Ensulizole

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Ensulizole
Ensulizole.svg
Phenylbenzimidazole-sulfonic-acid-3D-spacefill.png
Names
IUPAC name
2-Phenyl-3H-benzimidazole-5-sulfonic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.044.078 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C13H10N2O3S/c16-19(17,18)10-6-7-11-12(8-10)15-13(14-11)9-4-2-1-3-5-9/h1-8H,(H,14,15)(H,16,17,18) Yes check.svgY
    Key: UVCJGUGAGLDPAA-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C13H10N2O3S/c16-19(17,18)10-6-7-11-12(8-10)15-13(14-11)9-4-2-1-3-5-9/h1-8H,(H,14,15)(H,16,17,18)
    Key: UVCJGUGAGLDPAA-UHFFFAOYAY
  • O=S(=O)(O)c3ccc2[nH]c(c1ccccc1)nc2c3
Properties
C13H10N2O3S
Molar mass 274.29 g·mol−1
Hazards
Safety data sheet (SDS) Cole Parmer Material Safety Data Sheet
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Ensulizole (INN; [1] also known as phenylbenzimidazole sulfonic acid) is a common sunscreen agent. In 1999, the United States Food and Drug Administration regulated that the name ensulizole be used on sunscreen labels in the United States. Ensulizole is primarily a UVB protecting agent providing only minimal UVA protection. The scope of UVB is 290 to 340 nanometers whereas the UVA range is 320 to 400 nanometers. [2] For better UVA protection, it must be paired with avobenzone, titanium dioxide, or zinc oxide; outside of the United States it can also be paired with a UV absorber of the Tinosorb or Mexoryl types. Because ensulizole is water-soluble, it has the characteristic of feeling lighter on skin. As such, it is often used in sunscreen lotions or moisturizers whose aesthetic goal is a non-greasy finish. [3] The free acid is poorly soluble in water, so it is only used as its soluble salts. [4]

Related Research Articles

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Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm to 400 nm, shorter than that of visible light, but longer than X-rays. UV radiation is present in sunlight, and constitutes about 10% of the total electromagnetic radiation output from the Sun. It is also produced by electric arcs and specialized lights, such as mercury-vapor lamps, tanning lamps, and black lights. Although long-wavelength ultraviolet is not considered an ionizing radiation because its photons lack the energy to ionize atoms, it can cause chemical reactions and causes many substances to glow or fluoresce. Consequently, the chemical and biological effects of UV are greater than simple heating effects, and many practical applications of UV radiation derive from its interactions with organic molecules.

Dioxybenzone Chemical compound

Dioxybenzone (benzophenone-8) is an organic compound used in sunscreen to block UVB and short-wave UVA (ultraviolet) rays. It is a derivative of benzophenone. It is a yellow powder with a melting point of 68 °C. It is insoluble in water, but moderately soluble in ethanol and isopropanol.

Sunscreen Topical skin product that helps protect against sunburn

Sunscreen, also known as sunblock, sun cream or suntan lotion, is a photoprotective topical product for the skin that absorbs or reflects some of the sun's ultraviolet (UV) radiation and thus helps protect against sunburn and most importantly prevent skin cancer. Sunscreens come as lotions, sprays, gels, foams, sticks, powders and other topical products. Sunscreens are common supplements to clothing, particularly sunglasses, sunhats and special sun protective clothing, and other forms of photoprotection.

4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA because the two functional groups are attached to the benzene ring across from one another in the para position) is an organic compound with the formula H2NC6H4CO2H. PABA is a white solid, although commercial samples can appear gray. It is slightly soluble in water. It consists of a benzene ring substituted with amino and carboxyl groups. The compound occurs extensively in the natural world.

Sun tanning The darkening of skin in response to ultraviolet light

Sun tanning or simply tanning is the process whereby skin color is darkened or tanned. It is most often a result of exposure to ultraviolet (UV) radiation from sunlight or from artificial sources, such as a tanning lamp found in indoor tanning beds. People who deliberately tan their skin by exposure to the sun engage in a passive recreational activity of sun bathing. Some people use chemical products which can produce a tanning effect without exposure to ultraviolet radiation, known as sunless tanning.

Photodermatitis Skin condition

Photodermatitis, sometimes referred to as sun poisoning or photoallergy, is a form of allergic contact dermatitis in which the allergen must be activated by light to sensitize the allergic response, and to cause a rash or other systemic effects on subsequent exposure. The second and subsequent exposures produce photoallergic skin conditions which are often eczematous. It is distinct from sunburn.

Ecamsule Chemical compound

Ecamsule is an organic compound which is added to many sunscreens to filter out UVA rays. It is a benzylidene camphor derivative, many of which are known for their excellent photostability.

Avobenzone Oil-soluble ingredient used in sunscreen products

Avobenzone is an oil-soluble ingredient used in sunscreen products to absorb the full spectrum of UVA rays.

Octyl methoxycinnamate Organic chemical compound

Octyl methoxycinnamate or ethylhexyl methoxycinnamate (INCI) or octinoxate (USAN), trade names Eusolex 2292 and Uvinul MC80, is an organic compound that is an ingredient in some sunscreens and lip balms. It is an ester formed from methoxycinnamic acid and 2-ethylhexanol. It is a liquid that is insoluble in water.

UV filter Camera parts, features and technologies

UV filters are compounds, mixtures, or materials that block or absorb ultraviolet (UV) light. One of the major applications of UV filters is their use as sunscreens to protect skin from sunburn and other sun/UV related damage. After the invention of digital cameras changed the field of photography, UV filters have been used to coat glass discs fitted to camera lenses to protect hardware that is sensitive to UV light.

Padimate O Water-insoluble oily ingredient used in some sunscreens

Padimate O is an organic compound related to the water-soluble compound PABA that is used as an ingredient in some sunscreens. This yellowish water-insoluble oily liquid is an ester formed by the condensation of 2-ethylhexanol with dimethylaminobenzoic acid. Other names for padimate O include 2-ethylhexyl 4-dimethylaminobenzoate, Escalol 507, octyldimethyl PABA, and OD-PABA.

Octyl salicylate Chemical compound

Octyl salicylate, or 2-ethylhexyl salicylate, is an organic compound used as an ingredient in sunscreens and cosmetics to absorb UVB (ultraviolet) rays from the sun. It is an ester formed by the condensation of salicylic acid with 2-ethylhexanol. It is a colorless oily liquid with a slight floral odor.

Bemotrizinol Chemical compound

Bemotrizinol is an oil-soluble organic compound that is added to sunscreens to absorb UV rays. It is marketed as Parsol Shield, Tinosorb S, and Escalol S.

Bisoctrizole Chemical compound

Bisoctrizole is a phenolic benzotriazole that is added to sunscreens to absorb UV rays.

Bisdisulizole disodium Chemical compound

Bisdisulizole disodium is a water-soluble organic compound which is added to sunscreens to absorb UVA rays. It is marketed by Symrise.

Direct DNA damage can occur when DNA directly absorbs a UVB photon, or for numerous other reasons. UVB light causes thymine base pairs next to each other in genetic sequences to bond together into pyrimidine dimers, a disruption in the strand, which reproductive enzymes cannot copy. It causes sunburn and it triggers the production of melanin.

Drometrizole trisiloxane Chemical compound

Drometrizole trisiloxane (INCI) is a lipophilic benzotriazole derivative marketed as Mexoryl XL by L'Oréal and is used in sunscreens to absorb UV radiation. It is a broad-spectrum UV absorber with two absorption peaks, one at 303 nm (UVB) and one at 344 nm (UVA). Just like Mexoryl SX (ecamsule), it is used exclusively in products by L'Oréal owned brands. Drometrizole trisiloxane and ecamsule are often used together, because they show a synergistic effect in protection.

Sunburn Burning of the skin by the suns radiation

Sunburn is a form of radiation burn that affects living tissue, such as skin, that results from an overexposure to ultraviolet (UV) radiation, usually from the Sun. Common symptoms in humans and animals include: red or reddish skin that is hot to the touch or painful, general fatigue, and mild dizziness. Other symptoms include blistering, peeling skin, swelling, itching, and nausea. Excessive UV radiation is the leading cause of (primarily) non-malignant skin tumors, and in extreme cases can be life-threatening. Sunburn is an inflammatory response in the tissue triggered by direct DNA damage by UV radiation. When the cells' DNA is overly damaged by UV radiation, type I cell-death is triggered and the tissue is replaced.

Photoaging or photoageing is a term used for the characteristic changes to skin induced by chronic UVA and UVB exposure. Tretinoin is the best studied retinoid in the treatment of photoaging.

Sunscreen Innovation Act

The Sunscreen Innovation Act is a 2014 law that amended the Federal Food, Drug, and Cosmetic Act to establish an expedited process for the review and approval of over-the-counter (OTC) sunscreens. The US Food and Drug Administration (FDA) had not approved a new active ingredient in sunscreen since 1999, despite some sunscreens having been approved and used overseas for a decade. The new law gave the FDA one year to respond to the existing backlog of sunscreen ingredient approval requests, and then 18 months to reply to any future applications.

References

  1. "International non-proprietary name". Medinet. Retrieved 6 May 2016.
  2. "Archived copy" (PDF). www.uspdqi.org. Archived from the original (PDF) on 14 December 2003. Retrieved 22 May 2022.{{cite web}}: CS1 maint: archived copy as title (link)
  3. eMedicine - Sunscreens and Photoprotection : Article by Stanley B Levy
  4. "Vibrant Science & Technology - EMD Group".