BENZOPHENONE-6

Benzophenone-6 is a light stabilizer for protecting plastics like polyester film, rubber. 
Benzophenone-6 is used for decreasing the UV transmittance of polyester window film and increasing the lightfastness of dyes on both window film and fabrics. 
Benzophenone-6 is lower in cost than equivalent tetra-substituted benzophenone UV stabilizers.

CAS Number: 131-54-4
Molecular Formula: C15H14O5
Molecular Weight: 274.27
EINECS Number: 205-027-3

Synonyms: 131-54-4, 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone, Benzophenone-6, Bis(2-hydroxy-4-methoxyphenyl)methanone, Methanone, bis(2-hydroxy-4-methoxyphenyl)-, Cyasorb UV 12, Uvinul D 49, 2,2-Dihydroxy-4,4-Dimethoxybenzophenone, Caswell No. 353C, 4,4'-Dimethoxy-2,2'-dihydroxybenzophenone, EINECS 205-027-3, NSC 40149, BRN 1887087, DTXSID6038875, BENZOPHENONE 6, BENZOPHENONE, 2,2'-DIHYDROXY-4,4'-DIMETHOXY-, 7813J9CS1G, HELISORB 11, NSC-40149, Benzophenone-6 [MI], DTXCID4018875, Benzophenone-6 [MART.], HSDB 8473, Benzophenone-6 [WHO-DD], Benzophenone-6 (MART.), RefChem:566261, 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone (8CI), Benzophenone-6 [INCI], 205-027-3, MFCD00009606, di2-hydroxy-4-methoxyphenyl ketone, UNII-7813J9CS1G, bis(2-hydroxy-4-methoxy-phenyl)methanone, 4,2'-dihydroxybenzophenone, 2-(2-hydroxy-4-methoxybenzoyl)-5-methoxyphenol, Oprea1_596131, SCHEMBL38652, MLS000078302, BIDD:ER0037, CHEMBL1598017, SCHEMBL29365072, CHEBI:229993, HMS1607E21, HMS2337I05, NSC40149, Tox21_200543, BBL027762, SBB057212, STK835235, AKOS001483238, CCG-103162, NCGC00066968-02, NCGC00258097-01, AS-14402, Bis(2-hydroxy-4-methoxyphenyl) methanone, CAS-131-54-4, SMR000034072, Benzophenone,2'-dihydroxy-4,4'-dimethoxy-, DB-042042, 2,2'-dihydroxy-4,4'-dimethoxy-benzophenone, CS-0204684, D0575, NS00008303, ST50308262, 2,2/'-Dihydroxy-4,4/'-dimethoxybenzophenone, 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone, D89680, 2,2'-Dihydroxy-4,4'-dimethoxybenzophenone, 98%, SR-01000389299, SR-01000389299-1, Benzophenone, 2,2'-dihydroxy-4,4'-dimethoxy-;bis(2-hydroxy-4-methoxyphenyl)-methanon;Cyasorb UV 12;2,2-DIHDROXY-4,4-DIMETHOXYBENZOPHENONE;UV-6,BP-6;UV absorber UV BP-6;2,2'-Dihydroxy-4,4'-dimethoxybenzophenone≥99%;Benzophenone-6

Benzophenone-6 is a type of organic compound in the benzophenone family that functions primarily as a UV filter or UV absorber in a wide range of cosmetic, personal care, and industrial products. 
Benzophenone-6 is known as 2,2’-Dihydroxy-4,4’-dimethoxybenzophenone or bis(2-hydroxy-4-methoxyphenyl)methanone, which describes its structure consisting of two benzene rings linked by a central ketone (carbonyl) group. 
On each aromatic ring, it has hydroxyl (-OH) groups at the 2-positions and methoxy (-OCH₃) groups at the 4-positions, giving it both hydrophilic and electron-donating properties that enhance its ability to absorb ultraviolet (UV) radiation efficiently.

Benzophenone-6 belongs to the class of benzophenone UV absorbers, which are widely used because they can stabilize formulations by absorbing harmful UVA and UVB rays, thereby protecting the product and the skin from UV-induced damage. 
Unlike physical blockers such as zinc oxide or titanium dioxide, Benzophenone-6 chemically absorbs UV energy, dissipating it as low-level heat, which helps prevent degradation of sensitive ingredients in sunscreens, lotions, hair care products, and other cosmetic formulations.

Benzophenone-6 and -8 are compounds made from 2-hydroxybenzophenone. 
In cosmetics and personal care products, Benzophenone-2, -6 and -8 are used in the formulation of aftershave lotion, bath products, bubble baths, colognes, perfumes, eye makeup removers, and other skin and hair care products.
Benzophenone-6 is a naturally occurring organic compound with the formula (C6H5)2CO, generally abbreviated Ph2CO. 

Benzophenone-6 has been found in some fungi, fruits and plants, including grapes.
Benzophenone-6 is a white solid with a low melting point and rose-like odor that is soluble in organic solvents. 
Benzophenone-6 is the simplest diaromatic ketone. 

Benzophenone-6 is a widely used building block in organic chemistry, being the parent diarylketone.
Benzophenone-6 is a highly effective photo-reactive dyes that can be used for a variety of applications in organic chemistry. 
It was first synthesized in 1955, but has not been used in organic chemistry since. It is also a common chemical that belongs to the benzophenone group of compounds. 

Benzophenone-6 is commonly used as an ultraviolet (UV) absorber and is therefore often added to many everyday products to protect them from the damaging effects of UV radiation.
Benzophenone-6s molecular structure allows it to be moderately soluble in water, but it is more commonly used in emulsions, gels, creams, and sunscreen formulations, where it can blend evenly with other active ingredients. 
It is often combined with other UV filters to provide broad-spectrum protection, as it primarily absorbs UVA and part of UVB radiation, helping to reduce skin photoaging, DNA damage, and product instability caused by sunlight exposure.

Benzophenone-6 is sometimes listed under INCI (International Nomenclature of Cosmetic Ingredients) as Benzophenone-6, and it is recognized by multiple regulatory bodies and chemical databases, including CAS number 131-54-4, EINECS 205-027-3, and UNII 7813J9CS1G. 
In industrial and laboratory contexts, it may also be referred to as Cyasorb UV 12, Uvinul D 49, or Helisorb 11, among other trade names.

Melting point: 133-136 °C (lit.)
Boiling point: 377.26 °C (rough estimate)
Density: 1.2662 (rough estimate)
Refractive index: 1.5000 (estimate)
Storage temp.: 2-8 °C (protect from light)
Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
Form: Solid
pKa: 6.81 ± 0.35 (Predicted)
Color: Pale Yellow to Light Yellow
Water Solubility: Negligible
Merck: 14,1099
BRN: 1887087
Stability: Hygroscopic
InChIKey: SODJJEXAWOSSON-UHFFFAOYSA-N
LogP: 3.9-4.1

Benzophenone-6 is a common photosensitizer in photochemistry. 
Benzophenone-6 crosses from the S1 state into the triplet state with nearly 100% yield. 
The resulting diradical will abstract a hydrogen atom from a suitable hydrogen donor to form a ketyl radical.

Preparation by reaction of 2-hydroxy-4-methoxy-benzoic acid with resorcinol monomethyl ether in the presence of zinc chloride and phosphorous oxychloride at 7075° for 2.
Benzophenone-6 acts as a UV absorber. 
It is a 2,2'-dihydroxy-4,4'-dimethoxybenzophenone. 

Benzophenone-6 can absorb ultraviolet light in the range of 290-400 nm. 
Benzophenone-6 is used in sun care and other cosmetic care products.
Benzophenone-6 is frequently incorporated into sunscreen lotions, SPF creams, and day creams, where it acts as a chemical UV filter that absorbs UVA rays responsible for skin photoaging, hyperpigmentation, and DNA damage.

In shampoos, conditioners, and styling products, it helps protect hair fibers from UV-induced color fading, brittleness, and degradation, which is particularly important for dyed or chemically treated hair.
Benzophenone-6 and -8 protect cosmetics and personal care products from deterioration by absorbing, reflecting, or scattering UV rays.
Benzophenone-6 when applied to the skin, absorbs UV rays. 

In addition to causing sunburn, UV radiation is a significant cause of premature aging of the skin and contributes to the development of melanoma and other forms of skin cancer. 
When used in OTC sunscreen drug products, Benzophenone-6 must be called Dioxybenzone.
Benzophenone-6 is produced by the copper-catalyzed oxidation of diphenylmethane with air.

A laboratory route involves the reaction of benzene with carbon tetrachloride followed by hydrolysis of the resulting diphenyldichloromethane.
Benzophenone-6 can also be prepared by Friedel–Crafts acylation of benzene with benzoyl chloride in the presence of a Lewis acid (e.g. aluminium chloride) catalyst: since benzoyl chloride can itself be produced by the reaction of benzene with phosgene the first synthesis proceeded directly from those materials.
Another route of synthesis is through a palladium(II)/oxometalate catalyst. This converts an alcohol to a ketone with two groups on each side.

Another, less well-known reaction to produce Benzophenone-6 is the pyrolysis of anhydrous calcium benzoate.
Alkali metals reduce Benzophenone-6 to the deeply blue colored radical anion, diphenylketyl: M + Ph2CO → M+Ph2CO•−
Generally sodium is used as the alkali metal. 

Sodium-benzophenone ketyl is used in the purification of organic solvents, particularly ethers, because it reacts with water and oxygen to give non-volatile products.
Adsorbents such as alumina, silica gel, and especially molecular sieves are superior and far safer.
The sodium-benzophenone method is common since it gives a visual indication that water, oxygen, and peroxides are absent from the solvent. 

Large scale purification may be more economical using devices which utilize adsorbents such as the aforementioned alumina or molecular sieves.
The ketyl is soluble in the organic solvent being dried, which leads to faster purification. 
In comparison, sodium is insoluble, and its heterogeneous reaction is much slower. 

When excess alkali metal is present a second reduction may occur, resulting in a color transformation from deep blue to purple: M + M+Ph2CO•− → (M+)2(Ph2CO)2−
Benzophenone-6 is a substituted benzophenone compound with the chemical formula C15H14O5, where the central carbonyl group (C=O) links two aromatic rings. 
The hydroxyl groups (-OH) at the 2-positions on each benzene ring increase its hydrogen-bonding capacity, improving solubility in certain polar solvents and enhancing its photostabilizing properties. 

The methoxy groups (-OCH₃) at the 4-positions donate electrons to the aromatic system, which shifts the absorption maxima toward the UVA range, making it effective for broad-spectrum UV protection. 
This unique combination of electron-donating and hydrogen-bonding substituents allows Benzophenone-6 to absorb and dissipate high-energy UV photons safely as heat, preventing photodegradation of other formulation ingredients.

Benzophenone-6 works by absorbing ultraviolet light in the UVA (320–400 nm) and partially UVB (280–320 nm) regions, converting it into harmless energy in the form of low-level heat, a process known as photochemical quenching. 
By doing so, it protects sensitive compounds in formulations, such as vitamins, antioxidants, fragrances, and colorants, from UV-induced breakdown. 
This also helps maintain the stability, color, and effectiveness of products exposed to sunlight, extending their shelf life and performance.

Uses Of Benzophenone-6:
Benzophenone-6 is primarily used as a UV filter and photostabilizer in a wide range of products, including sunscreens, anti-aging creams, moisturizers, hair care products, and industrial materials. 
Its ability to absorb UVA and partially UVB radiation makes it essential for protecting both skin and formulations from the harmful effects of sunlight, preserving ingredient stability, color, texture, and efficacy. 
Additionally, its versatility allows it to be combined with other UV filters and cosmetic ingredients to achieve broad-spectrum protection and formulation stability.

As ultraviolet light absorber, especially in paints, plastics.
Benzophenone-6 can be used as a photo initiator in ultraviolet (UV)-curing applications such as inks, imaging, and clear coatings in the printing industry. 
Benzophenone-6 prevents UV light from damaging scents and colors in products such as perfumes and soaps.

Benzophenone-6 can also be added to plastic packaging as a UV blocker to prevent photo-degradation of the packaging polymers or its contents. 
Its use allows manufacturers to package the product in clear glass or plastic (such as a PETE water bottle).
Without it, opaque or dark packaging would be required.

In biological applications, Benzophenone-6 have been used extensively as photophysical probes to identify and map peptide–protein interactions.
Benzophenone-6 is used as an additive in flavorings or perfumes for "sweet-woody-geranium-like notes".
Benzophenone-6 is widely used in sunscreen formulations, day creams, and protective skincare products because it functions as a chemical UV filter, effectively absorbing UVA radiation and partially UVB radiation. 

By doing so, it prevents harmful ultraviolet rays from penetrating the skin, which helps to reduce photoaging, sunburn, DNA damage, and the formation of free radicals. 
Its use in cosmetic formulations enhances the overall UV protection offered by the product, especially when combined with other UV filters for broad-spectrum coverage.
In shampoos, conditioners, hair masks, and leave-in treatments, Benzophenone-6 helps protect hair from the damaging effects of sunlight, including color fading, loss of shine, dryness, and brittleness. 

Its ability to absorb UV radiation before it interacts with hair proteins or pigments ensures that color-treated, highlighted, or chemically processed hair maintains vibrancy and strength over time.
Benzophenone-6 is incorporated into formulations that contain vitamins, antioxidants, essential oils, and fragrances, as it prevents these compounds from breaking down when exposed to sunlight. 
This preserves the efficacy, scent, color, and texture of the product, making it particularly valuable in high-end cosmetic and anti-aging formulations where ingredient stability is critical for performance.

By reducing the amount of UV energy reaching the skin, Benzophenone-6 minimizes oxidative stress and the formation of reactive oxygen species (ROS), which can cause premature skin aging, wrinkles, and hyperpigmentation. 
Its inclusion in creams, lotions, and serums contributes to maintaining skin health and appearance while complementing other active ingredients.
Beyond personal care, Benzophenone-6 is also used in plastics, coatings, and polymeric materials to absorb UV radiation and prevent photodegradation. 

Benzophenone-6 helps maintain the color, flexibility, and mechanical integrity of plastics and coatings exposed to sunlight, which is important for packaging, outdoor furniture, automotive parts, and other materials that require long-term UV stability.
Due to its moderate solubility and chemical stability, Benzophenone-6 can be blended effectively with a variety of oils, emollients, and other UV filters, allowing formulators to create stable emulsions, gels, creams, and lotions with consistent protective properties. 
This versatility ensures that it can be used in both leave-on and rinse-off products, depending on the formulation goals.

Safety Profile Of Benzophenone-6:
Benzophenone-6 is considered "essentially nontoxic".
Benzophenone-6 is however banned as a food additive by the US Food and Drug Administration, despite the FDA's continuing stance that this chemical does not pose a risk to public health under the conditions of its intended use.
The European Union permits it as a flavouring substance, having established a Total Dietary Intake of 0.3mg/kg of body weight per day.

Benzophenone-6 derivatives are known to be pharmacologically active. 
From a molecular chemistry point of view interaction of benzophenone with B-DNA has been demonstrated experimentally.
The interaction with DNA and the successive photo-induced energy transfer is at the base of the Benzophenone-6 activity as a DNA photosensitizer and may explain part of its therapeutic potentialities.

In 2014, benzophenones were named Contact Allergen of the Year by the American Contact Dermatitis Society.
Benzophenone-6 is an endocrine disruptor capable of binding to the pregnane X receptor.
Benzophenone-6, when used in concentrated form or raw material, may cause mild to moderate skin irritation, particularly in individuals with sensitive, damaged, or compromised skin. 

Symptoms of irritation can include redness, itching, or a burning sensation, which typically resolve after removal of the substance and rinsing with water. 
In finished cosmetic formulations, where it is used at regulated concentrations, the risk of skin irritation is significantly reduced.
Direct contact of Benzophenone-6 with the eyes can lead to temporary irritation, watering, or redness, especially in its undiluted form. 

Proper handling, protective eyewear in manufacturing settings, and formulation at safe concentrations are important to minimize the risk of eye damage.
Although uncommon, repeated or prolonged exposure to Benzophenone-6 may trigger allergic contact dermatitis in susceptible individuals. 

Symptoms may include localized redness, itching, and rash, which generally subside when exposure is discontinued. 
Consumers with known sensitivity to benzophenone derivatives should avoid prolonged contact with products containing this ingredient.