Physcion
Basic information
- CAS
521-61-9- Standard SMILES
COc1cc(O)c2c(c1)C(=O)c1cc(C)cc(O)c1C2=O- InChIKey
FFWOKTFYGVYKIR-UHFFFAOYSA-N- Molecular formula
- C16H12O5
- Average molar mass
- 284.26 g/mol
- Monoisotopic mass
- 284.06847348
Overview
Physcion is a dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6. It has been widely isolated and characterised from both terrestrial and marine sources. It has a role as a metabolite, an antibacterial agent, an antineoplastic agent, an antifungal agent, a hepatoprotective agent, an anti-inflammatory agent and an apoptosis inducer. It is functionally related to a 2-methylanthraquinone.
Names & identifiers
- Preferred name
- Physcion
- IUPAC
- 1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione
- English name
- Emodin-3-methyl ether
- Molecular formula
- C16H12O5
- Molecular weight
- 284.26
Names & synonyms
Physcion521-61-9PhyscioneRheochrysidinEmodin 3-methyl ether1,8-dihydroxy-3-methoxy-6-methylanthracene-9,10-dione1,8-Dihydroxy-3-methoxy-6-methyl-9,10-anthracenedioneParieninEmodin monomethyl etherH6PT94IV61ANTHRAQUINONE, 1,8-DIHYDROXY-3-METHOXY-6-METHYL-NSC-251670
Show more names
parietinMethyleModinRheochrysidin (Physcion)Emodin-3-methyl ether 521-61-9Physcion-RMPhyscic acid
CHEBI:38167DTXSID20200101RefChem:45131DTXCID80122592208-315-7Emodin-3-methyl ether1,8-Dihydroxy-3-methoxy-6-methylanthraquinoneMFCD00017374
Database identifiers
- CAS
521-61-9- PubChem CID
- 10639
- DTXSID
DTXSID20200101- ChEMBL
CHEMBL42624- ChEBI
CHEBI:38167
Properties
Computed structural properties
- XLogP
- 3
- Topological polar surface area
- 83.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 1
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 448
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Aromatic polyketides [PK13] -> Anthracenes and phenanthrenes [PK1304]
LogP4.93
Collision Cross Section152.86 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 196 · 196-206°C
- Boiling point
- 560.5 · 560.5±50.0 °C(Predicted)
- Density
- 1.448 · 1.448±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer, Under Inert Atmosphere
- solubility
- Chloroform (Slightly, Heated), Ethyl Acetate (Slightly, Heated), Methanol (Slightly)
- form
- Solid
- pka
- 6.23 · 6.23±0.20(Predicted)
- color
- Yellow to Dark Yellow to Dark Orange
- BRN
- 6770499 · 6770499
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
H315 (93.3%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (93.3%)
Safety data
- F
- 10
- wgk
- 3
- rtecs
- CB6720000
- hs_code
- 29146990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 26
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302
- Hazard Classifications
- Acute Tox. 4 Oral
- Precautionary statements
- P264-P270-P301+P312-P501
Chemistry & industry
Applications
Usesantibacterial, cathartic
UsesA natural anthraquinone derivative, on the infection process of Blumeria graminis on wheat. Physcion is one of the important active ingredients of ethanol extract from the roots of Chinese rhubarb (Rheum officinale) for controlling powdery mildew.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: A dihydroxyanthraquinone that is 9,10-anthraquinone bearing hydroxy substituents at positions 1 and 8, a methoxy group at position 3, and a methyl group at position 6.
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Compound notes
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