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Home > Encyclopedia > Phenyl salicylate

Phenyl salicylate

pharmaceutical raw materials
Phenyl salicylate structure

Phenyl salicylate 

structure
  • CAS No:

    118-55-8

  • Formula:

    C13H10O3

  • Chemical Name:

    Phenyl salicylate

  • Synonyms:

    Benzoic acid,2-hydroxy-,phenyl ester;Salicylic acid,phenyl ester;Phenol salicylate;Phenyl salicylate;Salol;Phenyl 2-hydroxybenzoate;Salphenyl;2-Phenoxycarbonylphenol;Seesorb 201;Seesorb K 201;NSC 33406;Phenyl o-hydroxybenzoate;YC 136;2-Hydroxy-benzoic acid phenyl ester

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

white crystalline solid with an aromatic odour Phenyl salicylate has a distinctive aromatic odor and taste.ChEBI: A benzoate ester that is the phenyl ester of salicylic acid. Also known as salol, it can be formed by heating salicylic acid with phenol and is used in the manufacture of some polymers, lacquers, adhesives, waxes and polishes.Phenyl salicylate (chemical formula: C13H10O3) belongs to the family of hydroxybenzoic acid which are compound containing a hydroxybenzoic acid or its deri


Phenyl salicylate appears as white crystals. Insoluble in water. (NTP, 1992)|Solid|White crystalline solid


Phenyl salicylate appears as white crystals. Insoluble in water. (NTP, 1992)|Phenyl salicylate is a benzoate ester that is the phenyl ester of salicylic acid. Also known as salol, it can be formed by heating salicylic acid with phenol and is used in the manufacture of some polymers, lacquers, adhesives, waxes and polishes. It has a role as an ultraviolet filter. It is a benzoate ester, a member of phenols and a member of salicylates. It derives from a salicylic acid.|Phenyl salicylate is a 2-hydroxybenzoic acid phenyl ester. It is utilized in some manufacturing processes of polymers, lacquers, adhesives, waxes, as well as polishes. It is an active ingredient in some pharmaceutical products as a mild analgesic for pain relief by releasing salicylate (found in [DB00945] ). Phenyl salicylate may also be found in some antiseptic agents. It is synthesized by heating salicylic acid with phenol, [MSDS]. Phenyl salicylate is used as a food additive in the USA. This compound belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Phenyl salicylate Basic Attributes

214.22

214.22

393969

204-259-2

28A37T47QO

33406

DTXSID6021957

G - Genito urinary system and sex hormones

29182300

Characteristics

46.5

3.8

White Fine Crystalline Powder

1.25 g/cm3

130.5 °C

173 °C

>230 °F

1.5090 (estimate)

soluble in alcohol, ether, chloroform, turpentine, acetone and benzene. Sparingly soluble in chloroformbenzene. Insoluble in water.dioxane: 0.1 g/mL, clear, colorless

room temp

0.000421mmHg at 25°C

The acute oral LD
50
value in rats was reported as 3 g/kg and the acute dermal LD
50
value in rabbits exceeded 5 g/kg (Levenstein, 1975). The probable LD in man is 50-500 mg/kg. The toxic effects of phenyl salicylate are similar to those of phenol but do not include a corrosive action on the alimentary canal (Dittmer, 1959).

Insoluble in water.

Esters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Incompatible with bromine water, ferric salts, camphor, phenol, chloral hydrate, monobrominated camphor, thymol, or urethane in trituration. (NTP, 1992).

Safety Information

UN 3077 9 / PGIII

2

36/37/38

26-36-24/25

VO6125000

Xi

Light sensitive. Incompatible with strong oxidants. Flammable.

P261-P305 + P351 + P338

H315-H319-H335

Flash point data for this chemical are not available, however it is probably combustible. (NTP, 1992)

|Warning|H315 (98.45%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, 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 802 companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol followed by washing with a 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. (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)

Toxicity

Oral LD50 in the rat is 3000 mg/kg Adverse effects can be divided into several categories,: Eyes: irritation Skin: skin irritation Cardiovascular: rapid pulse, flushing Central Nervous System —blurred vision, dizziness Respiratory —shortness of breath or troubled breathing, irritation of respiratory system Genitourinary —difficult micturition, acute urinary retention Gastrointestinal —dry mouth, nausea/vomiting Overdosage may be managed by inducing emesis or gastric lavage. Slow intravenous administration of physostigmine in doses of 1 to 4 mg (0.5 to 1 mg in children) repeated as needed in 1-2 h to relieve severe antimuscarinic symptoms. Administration of small doses of diazepam to control excitement and seizures may be warranted. Artificial respiration with oxygen can be used if needed for respiratory depression. Adequate hydration is important, as well as symptomatic treatment, provided as necessary.

Please refer to [DB00945] for protein binding of salicylates.

Drug Information

Pain and fever.

Phenyl salicylate has several medical uses. It can be used as an analgesic to relieve pain, as an antiseptic with antibacterial effect as well as a kind of antipyretic for the treatment of fever. It is also used for the treatment of inflammation in the lower urinary tract. It is no longer commonly applied to human medical practice but is still used in veterinary medicine [MSDS]. When it is combined with methenamine, benzoic acid, phenyl salicylate, methylene blue, and hyoscyamine sulfate, it is used to relieve the discomfort, pain, frequent urge to urinate, and cramps/spasms of the urinary tract caused by a urinary tract infection or a diagnostic procedure.

Rapidly absorbed. Refer to [DB00945] for detailed salicylate absorption information.|Please refer to [DB00945] for the route of elimination.|Steady-state plasma salicylate concentrations increase more than proportionally with increasing dosages; the time required to reach steady state increases with increasing daily dose. Dosage intervals of 8-12 h are sufficient to maintain plasma salicylate concentrations in the normal therapeutic anti-inflammatory concentration range.|Please refer to [DB00945] for more information.

Hydrolyzed to salicylic acid. Salicylic acid elimination kinetics are dependent on drug concentration because of the limited capacity of two major biotransformation pathways: formation of salicyluric acid and of salicyl phenolic glucuronide. Metabolism of this drug occurs mainly in the liver, like other salicylates. Metabolism of salicylic acid occurs through glucuronide formation (to produce salicyluric acid), and salicyl phenolic glucuronide), conjugation with glycine (to produce salicyluric acid), and oxidation to form gentisic acid. The rate of formation of salicyl phenolic glucuronide and salicyluric acid are easily saturated at low salicylic acid concentrations and their formation can be described by Michaelis-Menten kinetics.

Mean half-life of 1.1 h.

Inhibits the activity of the enzyme known as cyclooxygenase (COX) which causes the formation of prostaglandins, substances which cause inflammation, swelling, pain, and fever. For more information, refer to the drug entry [DB00945].

SYMPTOMS: Symptoms of exposure to this compound include skin, eye and mucous membrane irritation. ACUTE/CHRONIC HAZARDS: This compound is a mild skin and eye irritant. (NTP, 1992)

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)

phenyl salicylate

Phenyl salicylate Use and Manufacturing

Methods of Manufacturing

Salicylic acid and phenol are esterified in the presence of catalyst sulfuric acid. The esterified liquid is neutralized, washed and distilled to obtain the finished product. Raw material consumption quota: 850kg/t for salicylic acid and 850kg/t for phenol.

Uses

In the manufacture of various polymers for the plastics industry, also in lacquers, adhesives, waxes, polishes.In suntan oils and cremes.As light absorber to prevent discoloration of plastics.Has some plasticizer properties.

Benzoic acid, 2-hydroxy-, phenyl ester: ACTIVE

Food additives -> Flavoring Agents|Flavoring Agents -> JECFA Flavorings Index|Cosmetics -> Antimicrobial; Denaturant

Flavoring Agents

Computed Properties

Molecular Weight:214.22
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:214.062994177
Monoisotopic Mass:214.062994177
Topological Polar Surface Area:46.5
Heavy Atom Count:16
Complexity:233
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Downstream Products

Drug Function and Efficacy

Sterilization and antiseptic effect

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Recommended Suppliers of Phenyl salicylate

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