Showing Compound Scoparone (FDB002774)

Record Information

Version

1.0

Creation date

2010-04-08 22:05:31 UTC

Update date

2025-11-18 22:40:34 UTC

Primary ID

FDB002774

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Scoparone

Description

Scoparone belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Scoparone is found, on average, in the highest concentration within sweet oranges (Citrus sinensis) and tarragons (Artemisia dracunculus). Scoparone has also been detected, but not quantified in, several different foods, such as wild celeries (Apium graveolens), citrus, fennels (Foeniculum vulgare), anises (Pimpinella anisum), and mandarin orange (clementine, tangerine). This could make scoparone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Scoparone.

CAS Number

120-08-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
6,7-Dimethoxycoumarin	Kegg
6,7-Dimethoxy-2-benzopyrone	HMDB
6,7-Dimethoxy-2H-1-benzopyran-2-one	HMDB
6,7-Dimethoxy-2H-chromen-2-one	HMDB
6,7-Dimethoxy-benzopyran-2-one	HMDB
6,7-Dimethoxy-coumarin	HMDB, MeSH
6,7-Dimethoxybenzopyran-2-one	HMDB
6,7-Dimethylesculetin	HMDB, MeSH
Aesculetin dimethyl ether	HMDB
Benzopyran-2-one, 6,7-dimethoxy- (9ci)	HMDB
Dimethyl esculetin	HMDB
Dimethylaesculetin	HMDB
Escoparone	HMDB
Esculetin 6,7-dimethyl ether	HMDB
Esculetin dimethyl ether	HMDB
O,O-Dimethylesculetin	HMDB
O-Methylisoscopoletin	HMDB
O-Methylscopoletin	HMDB
Scoparin?	HMDB
Scoparon	HMDB
Scopoletin methyl ether	HMDB
2H-1-Benzopyran-2-one, 6,7-dimethoxy-	biospider
Benzopyran-2-one, 6,7-dimethoxy-	biospider
Benzopyran-2-one, 6,7-dimethoxy- (9CI)	biospider
Coumarin, 6,7-dimethoxy-	biospider
O-methylisoscopoletin	biospider
O-methylscopoletin	biospider
O,o-dimethylesculetin	biospider
Scoparone	db_source

Predicted Properties

Property	Value	Source
Water Solubility	0.41 g/L	ALOGPS
logP	1.8	ALOGPS
logP	1.47	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.48 m³·mol⁻¹	ChemAxon
Polarizability	20.38 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C11H10O4

IUPAC name

6,7-dimethoxy-2H-chromen-2-one

InChI Identifier

InChI=1S/C11H10O4/c1-13-9-5-7-3-4-11(12)15-8(7)6-10(9)14-2/h3-6H,1-2H3

InChI Key

GUAFOGOEJLSQBT-UHFFFAOYSA-N

Isomeric SMILES

COC1=C(OC)C=C2C=CC(=O)OC2=C1

Average Molecular Weight

206.197

Monoisotopic Molecular Weight

206.057908802

Classification

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Coumarin
Benzopyran
1-benzopyran
Anisole
Alkyl aryl ether
Pyranone
Pyran
Benzenoid
Heteroaromatic compound
Lactone
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

coumarins (CHEBI:9055 )
coumarins (C09311 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
Physical Description	Not Available
Mass Composition	C 64.07%; H 4.89%; O 31.04%	DFC
Melting Point	Mp 144°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Scoparone, non-derivatized, GC-MS Spectrum	splash10-0bvu-6930000000-ced173387f2077948312	Spectrum
GC-MS	Scoparone, non-derivatized, GC-MS Spectrum	splash10-0a4i-7980000000-bac19c33733285c01d2e	Spectrum
GC-MS	Scoparone, non-derivatized, GC-MS Spectrum	splash10-0bvu-6930000000-ced173387f2077948312	Spectrum
GC-MS	Scoparone, non-derivatized, GC-MS Spectrum	splash10-0a4i-7980000000-bac19c33733285c01d2e	Spectrum
Predicted GC-MS	Scoparone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01t9-1910000000-49576d749f9a27e74639	Spectrum
Predicted GC-MS	Scoparone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Scoparone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4i-1920000000-9bd0d132645d4ed6bc1c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0490000000-6ba38bf256267dc79574	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0k96-0900000000-aa6111d1cffc77ac9e90	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0490000000-eeed81a14383625d7bf3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0f6x-0900000000-dfc6fbc2696bac03caa3	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0490000000-b740c17de432f1e6a236	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0f6x-0900000000-acf2d8ef9a78b346ec0a	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0390000000-fe20d160d812860d12df	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pbc-0920000000-283a15c7999af7cccb15	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0190000000-a354b13b55c501391e59	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0900000000-bb1cabccc184b742df3f	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-6ff0954c5cfe49286580	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0490000000-89ad655054326a39f101	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0a6u-4900000000-ae0decb43930d6b0fbfd	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0pbc-0930000000-7618d733b5a16befcbf4	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 6V, Positive	splash10-0a4i-0490000000-25b3b6e4b37d1caede53	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-80d2cec4f0f08e37a84d	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0490000000-ff9f81eadfea79cd2bc2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 50V, Positive	splash10-0a4i-3900000000-3f388422d31ee01c11c8	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0090000000-3ea9dfc965f95368cbc7	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0190000000-da5c9b027559bd7e9786	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0bvi-1910000000-dbe9795947b065d85bc1	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0190000000-5054bd554f5a32a27974	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0490000000-5077dddb7176cefd49da	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a5a-3900000000-34600055b290259d617d	2016-08-03	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB30818

CRC / DFC (Dictionary of Food Compounds) ID

CNP29-S:CNP27-Q

EAFUS ID

Not Available

Dr. Duke ID

6,7-DIMETHOXYCOUMARIN|SCOPARONE

BIGG ID

Not Available

KNApSAcK ID

C00002498

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Scoparone

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Aldose reductase inhibitor	48550	An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.	DUKE
Analgesic	35480	An agent that relieves pain by reducing or blocking pain signals in the brain, commonly used to manage acute or chronic pain, inflammation, and fever, with therapeutic applications in surgery, injury, and disease treatment.	DUKE
Anti-atherogenic	38070	An agent that prevents or reduces the formation of atheromas (plaques) in arteries, thereby lowering the risk of cardiovascular disease. It inhibits the biological processes leading to atherosclerosis, and has therapeutic applications in managing hyperlipidemia, hypertension, and cardiovascular disease, with key medical uses including reducing inflammation and improving lipid profiles.	DUKE
Anti hepatotoxic	62868	An agent that protects the liver from damage, reducing toxicity and promoting liver health. It plays a biological role in preventing liver injury and supporting liver function. Therapeutically, it is used to treat liver diseases, such as hepatitis and cirrhosis, and to counteract liver-damaging effects of certain medications and toxins.	DUKE
Anti implantation		An agent that prevents the adherence of the blastocyst to the uterine wall, playing a biological role in regulating fertility. Therapeutically, it is used to prevent pregnancy, with key medical applications in contraception and family planning.	DUKE
Anti-inflammatory	35472	An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.	DUKE
Anti-ischemic	52217	An agent that reduces or prevents tissue damage from inadequate blood flow, commonly used to manage angina, heart attacks, and strokes by improving oxygen delivery and reducing cardiac workload.	DUKE
Anti proliferant		An agent that prevents or inhibits cell growth and division, used therapeutically to treat cancer, manage tumor growth, and prevent restenosis after angioplasty, reducing abnormal cell proliferation.	DUKE
Anti radicular		An agent that relieves inflammation or irritation of the nerve root of a tooth, reducing pain and discomfort. Its biological role is to target and alleviate radicular pain, with therapeutic applications in endodontics and key medical uses in root canal treatments and tooth sensitivity management.	DUKE
Anti retinopathic	52217	An agent that prevents or treats retinopathy, a disease damaging the retina. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing diabetic retinopathy and other retinal disorders, with key medical uses including preserving vision and preventing blindness.	DUKE
Anti-spasmodic	52217	An agent that relaxes smooth muscle, reducing muscle spasms and cramps. It plays a biological role in regulating muscle tone and is therapeutically applied to treat conditions such as irritable bowel syndrome, menstrual cramps, and muscle spasms, providing relief from abdominal pain and discomfort.	DUKE
Cardiac	38070	Relating to the heart, referring to agents or functions that support heart health, treat cardiovascular diseases, or regulate heart rhythm, commonly used in managing conditions such as arrhythmias, heart failure, and hypertension.	DUKE
Cholagogue		An agent that stimulates the release of bile from the gallbladder, promoting digestion and relieving bile duct issues. Therapeutically, it aids in treating gallstones, jaundice, and liver disorders, while also supporting digestive health.	DUKE
Choleretic		An agent that increases bile production and secretion from the liver, enhancing digestion and fat absorption. Therapeutically, it's used to treat gallstones, liver disease, and indigestion, promoting healthy bile flow and liver function.	DUKE
Central nervous system depressant	35470	An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.	DUKE
Hepatoprotective	62868	An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.	DUKE
Hypocholesterolemic		An agent that lowers cholesterol levels in the blood, playing a crucial role in preventing cardiovascular disease. Therapeutically, it is used to manage hyperlipidemia and reduce the risk of heart disease, with key medical applications including the treatment of high cholesterol, atherosclerosis, and coronary artery disease.	DUKE
Hypotensive		An agent that lowers blood pressure, playing a biological role in regulating cardiovascular function. Therapeutically, it's used to manage hypertension, heart failure, and angina, with key medical applications in preventing stroke, kidney disease, and cardiac complications.	DUKE
Immunosuppressant	35705	An agent that suppresses the immune system, reducing inflammation and preventing rejection in organ transplants, and treating autoimmune diseases such as rheumatoid arthritis and lupus.	DUKE
Myorelaxant		An agent that reduces muscle contractility by blocking nerve impulses or decreasing motor end plate excitability, used therapeutically to relieve muscle spasms, tension, and pain, commonly in managing musculoskeletal disorders, anxiety, and insomnia.	DUKE
Tranquilizer		An agent that induces relaxation and reduces anxiety, used therapeutically to manage anxiety disorders, insomnia, and restlessness, promoting calmness and sedation in individuals.	DUKE
Vasodilator	35620	An agent that widens blood vessels, reducing blood pressure and increasing blood flow. It plays a biological role in regulating cardiovascular function. Therapeutically, vasodilators are used to treat conditions such as hypertension, angina, and heart failure, improving oxygen delivery and reducing cardiac workload.	DUKE