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サリチル酸 フェニル

Phenyl Salicylate

HCID 8361
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基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
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基本情報

CAS
118-55-8
標準SMILES
O=C(Oc1ccccc1)c1ccccc1O
InChIKey
ZQBAKBUEJOMQEX-UHFFFAOYSA-N
分子式
C13H10O3
平均分子量
214.22 g/mol
単同位体質量
214.06299418

概要

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 member of salicylates, a member of phenols and a benzoate ester. It is functionally related to a salicylic acid.

名称と識別子

優先名称
Phenyl Salicylate
IUPAC
phenyl 2-hydroxybenzoate
現地名
サリチル酸 フェニル
英語名
Phenyl salicylate
分子式
C13H10O3
分子量
214.22

名称と別名

Phenyl salicylate118-55-8PHENYL 2-HYDROXYBENZOATESalolSalphenylPhenol salicylateMusol2-PhenoxycarbonylphenolBenzoic acid, 2-hydroxy-, phenyl ester2-Hydroxybenzoic acid phenyl esterSalicylic acid, phenyl esterFenylester kyseliny salicylove
名称をさらに表示
サリチル酸 フェニルo-ヒドロキシ安息香酸フェニルサロール2-ヒドロキシ安息香酸フェニル2-ヒドロキシベンゼンカルボン酸フェニルサリチル酸フェニルザロール(サリチル酸フェニル)ヒドロキシ安息香酸フェニルザロール( サリチル酸フェニル)フェニルサリシレートフェニル 2-ヒドロキシベンゾアートFEMA 3960SALICYLIC ACID PHENYL ESTERNSC33406NSC 33406
Phenyl-2-hydroxybenzoate2-Hydroxy-benzoic acid phenyl esterDTXSID6021957Seesorb 201Seesorb K 2012-Hydroxybenzoic acid, phenyl esterNSC-33406FEMA NO. 3960

データベース識別子

物性

構造計算による物性

XLogP
3.8
極性表面積
46.5 Ų
水素結合供与体数
1
水素結合受容体数
3
回転可能結合数
3
重原子数
16
形式電荷
0
複雑度
233

実験および物理化学的性質

Chemical ClassesOther Classes -> Esters, Other
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsAntimicrobial; Denaturant
SpringerMaterials PropertiesAngular frequency
FragrancesFragrance Ingredient (Phenyl salicylate) -> IFRA transparency List
Food AdditivesANTIOXIDANT, STABILIZER OR THICKENER -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility · 4 件

insoluble

0.15 mg/mL at 25 °C

insoluble in water; soluble in 50% Heptane

moderately soluble (in ethanol)

Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 3 件

172-173

172.00 to 173.00 °C. @ 12.00 mm Hg

172-173 °C (12 mm Hg)

Melting Point · 2 件

安全と法規制

安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。

GHS分類

GHS Classification · 5 件

This chemical does not meet GHS hazard criteria for 12.6% (92 of 729) of reports.

Warning

H315 (85.9%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 729 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Regulatory Information · 5 件

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

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Benzoic acid, 2-hydroxy-, phenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 2-hydroxy-, phenyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

REACH registered substance: Phenyl salicylate (EC: 204-259-2)

Benzoic acid, 2-hydroxy-, phenyl ester: Non hazardous

Hazards Summary · 1 件

Causes convulsions and decreased body temperature in oral lethal-dose studies of rabbits; [RTECS] Mildly irritating to skin and eyes; [NTP] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Sigma-Aldrich MSDS] See Methyl salicylate. See Acetylsalicylic acid.

Hazard Classes and CategoriesSkin Irrit. 2 (85.9%)

毒性情報

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).

化学と産業

薬理情報

ATC Code · 2 件

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

Protein BindingPlease refer to [DB00945] for protein binding of salicylates.
Pharmacodynamics · 1 件

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.

Mechanism of ActionInhibits 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].
Biological Half-LifeMean half-life of 1.1 h.
Metabolism/Metabolites · 1 件

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.

Absorption, Distribution and Excretion

関連反応

25 件
反応記録を作成
HRID 187252 の反応式
HRID 187252反応物としてTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 375769 の反応式
HRID 375769反応物としてuspto-grants-1996_01
HRID 433025 の反応式
HRID 433025反応物としてuspto-grants-2003_12
HRID 433026 の反応式
HRID 433026反応物としてuspto-grants-2003_12
HRID 433027 の反応式
HRID 433027反応物としてuspto-grants-2003_12
HRID 433028 の反応式
HRID 433028反応物としてuspto-grants-2003_12
HRID 433029 の反応式
HRID 433029反応物としてuspto-grants-2003_12
HRID 433030 の反応式
HRID 433030反応物としてuspto-grants-2003_12
1 / 4 ページ

化合物ノート

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このページの内容基本情報概要名称と識別子物性安全と法規制化学と産業関連反応化合物ノート
その他の操作
ノートを作成反応を作成見積依頼を出す
CAS
118-55-8
PubChem CID
8361
DTXSID
DTXSID6021957
ChEMBL
CHEMBL1339216
ChEBI
CHEBI:34918
UNII
28A37T47QO
EC Number
204-259-2
Nikkaji
J5.300G

41-43

43 °C

Vapor Pressure0.00000817 [mmHg]

物理化学的性質

融点
41 · 41-43 °C (lit.)
沸点
172 · 172-173 °C/12 mmHg (lit.)
比重(密度)
1.25 g/cm3 · 1.250g/cm3
屈折率
1.509 · 1.5090 (estimate)
FEMA
3960 · 3960 | PHENYL SALICYLATE
闪点
230 °F · >230 °F
貯蔵温度
2 · 2-8°C
溶解性
0.1 g/mL、透明、無色 · ジオキサン: 0.1 g/mL、透明、無色
酸解離定数(Pka)
8.71 · 8.71±0.10(Predicted)
外見
微結晶性粉末
色
白い
臭い (Odor)
100 %で。マイルドな甘いフルーティバルサム · 100.00%で。マイルドな甘いフルーティバルサム
においのタイプ
バルサミコ
由来生物
synthetic
水溶解度
アルコール、エーテル、クロロホルム、テレビン油、アセトン、ベンゼンに可溶。クロロホルム、ベンゼンに溶けにくい。水に溶けません。
JECFA Number
736 · 736
Merck
14 · 14,7310
BRN
393969 · 393969
Dielectric constant
6.3 · 6.3(50.0℃)
安定性
光に敏感。強力な酸化剤と互換性がありません。可燃性。
化粧品成分の機能
抗菌剤香料変性剤
InChI
1S/C13H10O3/c14-12-9-5-4-8-11(12)13(15)16-10-6-2-1-3-7-10/h1-9,14H
InChIKey
ZQBAKBUEJOMQEX-UHFFFAOYSA-N
SMILES
Oc1ccccc1C(=O)Oc2ccccc2
LogP
3.55 · 3.55
CAS データベース
118 · 118-55-8(CAS DataBase Reference)
NISTの化学物質情報
2 · Benzoic acid, 2-hydroxy-, phenyl ester(118-55-8)
EPAの化学物質情報
Phenyl salicylate (118-55-8)

化学的性質

化学的特性Phenyl salicylate is a white crystalline solid that has a balsamic type odor. It readily dissolves in ether, benzene, and chloroform, and can be dissolved in ethanol, but is almost insoluble in water and glycerol.

安全データ

wgk
2
tsca
TSCA listed
rtecs
VO6125000
ridadr
UN 3077 9 / PGIII
hs_code
29182300
risk_code
36/37/38
化審法
(3)-1597
hazard_code
Xi
safety_code
26-36-24/25
Hazard Classifications
Aquatic Chronic 2Eye Irrit. 2Skin Irrit. 2Skin Sens. 1
ストレージクラス
11 - Combustible Solids
· 4 件

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.

Cellular LocationsMembrane

用途と製造

Uses · 2 件

Used to make polymers; Also used as a drug (analgesic/antipyretic/anti-inflammatory) and ingredient in lacquers, adhesives, waxes, polishes, suntan products, and plastics (absorbs light and prevents discoloration); [Merck Index] Used as an antioxidant and stabilizer/thickener for foods; [FDA]

Painting (Pigments, Binders, and Biocides) [Category: Paint]

U.S. Production2023: 19,842 lb
Industry UsesAbsorbent
Use Classification · 5 件

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Antimicrobial; Denaturant

General Manufacturing Information · 2 件

Plastics Product Manufacturing

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

応用分野 · 5 件

解説サリチル酸フェニル，(フェニルはphenyl) 化学式 C6H4(OH)COOC6H5 白色の結晶性粉末で、かすかな芳香と特異な味があり、腸内の殺菌薬（商標名ザロール）として用いられる。

用途薬理研究用、医薬品原料、樹脂の紫外線(吸収剤)安定剤。

説明Phenyl salicylate, also referred to as salol, is a member of the hydroxybenzoic acid family of organic compounds. Its chemical formula is C13H10O3. It is manufactured through the chemical reaction between phenol and salicylic acid. Phenyl salicylate is a good antiseptic that is used in the production of toothpaste. It has several medical properties, including its ability to act as an analgesic, anti-septic with antibacterial properties, and antipyretic to reduce fever. Additionally, it can be utilized for treating lower urinary tract inflammation. Although it is no longer widely used in human medicine, it is still employed in veterinary medicine.

使用Phenyl salicylate is used as an analgesic and antipyretic. It is also used in the manufacture of polymer plastics, lacquers, waxes, polishes, adhesives, and sunscreen products(suntan oils and cremes). As light absorber to prevent discoloration of plastics. It is also a fragrance ingredient, but has limited use. in veterinary use as an external disinfectant and intestinal antiseptic agent.

一般的な説明Phenyl salicylate is a phenyl ester of salicylic acid and is used as a medicine under the name ′salol′ as an internal antiseptic. It finds its application in paints, waxes, and varnishes as it is found to absorb UV radiation in the range of 290-325 nm. It also shows its presence in cosmetics and sunscreens as a UV filter.

調製方法 · 2 件

製造方法Phenyl salicylate was synthesized by esterification of salicylic acid and phenol in the presence of catalyst sulfuric acid. The esterification liquid is neutralized, washed with water and distilled to obtain the finished product. It also can preparation by the action of phosphorus oxychloride on a mixture of phenol and salicylic acid (Merck Index, 1968).

純化方法Fractionally crystallise salol from its melt, then crystallise it from *benzene. [Beilstein 10 IV 154.]

上流・下流製品情報

上流原料

2-ヒドロキシ安息香酸Esterification solutionフェノール-OD2-フェノキシ安息香酸ジフェニルヨードニウム トリフルオロメタンスルホン酸フェニルボロン酸フェノール

下流製品

オサルミドキサントンサリチルアニリド5-スルホ-2-ヒドロキシ安息香酸エチレン グリコール モノサリチラートジサリチルイミドN-(2H-1,2,4-トリアゾール-5-イル)サリチルアミド3,4-[1,3]ブタジエノ-2H-1-ベンゾピラン-2-オン1,6-2-Hydroxybenzoylaminohexane
補足説明 · 2 件

定義本品は、サリチル酸(*)とフェノールのエステルであり、次の化学式で表される。参照表示名称：サリチル酸

定義ChEBI: 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.