Ecamsule

Last updated
Ecamsule
Ecamsule.png
Ecamsule-3D-spacefill.png
Names
IUPAC name
[(3Z)-3-[[4-[(Z)-[7,7-Dimethyl-2-oxo-1-(sulfomethyl)-3-bicyclo[2.2.1]heptanylidene]methyl]phenyl]methylidene]-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonic acid
Other names
Mexoryl SX; Terephthalylidene dicamphor sulfonic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.101.049 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C28H34O8S2/c1-25(2)21-9-11-27(25,15-37(31,32)33)23(29)19(21)13-17-5-7-18(8-6-17)14-20-22-10-12-28(24(20)30,26(22,3)4)16-38(34,35)36/h5-8,13-14,21-22H,9-12,15-16H2,1-4H3,(H,31,32,33)(H,34,35,36)/b19-13-,20-14- Yes check.svgY
    Key: HEAHZSUCFKFERC-AXPXABNXSA-N Yes check.svgY
  • InChI=1/C28H34O8S2/c1-25(2)21-9-11-27(25,15-37(31,32)33)23(29)19(21)13-17-5-7-18(8-6-17)14-20-22-10-12-28(24(20)30,26(22,3)4)16-38(34,35)36/h5-8,13-14,21-22H,9-12,15-16H2,1-4H3,(H,31,32,33)(H,34,35,36)/b19-13-,20-14-
    Key: HEAHZSUCFKFERC-AXPXABNXBW
  • O=S(=O)(O)CC45C(=O)\C(=C/c1ccc(cc1)/C=C2\C(=O)C3(CCC2C3(C)C)CS(=O)(=O)O)C(CC4)C5(C)C
Properties
C28H34O8S2
Molar mass 562.69 g·mol−1
Melting point 255 °C (491 °F; 528 K)(dec) [1]
log P 1.35 [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Ecamsule (USAN, trade name Mexoryl SX, INCI terephthalylidene dicamphor sulfonic acid) 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. [2]

Contents

Although there are a few different UV absorbers with the trade name Mexoryl, only two of them are widely used where approved. Mexoryl SX (water-soluble) and Mexoryl XL (INCI Drometrizole trisiloxane, oil-soluble). Together they show a synergistic effect in protection. [3] The patents are held by L'Oréal. Sunscreens containing ecamsule are exclusive to L'Oréal and its brands.

Mode of action

Exposed to UV, ecamsule undergoes reversible photoisomerization, followed by photoexcitation. The absorbed UV is then released as thermal energy, without penetrating the skin.

UVB rays cause short-term sunburn and skin cancer; UVA rays cause wrinkling and may have some role in development of skin cancer. There is no official rating for UVA protection in the US. In Europe, there are several different rating systems that are used to measure effectiveness in blocking UVA rays, including the IPD (immediate pigment darkening assay) and the PPD (persistent pigment darkening assay). The UVB range is 280 to 320 nanometers, and the UVA range is 320 to 400. Ecamsule protects against UV wavelengths in the 290–400 nanometer range, with peak protection at 345 nm. [4] [5] Because ecamsule does not cover the entire UV spectrum, it should be combined with other active sunscreen agents to ensure broad-spectrum UV protection. Ecamsule is a photostable organic UVA absorber, meaning it doesn't degrade significantly when exposed to light. This is in contrast to the widely used UVA absorber avobenzone that is not intrinsically photostable and requires photostabilizers to prevent significant degradation in light. [6] [7] [8]

Efficacy

A 5% ecamsule containing sunscreen can prevent early changes leading to photoaging in humans. A broad spectrum sunscreen with ecamsule, avobenzone and octocrylene significantly reduces the skin damage associated with UV exposure in human subjects. [9]

In studies done in mice it reduces the formation of UV induced pyrimidine dimers and delays the onset of skin cancer. In vitro ecamsule effectively protects against the harmful effects of UV. [10]

Safety

Ecamsule has little percutaneous absorption and little systemic effects, therefore it is considered relatively safe. [11] A mouse study shows that it does not increase the probability of promoting skin cancer. [12] Studies done in vitro show that it is not photomutagenic. [13]

Because ecamsule is an acid it needs to be neutralized in order to be used without offsetting the final pH of the sunscreen too much. Usually this is done with triethanolamine.

Availability

L'Oréal patented ecamsule first in 1982. It was approved in the EU in 1991. Sunscreens based on ecamsule have been available in Europe, Canada and other parts of the world since 1993. Ecamsule was given approval by the FDA in 2006 to be used in the U.S. [14] However this approval only extends to ecamsule containing sunscreens registered under a New Drug Application, not ecamsule itself. [15] [16]

Related Research Articles

Ultraviolet Light with wavelength shorter than visible light

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.

Oxybenzone Chemical compound


Oxybenzone or benzophenone-3 or BP-3 is an organic compound. It is a pale-yellow solid that is readily soluble in most organic solvents. Oxybenzone belongs to the class of aromatic ketones known as benzophenones. It is a naturally occurring chemical found in various flowering plants as well as being an organic component of many sunscreen lotions. It is widely used in plastics, toys, furniture finishes, and other products to limit UV degradation.

Sunscreen Topical skin product that helps protect against sunburn

Sunscreen, also known as sunblock 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.

Sunless tanning, also known as UV filled tanning, self tanning, spray tanning, or fake tanning, refers to the effect of a suntan without the Sun. The popularity of sunless tanning has risen since the 1960s after health authorities confirmed links between UV exposure and the incidence of skin cancer.

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.

Ensulizole Chemical compound

Ensulizole 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. 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. The free acid is poorly soluble in water, so it is only used as its soluble salts.

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.

Homosalate Chemical compound

Homosalate is an organic compound used in some sunscreens. It is made by the Fischer–Speier esterification of salicylic acid and 3,3,5-trimethylcyclohexanol, the latter being a hydrogenated derivative of isophorone. Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter. The salicylic acid portion of the molecule absorbs ultraviolet rays with a wavelength from 295 nm to 315 nm, protecting the skin from sun damage. The hydrophobic trimethyl cyclohexane functional group provides greasiness that prevents it from dissolving in water.

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.

Pyrimidine dimer

Pyrimidine dimers are molecular lesions formed from thymine or cytosine bases in DNA via photochemical reactions. Ultraviolet light (UV) induces the formation of covalent linkages between consecutive bases along the nucleotide chain in the vicinity of their carbon–carbon double bonds. The dimerization reaction can also occur among pyrimidine bases in dsRNA —uracil or cytosine. Two common UV products are cyclobutane pyrimidine dimers (CPDs) and 6–4 photoproducts. These premutagenic lesions alter the structure and possibly the base-pairing. Up to 50–100 such reactions per second might occur in a skin cell during exposure to sunlight, but are usually corrected within seconds by photolyase reactivation or nucleotide excision repair. Uncorrected lesions can inhibit polymerases, cause misreading during transcription or replication, or lead to arrest of replication. Pyrimidine dimers are the primary cause of melanomas in humans.

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.

Diethylamino hydroxybenzoyl hexyl benzoate Chemical compound

Diethylamino hydroxybenzoyl hexyl benzoate (INCI) is an organic compound used in sunscreens to absorb UVA radiation. It is marketed as Uvinul A Plus by BASF. DHHB has an absorption maximum of 354 nm.

Mycosporine-like amino acids (MAAs) are small secondary metabolites produced by organisms that live in environments with high volumes of sunlight, usually marine environments. The exact number of compounds within this class of natural products is yet to be determined, since they have only relatively recently been discovered and novel molecular species are constantly being discovered; however, to date their number is around 30. They are commonly described as “microbial sunscreens” although their function is believed not to be limited to sun protection.

References

  1. 1 2 "ecamsule". www.chemsrc.com.
  2. ↑ Deflandre A, Lang G (April 1988). "Photostability assessment of sunscreens. Benzylidene camphor and dibenzoylmethane derivatives". International Journal of Cosmetic Science. 10 (2): 53–62. doi:10.1111/j.1467-2494.1988.tb00002.x. PMID   19456910.
  3. ↑ Moyal D. (October 2004). "Prevention of ultraviolet-induced skin pigmentation". Photodermatol Photoimmunol Photomed. 20 (5): 243–7. doi:10.1111/j.1600-0781.2004.00111.x. PMID   15379874.
  4. ↑ Fourtanier A, Labat-Robert J, Kern P, Berrebi C, Gracia AM, Boyer B (April 1992). "In vivo evaluation of photoprotection against chronic ultraviolet-A irradiation by a new sunscreen Mexoryl SX". Photochem Photobiol. 55 (4): 549–60. doi:10.1111/j.1751-1097.1992.tb04277.x. PMID   1320278.
  5. ↑ Seite S, Moyal D, Richard S, de Rigal J, Leveque JL, Hourseau C, Fourtanier A (June 1998). "Mexoryl SX: a broad absorption UVA filter protects human skin from the effects of repeated suberythemal doses of UVA". J Photochem Photobiol B. 44 (1): 69–76. doi:10.1016/S1011-1344(98)00122-5. PMID   9745729.
  6. ↑ Chatelain E, Gabard B (September 2001). "Photostabilization of Butyl methoxydibenzoylmethane (Avobenzone) and Ethylhexyl methoxycinnamate by Bis-ethylhexyloxyphenol methoxyphenyl triazine (Tinosorb S), a new UV broadband filter". Photochemistry and Photobiology. 74 (3): 401–6. doi:10.1562/0031-8655(2001)074<0401:POBMAA>2.0.CO;2. ISSN   0031-8655. PMID   11594052.
  7. ↑ Free text.png Tarras-Wahlberg N, Stenhagen G, Larko O, Rosen A, Wennberg AM, Wennerstrom O (October 1999). "Changes in ultraviolet absorption of sunscreens after ultraviolet irradiation". J Invest Dermatol. 113 (4): 547–53. doi: 10.1046/j.1523-1747.1999.00721.x . PMID   10504439.
  8. ↑ Wetz F, Routaboul C, Denis A, Rico-Lattes I (Mar–Apr 2005). "A new long-chain UV absorber derived from 4-tert-butyl-4'-methoxydibenzoylmethane: absorbance stability under solar irradiation". Journal of Cosmetic Science. 56 (2): 135–48. doi:10.1562/2004-03-09-ra-106. PMID   15870853.
  9. ↑ Seité S, Colige A, Piquemal-Vivenot P, Montastier C, Fourtanier A, Lapière C, Nusgens B (August 2000). "A full-UV spectrum absorbing daily use cream protects human skin against biological changes occurring in photoaging". Photodermatol Photoimmunol Photomed. 16 (4): 147–55. doi:10.1034/j.1600-0781.2000.160401.x. PMID   11019938.
  10. ↑ Marrot L, Belaidi JP, Chaubo C, Meunier JR, Perez P, Agapakis-Causse C (September 1998). "An in vitro strategy to evaluate the phototoxicity of solar UV at the molecular and cellular level: application to photoprotection assessment". Eur J Dermatol. 8 (6): 403–12. PMID   9729050.
  11. ↑ Benech-Kieffer F, Meuling WJ, Leclerc C, Roza L, Leclaire J, Nohynek G (Nov–Dec 2003). "Percutaneous absorption of Mexoryl SX in human volunteers: comparison with in vitro data". Skin Pharmacol Appl Skin Physiol. 16 (6): 343–55. doi:10.1159/000072929. PMID   14528058.
  12. ↑ Fourtanier A (October 1996). "Mexoryl SX protects against solar-simulated UVR-induced photocarcinogenesis in mice". Photochem Photobiol. 64 (4): 688–93. doi:10.1111/j.1751-1097.1996.tb03125.x. PMID   8863475.
  13. ↑ Dean SW, Dunmore RH, Ruddock SP, Dean JC, Martin CN, Kirkland DJ (May 1992). "Development of assays for the detection of photomutagenicity of chemicals during exposure to UV light. II. Results of testing three sunscreen ingredients". Mutagenesis. 7 (3): 179–82. doi:10.1093/mutage/7.3.179. PMID   1602971.
  14. ↑ "Long-awaited sunscreen approved for sale in U.S." USA Today. 2006-07-24.
  15. ↑ "FDA approves Mexoryl in L'Oreal sunscreen". cosmeticsdesign.com.
  16. ↑ "redirecting". www.cosmeticsandtoiletries.com.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.