Aloin B
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Basic information
- CAS
28371-16-6- Standard SMILES
O=C1c2c(O)cccc2[C@@H]([C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)c2cc(CO)cc(O)c21- InChIKey
AFHJQYHRLPMKHU-WEZNYRQKSA-N- Molecular formula
- C21H22O9
- Average molar mass
- 418.4 g/mol
- Monoisotopic mass
- 418.12638228
Overview
Aloin B is a C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9R diastereoisomer). It has a role as a metabolite and a laxative. It is a C-glycosyl compound, a member of phenols, a cyclic ketone and a member of anthracenes.
Names & identifiers
- Preferred name
- Aloin B
- IUPAC
- (10R)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one
- English name
- Aloin B
- Molecular formula
- C21H22O9
- Molecular weight
- 418.4
Names & synonyms
Aloin B28371-16-6Isobarbaloin69VIB0J2WKCHEBI:74131DTXSID70904581(10R)-1,8-dihydroxy-3-(hydroxymethyl)-10-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-10H-anthracen-9-one(1S)-1,5-anhydro-1-[(9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl]-D-glucitol(10R)-1,8-dihydroxy-3-(hydroxymethyl)-10-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)-10H-anthracen-9-one(1S)-1,5-anhydro-1-((9R)-4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl)-D-glucitolRefChem:27242DTXCID901333710
Show more names
ALOIN B(P)Aloin B-RMBarbaloin BAloin B, >99%Aloin B (10 mg)Aloin B (Aloin-BAloin B (Standard)
(R)-1,8-dihydroxy-3-(hydroxymethyl)-10-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)anthracen-9(10H)-oneSCHEMBL181616CHEMBL3617994(10R)-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-10-[(2S,3R,4R,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]-9,10-DIHYDROANTHRACEN-9-ONEAloin-B;Isobarbaloin(10R)-10-.BETA.-D-GLUCOPYRANOSYL-1,8-DIHYDROXY-3-(HYDROXYMETHYL)-9(10H)-ANTHRACENONE5133-19-7UNII-69VIB0J2WK
Properties
Computed structural propertiesFilling in
- XLogP
- -0.1
- Topological polar surface area
- 168 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 3
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 630
Physicochemical properties
- Melting point
- 147 · 147~148℃
- Boiling point
- 752.6 · 752.6±60.0 °C(Predicted)
- Density
- 1.647 · 1.647±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- 2 · 2-8°C
- solubility
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 0.25 mg/ml; PBS (pH 7.2): 0.5 mg/ml
- form
- A crystalline solid
- pka
- 7.12 · 7.12±0.40(Predicted)
- color
- Light yellow to yellow
- Major Application
- (pharmaceutical small molecule)
- InChIKey
- AFHJQYHRLPMKHU-GQMFJIQQNA-N
- SMILES
- O[C@@H]1[C@H]([C@H](O)[C@@H](CO)O[C@@]1([H])[C@]1([H])C2=CC=CC(O)=C2C(=O)C2C(=CC(CO)=CC1=2)O)O |&1:1,2,3,5,9,11,r|
- FDA UNII
- 69 VIB0J2WK · 69VIB0J2WK
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
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
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Hazard information
Regulatory InformationChemical: 9(10H)-Anthracenone, 10-.beta.-D-glucopyranosyl-1,8-dihydroxy-3-(hydroxymethyl)-, (R)-
Hazard Classes and Categories
Acute Tox. 4 (100%)
Acute Tox. 4 (100%)
Safety data
- wgk
- WGK 3
- hs_code
- 29389090
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H314-H290
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P501-P234-P264-P280-P390-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P406-P405
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationAgents that are used to stimulate evacuation of the bowels.
Applications
UsesAloin B is an aloe exudate and a phytochemical constituent. It is one isomer of Aloin, the other being Aloin A (A575415)
Additional notes
DefinitionChEBI: A C-glycosyl compound that is beta-D-glucopyranose in which the anomeric hydroxy group is replaced by a 4,5-dihydroxy-2-(hydroxymethyl)-10-oxo-9,10-dihydroanthracen-9-yl moiety (the 9R d astereoisomer).
Related reactions
0 records
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Compound notes
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