Homosalate
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Homosalate
structure -
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CAS No:
118-56-9
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Formula:
C16H22O3
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Chemical Name:
Homosalate
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Synonyms:
Benzoic acid,2-hydroxy-,3,3,5-trimethylcyclohexyl ester;Salicylic acid,3,3,5-trimethylcyclohexyl ester;Cyclohexanol,3,3,5-trimethyl-,salicylate;Heliophan;Homosalate;3,3,5-Trimethylcyclohexyl salicylate;Heliopan;Homomenthyl salicylate;Filtrosol A;Kemester;Neo Heliopan;Eusolex HMS;Kemester HMS;Neo Heliopan HMS;Heliopan HMS;Uniderm Homsal;NSC 164918;Parsol HMS;3,3,5-Trimethylcyclohexyl 2-hydroxybenzoate;Escalol HMS;8045-71-4;50610-40-7;52253-93-7;194304-23-9
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CAS No:
Description
Liquid.A homolog of menthyl salicylate.Viscous or light yellow to slightly tan liquid or oil.
3,3,5-trimethylcyclohexylsalicylate appears as viscous or light yellow to slightly tan liquid or oil. (NTP, 1992)|Liquid
3,3,5-trimethylcyclohexylsalicylate appears as viscous or light yellow to slightly tan liquid or oil. (NTP, 1992)|2-hydroxybenzoic acid (3,3,5-trimethylcyclohexyl) ester is a benzoate ester and a member of phenols. It derives from a salicylic acid.|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.
Characteristics
46.5
5
3,3,5-trimethylcyclohexylsalicylate appears as viscous or light yellow to slightly tan liquid or oil. (NTP, 1992)
1.045-1.048 g/cm3 @ Temp: 25 °C
163 °C
169 - 173℃
n20 1.516 to 1.518
H2O: <0.1 g/100 mL at 26 ºC
4.17E-05mmHg at 25°C
This compound will hydrolyze under basic conditions. (NTP, 1992). Insoluble in water.
Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
An ester and a phenol. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.
Safety Information
NONH for all modes of transport
2
36/37/38
26-36/39
YK0493000
Xi
P261-P305 + P351 + P338
H315-H319-H335
This chemical is probably combustible. (NTP, 1992)
|Warning|H315 (77.55%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 160 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Fires involving this materical can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
SMALL SPILLS AND LEAKAGE: If you spill this chemical, use absorbent paper to pick up all liquid spill material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with alcohol followed by washing with a strong soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Drug Information
As ingredient in many sunscreen for protection against sunburn, skin aging and skin cancer.
Acts as UV filters.
Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)
For local use only, no systemic absorption.
For local use only, no systemic absorption.
For local use only, no systemic absorption.
Homosalate has the ability to convert incident ultraviolet radiation into less damaging infrared radiation (heat).
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
3,3,5-trimethylcyclohexyl salicylate
Homosalate Use and Manufacturing
250 ml three-necked flask, 10.0 g of methyl salicylate, 23.3 g of 3, 3, 5-trimethylcyclohexanol, 0.50 g of potassium carbonate, Ammonium bromide 0.1g, heated to 180 reaction 13h, gas chromatography detection reaction system methyl salicylate conversion was 97.2percent.To vacuum distillation unit, the former fraction recovery to be applied, ColorlessMing of the Hu Moluo13.98 g, Yield 81.1percent, GCPurity greater than 99percent.250 ml three-necked flask, 10.0 g of methyl salicylate, 23.3 g of 3, 3, 5-trimethylcyclohexanol, 0.50 g of potassium carbonate, Ammonium bromide 0.1g, heated to 180 reaction 13h, gas chromatography detection reaction system methyl salicylate conversion was 97.2%.To vacuum distillation unit, the former fraction recovery to be applied, ColorlessMing of the Hu Moluo13.98 g, Yield 81.1%, GCPurity greater than 99%.50 g of 3, 3, 5-trimethylcyclohexyl ester (Salicylate derivatives, such as: 2-ethylhexyl salicylate (e.g. Eusolex OS), 4-isopropylbenzyl salicylate (e.g. Megasol), or 3, 3, 5-trimethylcyclohexyl salicylate (e.g. Salicylate derivatives, such as 2-ethylhexyl salicylate (e.g. Eusolex OS), 4-isopropylbenzyl salicylate (e.g. Megasol) or 3, 3, 5-trimethylcyclohexyl salicylate (e.g. salicylate derivatives, such as 2-ethylhexyl salicylate (eg, Eusolex OS), 4-isopropylbenzyl salicylate (eg, Megasol) or 3, 3, 5-trimethylcyclohexyl salicylate (eg, salicylate derivatives, such as 2-ethylhexyl salicylate (e.g. Eusolex OS), 4-isopropylbenzyl salicylate (e.g. Megasol), or 3, 3, 5-trimethyl cyclohexyl salicylate (e.g. salicylate derivatives, such as 2-ethylhexyl salicylate (e.g. Eusolex OS), 4-isopropylbenzyl salicylate (e.g. Megasol) or 3, 3, 5-trimethylcyclohexyl salicylate (e.g. the following salicylates: Potassium or triethanolamine salicylate Amyl salicylate Menthyl salicylate Homomenthyl salicylate 2-Ethylhexyl salicylate Phenyl salicylate Benzyl salicylate para-Isopropanolphenyl salicylate Isodecyl salicylate Homomenthyl N-acetylanthranilateAt least one of the following compounds is preferably employed as an agent absorbing the UV rays: 2-ethylhexyl p-(dimethylamino)benzoate (Escalot 507) 2-ethylhexyl p-methoxycinnamate (Parsol MCX) 3-benzylidene-d, l-camphor 3-(4'-methylbenzylidene)-d, l-camphor (Eusolex 6300) amyl 4-(dimethylamino)benzoate (Escalol 506) homomenthyl salicylate (Filtrasol A) 2-hydroxy-4-methoxybenzophenone (Uvinul M 40 - SpectraSorb UV 9) N-(2-ethylhexyl)-4-(3'-methylidenecamphor)benzene sulphonamidesalicylate derivatives, such as 2-ethylhexyl salicylate (for example Eusolex OS), 4-isopropylbenzyl salicylate (for example Megasol) or 3, 3, 5-trimethylcyclohexyl salicylate (for example PEG-25 PABA, The preferred organic screening agents are selected from among: Ethylhexyl methoxycinnamate, Ethylhexyl salicylate, The preferential additional organic photoprotective agents are chosen from: Ethylhexyl methoxycinnamate, The preferred additional organic photoprotective agents are selected from among: Ethylhexyl Methoxycinnamate; The preferred organic screening agents are selected from: Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, The preferred additional organic screening agents are selected from among: Ethylhexyl methoxycinnamate, The preferred additional organic photoprotective agents are selected from among: Ethylhexyl methoxycinnamate, The preferred organic photoprotective agents are selected from among: Ethylhexyl methoxycinnamate, Ethylhexyl salicylate, In the context of the invention and in one particular embodiment, the following hydrophobic sunscreen agents (B) are employed in the kit according to the invention: derivative of dioctylbutylamidotriazone chemically bonded thereto plus ethylhexyl salicylate dimethicodiethyl benzalmalonate homosalatederivative of hexyl 2-(4'-(diethylamino)-2'-hydroxybenzoyl)benzoate chemically bonded thereto plus ethylhexyl salicylate dimethicodiethyl benzalmalonate homosalatederivative of tris(2-ethylhexyl) 4, 4', 4'-(1, 3, 5-triazine-2, 4, 6-triyltriimino)trisbenzoate chemically bonded thereto plus ethylhexyl salicylate dimethicodiethyl benzalmalonate homosalate4, 4'-diarylbutadiene derivative chemically bonded thereto plus ethylhexyl salicylate dimethicodiethyl benzalmalonate homosalateThe preferred organic screening agents are selected from: Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, The preferred additional organic screening agents are selected from among: Butyl methoxydibenzoylmethane, Ethylhexyl methoxycinnamate, Ethylhexyl salicylate, The preferred organic screening agents are chosen from: Butylmethoxydibenzoylmethane, Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, The preferred organic photoprotective agents are chosen from: Ethylhexyl methoxycinnamate, Ethylhexyl salicylate, The preferred ones are The preferred organic screens are chosen from: ethylhexyl methoxycinnamate, ethylhexyl salicylate, homosalate, butylmethoxydibenzoylmethane, phenylbenzimidazolesulphonic acid, Those preferred are: The preferred organic screening agents are chosen from: Butyl methoxydibenzoylmethane, Ethylhexyl methoxycinnamate, Ethylhexyl salicylate, The preferred organic screening agents are chosen from: Butyl methoxydibenzoylmethane, Ethylhexyl methoxycinnamate, Ethylhexyl salicylate, Benzoxazole Derivatives: 2, 4-Bis[4-[5-(1, 1-dimethylpropyl)benzoxazol-2-yl]phenylimino]-6-[(2-ethylhexyl)imino]-1, 3, 5-triazine, sold under the name of Uvasorb K2A by Sigma 3V, and mixtures thereof. The preferential organic screening agents are chosen from: Ethylhexyl Methoxycinnamate, Ethylhexyl Salicylate, salicylate derivatives, such as 2-ethylhexyl salicylate (for example Neo Heliopan OS, sold by Symrise), 4-isopropylbenzyl salicylate (for example Megasol), 3, 3, 5-trimethylcyclohexyl salicylate (A preparation according to claims 1 or 2, wherein the preparation comprises at least an additional UV absorbing substance selected from the group consisting of: - 3-(4'-trimethylammonium)benzylidenebornan-2-one methyl sulphate- homomenthyl salicylate- 2-ethylhexyl 2-cyano-3, 3-diphenylacrylate- N-[(2 and 4)-[2-(oxoborn-3-ylidene)methyl]benzyl]acrylamide polymer- 2-ethylhexyl p-methoxycinnamate
UV screen, analgesic
Odor agents
Personal care products
100,000 - 500,000 lb
Fragrances|Benzoic acid, 2-hydroxy-, 3,3,5-trimethylcyclohexyl ester: ACTIVE
Cosmetics -> Skin conditioning; Uv absorber; Uv filter
Computed Properties
Molecular Weight:262.34
XLogP3:5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:262.15689456
Monoisotopic Mass:262.15689456
Topological Polar Surface Area:46.5
Heavy Atom Count:19
Complexity:324
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Absorbs UVB radiation in the 295-315nm range, enhancing the overall UVB protection of the sunscreen formulation.
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