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rel-2-ヒドロキシ安息香酸(1S*)-5α*-メチル-2β*-イソプロピルシクロヘキサン-1α*-イル

Menthyl Salicylate

HCID 20055232
ノート反応
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
部分構造検索類似構造を探す

基本情報

CAS
89-46-3
標準SMILES
CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(=O)c1ccccc1O
InChIKey
SJOXEWUZWQYCGL-DVOMOZLQSA-N
分子式
C17H24O3
平均分子量
276.4 g/mol
単同位体質量
276.17254462

概要

Menthyl salicylate is 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
Menthyl Salicylate
IUPAC
[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-hydroxybenzoate
現地名
rel-2-ヒドロキシ安息香酸(1S*)-5α*-メチル-2β*-イソプロピルシクロヘキサン-1α*-イル
英語名
MENTHYL SALICYLATE
分子式
C17H24O3
分子量
276.37

名称と別名

MENTHYL SALICYLATE89-46-31-Menthyl salicylateDTXSID804682243XOA705ZDBenzoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, rel-EINECS 201-909-7MENTHYL SALICYLATE [MI]DTXCID80809573(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl 2-hydroxybenzoateBenzoic acid, 2-hydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl esterBenzoic acid, 2-hydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, (1alpha,2beta,5alpha)-
名称をさらに表示
rel-2-ヒドロキシ安息香酸(1S*)-5α*-メチル-2β*-イソプロピルシクロヘキサン-1α*-イルサリチル酸メンチルサリメントールコントラソールサモールメンチルサリチレ-トmenthylSamolContrasolSalimentholMENTHYL SALICYLATE(RG)Sunburn preventive No.1Menthol salicylate ester
5-Methyl-2-(1-methylethyl)cyclohexyl 2-hydroxybenzoate2-Hydroxybenzoic acid, 5-methyl-2-(1-methylethyl)cyclohexyl esterBenzoic acid, 2-hydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, (1.alpha.,2.beta.,5.alpha.)-RefChem:810983MENTHYL SALICYLATE [INCI]menthyl salicylate, (+/-)-rel-(1R,2S,5R)-2-Isopropyl-5-methylcyclohexyl 2-hydroxybenzoateNCGC00181042-01

物性

構造計算による物性

XLogP
5.4
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
4
重原子数
20
形式電荷
0
複雑度
326

実験および物理化学的性質

DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsMasking; Uv absorber
Flavoring AgentsEU Flavoring substances

物理化学的性質

融点
25 °C · <25 °C
沸点
186 · 186-190 °C/12 mmHg (lit.)
比重(密度)
1.04 g/mL · 1.04 g/mL at 20 °C (lit.)
屈折率
20 · n20/D 1.52
闪点
100 ℃ · 100℃
酸解離定数(Pka)
8.1 · 8.10±0.30(Predicted)
外見
liquid
比重
1.05 · 1.05
臭い (Odor)
無臭またはわずかにフルーティーな香り
BRN
3097754 · 3097754
安定性
安定。強力な酸化剤とは相容れない。可燃性。
化粧品成分の機能
紫外線吸収剤香料
InChI
1S/C17H24O3/c1-11(2)13-9-8-12(3)10-16(13)20-17(19)14-6-4-5-7-15(14)18/h4-7,11-13,16,18H,8-10H2,1-3H3
InChIKey
SJOXEWUZWQYCGL-UHFFFAOYSA-N

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 · 3 件

H413 (100%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

P273, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

危険有害性情報

Regulatory Information · 3 件

Chemical: Benzoic acid, 2-hydroxy-, 5-methyl-2-(1-methylethyl)cyclohexyl ester, (1.alpha.,2.beta.,5.alpha.)-

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

Benzoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, rel-: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesAquatic Chronic 4 (100%)

安全データ

wgk
3
tsca
TSCA listed
Hazard Classifications
Aquatic Chronic 4
ストレージクラス
10 - Combustible liquids

化学と産業

薬理情報

Pharmacodynamics · 1 件

Menthol and methyl salicylate are known as counterirritants. They work by causing the skin to feel cool and then warm. Used together, they provide symptomatic relief for mild to moderate muscular and joint aches and pains, muscle cramps, shoulder aches and stiff neck..

Mechanism of Action · 1 件

Menthol dilates the blood vessels causing a sensation of coldness, followed by an analgesic effect. Menthol also acts as a penetration enhancer, increasing the penetration of drugs when applied on the skin, to give a faster onset of action. Methyl salicylate is a salicylic acid derivative, and when combined with menthol, produces menthyl salicylate. Salicylates inhibit cyclooxygenase, thereby reducing the formation of prostaglandins, and cause platelet dysfunction Methyl salicylate is used topically as a counter-irritant. Upon application, it is absorbed through the skin and is applied for the relief of pain in rheumatic conditions and painful muscle or joints. The menthol dilates blood vessels, why the salicylate portion provides a topical anesthetic and analgesic action on the affected area. The cooling and warning action may interfere with the transmission of pain signals through nerves.

Absorption, Distribution and Excretion · 1 件

May be absorbed through intact skin. The absorption of topical salicylates is proportional to the surface area exposed, the duration of exposure, concentration and skin integrity. Absorption characteristics of salicylates vary with the dose, formulation, and route of administration. Percutaneous absorption is enhanced by exercise, heat, occlusion, or disruption of the integrity of the skin or application to large areas of skin. Both the rate and extent of absorption increases after continuous application, increasing its bioavailability.

用途と製造

Use ClassificationCosmetics -> Masking; Uv absorber
General Manufacturing InformationBenzoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, rel-: INACTIVE

関連反応

0 件
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化合物ノート

読み込み中…

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

データベース識別子

CAS
89-46-3
PubChem CID
20055232
DTXSID
DTXSID8046822
ChEBI
CHEBI:135976
UNII
43XOA705ZD
EC Number
201-909-7
Nikkaji
J276.317F
SMILES
CC(C)C1CCC(C)CC1OC(=O)c2ccccc2O
LogP
6.429 · 6.429 (est)
EPAの化学物質情報
2 · Benzoic acid, 2-hydroxy-, (1R,2S,5R)-5-methyl-2-(1-methylethyl)cyclohexyl ester, rel- (89-46-3)

化学的性質

化学的特性colourless to light yellow liquid

応用分野 · 2 件

説明Menthyl salicylate is almost odorless when pure. Slightly bitter-astringent taste. It carries the usual characteristics of a phenol, which are not exactly welcome by the perfumer.

使用Menthyl salicylate is an ester of menthol and salicylic acid. This product is used to treat minor aches and pains of the muscles/joints (e.g., arthritis, backache, sprains). It also as a "sun screen" to filter out ultraviolet light in Preparations for preventing sunburn.

調製方法

製造方法Menthyl salicylate is produced by azeotropic esterification of Menthol with Salicylic acid, using a Benzene- or Toluene sulfonic acid catalyst.

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