1,8-dihydroxy-3-(hydroxymethyl)-10-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one

Base Information

• Chemical Name: 1,8-dihydroxy-3-(hydroxymethyl)-10-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
• CAS No.: 1415-73-2
• Molecular Formula: C₂₁H₂₂O₉
• Molecular Weight: 418.4
• Hs Code.: 29329990
• Mol file: 1415-73-2.mol

Synonyms:barbaloin;barbaloin, (S)-isomer;barbaloin, beta-D-isomer;barbaloin, monoglucoside;isobarbaloin

Chemical Property of 1,8-dihydroxy-3-(hydroxymethyl)-10-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one

Chemical Property:

• Appearance/Colour: yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 148-149oC
• Refractive Index: 1.741
• Boiling Point: 752.6 ºC at 760 mmHg
• PKA: 7.12±0.40(Predicted)
• Flash Point: 268 ºC
• PSA: 167.91000
• Density: 1.647 g/cm³
• LogP: -0.89120
• Storage Temp.: 2-8°C
• Solubility.: pyridine: 50 mg/mL, clear, dark red
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 3
• Exact Mass: 418.12638228
• Heavy Atom Count: 30
• Complexity: 630

Purity/Quality:

98% min ^*data from raw suppliers

Aloin A ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2C4C(C(C(C(O4)CO)O)O)O)C=C(C=C3O)CO
• Isomeric SMILES: C1=CC2=C(C(=C1)O)C(=O)C3=C(C2C4[C@@H]([C@@H]([C@@H]([C@H](O4)CO)O)O)O)C=C(C=C3O)CO
• Uses: Aloin is a naturally occurring substance found in various Aloe plant species. Aloin was originally used as a laxative in the treatment of constipation. Recent studies have investigated Aloin as an ant ineoplastic agent that enhances melanogenesis and transglutaminase activity. Aloe exudant, used as a stimulant-laxative

Technology Process of 1,8-dihydroxy-3-(hydroxymethyl)-10-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one

There total 4 articles about 1,8-dihydroxy-3-(hydroxymethyl)-10-[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one 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:

→ 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2,28371-16-6,73649-93-1,5133-19-7)

Guidance literature:

With ethanol; sodium ethanolate; unter vermindertem Druck;

Reference yield:

1,8-dihydroxy-3-hydroxymethyl-10-(tetra-O-acetyl-ξ-D-glucopyranosyl)-anthrone → 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2,28371-16-6,73649-93-1,5133-19-7)

Guidance literature:

With ethanol; sodium ethanolate; unter vermindertem Druck;

Reference yield:

1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (6247-99-0) → 10-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone (1415-73-2,28371-16-6,73649-93-1,5133-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH solution; acetone / unter Ausschluss von Licht und Luft

2: sodium ethylate; ethanol / unter vermindertem Druck

With sodium hydroxide; ethanol; sodium ethanolate; acetone;

upstream raw materials:

1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

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

Downstream raw materials:

1,8-dihydroxy-3-hydroxymethyl-9,10-anthracenedione

Chrysophanol

1,8-dihydroxy-3-(hydroxymethyl)-9(10H)-anthracenone

4,5-dihydroxy-2-hydroxymethyl-1,3,6,8-tetranitro-anthraquinone