Sitogluside

Base Information

• Chemical Name: Sitogluside
• CAS No.: 474-58-8
• Molecular Formula: C35H60O6
• Molecular Weight: 576.858
• Hs Code.: 29389090
• European Community (EC) Number: 685-415-0
• UNII: U45VN859W3
• DSSTox Substance ID: DTXSID301045674
• Nikkaji Number: J5.961G
• Wikipedia: Daucosterol,Eleutheroside A
• Wikidata: Q15410900
• NCI Thesaurus Code: C90816
• Metabolomics Workbench ID: 140389
• ChEMBL ID: CHEMBL506678
• Mol file: 474-58-8.mol

Synonyms:beta-sitosterol glucoside;beta-sitosterol glucutonide;beta-sitosterol-beta-D-glycoside;beta-sitosteryl-beta-D-glucopyranoside;daucosterol;eleutheroside A;lyoniside;sitosterol beta-D-glucoside;sitosterol glucuronide

Chemical Property of Sitogluside

Chemical Property:

• Appearance/Colour: off white powder
• Vapor Pressure: 4.95E-21mmHg at 25°C
• Melting Point: 283～286℃
• Refractive Index: 1.553
• Boiling Point: 673.6 °C at 760 mmHg
• PKA: 12.91±0.70(Predicted)
• Flash Point: 361.2 °C
• PSA: 99.38000
• Density: 1.13 g/cm³
• LogP: 5.84900
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly,Heated), Pyridine (Slightly, Sonicated)
• XLogP3: 7.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 576.43898963
• Heavy Atom Count: 41
• Complexity: 920

Purity/Quality:

98%,99%, ^*data from raw suppliers

Eleutheroside A ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)C(C)C
• Isomeric SMILES: CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)C(C)C
• Uses: Daucosterol can be used as an efficient and inexpensive neuroprotectants, to which the IGF1-like activity of daucosterol contributes and it could be potentially developed as a medicine for ischemic stroke treatment. Moreover, daucosterol has neuroprotective activity, it has proliferation-enhancing activity of neural stem cells (NSCs), and it as an efficient and inexpensive growth factor alternative that could be potentially developed as a medicine for ischemic stroke treatment, can significantly reduce neuronal loss. The study demonstrated that daucosterol works as an efficient and inexpensive growth factor alternative that could be used in clinical medicine and research applications. β-Sitosterol and β-sitosteryl-β-D-glucoside were isolated as analgesic constituents from the leaves of Mentha cordifolia Opiz.
• Description: Daucosterol, alias: Citoside, β-Sitosterol β-D-glucoside, and the molecular formula is C35H6. The compound of the formula (description column) belongs to a carotene compound, which is present in mallow family plants, and figs and other plants also contain carotene. Daucosterol exhibits anti-tumor, anti-inflammatory and acaricidal activities, also moderate antibacterial activity against Bacillus subtilis and Staphylococcus aureus, and it has anti-cancer and apoptotic effects in human colon cancer cell line HCT-116.

Technology Process of Sitogluside

There total 2 articles about Sitogluside 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:

β-sitosteryl glucoside-3'-O-linoleate (1192023-60-1) → Daucosterol (474-58-8) + linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3)

Guidance literature:

β-sitosteryl glucoside-3'-O-linoleate; With sodium hydroxide; In tetrahydrofuran; methanol; at 50 ℃; for 2h;

With hydrogenchloride; In tetrahydrofuran; methanol; water;

DOI:10.1007/s10600-009-9342-x

Reference yield:

β-sitosterol 3-O-(6'-octadecanoyl) β-D-glucopyranoside (53657-30-0) → Daucosterol (474-58-8) + Methyl stearate (112-61-8)

Guidance literature:

With sodium methylate; In methanol; for 2h; Ambient temperature;

DOI:10.1016/0031-9422(88)80475-8

Reference yield:

Daucosterol (474-58-8) → D-glucose (50-99-7)

Guidance literature:

With hydrogenchloride; In methanol; water; for 15h; Reflux;

DOI:10.1002/rcm.6219

upstream raw materials:

β-sitosterol 3-O-(6'-octadecanoyl) β-D-glucopyranoside

β-sitosteryl glucoside-3'-O-linoleate

Downstream raw materials:

D-Glucose

β-sitosterol

2,3,4,6-tetra-O-methyl-D-glucopyranose

D-glucose

Refernces

• 1、 Pei-Wu, Geng,Fukuyama, Yoshiyasu,Rei, Wang,Jinxian, Bao,Nakagawa,Kazuyuki. "AN ACYLATED SITOSTEROL GLUCOSIDE FROM ALISMA PLANTAGO-AQUATICA". . p. 1895 - 1896. Retrieved 2007/10/02.