXJC-UHFFFAOYSA-N
Boiling Point
150-160 °C / 5 mmHg
Melting Point
62-64 °C
Flash Point
100 °C (212 °F) - closed cup
Purity
> 98 %
Density
0.8 g/cm3 (25 °C)
Solubility
less than 1 mg/mL at 68 °F
Appearance
White to light yellow to green powder to crystal
Application
Used as an ultraviolet light absorber and stabilizer (especially in plastics), photostabilizer for synthetic resins, and topical sunscreen agent.
Storage
Inert atmosphere, Room Temperature
Stability
Stable under recommended storage conditions
LogP
2.63180
Vapor Pressure
0.00000142 [mmHg]
Henry's Law Constant
1.5X10-8 atm-cu m/mol at 25 °C (est)
Decomposition
When heated to domposition it emits acrid smoke and irritating fumes
Dissociation Constants
pKa = 7.1 (phenol) (est)
Odor
Weak odor
Safety Information
Hazards
H315:
Causes skin irritation.
H319:
Causes serious eye irritation.
H410:
Very toxic to aquatic life with long-lasting effects.
Causes skin irritation.
H319:
Causes serious eye irritation.
H410:
Very toxic to aquatic life with long-lasting effects.
Precautionary Statement
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P391, P403+P233, P405, and P501
Signal Word
Warning
Computed Properties
XLogP3
3.6
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Exact Mass
228.078644241 g/mol
Monoisotopic Mass
228.078644241 g/mol
Topological Polar Surface Area
46.5Ų
Heavy Atom Count
17
Formal Charge
0
Complexity
258
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| US-10980756-B1 | Methods of treatment | 2020-03-16 |
| US-2021186857-A1 | Skin rejuvenating composition | 2019-12-20 |
| WO-2021122491-A1 | Catheter sheath for acoustically amplifying laser-induced pressure waves | 2019-12-20 |
| WO-2021125323-A1 | Pink bollworm control method | 2019-12-20 |
| WO-2021125325-A1 | Method for simultaneously preventing pink bollworm and american bollworm | 2019-12-20 |
| WO-2021119770-A1 | Cosmetic composition for a keratin substance, process for manufacturing a cosmetic composition and use of the cosmetic composition | 2019-12-19 |
| WO-2021119771-A1 | Cosmetic composition, process of manufacturing the cosmetic composition and use of the cosmetic composition | 2019-12-19 |
| WO-2021123116-A1 | Adhesive photoprotective compounds and uses thereof | 2019-12-19 |
| WO-2021125219-A1 | Oil-in-water emulsion composition | 2019-12-19 |
| US-2021186845-A1 | Vitamin a and vitamin c combinations with enhanced stability | 2019-12-18 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 34864131 | 2022-02-01 | Sunscreen filter octocrylene is a potential obesogen by acting as a PPARγ partial agonist | Toxicology letters |
| 34523531 | 2021-12-01 | Pregnancy exposure to synthetic phenols and placental DNA methylation - An epigenome-wide association study in male infants from the EDEN cohort | Environmental pollution (Barking, Essex : 1987) |
| 33049310 | 2021-04-01 | Evaluation of a multiplexed, multispecies nuclear receptor assay for chemical hazard assessment | Toxicology in vitro : an international journal published in association with BIBRA |
| 33405908 | 2021-02-15 | A Gene Expression Biomarker Identifies Chemical Modulators of Estrogen Receptor α in an MCF-7 Microarray Compendium | Chemical research in toxicology |
| 32946892 | 2020-12-01 | Bisphenol A and benzophenone-3 exposure alters milk protein expression and its transcriptional regulation during functional differentiation of the mammary gland in vitro | Environmental research |
| 32861021 | 2020-10-01 | Prodiamesa olivacea: de novo biomarker genes in a potential sentinel organism for ecotoxicity studies in natural scenarios | Aquatic toxicology (Amsterdam, Netherlands) |
| 32407875 | 2020-09-01 | Benzophenone-3 and benzophenone-8 exhibit obesogenic activity via peroxisome proliferator-activated receptor γ pathway | Toxicology in vitro : an international journal published in association with BIBRA |
| 31939680 | 2020-01-01 | Effects of Benzophenone-3 and Propylparaben on Estrogen Receptor-Dependent R-Loops and DNA Damage in Breast Epithelial Cells and Mice | Environmental health perspectives |
| 31368502 | 2019-10-01 | Benzophenone-3 Passes Through the Blood-Brain Barrier, Increases the Level of Extracellular Glutamate, and Induces Apoptotic Processes in the Hippocampus and Frontal Cortex of Rats | Toxicological sciences : an official journal of the Society of Toxicology |
| 30599193 | 2019-03-15 | The UV filter benzophenone 3, alters early follicular assembly in rat whole ovary cultures | Toxicology letters |
