Salidroside

Base Information

• Chemical Name: Salidroside
• CAS No.: 10338-51-9
• Molecular Formula: C14H20O7
• Molecular Weight: 300.309
• Hs Code.: 29389090
• European Community (EC) Number: 695-621-2
• NSC Number: 741643
• UNII: M983H6N1S9
• DSSTox Substance ID: DTXSID4049034
• Nikkaji Number: J15.618C
• Wikipedia: Salidroside
• Wikidata: Q7404463
• Pharos Ligand ID: 3R4HFSJ558W6
• Metabolomics Workbench ID: 49888
• ChEMBL ID: CHEMBL465208
• Mol file: 10338-51-9.mol

Synonyms:Rhodiola roseal.P.E;b-D-Glucopyranoside, 2-(4-hydroxyphenyl)ethyl;Glucopyranoside,p-hydroxyphenethyl (7CI);Salidroside (8CI);2-(4-Hydroxyphenyl)ethyl-b-D-glucopyranoside;4-Hydroxy-phenyl-2-ethyl-b-D-glucopyranoside;Rhodioloside;Rhodosin;Tyrosol a-(b-D-glucopyranoside);

Chemical Property of Salidroside

Chemical Property:

• Appearance/Colour: Red-brown fine powder
• Vapor Pressure: 6.54E-13mmHg at 25°C
• Melting Point: 159～160℃
• Refractive Index: 1.628
• Boiling Point: 549.5 °C at 760 mmHg
• PKA: 9.98±0.15(Predicted)
• Flash Point: 286.2 °C
• PSA: 119.61000
• Density: 1.46 g/cm³
• LogP: -1.24880
• Storage Temp.: ?20°C
• Solubility.: Methanol (Slightly), Pyridine (Slightly)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 300.12090297
• Heavy Atom Count: 21
• Complexity: 306

Purity/Quality:

Salidroside 3-5%, Rosavins 3-5%, Rosavin 2% up ^*data from raw suppliers

Salidroside ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CCOC2C(C(C(C(O2)CO)O)O)O)O
• Isomeric SMILES: C1=CC(=CC=C1CCO[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)O
• Description: Rosavins are a collection of compounds which include, rosavin, rosin and rosarin. They are known as a cinnamyl alcohol glycoside belonging to a group of compounds known as phenylpropanoids. They are amongst the main active phytochemical components in Rhodiola rosea, but studies remain inconclusive on how they specifically operate and their mechanisms of action. Some research suggests that rosavins may not be effective on their own, but must be combined with other more powerful compounds, like salidroside, to exhibit potential effects.
• Uses: Antibacterial effects; cardiovascular protection, effective anti-oxidant, anti-cancer activity, enhancing memory, anti-radiation effect. Salidroside is a phenylpropanoid glycoside that exhibits a wide range of pharmacological effects. This include protective effects against neuronal death which can be applied to the treatment of Alzheimer’s disease. Cardioprotecticve, countering oxidative stress in cardiac related malignanied=v

Technology Process of Salidroside

There total 45 articles about Salidroside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

tetraacetyl salidroside (28251-63-0) → Salidroside (10338-51-9)

Guidance literature:

With methanol; potassium carbonate;

DOI:10.1016/S0040-4020(01)89229-2

Reference yield: 97.7%

(2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(4-acetoxyphenethoxy)tetrahydro-2Hpyran-3,4,5-triyl triacetate (39032-08-1) → Salidroside (10338-51-9)

Guidance literature:

With sodium methylate; In methanol; for 1h; Ambient temperature;

DOI:10.1248/cpb.46.581

Reference yield: 94.9%

β-D-glucose (492-61-5) + p-hydroxyphenethyl alcohol (501-94-0) → Salidroside (10338-51-9)

Guidance literature:

With E_.coli (BLPad-StyAB-RostyC-SlPAR₁-UGT₈₅A₁); In aq. phosphate buffer; at 37 ℃; for 12h; pH=7.0; Reagent/catalyst; Enzymatic reaction;

DOI:10.1039/d0gc03595e

upstream raw materials:

methanol

cornoside

tetraacetyl salidroside

p-hydroxyphenethyl alcohol 1-O-β-D-(6''-O-galloyl)-glucopyranoside

Downstream raw materials:

cornoside

alpha-D-glucopyranose

((2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-(4-hydroxyphenethoxy)tetrahydro-2H-pyran-2-yl)methyl acetate

Refernces

• 1、 Bi, Yanhong,Zhu, Chun,Wang, Zhaoyu,Jia, Jianbo. "Influence of the ionic liquid cosolvent on glucosylation reactions catalyzed by b-glycosidase for production of salidroside". . p. 5095 - 5098. Retrieved 2013.
• 2、 Bassanini, Ivan,Krejzová, Jana,Panzeri, Walter,Monti, Daniela,K?en, Vladimir,Riva, Sergio. "A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides". . p. 2040 - 2045. Retrieved 2017.
• 3、 Tong, Ai Min,Lu, Wen Ya,Xu, Jian He,Lin, Guo Qiang. "Use of apple seed meal as a new source of β-glucosidase for enzymatic glucosylation of 4-substituted benzyl alcohols and tyrosol in monophasic aqueous-dioxane medium". . p. 2095 - 2097. Retrieved 2004.
• 4、 Schwab, Wilfried,Schreier, Peter. "Aryl β-d-glucosides from Carica papaya fruit". . p. 1813 - 1816. Retrieved 1988.
• 5、 Shimomura, Hiroko,Sashida, Yutaka,Adachi, Tokuo. "PHENOLIC GLUCOSIDES FROM PRUNUS GRAYANA". . p. 249 - 252. Retrieved 1987.
• 6、 Wang, Feng,Huang, Dengfa,Ma, Yong,Zhang, Fuming,Linhardt, Robert J.. "Preparation of salidroside with n-butyl β-D-glucoside as the glycone donor via a two-step enzymatic synthesis catalyzed by immobilized β-glucosidase from bitter almonds". . p. 246 - 260. Retrieved 2019/02/03.