基本情報
- CAS
138-52-3- 標準SMILES
OCc1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
NGFMICBWJRZIBI-UJPOAAIJSA-N- 分子式
- C13H18O7
- 平均分子量
- 286.28 g/mol
- 単同位体質量
- 286.10525291
概要
Salicin is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue. It has a role as a metabolite, a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, an antipyretic, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a prodrug. It is a member of benzyl alcohols, an aryl beta-D-glucoside and an aromatic primary alcohol. It is functionally related to a salicyl alcohol.
名称と識別子
- 優先名称
- Salicin
- IUPAC
- (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
- 現地名
- サリシン
- 英語名
- D-(-)-Salicin
- 分子式
- C13H18O7
- 分子量
- 286.28
名称と別名
salicin138-52-3SalicosideD-(-)-SalicinSalicyl alcohol glucosideD(-)-Salicin2-(Hydroxymethyl)phenyl beta-D-glucopyranosideSaligenin beta-D-glucopyranosideSalicinum2-(Hydroxymethyl)phenyl-beta-d-glucopyranosideo-(Hydroxymethyl)phenyl beta-D-glucopyranoside(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
名称をさらに表示
サリシンD(-)-サリシン２（ヒドロキシメチル）フェニルβＤグルコピラノシド(-)-サリシン2-(ヒドロキシメチル)フェニルβ-D-グルコピラノシドD(-)‐サリシン2-(ヒドロキシメチル)フェニル Β-D-グルコピラノシドD-(-)-サリシンサリシン (AHP VERIFIED)D-(−)-サリシンD-(-)-サリシン, 99%2-(ヒドロキシメチル)フェニル-β-Ｄ-グルコシドD-SALICINWHITE WILLOWSalicylinSalicin-RMSALICIN(RG)SALICIN(SH)Salicin >
4649620TBZDTXSID10883326NSC-5751CHEBI:17814(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-(hydroxymethyl)phenoxy)oxane-3,4,5-triolRefChem:884384DTXCID901022864Salicine
物性
構造計算による物性
- XLogP
- -1.2
- 極性表面積
- 120 Ų
- 水素結合供与体数
- 5
- 水素結合受容体数
- 7
- 回転可能結合数
- 4
- 重原子数
- 20
- 形式電荷
- 0
- 複雑度
- 300
実験および物理化学的性質
LogP
-1.22
-1.22
Solubility40 mg/mL at 25 °C
Melting Point207 °C
Physical DescriptionSolid
Collision Cross Section
162.78 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
163.2 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
物理化学的性質
- 融点
- 196 · 196-202 °C
- 比旋光度
- -61.5 · -61.5 º (c=5, water)
- 沸点
- 388.65 °C · 388.65°C (rough estimate)
- 比重(密度)
- 1.434 · 1.4340
- 屈折率
- -62 ° · -62 ° (C=3, H2O)
- 貯蔵温度
- 2 · 2-8°C
- 溶解性
- 36 g/リットル · 36g/リットル
- 外見
- 微結晶性粉末
- 酸解離定数(Pka)
- 12.8 · 12.80±0.70(Predicted)
- 色
- 白い
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
This chemical does not meet GHS hazard criteria for 31.3% (26 of 83) of reports.
Warning
H317 (68.7%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P261, P272, P280, P302+P352, P321, P333+P317, P362+P364, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 83 reports by companies from 3 notifications to the ECHA C&L Inventory.
危険有害性情報
Regulatory Information.beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - .beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl: Environment tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (68.7%)
安全データ
- F
- 3-10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LZ5901700
- hs_code
- 29389090
- risk_code
- 43
- hazard_code
- Xi
- safety_code
- 36/37-37-24/25-36
- Hazard Classifications
- Skin Sens. 1
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
MeSH Pharmacological ClassificationCompounds or agents that combine with cyclooxygenase (PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES) and thereby prevent its substrate-enzyme combination with arachidonic acid and the formation of eicosanoids, prostaglandins, and thromboxanes.
Cellular LocationsCytoplasm
用途と製造
General Manufacturing Information.beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl: ACTIVE
応用分野
解説salicyl alcohol glycoside．C13H18O7(286.28)．サリコシド(salicoside)ともいう．配糖体の一種．ヤナギ科シダレヤナギSalix purpureaなどの樹皮，葉などから得られる．"白色の柱状晶．融点201 ℃．[α]D－45.6°(エタノール)．酸またはエムルシン(β-グルコシダーゼ)により加水分解され，D-グルコースとアグリコンのサリゲニンを生じる．β-グリコシダーゼ含有酵素の検定試薬，鎮痛剤に使用される．[CAS 138-52-3]森北出版「化学辞典（第2版）
用途酵素 β-グルコシダーゼの活性度試験に用いられる。
使用D-(-)-Salicin has been used:to study its in vitro anticoagulant and antiplatelet activitiesas a standard in high performance liquid chromatography method (HPLC) for quantitation of salicin from willow plantas a tastant in taste threshold assayas a constituent of nutrient agar-salicin medium for selective isolation of Lactobacillus paracasei
一般的な説明Salicin is a non-phenolic glucosidic compound extracted from meadowsweet (Filipendula ulmaria L). It is majorly used as a substitute for quinine. Salicin can be used as a therapeutic for patients suffering from rheumatic fever. Salicin acts a metabolic precursor for salicylic acid. It is a novel phytochemical that exhibits immunological cross functions in plants and humans. Salicin facilitates growth and reproduction in plants. In addition, It also protects plants against biotic and abiotic stress.
調製方法
Crystallise D(-)-salicin from EtOAc, EtOH or water and sublime it at 190-195o/12mm. [Armour et al. J Chem Soc 412 1961, IR: Pearl & Darling J Org Chem 24 731 1959, Beilstein 17 III/IV 2986, 17/7 V 113.]
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