beta-Sitosterol 3-O-(6-O-oleoyl)-beta-D-glucopyranoside

Base Information

• Chemical Name: beta-Sitosterol 3-O-(6-O-oleoyl)-beta-D-glucopyranoside
• CAS No.: 53657-29-7
• Molecular Formula: C53H92 O7
• Molecular Weight: 841.309
• DSSTox Substance ID: DTXSID101317097
• Nikkaji Number: J652.106A
• Wikidata: Q105162176
• Mol file: 53657-29-7.mol

Synonyms:beta-sitosterol 3-O-(6-O-oleoyl)-beta-D-glucopyranoside;sitoindoside II

Chemical Property of beta-Sitosterol 3-O-(6-O-oleoyl)-beta-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 4E-32mmHg at 25°C
• Boiling Point: 832°C at 760 mmHg
• Flash Point: 222.1°C
• PSA: 105.45000
• Density: 1.05g/cm³
• LogP: 12.43740
• Storage Temp.: -20°C
• XLogP3: 15.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 26
• Exact Mass: 840.68430527
• Heavy Atom Count: 60
• Complexity: 1330

Purity/Quality:

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCC=CCCCCCCCC(=O)OCC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(C4CC=C3C2)CCC5C(C)CCC(CC)C(C)C)C)C)O)O)O
• Isomeric SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@]5([C@H]([C@@H]4CC=C3C2)CC[C@@H]5[C@H](C)CC[C@@H](CC)C(C)C)C)C)O)O)O
• Uses: Sitoindoside II is an acyl steryl glycoside used in pharmacological studies to determine inhibitory effects on proliferation of various cancer cell lines.

Technology Process of beta-Sitosterol 3-O-(6-O-oleoyl)-beta-D-glucopyranoside

There total 3 articles about beta-Sitosterol 3-O-(6-O-oleoyl)-beta-D-glucopyranoside 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:

Daucosterol (474-58-8) + (Z)-9-octadecenoyl chloride (112-77-6) → 3-O-(6'-O-oleoyl-β-D-glucopyranosyl)-β-sitosterol (53657-29-7)

Guidance literature:

With pyridine; In benzene; at 4 ℃; for 48h;

DOI:10.1021/np000592z

Reference yield:

β-sitosterol (83-46-5) → 3-O-(6'-O-oleoyl-β-D-glucopyranosyl)-β-sitosterol (53657-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.80 g / silver oxide; MgSO₄ / diethyl ether / 24 h / 20 °C

2: pyridine / benzene / 48 h / 4 °C

With pyridine; magnesium sulfate; silver(l) oxide; In diethyl ether; benzene;

DOI:10.1021/np000592z

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3-O-(6'-O-oleoyl-β-D-glucopyranosyl)-β-sitosterol (53657-29-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.80 g / silver oxide; MgSO₄ / diethyl ether / 24 h / 20 °C

2: pyridine / benzene / 48 h / 4 °C

With pyridine; magnesium sulfate; silver(l) oxide; In diethyl ether; benzene;

DOI:10.1021/np000592z

upstream raw materials:

Daucosterol

(Z)-9-octadecenoyl chloride

β-sitosterol

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

Methyl oleate

β-sitosterol