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HOMOSALATE

Homosalate is an organic compound used in some sunscreens. 
Homosalate 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.

CAS No: 118-56-9
IUPAC Name: 3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate
EC No:204-260-8
Chemical formula: C16H22O3

Other names: Homosalate, 118-56-9, Homomenthyl salicylate, Coppertone, 3,3,5-TRIMETHYLCYCLOHEXYL SALICYLATE, Heliopan, Heliophan, Filtersol ''A'', 3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate, m-Homomenthyl salicylate, Homosalatum, Homosalato, (3,3,5-trimethylcyclohexyl) 2-hydroxybenzoate, Caswell No. 482B, Benzoic acid, 2-hydroxy-, 3,3,5-trimethylcyclohexyl ester, 52253-93-7, CCRIS 4885, NSC 164918, Metahomomenthyl salicylate, Salicylic acid, m-homomenthyl ester, EINECS 204-260-8, 2-Hydroxybenzoic acid 3,3,5-trimethylcyclohexyl ester, UNII-V06SV4M95S, Salicylic Acid 3,3,5-Trimethylcyclohexyl Ester, EPA Pesticide Chemical Code 076603, NSC-164918, V06SV4M95S, MFCD00019377, DTXSID1026241, EC 204-260-8, Salicylic acid, 3,3,5-trimethylcyclohexyl ester, NCGC00091888-01, DTXCID606241, Salicylic acid, 3,3,5-trimethylcyclohexyl ester (8CI), Filtrosol A, component of Coppertone, SR-05000001884, Homosalat, Kemester HMS, CAS-118-56-9, Homosalate; Salicylic acid 3,3,5-trimethylcyclohexyl ester; 3,3,5-Trimethylcyclohexyl salicylate, Filtersol''A'', Prestwick1_001090, Prestwick2_001090, Prestwick3_001090, SCHEMBL16207, BSPBio_001140, SPECTRUM1505020, SPBio_003030, BPBio1_001254, CHEMBL1377575, CHEBI:91642, 3,5-Trimethylcyclohexyl salicylate, HMS1571I22, HMS2093G22, HMS2098I22, HMS3715I22, Pharmakon1600-01505020, HY-B0928, 3,3,5-Trimethylcyclohexylsalicylate, Tox21_111174, Tox21_202109, Tox21_303082, NSC164918, NSC758908, s4572, AKOS015904082, Tox21_111174_1, CCG-213330, DB11064, NSC-758908, NCGC00091888-02, NCGC00091888-03, NCGC00091888-04, NCGC00091888-05, NCGC00091888-06, NCGC00091888-09, NCGC00257063-01, NCGC00259658-01, AS-10409, SY051923, SBI-0206787.P001, AB00514041, NS00009551, Salicylic acid,3,5-trimethylcyclohexyl ester, T2278, Benzoic acid, 3,3,5-trimethylcyclohexyl ester, D04450, E78223, AB00514041_02, EN300-7381967, A921433, J-519754, Q2260189, SR-05000001884-1, SR-05000001884-2, BRD-A34751532-001-03-6, BRD-A34751532-001-04-4

Homosalate is a widely used chemical in sunscreens and skin care products with SPF. 
Homosalate is a potential endocrine disruptor and studies in cells suggest it may impact hormones. 
In addition to direct health concerns following homosalate exposure, the chemical may also enhance the absorption of pesticides in the body.

"Homosalate is an organic compound belonging to a class of chemicals known as salicylates," explains Petrillo. 
It's a chemical sunscreen that shields the skin from sun exposure by absorbing UV light and converting it to heat so that it can't cause DNA damage to the skin cells, he adds. 
There are plenty of other chemical sunscreen ingredients, but homosalate is incredibly common. 
In fact, it's found in almost half of commercially-available sunscreens, notes Fincher.

Homosalate's mechanism of action—and that of any chemical sunscreen—depends on it being absorbed into the skin (unlike physical sunscreens, which sit on top of the skin). 
Homosalate this absorption into the body that's incited talk about the safety of these ingredients.

According to Petrillo, there isn't a huge difference between the various chemical sunscreen ingredients, all of which work the same way. 
The differences lay in terms of which specific UV rays they can absorb and protect against.

UVB-blocker: Homosalate, in particular, is a UVB-blocker, protecting against the UV damage that is known to cause skin cancer, says Fincher. 
To that point, "since it has very limited efficacy against UVA rays, it needs to be combined with other agents to ensure complete protection," adds Idriss.

Broad-spectrum sunscreen ingredient: 
Homosalate this combination of chemical sunscreen ingredients, some of which work against UVA rays and some of which work against UVB rays, that will offer a larger range of protection so that a sunscreen can be called "broad-spectrum," notes Fincher.

Homosalate is an organic compound that belongs to salicylates. It is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. Salicylates prevent direct skin exposure to the sun’s harmful rays by absorbing ultraviolet (UV) light.

Homosalate specifically absorbs short-wave UVB rays, which are associated with DNA damage and increased risk of skin cancer. It is a common ingredient in many commercially available sunscreens. There are no reported adverse effects from homosalate.

Molar mass: 262.349 g·mol−1
Density: 1.05 g/cm3 (20 °C)
Melting point: < -20 °C
Boiling point: 181–185 °C

Solubility in water: 0.4 mg/L
XLogP3-AA: 5
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 3

Rotatable Bond Count: 3
Exact Mass: 262.15689456 g/mol
Monoisotopic Mass: 262.15689456 g/mol
Topological Polar Surface Area: 46.5Ų

Heavy Atom Count: 19
Complexity: 324
Undefined Atom Stereocenter Count: 2
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Homosalate is one of the most commonly used UVB filters in sunscreens in the US market. 
Homosalate belongs to the salicylate class and has a peak absorption of 306 nm. 
Homosalate is approved by the FDA for a maximum concentration of 15%. 
Along with other salicylates such as octisalate, it is a weak absorber and is often used in combination with other organic absorbers.

Octocrylene is another widely used UVB filter. 
This molecule has the unique role in stabilizing avobenzone, the only long-range organic UVA filter available in the United States. 
Without octocrylene, avobenzone is degraded by 50% upon 1 hour of UV exposure, rendering the sunscreen less effective. 
Octocrylene has a thick, oily texture, and a peak absorption at 303 nm (range 290–360 nm).

Homosalate is an organic compound that belongs to salicylates. 
Homosalate is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. 
Salicylates prevent direct skin exposure to the sun’s harmful rays by absorbing ultraviolet (UV) light.

Homosalate specifically absorbs short-wave UVB rays, which are associated with DNA damage and increased risk of skin cancer. 
Homosalate is a common ingredient in many commercially available sunscreens. 
There are no reported adverse effects from homosalate.

Homosalate is an organic compound that belongs to salicylates. 
Homosalate is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. 
Salicylates prevent direct skin exposure to the sun’s harmful rays by absorbing ultraviolet (UV) light. 
Homosalate specifically absorbs short-wave UVB rays, which are associated with DNA damage and increased risk of skin cancer.

Homosalate is a common ingredient in many commercially available sunscreens. 
There are no reported adverse effects from homosalate.

Homosalate is an FDA-approved sunscreen active ingredient that provides primarily UVB protection, stopping where the UVA range begins. 
Homosalate internationally approved for use in sunscreens, up to a maximum concentration of 15%.

Since the UVA-protecting range of homosalate is very narrow, it’s not used alone in sunscreens, but is often used with UVA filters such as avobenzone, where it can help improve stability. 
Homosalate considered non-sensitizing and is most often seen in sunscreens rated SPF 30 and greater.

Interestingly, since homosalate is a salicylate ingredient just like salicylic acid, part of how it works to reduce signs of UV-triggered redness is from its calming benefit. 
Some researchers speculate that this could mean people stay out in the sun longer since they won’t see their skin turn color, but since homosalate is never used alone and the redness-producing damage it offsets is a benefit, it’s not considered a valid concern. 
Other studies have shown that homosalate suppresses the formation of a type of free radical known as singlet oxygen which is formed when skin is exposed to UV light.

Turning to safety, studies have shown that homosalate has low penetration into skin, is not an endocrine disruptor, and is unlikely to provoke an allergic reaction on skin. 
In vitro studies on breast cancer cells have shown that homosalate has cytotoxic effects; however, this does not apply to how sunscreen is used on skin, and the amounts shown to provoke this effect are much greater than what could be absorbed into the body from topical application.

Despite an impressive safety profile, this sunscreen active is one of several currently undergoing further safety and toxicology testing under the purview of the United States Food and Drug Administration (FDA). 
This testing is to gain a better understanding of the systemic absorption, metabolism, and elimination of these sunscreen actives when small amounts enter the body via topical use.

Homosalate important to know that the presence of this or other sunscreen actives in the body does not mean your health is at risk. 
Homosalate is anticipated that the additional testing being done will reaffirm the safety of these ingredients; however, those who remain concerned can choose sunscreens with mineral actives (titanium dioxide and zinc oxide) which are not included in the FDA’s new call for additional testing.
Sunscreens are used to protect the skin from the harmful effects of the sun.

They help to prevent sunburn and premature aging (such as wrinkles, leathery skin). 
Sunscreens also help to decrease the risk of skin cancer and also of sunburn-like skin reactions (sun sensitivity) caused by some medications (including tetracyclines, sulfa drugs, phenothiazines such as chlorpromazine).
The active ingredients in sunscreens work either by absorbing the sun's ultraviolet (UV) radiation, preventing it from reaching the deeper layers of the skin, or by reflecting the radiation.

Wearing sunscreen does not mean that you can stay out longer in the sun. 
Sunscreens cannot protect against all of the sun's radiation.
There are various types of sunscreens available in many forms (e.g., cream, lotion, gel, stick, spray, lip balm). 
See the Notes section for information about selecting a sunscreen.

Sunscreens are for use on the skin only. 
Follow all directions on the product package. 
If you have any questions, ask your doctor or pharmacist.

Apply sunscreen generously to all exposed skin 30 minutes before sun exposure. 
As a general guide, use 1 ounce (30 grams) to cover your entire body. 
Reapply the sunscreen after swimming or sweating or drying off with a towel or if it has rubbed off. 
If you are outside for long periods, reapply sunscreen every 2 hours. 
If you are using the lip balm form, apply to the lip area only.

The spray form is flammable. 
If using the spray, avoid smoking when applying this medication and do not use or store it near heat or open flame.

When applying sunscreen to the face, be careful to avoid contact with the eyes. 
If the sunscreen gets in your eyes, rinse thoroughly with water.

Homosalate is an organic sun filter (from carbon). 
This filter mainly absorbs UVB radiation, which is responsible for tanning but also for sunburn and skin cancer. 

In our products, Homosalate appears in the list of ingredients on the packaging, under the name Homosalate.

Homosalate is an oil-soluble chemical sunscreen ingredient used to absorb UVB rays (the rays produce sunburns in the upper layer of skin). 
Ironically it is a weak UV filter (at 10% concentration it is an SPF 4) and is not photostable (meaning it breaks down in sunshine). 
Homosalate is a derivative of salicylic acid. 
Salicylic acid is used to remove the outer layer of skin and treat warts and acne.

Because homosalate only covers the UVB spectrum, it is usually combined with avobenzone (a chemical UVA filter) to get broad-spectrum coverage.

As most ingredients in chemical sunscreens homosalate works by absorbing into skin — it does not sit on top of skin like zinc oxide.

On labels, homosalate might also be listed as Homomenthyl salicylate, or HMS.

Homosalate is an ingredient used in the formulation of sunscreen products. 
Homosalate is also used in some eyebrow pencils, skincare, and lipsticks.

Homosalate is used mainly as a sunscreen ingredient, protecting the skin against UV rays.  
As you probably know by now, sun damage from UV rays contributes to the risk of skin cancers such as melanoma, as well as contributing to premature aging.

Another way in which homosalate is used is to protect ingredients in other formulations from degrading or absorbing UV rays. 
Homosalate does this by converting UV rays into less damaging infrared heat. 

In terms of chemistry, homosalate is formed by reacting salicylic acid and another compound 3,3,5-trimethylcyclohexanol. 
Understandably the second ingredient may sound scary however, it is actually used as a food additive to improve the minty taste of products.

The main benefit of homosalate is that it is able to protect the skin from the harmful effects of the sun. 
Sunscreens generally reduce the risk of skin cancers such as melanoma. 
As well as this important benefit sunscreens can also reduce sun sensitivity that is often experienced by those on medications that increase your sensitivity to the sun such as tetracyclines, sulfa drug, and isotretinoin. 

The other main benefit to sunscreens is that they also protect the skin from sunburn and premature aging. 
Sun damage is one of the major contributing factors to premature aging, leading to more visible wrinkles, and fine lines. 

Sunscreens work in either of two ways, the first is physical sunscreens like zinc and titanium dioxide, which reflect the sun’s rays preventing it from penetrating into the deeper layers of the skin where damage can be caused. 
The issue with physical sunscreens is that they need to be applied in a thick layer that often leaves a white layer of product on the skin in order for the sunscreen to reflect the UV rays properly. 

The other is a chemical sunscreen like homosalate which absorbs UV rays and transfers them into infrared heat. 
Keep in mind that the heat that is produced from using chemical sunscreens is very minimal and unlikely to cause any irritation or damage by itself. 

As always, make sure to regularly apply sunscreen and protect your skin from sun exposure by wearing long sleeve shirts, hats and avoiding extended periods of time in the sun. 

Homosalate (HMS) is a salicylate molecule that is commonly included within commercial sunscreen formulations to provide protection from the adverse effects of ultraviolet (UV) radiation exposure. 
In the present work, the mechanisms by which HMS provides UV photoprotection are unravelled, using a multi-pronged approach involving a combination of time-resolved ultrafast laser spectroscopy in the gas-phase and in solution, laser-induced fluorescence, steady-state absorption spectroscopy, and computational methods.

The unique combination of these techniques allow us to show that the enol tautomer of HMS undergoes ultrafast excited state intramolecular proton transfer (ESIPT) upon photoexcitation in the UVB (290–320 nm) region; once in the keto tautomer, the excess energy is predominantly dissipated non-radiatively.

Sharp transitions are observed in the LIF spectrum at close-to-origin excitation energies, which points towards the potential presence of a second conformer that does not undergo ESIPT. 
These studies demonstrate that, overall, HMS exhibits mostly favourable photophysical characteristics of a UV filter for inclusion in sunscreen formulations.

Salicylates are defined as salts or esters derived from salicylic acid, several of which have uses within the personal care and pharmaceutical industries.
In addition to being included in cosmetics for fragrance and antioxidant properties,1,2 salicylates are used as chemical (organic) filters in sunscreen blends, for solar protection via absorption of ultraviolet (UV) radiation, specifically UVB radiation (290–320 nm).

Even though regulated exposure to UV radiation has positive effects on human health, such as facilitating the synthesis of vitamin D, the use of UV filters in sunscreen formulations is necessary to prevent the adverse effects of overexposure, such as an increased risk of skin cancers.

Despite having a low extinction coefficient compared to other available UV filters,13 salicylates are an appealing choice for sunscreen formulators for several reasons. 
Firstly, the minimal solvatochromic shift that is observed in salicylates upon significant changes in solvent polarity has been demonstrated in at least 13 different solvents.

This negligible shift in peak absorption implies that a range of excipients may be used in a formulation without changing the protection range of wavelengths afforded by these molecules. 
Furthermore, salicylates contained within sunscreen formulations can serve as solubilizers for other UV filters such as avobenzone, which to date remains the most widely implemented UVA (320–400 nm) filter in the world.

In addition, salicylates have a favourable safety record, with few reports of allergenic effects of these compounds.
However, a consensus is yet to be reached on whether salicylates used in sunscreens are photostable, that is, if they do not degrade upon prolonged UV exposure. 
Many publications report that they are indeed photostable,18,21–23 while other reports also exist to the contrary.

Homosalate is an organic compound most often used in sunscreens as a chemical UV filter. 
Ungraded products supplied by Spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for human consumption or therapeutic use.

Homosalate is an ingredient used in sunscreens and fragrances. 
Homosalate is a UV-absorber, filter, and a skin conditioner 
Homosalate absorbs UVB rays specifically.

Homosalate is found in fragrances and sunscreens 

Homosalate (HMS, Homomenthyl salicylate) is an organic ultraviolet filter used in most sunscreens but has been reported to be toxic to marine organisms. 
Homosalate aggravates the invasion of human trophoblast cells as well as regulates intracellular signaling pathways including PI3K/AKT and MAPK pathways.

Homosalate is a chemical sunscreen based on the naturally occurring molecule salicylic acid. 
Salicylic acid is found in willow plants but for industrial use it is typically made synthetically. 
Another molecule is stuck onto the salicylic acid to make it less soluble in water so the sunscreen doesn’t get washed off easily. 
Homosalate is good at absorbing UVB rays, however there are some concerns about it’s safety (see below)

Chemical sunscreens are one of two classes of sunscreen, the other being mineral sunscreens like titanium dioxide or zinc oxide.

Homosalate is also sometimes used in fragrances.

Sunscreens protect your skin from the sun’s harmful UV rays.
When it hits your skin, UV light can enter your skin cells and damage their DNA. 
This DNA damage can cause mutations which can lead to cancer. 

Some wavelengths of UV called UVB directly damage the DNA while other wavelengths called UVA create reactive free radicals which attack the DNA. 
Your body tries to prevent these mutations progressing into cancer by triggering inflammation and sunburn. 
As well as being painful, this inflammation also damages the collagen in your skin, leading to wrinkled and aged looking skin.

When sunscreens like homosalate are applied to the skin, they create a protective barrier which absorbs UV light before it can get inside your skin cells. 
The salicylic acid part of homosalate is good at absorbing UVB rays and small amount of UVA. 
As chemical sunscreens have different wavelengths they’re best at absorbing, homosalate is usually mixed with a molecule that absorbs UVA well to increase protection.

Homosalate is an organic compound used in some sunscreens. 
Homosalate 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.
In short, homosalate is the main ingredients in chemical sunscreens. 
Scientifically, it’s an organic salicylate compound that helps to absorb UV light by converting it to heat so that the sun damage won’t hinder the skin cells.

Although there are many ingredients in chemical sunscreens, homosalate is one of the most common — found in nearly half of commercial sunscreens on the market.
Homosalate is used as an UV adsorbing agent in subscreen cosmetics such as creams, lotions, lipsticks and sun oils. 
Further research may identify additional product or industrial usages of this chemical.

Homosalate is an organic compound used in some sunscreens. 
Homosalate is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. 
Contained in 45% of U.S. sunscreens, it is used as a chemical UV filter.

UV filters should be determined a strict toxicological safety prior to approval. 
Homosalate (HMS) is one of the most widely used organic UV filter. 
HMS accumulates in aquatic biota ecosystems and humans through the food chain; therefore, it is important to consider the effects on health and know its mechanisms of action.

Homosalate is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol. 
Homosalate is used in some sunscreens. 
Reference standards of Homosalate API, and its pharmacopeial, non pharmacopeial impurities, and stable isotopes are listed below.

Homosalate is a UV filtering agent used in sunscreens and cosmetics for skin protection purposes. 
Despite the widespread use of these products, the extent of in vivo exposure to homosalate has not been elucidated. 
This study first reports the development of a rapid and sensitive high performance liquid chromatography-tanden mass spectrometry (HPLC-MS/MS) method for the analysis of homosalate in rat plasma and its pharmacokinetic characterization after topical application.

Chromatographic separation was achieved using a Kinetex C18 column (50 mm × 2.1 mm, 2.6 µm). 
The mobile phase was a mixture of acetonitrile and 0.05% formic acid (82.5:17.5 v/v). 
The multiple reaction monitoring was based on the transition of m/z 263.2 → 139.0 for homosalate and 251.2 → 139.0 for octyl salicylate (internal standard). 
The present method was found to be linear in the concentration range of 0.2–400 ng/mL (r > 0.999). 
The intra- and inter-day assay accuracy and precision ranged from 92.8 to 107.6% and 3.9 to 7.0%, respectively.

The developed assay was successfully applied to a pharmacokinetic study in rats after topical application of gel containing homosalate (dose 1.8 mg). 
The maximum plasma concentration (7.9 ± 2.7 ng/mL) was achieved at 11.3 ± 1.6 hr, indicating a prolonged absorption of homosalate after topical application.

The molecule chosen as the focus of this study is homomenthyl salicylate (herein referred to as homosalate, HMS); its molecular structure and the range of UV protection it provides is shown in . 
This molecule is approved for use in sunscreen formulations worldwide and can be employed in substantial quantities (e.g. up to 15% w/w in the United States).

Recent studies in rat models have shown that HMS has low dermal permeability and does not cause any endocrine disruption, both of which are major concerns for many existing UV filters used in sunscreen formulations.

In addition, HMS has been deemed to have a favourable toxicological profile.
However, in the MCF-7 cell line, HMS was shown to have cytotoxic and genotoxic characteristics, and extensive studies on the toxicological effects of HMS are recommended.

Homosalate is an organic compound used in some sunscreens. 
Homosalate is an ester formed from salicylic acid and 3,3,5-trimethylcyclohexanol, a derivative of cyclohexanol.

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 cyclohexanol portion provides greasiness that prevents it from dissolving in water.

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