CHROMONE

Chromone is a distinctive benzopyranone scaffold valued for its role in molecular design, heterocyclic chemistry, and the preparation of specialized organic compounds.
Chromone's conjugated structure offers a useful balance of aromatic stability and synthetic flexibility, allowing chemists to build a wide variety of substituted and functionally tailored derivatives.
This makes chromone especially attractive for research-driven applications involving advanced intermediates, optical systems, and structurally complex fine chemicals.

CAS Number: 491-38-3
EC Number: 207-737-9
Molecular Formula: C9H6O2
Molecular Weight: 146.14 g/mol

Synonyms: CHROMONE, 4H-Chromen-4-one, 491-38-3, 4-Chromone, Chromen-4-one, Benzo-gamma-pyrone, 1,4-benzopyrone, DTXSID40197680, 20C556MJ76, CHEBI:72013, RefChem:125916, DTXCID00120171, 207-737-9, 4H-1-Benzopyran-4-one, 1-Benzopyran-4-one, 4H-Benzo(b)pyran-4-one, MFCD00024064, 4-oxo-4H-1-benzopyran, Benzopyrone, 4-chromenone, benzopyran-4-one, EINECS 207-737-9, BRN 0114087, Chromone-, Benz-g-pyrone, UNII-20C556MJ76, benzo-|A-pyrone, chromone, 12, Chromone, 99%, Benzo-.gamma.-pyrone, 4H-Chromen-4-one #, SCHEMBL37994, 5-17-10-00139 (Beilstein Handbook Reference), MLS002473394, CHEMBL13311, SCHEMBL207427, SCHEMBL466442, 4H-chromen-4-one [M+H]+, FC13, orb3029397, SCHEMBL1460498, SCHEMBL2873532, SCHEMBL3354660, SCHEMBL7085952, SCHEMBL12612291, SCHEMBL12612324, SCHEMBL29369932, BDBM24783, PDK0235, EBC-14268, MSK164076, SBB086467, XH0839, AKOS000521772, CS-W005942, FC54286, GS-6824, SMR001397486, ST092368, SY020315, DB-051603, NS00031861, EN300-80154, H10070, AF-407/03086014, F319145, Q420156, Z1218937140, InChI=1/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6, CHROMONE, 4-Chromone, Benzo-gamma-pyrone, 4H-Chromen-4-one, 4H-1-Benzopyran-4-one, chromone, 12, 1-Benzopyran-4-one, 4H-Benzo(b)pyran-4-one, 199222_ALDRICH, EINECS 207-737-9, CID10286, BRN 0114087, LS-53467, ST5331439, 5-17-10-00139 (Beilstein Handbook Reference), AF-407/03086014, InChI=1/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6, 491-38-3, 1-Benzopyran-4-one, 2,3-Benzo-4-pyrone, 207-737-9, 4-Chromone, 491-38-3, 4H-1-Benzopyran-4-one, 4H-Benzo(b)pyran-4-one, 4H-benzo[b]pyran-4-one, 4H-Chromen-4-on, 4H-Chromen-4-one, 4H-Chromén-4-one, Benzo-g-pyrone, Benzo-γ-pyrone, Chromen-4-one, Chromone, T66 BO EVJ, 1,4-benzopyrone, 1-BENZOPYRAN-4(4H)-ONE, 3-dihydrochromen-4-one, 4-chromenone, 4-OXO-4H-1-BENZOPYRAN, 4H-chromen-4-one::chromone, 12, 5-17-10-00139, Benz-g-pyrone, Benzopyrone, Chromone [491-38-3], chromone, 12, EINECS 207-737-9, FUCO_BOVIN, I23O1_HUMAN, Indoleamine 2,3-dioxygenase 1, MANA_CANEN, Tissue α-L-fucosidase, α-mannosidase

Chromone is the simplest member of the class of chromones that is 4H-chromene with an oxo group at position 4.
Chromone is a member of chromones and an enone.

Chromone compounds belong to a class of organic compounds closely related to benzopyrones.
They are distinguished by their chromone moiety, featuring a benzopyrone ring system with a C-2 ketone group.

The interaction of chromones with various molecular targets has been elucidated.
These compounds have been found to modulate the activity of enzymes including c-Jun N-terminal kinase, cyclooxygenase-2, and lipoxygenase.
Additionally, chromones have demonstrated the ability to modulate the activity of ion channels, such as the voltage-gated calcium channel and voltage-gated potassium channel.

Chromone is a derivative of benzopyran with a substituted keto group on the pyran ring.
Chromone is an isomer of coumarin.

Derivatives of chromone are collectively known as chromones.
Most, though not all, chromones are also phenylpropanoids.

Chromone is defined as a bicyclic compound belonging to the flavonoid family, characterized by a 1-benzopyran-4-one structure, which contains a heterocyclic ring with an oxygen atom.
Chromone exhibits various medicinal and biological properties, including the ability to inhibit specific enzymes and serve as a pharmacophore in medicinal applications.

Chromone is a versatile chemical compound known for its unique structure and diverse applications across various industries.
Chromone, characterized by its chromen-4-one structure, exhibits significant biological activity, making it a valuable asset in pharmaceutical research and development.

Chromone derivatives are widely studied for their potential in anti-inflammatory, antioxidant, and anticancer therapies, showcasing their relevance in modern medicine.
Additionally, Chromone serves as a key building block in the synthesis of various natural products and dyes, enhancing its utility in organic chemistry and materials science.

Researchers and industry professionals appreciate Chromone for its ability to act as a scaffold for the development of novel compounds, particularly in the field of medicinal chemistry.
Chromone's distinct properties allow for the exploration of new therapeutic agents, while its applications in the production of fluorescent materials and agrochemicals further highlight its versatility.
With ongoing studies revealing more about its potential, Chromone remains a compound of interest for those looking to innovate in chemical synthesis and drug discovery.

Chromone is an oxygen-containing heterocyclic aromatic compound with the molecular formula C9H6O2.
Chromone consists of a benzene ring fused to a pyrone ring and serves as an important structural framework in natural products, pharmaceuticals, dyes, and specialty organic compounds.
Chromone derivatives are widely studied and used in medicinal chemistry, fine chemical synthesis, fluorescent materials, and the development of functional molecules because of their versatile reactivity and conjugated ring system.

Chromone, belongs to the class of organic compounds known as chromones.
Chromones are compounds containing a benzopyran-4-one moiety. Chromone has been detected, but not quantified in, fats and oils and herbs and spices.

This could make chromone a potential biomarker for the consumption of these foods.
Based on a literature review a significant number of articles have been published on Chromone.

Chromone, with the CAS number 491-38-3, is a bicyclic organic compound characterized by a fused benzene and pyrone ring structure.
Chromone is a colorless to pale yellow solid that is soluble in organic solvents but has limited solubility in water.

Chromone exhibits a range of interesting chemical properties, including the ability to undergo various reactions such as electrophilic substitution and nucleophilic addition due to the presence of the carbonyl group in the pyrone ring.
Chromone is known for its biological activities, including anti-inflammatory, antioxidant, and antimicrobial properties, making it of interest in pharmaceutical research.

Additionally, chromone derivatives are often studied for their potential applications in the development of dyes, agrochemicals, and as fluorescent probes in biochemical assays.
Chromone's structure allows for the modification of its properties, leading to a diverse array of derivatives with tailored functionalities.
Overall, chromone serves as an important scaffold in organic chemistry and medicinal chemistry.

Examples:
6,7-dimethoxy-2,3-dihydrochromone has been isolated from Sarcolobus globosus.
Altechromone A can be isolated from fungi such as Alternaria sp.

Eucryphin, a chromone rhamnoside, can be isolated from the bark of Eucryphia cordifolia.
Cromolyn (disodium cromoglicate) was found to inhibit antigen challenge as well as stress induced symptoms.

Cromoglicate is used as a mast cell stabilizer in allergic rhinitis, asthma and allergic conjunctivitis.
Nedocromil sodium was found to have a somewhat longer half-life than cromolyn; however, production was discontinued in the US in 2008.
Xanthone with a second aromatic ring.

Uses of Chromone:
Chromone is widely used as a heterocyclic building block in pharmaceutical and medicinal chemistry for the synthesis of structurally diverse bioactive compounds.
Chromone serves as an important intermediate in the preparation of chromone derivatives used in fine chemical research and specialty organic synthesis.

Chromone's conjugated aromatic structure also makes it valuable in the development of fluorescent compounds, dyes, optical materials, and molecular probes.
Chromone-based structures are frequently employed in natural-product chemistry because the chromone nucleus occurs in many plant-derived compounds and related functional molecules.

Chromone is also used in the synthesis of agrochemical intermediates, advanced heterocycles, and research reagents.
In materials science, chromone derivatives are investigated for applications in photochemistry, sensors, electronic materials, and functional molecular systems.

Chromone's ability to undergo a variety of substitution and ring-transformation reactions makes chromone a useful platform for constructing more complex oxygen-containing aromatic compounds.
Overall, chromone is valued across pharmaceutical, analytical, research, and specialty chemical applications as a versatile precursor for high-value functional derivatives.

Production of Chromone:
Chromone is commonly produced through cyclization reactions involving ortho-hydroxy aromatic precursors, particularly 2′-hydroxyacetophenone derivatives.
Classical production routes include the Baker–Venkataraman and Kostanecki–Robinson approaches, in which acylation and rearrangement generate suitable diketone intermediates that subsequently undergo ring closure to form the chromone framework.

Another widely used route converts 2′-hydroxyacetophenones into enaminone intermediates followed by cyclization to obtain the chromone ring system.
Modern synthesis has expanded to include catalytic, metal-free, microwave-assisted, and tandem annulation processes designed to improve reaction efficiency and provide access to differently substituted chromone derivatives.

After synthesis, the crude chromone product is generally purified by suitable separation and crystallization techniques to obtain the required purity for pharmaceutical, research, or specialty chemical applications.

Synthesis of Chromone:
Chromone can be synthesized through several established cyclization strategies that construct its fused benzopyran-4-one ring system.
One of the most widely used approaches begins with 2′-hydroxyacetophenone derivatives, which can be converted into suitable intermediates and subsequently cyclized to form the chromone nucleus.

The Baker–Venkataraman rearrangement is particularly important for substituted chromones, involving acylation of an ortho-hydroxyacetophenone followed by base-promoted rearrangement to a 1,3-diketone and subsequent cyclocondensation.
Enaminone-based methods also provide efficient access to chromones through intramolecular annulation of ortho-hydroxyaryl enaminones.

Other synthetic strategies employ phenols, chalcones, salicylic acid derivatives, ynones, and hydroxyaryl ketones as starting materials.
Modern developments include metal-catalyzed, metal-free, microwave-assisted, tandem, and one-pot procedures designed to improve efficiency and expand the range of accessible chromone derivatives.

Stability and Reactivity of Chromone:

Chemical stability:
Chromone is stable under normal ambient temperatures and recommended storage conditions.

Reactivity:
No significant reactivity is expected under normal conditions of handling and use.

Conditions to avoid:
Avoid excessive heat, ignition sources, prolonged exposure to light, and contact with incompatible materials.

Incompatible materials:
Avoid strong oxidizing agents and highly reactive chemical substances.

Hazardous decomposition products:
Thermal decomposition or combustion may generate carbon monoxide, carbon dioxide, and irritating organic fumes.

Handling and Storage of Chromone:

Safe handling:
Avoid inhalation of dust and unnecessary contact with the skin and eyes.
Use adequate ventilation and minimize dust generation during handling.

Storage conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated place protected from direct light and incompatible materials.
Cool and dark storage is recommended.

First Aid Measures of Chromone:

Inhalation:
Move the affected person to fresh air and obtain medical attention if symptoms develop.

Skin contact:
Remove contaminated clothing and wash the affected area thoroughly with soap and water.

Eye contact:
Rinse cautiously with plenty of water for several minutes and obtain medical attention if irritation persists.

Ingestion:
Rinse the mouth with water and obtain medical advice if discomfort occurs.

Firefighting Measures of Chromone:

Suitable extinguishing media:
Use water spray, dry chemical, carbon dioxide, or suitable foam according to surrounding fire conditions.

Protective equipment:
Firefighters should wear appropriate protective equipment and self-contained breathing apparatus where necessary.

Hazardous combustion products:
Combustion may produce carbon oxides and irritating fumes.
Chromone is classified in storage class 11 for combustible solids by Sigma-Aldrich.

Accidental Release Measures of Chromone:

Personal precautions:
Ensure adequate ventilation, avoid dust formation, and wear suitable personal protective equipment.

Cleanup methods:
Carefully sweep or collect spilled material into a suitable closed container while minimizing airborne dust.

Environmental precautions:
Prevent unnecessary release into drains, surface water, and soil.

Exposure Controls/Personal Protection of Chromone:

Engineering controls:
Provide adequate general or local exhaust ventilation where dust may be generated.

Eye protection:
Wear suitable safety glasses or protective goggles.

Hand protection:
Wear appropriate chemical-resistant protective gloves.

Body protection:
Use suitable protective work clothing.

Respiratory protection:
Use suitable particulate respiratory protection when ventilation is insufficient or significant dust is generated.

Identifiers of Chromone:
Name: chromen-4-one
CAS Number: 491-38-3
FDA UNII: 20C556MJ76
Nikkaji Web: J6.056I
Beilstein Number: 0114087
MDL: MFCD00024064
XlogP3: 1.40 (est)
Molecular Weight: 146.14522000
Formula: C9 H6 O2

CAS No.: 491-38-3
EC Number: 207-737-9
Chemical Name: CHROMONE
CBNumber: CB6417590
Molecular Formula: C9H6O2
Molecular Weight: 146.14

CAS Number: 491-38-3
ChEBI: CHEBI:72013
ChEMBL: ChEMBL13311
ChemSpider: 9866
ECHA InfoCard: 100.007.035
PubChem CID: 10286
UNII: 20C556MJ76
CompTox Dashboard (EPA): DTXSID40197680
InChI: InChI=1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
Key: OTAFHZMPRISVEM-UHFFFAOYSA-N
InChI: InChI=1/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
Key: OTAFHZMPRISVEM-UHFFFAOYAY
SMILES: O=C1C=COc2ccccc12

Empirical Formula (Hill Notation): C9H6O2
CAS Number: 491-38-3
Molecular Weight: 146.14
NACRES: NA.22
PubChem Substance ID: 24851900
UNSPSC Code: 12352100
EC Number: 207-737-9
MDL Number: MFCD00024064
Assay: 99%

Properties of Chromone:
Chemical Formula: C9H6O2
Molar Mass: 146.145 g·mol−1
Acidity (pKa): −2.0 (of conjugate acid)

Quality Segment: 100
Assay: 99%
Melting Point: 55-60 °C (lit.)
Functional Group: ketone
SMILES String: O=C1C=COc2ccccc12
InChI: 1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
InChI Key: OTAFHZMPRISVEM-UHFFFAOYSA-N

Melting Point: 55-60 °C(lit.)
Boiling Point: 239℃
Density: 1.248
Refractive Index: 1.5100 (estimate)
Flash Point: 107℃
Storage Temperature: Keep in dark place,Sealed in dry,Room Temperature
Appearance: Light yellow to yellow Solid
InChI: 1S/C9H6O2/c10-8-5-6-11-9-4-2-1-3-7(8)9/h1-6H
InChIKey: OTAFHZMPRISVEM-UHFFFAOYSA-N
SMILES: O=C1C=COc2ccccc12
CAS DataBase Reference: 491-38-3(CAS DataBase Reference)

Molecular Weight: 146.14 g/mol
XLogP3: 1.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 146.036779430 Da
Monoisotopic Mass: 146.036779430 Da
Topological Polar Surface Area: 26.3 Ų
Heavy Atom Count: 11
Complexity: 196
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Names of Chromone:

IUPAC name:
Chromen-4-one

Preferred IUPAC name:
4H-1-Benzopyran-4-one

Other names:
4-Chromone
1,4-Benzopyrone
4H-Chromen-4-one
Benzo-gamma-pyrone
1-Benzopyran-4-one
4H-Benzo(b)pyran-4-one