Basic information
- CAS
138-52-3- Standard SMILES
OCc1ccccc1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O- InChIKey
NGFMICBWJRZIBI-UJPOAAIJSA-N- Molecular formula
- C13H18O7
- Average molar mass
- 286.28 g/mol
- Monoisotopic mass
- 286.10525291
Overview
Salicin is an aryl beta-D-glucoside that is salicyl alcohol in which the phenolic hydrogen has been replaced by a beta-D-glucosyl residue.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.
Names & identifiers
- Preferred name
- Salicin
- IUPAC
- (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
- English name
- D-(-)-Salicin
- Molecular formula
- C13H18O7
- Molecular weight
- 286.28
Names & synonyms
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
Show more names
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
Database identifiers
- CAS
138-52-3- PubChem CID
- 439503
- DTXSID
Properties
Computed structural properties
- XLogP
- -1.2
- Topological polar surface area
- 120 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 4
- Heavy atoms
- 20
- Formal charge
- 0
- Complexity
- 300
Experimental & physicochemical properties
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]
Physicochemical properties
- Melting point
- 196 · 196-202 °C
- alpha
- -61.5 · -61.5 º (c=5, water)
- Boiling point
- 388.65 °C · 388.65°C (rough estimate)
- Density
- 1.434 · 1.4340
- refractive index
- -62 ° · -62 ° (C=3, H2O)
- storage temp.
- 2 · 2-8°C
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
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.
Hazard information
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%)
Safety data
- F
- 3-10
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- LZ5901700
- hs_code
- 29389090
- risk_code
- 43
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 36/37-37-24/25-36
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Pharmacology
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
Uses & manufacturing
General Manufacturing Information.beta.-D-Glucopyranoside, 2-(hydroxymethyl)phenyl: ACTIVE
Applications
DescriptionD(-)-Salicin is a traditional medicine which has been known to exhibit anti-inflammation and other therapeutic activities, it can inhibit the LPS-induced inflammation in RAW264.7 cells and mouse models.
Usesanalgesic, antipyretic
UsesH1 antihistamine (nonsedating)
UsesStandard substrate in evaluating enzyme Preparations contg b-glucosidase: Weidenhagen, Z. Ver. Zucker-Ind. 79, 591 (1929).
UsesD-(-)-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
General DescriptionSalicin 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.
Related reactions
0 records
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Compound notes
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