(-)-Arctigenin
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Basic information
- CAS
144901-91-7- Standard SMILES
COc1cc(C[C@H]2C(=O)OC[C@@H]2Cc2ccc(OC)c(OC)c2)ccc1O- InChIKey
NQWVSMVXKMHKTF-JKSUJKDBSA-N- Molecular formula
- C21H24O6
- Average molar mass
- 372.4 g/mol
- Monoisotopic mass
- 372.15728848
Names & identifiers
- Preferred name
- (-)-Arctigenin
- IUPAC
- (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one
- English name
- (-)-Arctigenin
- Molecular formula
- C21H24O6
- Molecular weight
- 372.41
Names & synonyms
Arctigenin(-)-Arctigenin7770-78-7U76MR9VS6M(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R-trans)-2(3H)-Furanone, 4-((3,4-dimethoxyphenyl)methyl)dihydro-3-((4-hydroxy-3-methoxyphenyl)methyl)-, (3R,4R)-DTXSID60998919(3R,4R)-4-((3,4-dimethoxyphenyl)methyl)-3-((4-hydroxy-3-methoxyphenyl)methyl)oxolan-2-one2(3H)-Furanone, 4-[(3,4-dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-, (3R,4R)-RefChem:27994DTXCID201425899
Show more names
ARCTIGENIN(P)The arctigenin(?)-Arctigeninarctigenin powerArctigenin (Standard)(-)-Arctigenin USP/EP/BPArctigenin, 10 mM in DMSO(-)-Arctigenin, ≥98%(HPLC)
(+/-)-ArctigeninArctigenin, (+/-)-Arctigenin, trans-((+/-)-UNII-U76MR9VS6MC21H24O6MFCD00870597(3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone(3R,4R)-4-(3,4-dimethoxybenzyl)-3-(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
Database identifiers
- CAS
144901-91-7、7770-78-7- PubChem CID
- 64981
- DTXSID
DTXSID60998919- ChEMBL
CHEMBL435734- ChEBI
CHEBI:79- UNII
- 2FD8L150E7、U76MR9VS6M
- Nikkaji
- J16.086E
Properties
Computed structural propertiesFilling in
- XLogP
- 3.6
- Topological polar surface area
- 74.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 483
Physicochemical properties
- Melting point
- 98 to · 98.0 to 102.0 °C
- Boiling point
- 567 · 567.0±45.0 °C(Predicted)
- Density
- 1.227 · 1.227±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · Sealed in dry,Store in freezer, under -20°C
- solubility
- 34 mg/mL · DMSO: 34 mg/mL with heating and sonicating, soluble
- form
- solid
- pka
- 10.03 · 10.03±0.20(Predicted)
- color
- White to Light yellow
- λmax
- 280 nm · 280nm(EtOH)(lit.)
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- Cosmetics Ingredients Functions
- ANTIOXIDANT
- InChI
- InChI=1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1
- InChIKey
- NQWVSMVXKMHKTF-JKSUJKDBSA-N
- SMILES
- O1C[C@H](CC2=CC=C(OC)C(OC)=C2)[C@@H](CC2=CC=C(O)C(OC)=C2)C1=O
- LogP
- 2.47 · 2.470 (est)
- CAS DataBase Reference
- 7770 · 7770-78-7(CAS DataBase Reference)
- NCI Dictionary of Cancer Terms
- arctigenin
- FDA UNII
- 76 MR9VS6M · U76MR9VS6M
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Safety Statements
- 22 · 22-24/25
- WGK Germany
- 3 · 3
- RTECS
- 9247000 · LY9247000
- HS Code
- 2932.2 · 2932.20.4500
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- LY9247000
- hs_code
- 2932.20.4500
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 22-24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
Cellular LocationsMembrane
Applications
UsesArctigenin is a plant ligan associated with anticancer and antioxidant properties.
Additional notes
DefinitionChEBI: (-)-Arctigenin is a lignan.
Suppliers
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Related reactions
1 records
Compound notes
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