Menthyl anthranilate

Last updated
Menthyl anthranilate
Menthyl anthranilate.svg
Names
IUPAC name
(1R,3R,4S)-p-Menthan-3-yl 2-aminobenzoate
Systematic IUPAC name
(1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 2-aminobenzoate
Other names
Meradimate; Menthyl-o-aminobenzoate; Anthranilic acid menthyl ester; Anthranilic acid p-menth-3-yl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.664 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C17H25NO2/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16H,8-10,18H2,1-3H3/t12-,13+,16-/m1/s1
    Key: SOXAGEOHPCXXIO-DVOMOZLQSA-N
  • InChI=1/C17H25NO2/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16H,8-10,18H2,1-3H3/t12-,13+,16-/m1/s1
    Key: SOXAGEOHPCXXIO-DVOMOZLQBB
  • O=C(O[C@H]1[C@@H](CC[C@H](C1)C)C(C)C)c2ccccc2N
Properties
C17H25NO2
Molar mass 275.392 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Menthyl anthranilate (meradimate) is a sunscreening agent. It is one of the 17 ingredients approved by the Food and Drug Administration for use in over-the-counter sunscreen products. [1] [2] [3]

Related Research Articles

<span class="mw-page-title-main">Skin cancer</span> Medical condition involving uncontrolled growth of skin cells

Skin cancers are cancers that arise from the skin. They are due to the development of abnormal cells that have the ability to invade or spread to other parts of the body. Skin cancer is the most commonly diagnosed form of cancer in humans. There are three main types of skin cancers: basal-cell skin cancer (BCC), squamous-cell skin cancer (SCC) and melanoma. The first two, along with a number of less common skin cancers, are known as nonmelanoma skin cancer (NMSC). Basal-cell cancer grows slowly and can damage the tissue around it but is unlikely to spread to distant areas or result in death. It often appears as a painless raised area of skin that may be shiny with small blood vessels running over it or may present as a raised area with an ulcer. Squamous-cell skin cancer is more likely to spread. It usually presents as a hard lump with a scaly top but may also form an ulcer. Melanomas are the most aggressive. Signs include a mole that has changed in size, shape, color, has irregular edges, has more than one color, is itchy or bleeds.

<span class="mw-page-title-main">Oxybenzone</span> Chemical compound

Oxybenzone or benzophenone-3 or BP-3 is an organic compound belonging to the class of aromatic ketones known as benzophenones. It is a pale-yellow solid that is readily soluble in most organic solvents. It is widely used in sunscreen formulations, plastics, toys, furniture finishes, and other products to limit UV degradation. In nature, oxybenzone can be found in various flowering plants. The compound was first synthesised in Germany by chemists König and Kostanecki in 1906.

<span class="mw-page-title-main">Sunscreen</span> 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 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.

<span class="mw-page-title-main">Menthol</span> Organic compound used as flavouring and analgesic

Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature and melts slightly above.

<span class="mw-page-title-main">Basal-cell carcinoma</span> Most common type of skin cancer

Basal-cell carcinoma (BCC), also known as basal-cell cancer, basalioma or rodent ulcer, is the most common type of skin cancer. It often appears as a painless raised area of skin, which may be shiny with small blood vessels running over it. It may also present as a raised area with ulceration. Basal-cell cancer grows slowly and can damage the tissue around it, but it is unlikely to spread to distant areas or result in death.

<span class="mw-page-title-main">Sunless tanning</span> 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 exposure to the Sun. Sunless tanning involves the use of oral agents (carotenids), or creams, lotions or sprays applied to the skin. Skin-applied products may be skin-reactive agents or temporary bronzers (colorants).

<span class="mw-page-title-main">Ecamsule</span> 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.

<span class="mw-page-title-main">Octyl methoxycinnamate</span> 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.

<span class="mw-page-title-main">Retinyl palmitate</span> Vitamin A chemical compound

Retinyl palmitate, or vitamin A palmitate, is the ester of retinol (vitamin A) and palmitic acid, with formula C36H60O2. It is the most abundant form of vitamin A storage in animals.

<span class="mw-page-title-main">Padimate O</span> 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.

<span class="mw-page-title-main">Octocrylene</span> 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.

<span class="mw-page-title-main">2-Ethylhexyl salicylate</span> Chemical compound

2-Ethylhexyl salicylate, or octyl 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.

<span class="mw-page-title-main">Skin care</span> Range of practices that support skin integrity

Skin care or skincare is a range of practices that support skin integrity, enhance its appearance, and relieve skin conditions. They can include nutrition, avoidance of excessive sun exposure, and appropriate use of emollients. Practices that enhance appearance include the use of cosmetics, botulinum, exfoliation, fillers, laser resurfacing, microdermabrasion, peels, retinol therapy, and ultrasonic skin treatment. Skin care is a routine daily procedure in many settings, such as skin that is either too dry or too moist, and prevention of dermatitis and prevention of skin injuries.

<span class="mw-page-title-main">Pyrimidine dimer</span> Type of damage to DNA

Pyrimidine dimers represent molecular lesions originating from thymine or cytosine bases within DNA, resulting from photochemical reactions. These lesions, commonly linked to direct DNA damage, are induced by ultraviolet light (UV), particularly UVC, result in the formation of covalent bonds between adjacent nitrogenous bases along the nucleotide chain near their carbon–carbon double bonds, the photo-coupled dimers are fluorescent. Such dimerization, which can also occur in double-stranded RNA (dsRNA) involving uracil or cytosine, leads to the creation of cyclobutane pyrimidine dimers (CPDs) and 6–4 photoproducts. These pre-mutagenic lesions modify the DNA helix structure, resulting in abnormal non-canonical base pairing and, consequently, adjacent thymines or cytosines in DNA will form a cyclobutane ring when joined together and cause a distortion in the DNA. This distortion prevents DNA replication and transcription mechanisms beyond the dimerization site.

<span class="mw-page-title-main">Indirect DNA damage</span>

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.

Tanning activators are chemicals that increase the effect of UV-radiation on the human skin.

<span class="mw-page-title-main">Sulisobenzone</span> Chemical compound

Sulisobenzone (benzophenone-4) is an ingredient in some sunscreens which protects the skin from damage by UVB and UVA ultraviolet light.

<span class="mw-page-title-main">Sunburn</span> 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 other 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, which 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.

The Public Access to Sunscreens Coalition, or PASS Coalition, is a coalition of public health organizations, dermatologists and sunscreen product companies whose mission is to help prevent skin cancer and improve public health by ensuring Americans have access to safe and effective sunscreens and evidence-based education on sun-safe practices. It accomplishes these goals by lobbying for an efficient and transparent regulatory pathway to market for new sunscreens and advocating against proposals that limit access to FDA-approved sunscreens.

References

  1. "The Skin Cancer Foundation's Guide to Sunscreens". Skin Cancer Foundation . Retrieved March 15, 2013.
  2. Rodrigues, Natércia d.N.; Cole-Filipiak, Neil C.; Turner, Matt A.P.; Krokidi, Konstantina; Thornton, Georgia L.; Richings, Gareth W.; Hine, Nicholas D.M.; Stavros, Vasilios G. (2018). "Substituent position effects on sunscreen photodynamics: A closer look at methyl anthranilate". Chemical Physics. 515: 596–602. Bibcode:2018CP....515..596R. doi:10.1016/j.chemphys.2018.08.001.
  3. Rodrigues, N.D.N.; Cole-Filipiak, N.C.; Horbury, M.D.; Staniforth, M.; Karsili, T.N.V.; Peperstraete, Y.; Stavros, V.G. (2018). "Photophysics of the sunscreen ingredient menthyl anthranilate and its precursor methyl anthranilate: A bottom-up approach to photoprotection". Journal of Photochemistry and Photobiology A: Chemistry. 353: 376–384. doi:10.1016/j.jphotochem.2017.11.042.