Bisoctrizole

Last updated
Bisoctrizole
Bisoctrizole.svg
Bisoctrizole-3D-spacefill.png
Names
Preferred IUPAC name
2,2′-Methylenebis[6-(2H-1,2,3-benzotriazol-2-yl)-4-(2,4,4-trimethylpentan-2-yl)phenol]
Other names
UV-360
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.100.550 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C41H50N6O2/c1-38(2,3)24-40(7,8)28-20-26(36(48)34(22-28)46-42-30-15-11-12-16-31(30)43-46)19-27-21 -29(41(9,10)25-39(4,5)6)23-35(37(27)49)47-44-32-17-13-14-18-33(32)45-47/h11-18,20-23,48-49H,19,24-25H2,1-10H3 Yes check.svgY
    Key: FQUNFJULCYSSOP-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C41H50N6O2/c1-38(2,3)24-40(7,8)28-20-26(36(48)34(22-28)46-42-30-15-11-12-16-31(30)43-46)19-27-21- 29(41(9,10)25-39(4,5)6)23-35(37(27)49)47-44-32-17-13-14-18-33(32)45-47/h11-18,20-23,48-49H,19,24-25H2,1-10H3
    Key: FQUNFJULCYSSOP-UHFFFAOYAP
  • n1c6ccccc6nn1c2cc(cc(c2O)Cc5cc(cc(n3nc4ccccc4n3)c5O)C(C)(C)CC(C)(C)C)C(C)(C)CC(C)(C)C
Properties
C41H50N6O2
Molar mass 658.88 g/mol
Melting point 195.7 °C (384.3 °F; 468.8 K)
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 ?)

Bisoctrizole (INN [1] /USAN, [2] marketed by BASF as Tinosorb M, by DSM Nutritional Products as Parsol Max, by Everlight Chemical as Eversorb M, and by MPI as Milestab 360, INCI methylene bis-benzotriazolyl tetramethylbutylphenol) is a phenolic benzotriazole that is added to sunscreens to absorb UV rays. [3] It is a broad-spectrum ultraviolet radiation absorber, absorbing UVB as well as UVA rays. [3] It also reflects and scatters UV.[ citation needed ]

Bisoctrizole is what is termed is a hybrid UV absorber, which has been described as an organic UV filter produced in microfine organic particles (< 200 nm),[ verification needed ] [4] [ better source needed ] [5] [ non-primary source needed ] like microfine zinc oxide and titanium dioxide.[ dubious – discuss ][ citation needed ] Where other organic UV absorbers dissolved in either the oily or aqueous phases, bisoctrizole dissolves poorly in both.[ citation needed ]

Hence, bisoctrizole is formulated in sunscreen preparations as a 50% suspension, the absorber added to the water phase,[ contradictory ] and mineral micropigments usually added to the oil phase.[ citation needed ] The bisoctrizole particles are stabilized by the surfactant decyl glucoside.[ citation needed ] The compound shows very little photodegradation, and has a stabilizing effect on other UV absorbers, octyl methoxycinnamate (octinoxate) in particular.[ citation needed ]

In primary research reports, bisoctrizole has been reported to minimally penetrate skin, [6] [ non-primary source needed ] and has been described as lacking estrogenic effects in vitro. [7] [ non-primary source needed ]

As of this date,[ when? ] bisoctrizole had not been approved by the U.S. Food and Drug Administration (FDA),[ citation needed ] but is approved in the EU and other parts of the world. [8] [ better source needed ] [9] [10] [ full citation needed ]

Related Research Articles

Ultraviolet Form of electromagnetic radiation

Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm to 400 nm (750 THz), 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 sun cream, 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.

Sunless tanning Indoor tanning lotion

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. Sunless tanning involves the use of creams, lotions and sprays applied to the skin.

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.

Octocrylene Organic compound

Octocrylene is an organic compound used as an ingredient in sunscreens and cosmetics. It is an ester formed by the condensation of 2-ethylhexyl cyanoacetate with benzophenone. It is a viscous, oily liquid that is clear and colorless.

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.

Photoprotection is the biochemical process that helps organisms cope with molecular damage caused by sunlight. Plants and other oxygenic phototrophs have developed a suite of photoprotective mechanisms to prevent photoinhibition and oxidative stress caused by excess or fluctuating light conditions. Humans and other animals have also developed photoprotective mechanisms to avoid UV photodamage to the skin, prevent DNA damage, and minimize the downstream effects of oxidative stress.

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.

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.

Indirect DNA damage

Indirect DNA damage occurs when a UV-photon is absorbed in the human skin by a chromophore that does not have the ability to convert the energy into harmless heat very quickly. Molecules that do not have this ability have a long-lived excited state. This long lifetime leads to a high probability for reactions with other molecules—so-called bimolecular reactions. Melanin and DNA have extremely short excited state lifetimes in the range of a few femtoseconds (10−15s). The excited state lifetime of compounds used in sunscreens such as menthyl anthranilate, avobenzone or padimate O is 1,000 to 1,000,000 times longer than that of melanin, and therefore they may cause damage to living cells that come in contact with them.

Afimoxifene Chemical compound

Afimoxifene, also known as 4-hydroxytamoxifen (4-OHT) and by its tentative brand name TamoGel, is a selective estrogen receptor modulator (SERM) of the triphenylethylene group and an active metabolite of tamoxifen. The drug is under development under the tentative brand name TamoGel as a topical gel for the treatment of hyperplasia of the breast. It has completed a phase II clinical trial for cyclical mastalgia, but further studies are required before afimoxifene can be approved for this indication and marketed.

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.

Iscotrizinol Chemical compound

Iscotrizinol is an organic compound used in sunscreens to absorb UVB and some UVA radiation with a peak protection at 310 nm. It is one of the most photostable chemical sunscreens known today with 25 hours required to lose 10% of its SPF protection ability. It is marketed as Uvasorb HEB by 3V Sigma.

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. ↑ WHO Staff (2005). "Recommended International Nonproprietary Names: List 54, International Nonproprietary Names for Pharmaceutical Substances (INN) [Entry 'bisoctrizolum']". WHO Drug Information. 19 (3). Archived from the original on October 19, 2009. Retrieved July 5, 2022.
  2. ↑ National Library of Medicine Staff (July 5, 2022). "Bisoctrizole". Chem.NLM.NIH.gov. Retrieved July 5, 2022.
  3. 1 2 Latha, MS; Martis, Jacintha; Shobha, V; Shinde, Rutuja Sham; Bangera, Sudhakar; Krishnankutty, Binny; Bellary, Shantala; Varughese, Sunoj; Rao, Prabhakar; Naveen Kumar, B.R. (January 2013). "Sunscreening Agents A Review". Journal of Clinical and Aesthetic Dermatology. 6 (1): 16–26. PMC   3543289 . PMID   23320122.
  4. ↑ Ciba Staff (July 5, 2022). "TINOSORB® M, Broad-spectrum UV Filter for the Water Phase". BASF.com. Retrieved July 5, 2022.
  5. ↑ Herzog, B.; Mongiat, S.; Deshayes, C.; Neuhaus, M.; Sommer, K.; Mantler, A. (2002). "In vivo and in vitro assessment of UVA protection by sunscreen formulations containing either butyl methoxy dibenzoyl methane, methylene bis-benzotriazolyl tetramethylbutylphenol, or microfine ZnO". International Journal of Cosmetic Science. 24 (3): 170–85. doi:10.1046/j.1467-2494.2002.00137.x. PMID   18498509. S2CID   37553401.[ non-primary source needed ]
  6. ↑ Mavon A, Miquel C, Lejeune O, Payre B, Moretto P (2007). "In vitro percutaneous absorption and in vivo stratum corneum distribution of an organic and a mineral sunscreen". Skin Pharmacol Physiol. 20 (1): 10–20. doi:10.1159/000096167. PMID   17035717. S2CID   22041398.[ non-primary source needed ]
  7. ↑ Ashby J, Tinwell H, Plautz J, Twomey K, Lefevre PA (December 2001). "Lack of binding to isolated estrogen or androgen receptors, and inactivity in the immature rat uterotrophic assay, of the ultraviolet sunscreen filters Tinosorb M-active and Tinosorb S". Regul Toxicol Pharmacol . 34 (3): 287–91. doi:10.1006/rtph.2001.1511. PMID   11754532.[ non-primary source needed ]
  8. ↑ Kapes, Beth (July 1, 2005). "Docs Rally for Better Sun Protection". ModernMedicine.com. Archived from the original on October 9, 2007. Retrieved July 5, 2022.
  9. ↑ "Eur-Lex.Europa.eu PDF" (PDF). Archived from the original (PDF) on 2008-08-14. Retrieved 2007-08-19.
  10. ↑ Australian Regulatory Guidelines for OTC Medicines, Chapter 10. [ full citation needed ]
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.