XANTHONE

Xanthone is a versatile aromatic heterocyclic compound widely used as a building block in pharmaceutical, fine-chemical, and functional material synthesis.
Xanthone's rigid conjugated structure makes Xanthone valuable for preparing substituted derivatives, fluorescent compounds, dyes, and biologically active molecules.
Xanthone also serves as an important intermediate in medicinal chemistry, natural-product research, and the development of advanced organic compounds.

CAS Number: 90-47-1
EC Number: 201-997-7
Molecular Formula: C13H8O2
Molecular Weight: 196.2 g/mol

Synonyms: XANTHONE, 9H-Xanthen-9-one, 90-47-1, Xanthen-9-one, 9-Xanthenone, Benzophenone oxide, Xanthenone, 9-Oxoxanthene, Genicide, 9-Xanthone, Diphenylene ketone oxide, Dibenzo-gamma-pyrone, 9H-Xanthene, 9-oxo-, DTXSID6021795, 9749WEV0CA, NSC-14978, DTXCID201795, CHEBI:37647, RefChem:195149, 201-997-7, Xanthene, 9-oxo-, MFCD00005060, Dibenzo-.gamma.-pyrone, NSC 14978, Xanthone (Standard), CHEMBL186784, E 6, NSC14978, ST024714, Caswell No. 905, diphenyline ketone oxide, EINECS 201-997-7, EPA Pesticide Chemical Code 086503, UNII-9749WEV0CA, AI3-00077, xanthene-9-one, Xanthone, 97%, XANTHONE [MI], Spectrum2_000052, Spectrum3_001884, XANTHONE [USP-RS], SCHEMBL41161, BSPBio_003388, SPECTRUM200523, MLS002207109, SCHEMBL654268, SCHEMBL694630, SPBio_000203, ghl.PD_Mitscher_leg0.1212, orb1304774, SCHEMBL3286115, SCHEMBL3367763, SCHEMBL3368451, SCHEMBL29358061, SCHEMBL29398266, HY-N0126R, KBio3_002891, WLN: T C666 BO IVJ, HMS3651G22, HY-N0126, STR05546, Tox21_301151, BDBM50155411, CCG-38356, EBC-13728, MSK161079, s2372, SBB069491, STK372481, AKOS001213782, FX29267, SDCCGMLS-0066462.P001, CAS-90-47-1, NCGC00095484-01, NCGC00095484-02, NCGC00095484-03, NCGC00255049-01, DA-68731, SMR000112239, SY017687, CS-0007833, NS00039360, SW219800-1, X0005, EN300-20176, C22599, F15407, AC-907/21098006, F358255, Q421789, SR-05000002437, SR-05000002437-1, BRD-K27135764-001-08-7, F8889-9282, Z104477176, Xanthone, United States Pharmacopeia (USP) Reference Standard, InChI=1/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8

Xanthone is a polycyclic aromatic ketone consisting of a dibenzo-γ-pyrone skeleton.
Xanthone serves as a valuable intermediate in organic synthesis and is also used as a building block in the preparation of dyes, pigments, and functional organic materials.
Due to its aromatic and ketone functionalities, Xanthone exhibits interesting photochemical and electronic properties.

Xanthone is an organic compound with the molecular formula C13H8O2.
Xanthone is a white solid.

In 1939, xanthone was introduced as an insecticide and it currently finds uses as ovicide for codling moth eggs and as a larvicide.
Xanthone is also used in the preparation of xanthydrol, which is used in the determination of urea levels in the blood.
Xanthone can also be used as a photocatalyst.

Xanthone is the parent compound of the xanthone class consisting of xanthene bearing a single oxo substituent at position 9.
Xanthone has a role as an insecticide.

Xanthone is a compound that has been shown to have a significant cytotoxicity against HL-60 cells and to inhibit the cyclase enzyme.
Xanthone also inhibits the protein production of mcl-1, which is necessary for the development of cancer cells.

Xanthone is an aromatic oxygen-containing heterocyclic compound composed of two benzene rings fused to a central pyranone structure.
Xanthone serves as an important structural framework and intermediate in pharmaceutical, natural-product, dye, and specialty chemical research.
Xanthone derivatives are widely studied and utilized because their rigid conjugated ring system supports diverse chemical modification and the development of functional organic compounds.

Xanthones are naturally-occurring compounds characterized by a tricyclic aromatic system, known for their antibacterial properties and potential therapeutic applications in treating local infections, wounds, and lesions, particularly those involving antibiotic-resistant pathogens.

Xanthone is a phenolic compound classified as a secondary metabolite that occurs naturally in numerous plants and fungi.
Xanthone's diverse biological activities have drawn significant research interest.

In particular, xanthone has been widely utilized in various in vitro studies to investigate its impact on several cellular processes, including cell proliferation, apoptosis, and cell migration.
Additionally, researchers have explored Xanthone's effects on biochemical processes, such as enzyme activity and protein synthesis.

Xanthones are aromatic oxo compounds derived from the xanthene ring system and are the coloring substances of some plants in nature.
Xanthones are therefore secondary plant metabolites produced in plants as pigments, fragrances, and flavor compounds.

Xanthone is a naturally occurring polyphenolic compound recognized for its diverse range of applications in various fields, including pharmaceuticals, cosmetics, and food industries.
Xanthone is known for its antioxidant properties, making it a valuable ingredient in formulations aimed at combating oxidative stress.

Xanthone is particularly noted for its potential therapeutic effects, including anti-inflammatory, antimicrobial, and anticancer activities, which have been the subject of numerous studies.
Xanthone's ability to enhance the stability and efficacy of active ingredients in cosmetic products further underscores its relevance in the beauty industry.

In research, Xanthone serves as a vital building block for synthesizing more complex compounds, facilitating the development of new drugs and therapeutic agents.
Xanthone's unique structure allows for modifications that can lead to enhanced biological activity, making it a focus for medicinal chemistry.

Additionally, Xanthone's applications extend to the food industry, where it is utilized as a natural colorant and preservative.
With its multifaceted benefits and applications, Xanthone stands out as a compound of significant interest for researchers and industry professionals alike.

Xanthones are a class of naturally occurring organic compounds that belong to polyphenols and have powerful antioxidant properties.
Xanthones are found in various plants, in particular in mangosteens (Garcinia mangostana), which contain the highest amount of these compounds.
Xanthones are known for their wide range of biological activities, including anti-inflammatory, anti-cancer, antibacterial, antiviral, and neuroprotective properties.

Due to their antioxidant properties, xanthones help protect cells from damage caused by free radicals and thereby reduce the risk of developing chronic diseases such as cardiovascular disease and cancer.
In addition, xanthones help strengthen the immune system, reduce inflammation and maintain brain health.

Xanthones are used in dietary supplements and natural remedies to improve overall health and prevent disease.
Xanthone is important to consider the possible side effects and contraindications when using xanthones, so it is recommended to consult a doctor before using them.

Xanthone Derivatives:
Xanthone forms the core of a variety of natural products, such as mangostin or lichexanthone.
Xanthones are sometimes referred to as xanthones or xanthonoids.

Over 200 natural xanthones have been identified.
Many are phytochemicals found in plants in the families Bonnetiaceae, Clusiaceae, and Podostemaceae.

They are also found in some species of the genus Iris.
Some xanthones are found in the pericarp of the mangosteen fruit (Garcinia mangostana) as well as in the bark and timber of Mesua thwaitesii.

Uses of Xanthone:
Xanthone is used to make xanthydrol and as an ovicide for codling moth eggs (less effective as larvicide).
Xanthone is acts as an inhibitor of human cancer cell lines.

Xanthone is used predominantly as oxygenated polycyclic aromatic compounds, and as a vasorelaxant.
Xanthone can be used as a fluorescent agent, as well as an intermediate in organic synthesis and chemical research.

Xanthone has antiinflammatory activity and can be used in treating infectious diseases such as tuberculosis, malaria, and leprosy.
The biological properties of Xanthone are shown by its ability to scavenge anion radicals and to act as a fluorescence probe for coumarin derivatives.

Xanthone is used as an intermediate and structural building block in pharmaceutical and fine-chemical synthesis.
Xanthone is employed in the preparation of biologically active xanthone derivatives and natural-product analogues.

Xanthone is used in research involving fluorescent compounds, dyes, pigments, and optical materials.
Xanthone serves as a starting material for the synthesis of substituted aromatic and heterocyclic compounds.

Xanthone derivatives are investigated for applications in medicinal chemistry, agrochemical research, and functional material development.
Xanthone is also used in academic and industrial laboratories as a reference compound and synthetic intermediate.

Synthesis of Xanthone:
Xanthone can be prepared by the heating of phenyl salicylate.

Various other methods of synthesis given are:
Heating a mixture of salicylic acid, phenol, and acetic anhydride.
Warming o-phenoxybenzoic acid with sulfuric acid or phosphorous pentoxide.

Distillation of o-phenoxybenzoyl chloride under vacuum.
Heating of aspirin or o-hydroxybenzophenone.

Derivatives:

Multiple methods have been reported for synthesizing xanthone derivatives:
The Michael-Kostanecki method uses an equimolar mix of a polyphenol and a salicylic acid derivative, which are heated with a dehydrating agent in a condensation reaction.
The Friedel-Crafts method has a benzophenone intermediate.

The Robinson-Nishikawa method is a variant of the Hoesch synthesis but with low yields.
The Asahina-Tanase method synthesizes some methoxylated xanthones, and xanthones with acid-sensitive substituents.

The Tanase method is used to synthesize polyhydroxyxanthones.
The Ullman method condenses a phenol with an O-chlorobenzene and cyclizes the resulting diphenylether.

Stability and Reactivity of Xanthone:

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

Reactivity:
Xanthone may react with strong oxidizing agents and other highly reactive substances.

Conditions to avoid:
Avoid excessive heat, open flames, ignition sources, and prolonged exposure to incompatible materials.

Incompatible materials:
Keep away from strong oxidizing agents and other reactive chemicals.

Handling and Storage of Xanthone:

Safe handling:
Handle in a well-ventilated area and avoid inhalation of dust and unnecessary contact with the skin and eyes.

Storage conditions:
Keep the container tightly closed in a cool, dry, and well-ventilated place away from heat and incompatible materials.

First Aid Measures of Xanthone:

Inhalation:
Move the affected person to fresh air and seek medical attention if symptoms persist.

Skin contact:
Wash the affected area thoroughly with soap and plenty of water.

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

Ingestion:
Rinse the mouth and seek medical advice if discomfort develops.

Firefighting Measures of Xanthone:

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

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

Accidental Release Measures of Xanthone:

Personal precautions:
Ensure adequate ventilation and avoid generating or inhaling dust.

Cleanup methods:
Carefully collect or sweep up the material and place it in a suitable closed container for disposal.

Environmental precautions:
Prevent unnecessary release into drains, waterways, and the surrounding environment.

Exposure Controls/Personal Protective of Xanthone:

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

Eye protection:
Wear suitable safety glasses or chemical goggles.

Hand protection:
Use appropriate chemical-resistant protective gloves.

Skin protection:
Wear suitable protective clothing.

Respiratory protection:
Use suitable respiratory protection when ventilation is insufficient or significant dust exposure may occur.

Identifiers of Xanthone:
Empirical Formula (Hill Notation): C13H8O2
CAS Number: 90-47-1
Molecular Weight: 196.20
UNSPSC Code: 12352100
NACRES: NA.22
PubChem Substance ID: 24902151
EC Number: 201-997-7
Beilstein/REAXYS Number: 140443
MDL Number: MFCD00005060
Assay: 97%
Form: powder

CAS No.: 90-47-1
Chemical Name: Xanthone
CBNumber: CB3304187
Molecular Formula: C13H8O2
Molecular Weight: 196.2
MDL Number: MFCD00005060

CAS Number: 90-47-1
Beilstein Reference: 140443
ChEBI: CHEBI:37647
ChEMBL: ChEMBL186784
ChemSpider: 6753
ECHA InfoCard: 100.001.816
EC Number: 201-997-7
Gmelin Reference: 166003
PubChem CID: 7020
UNII: 9749WEV0CA
CompTox Dashboard (EPA): DTXSID6021795
InChI: InChI=1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
Key: JNELGWHKGNBSMD-UHFFFAOYSA-N
InChI: InChI=1/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
Key: JNELGWHKGNBSMD-UHFFFAOYAA
SMILES: O=C1c2ccccc2Oc3ccccc31

Properties of Xanthone:
Quality Segment: 100
Assay: 97%
Form: powder
Boiling Point: 349-350 °C/730 mmHg (lit.)
Melting Point: 172-174 °C (lit.)
Functional Group: ketone
SMILES String: O=C1c2ccccc2Oc3ccccc13
InChI: 1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
InChI Key: JNELGWHKGNBSMD-UHFFFAOYSA-N
Gene Information: mouse ... Prkch(18755)

Melting Point: 172-174 °C(lit.)
Boiling Point: 349-350 °C730 mm Hg(lit.)
Density: 1.1607 (rough estimate)
Refractive Index: 1.6000 (estimate)
Flash Point: 350-351°C
Storage Temperature: Sealed in dry,Room Temperature
Solubility: Chloroform (Slightly), Methanol (Slightly, Heated)
Form: Solid
Color: White to Light Purple
Water Solubility: Xanthone is Soluble in water (partly), chloroform, hot Toluene, ether (slightly), and hot alcohol.
Merck: 14,10062
BRN: 140443
Stability: Stable. Incompatible with strong oxidizing agents.
InChI: 1S/C13H8O2/c14-13-9-5-1-3-7-11(9)15-12-8-4-2-6-10(12)13/h1-8H
InChIKey: JNELGWHKGNBSMD-UHFFFAOYSA-N
SMILES: O=C1c2ccccc2Oc3ccccc13
CAS DataBase Reference: 90-47-1(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 9749WEV0CA
NIST Chemistry Reference: Xanthone(90-47-1)
EPA Substance Registry System: 9H-Xanthen-9-one (90-47-1)
UNSPSC Code: 41116107
NACRES: NA.24

Chemical Formula: C13H8O2
Molar Mass: 196.205 g·mol−1
Appearance: white solid
Melting Point: 174 °C (345 °F; 447 K)
Solubility in Water: Sl. sol. in hot water
Magnetic Susceptibility (χ): -108.1·10−6 cm3/mol

Molecular Weight: 196.20 g/mol
XLogP3: 3.4
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Rotatable Bond Count: 0
Exact Mass: 196.052429494 Da
Monoisotopic Mass: 196.052429494 Da
Topological Polar Surface Area: 26.3 Ų
Heavy Atom Count: 15
Complexity: 237
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

Related compounds of Xanthone:
xanthene

Names of Xanthone:

Preferred IUPAC name:
9H-Xanthen-9-one

Other names:
9-Oxoxanthene
Diphenyline ketone oxide