Astilbin
Basic information
- CAS
29838-67-3- Standard SMILES
C[C@@H]1O[C@@H](O[C@H]2C(=O)c3c(O)cc(O)cc3O[C@@H]2c2ccc(O)c(O)c2)[C@H](O)[C@H](O)[C@H]1O- InChIKey
ZROGCCBNZBKLEL-MPRHSVQHSA-N- Molecular formula
- C21H22O11
- Average molar mass
- 450.4 g/mol
- Monoisotopic mass
- 450.11621151
Overview
Astilbin is a flavanone glycoside that is (+)-taxifolin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as a radical scavenger, an anti-inflammatory agent and a plant metabolite. It is a member of 4'-hydroxyflavanones, an alpha-L-rhamnoside, a tetrahydroxyflavanone, a member of 3'-hydroxyflavanones, a monosaccharide derivative and a flavanone glycoside. It is functionally related to a (+)-taxifolin. It is an enantiomer of a neoastilbin.
Names & identifiers
- Preferred name
- Astilbin
- IUPAC
- (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
- English name
- Taxifolin 3-O-rhamnoside
- Molecular formula
- C21H22O11
- Molecular weight
- 450.4
Names & synonyms
Astilbin29838-67-3CHEBI:38200DTXSID501019948(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-3,4-dihydro-2H-1-benzopyran-4-one(2R,3R)-2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy)-3,4-dihydro-2H-1-benzopyran-4-one(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-2,3-dihydrochromen-4-oneRefChem:115311DTXCID7014778073-0-alpha-1-rhamnosyl-(2R,3R)-dihydroquercetinKA92CW3M68
Show more names
LoastilinAstilbin-RMAstilbin (Standard)Taxifolin 3-rhaMnosideAstilbin (6CI, 7CI, 8CI)Astilbin Taxifolin 3-O-rhaMnoside
NSC-245342Taxifolin 3-O-rhamnoside(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)chroman-4-one(2R,3R)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one4H-1-Benzopyran-4-one,3-[(6-deoxy-a-L-mannopyranosyl)oxy]-2-(3,4-dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-, (2R,3R)-Astilbin from Engelhardtia roxburghiana(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-chromen-3-yl 6-deoxy-alpha-L-mannopyranosideDihydroquercetin 3-rhamnoside
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 186 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 3
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 676
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
Melting Point179 - 180 °C
Physical DescriptionSolid
Collision Cross Section
212.64 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
211.3 Ų [M+Na]+
Physicochemical properties
- Melting point
- 180 °C · 180 °C (decomp)
- Boiling point
- 801.1 · 801.1±65.0 °C(Predicted)
- Density
- 1.74 · 1.74
- storage temp.
- 2 · Sealed in dry,2-8°C
- solubility
- 2 O: · H2O: soluble1mg/mL, clear, colorless
- pka
- 7.34 · 7.34±0.60(Predicted)
- form
- A crystalline solid
- color
- White to off-white
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
H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
P273, P391, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAquatic Acute 1 (100%)
Safety data
- wgk
- 3
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29389090
- risk_code
- 50
- Signal word
- Warning
- Symbol(GHS)
- GHS09
- hazard_code
- N
- safety_code
- 61
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H400
- Precautionary statements
- P273
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
DescriptionAstilbin is a flavonoid that has been found in S. glabra and has diverse biological activities. It inhibits cisplatin-induced increases in apoptosis and accumulation of reactive oxygen species (ROS) in HEK293 cells when used at a concentration of 200 μM. Astilbin (50 mg/kg) increases renal glutathione (GSH) levels and superoxide dismutase (SOD) and catalase activity and reduces serum creatinine and blood urea nitrogen (BUN) levels, renal IL-1β, IL-6, and TNF-α levels, apoptosis in kidney tissue, and kidney injury in a mouse model of cisplatin-induced nephrotoxicity. It reduces loss of dopaminergic neurons in the substantia nigra and increases striatal GSH levels and SOD activity in a mouse model of MPTP-induced Parkinson''s disease when administered at a dose of 50 mg/kg per day. Astilbin also reduces descent time in a pole test and increases traction test score in a mouse model of Parkinson''s disease, indicating reduced motor deficits. It reduces cell viability of MDA-MB-231 and MCF-7 cells (IC50s = 167.9 and 191.6 μM, respectively), as well as inhibits migration and increases apoptosis when used at concentrations of 50 and 200 μM. Astilbin (20 mg/kg every other day for 14 days) reduces tumor growth in an MCF-7 mouse xenograft model.
UsesAstilbin displays anti-depressant activity involving monoaminergic neurotransmitters an the BDNF signal pathway. Anti-oxidant.
Additional notes
DefinitionChEBI: A flavanone glycoside that is (+)-taxifolin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage.
Related reactions
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Compound notes
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