Basic information
- CAS
120-08-1- Standard SMILES
COc1cc2ccc(=O)oc2cc1OC- InChIKey
GUAFOGOEJLSQBT-UHFFFAOYSA-N- Molecular formula
- C11H10O4
- Average molar mass
- 206.19 g/mol
- Monoisotopic mass
- 206.0579088
Overview
Scoparone is a member of the class of coumarins that is esculetin in which the two hydroxy groups at positions 6 and 7 are replaced by methoxy groups. It is a major constituent of the Chinese herbal medicine Yin Chen Hao, and exhibits a variety of pharmacological activities such as anti-inflammatory, anti-allergic, and anti-tumor activities. It has a role as an antihypertensive agent, an antilipemic drug, an immunosuppressive agent, an anti-allergic agent, an anti-inflammatory agent and a plant metabolite. It is a member of coumarins and an aromatic ether. It is functionally related to an esculetin.
Names & identifiers
- Preferred name
- Scoparone
- IUPAC
- 6,7-dimethoxychromen-2-one
- English name
- SCOPARONE
- Molecular formula
- C11H10O4
- Molecular weight
- 206.19
Names & synonyms
Scoparone120-08-16,7-DIMETHOXYCOUMARIN6,7-DimethylesculetinEscoparoneScoparon6,7-Dimethoxy-2H-chromen-2-oneEsculetin dimethyl etherAesculetin dimethyl ether6,7-dimethoxychromen-2-oneScopoletin methyl ethero-Methylscopoletin
Show more names
AKOS 236-43Scoparone-RMSCOPARONE(RG)DIMETHYLESCULETINDIMETHOXYCOUMARIN
6,7-Dimethoxy-2H-1-benzopyran-2-oneo-Methylisoscopoletino,o-Dimethylesculetin6,7-Dimethoxy-Coumarin6,7-Dimethoxybenzopyran-2-oneEsculetin 6,7-dimethyl etherH5841PDT4YDTXSID10152640
Database identifiers
- CAS
120-08-1- PubChem CID
- 8417
- DTXSID
DTXSID10152640- ChEMBL
CHEMBL325864- ChEBI
CHEBI:9055- UNII
- H5841PDT4Y
- EC Number
- 204-369-0
- Nikkaji
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 44.8 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 2
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 274
Experimental & physicochemical properties
LogP2.45
Melting Point144 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 143 · 143-145 °C (lit.)
- Boiling point
- 265.04 °C · 265.04°C (rough estimate)
- Density
- 1.0858 · 1.0858 (rough estimate)
- refractive index
- 1.4389 · 1.4389 (estimate)
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- 8.4 mg/mL · >8.4mg/mL in DMSO
- form
- Powder
- color
- Light yellow to yellow
- Merck
- 13 · 13,8479
- Cosmetics Ingredients Functions
- ANTIOXIDANT
- InChI
- InChI=1S/C11H10O4/c1-13-9-5-7-3-4-11(12)15-8(7)6-10(9)14-2/h3-6H,1-2H3
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
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P264, P264+P265, P270, P280, P301+P316, P305+P351+P338, P321, P330, P337+P317, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- GN6550000
- ridadr
- 2811
- hs_code
- 29322090
- risk_code
- 23/24/25-36-22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn
- safety_code
- 27/28-36/37/39-45-26
- hazard_class
- 6.1(b)
- Storage Class
- 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
- packing_group
- III
- Hazard statements
- H301-H319
- Hazard Classifications
- Acute Tox. 3 OralEye Irrit. 2
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic).
Drugs used to cause dilation of the blood vessels.
Cellular LocationsCytoplasm
Applications
UsesScoparone-13C2D6 is a by-product in the synthesis of Scopoletin-13C,d3 (S200502). Scopoletin-13C,d3, is the labeled analogue of Scopoletin (S200500), used for cosmetics, topical formulations, and foods. Scoparone-13C2D6 is also the labeled form of Scoparone (S199980), which regulates the expression of Th1/Th2 cytokines and IgE and is effective in treating allergic rhinitis.
General Description6,7-Dimethoxycoumarin inhibits the in vitro growth of Phytophthora citrophthora, Verticillium dahliae, Penicillium digitatum, P. italicum, Colletotrichum gloeosporioides, Diplodia natalensis and Hendersonula toruloidea. Determination and pharmacokinetic study of 6,7-dimethoxycoumarin in rat plasma after intragastric administration of different decoctions of Yinchenhao Tang by reversed-phase HPLC method with UV detection has been reported.
Upstream & downstream products
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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