39731-48-1

Basic information

• Product Name: 3,4-dihydroxyxanthone
• Synonyms: 3,4-dihydroxyxanthone
• CAS NO: 39731-48-1
• Molecular Formula: C₁₃H₈O₄
• Molecular Weight: 0
• Mol File: 39731-48-1.mol

Chemical Properties

• Boiling Point: 419.4°Cat760mmHg
• Flash Point: 168°C
• Appearance: /
• Density: 1.516g/cm³
• Vapor Pressure: 1.25E-07mmHg at 25°C
• Refractive Index: 1.717
• CAS DataBase Reference: 3,4-dihydroxyxanthone(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydroxyxanthone(39731-48-1)
• EPA Substance Registry System: 3,4-dihydroxyxanthone(39731-48-1)

Safety Data

• Hazardous Substances Data: 39731-48-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H8O4/c14-9-6-5-8-11(15)7-3-1-2-4-10(7)17-13(8)12(9)16/h1-6,14,16H

Upstream product

• 147188-08-7 (2-hydroxy-3,4-dimethoxyphenyl)(2-methoxyphenyl)methanone 
• 5715-02-6 2-acetoxybenzonitrile 
• 87-66-1 2-hydroxyresorcinol 
• 24061-29-8 3,4-dimethoxyxanthen-9-one 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 79-37-8 oxalyl dichloride 
• 445-29-4 o-fluoro-benzoic acid 
• 1143-72-2 2,3,4-trihydroxybenzophenone 
• 1204201-92-2 (2-fluorophenyl)(2,3,4-trihydroxy-phenyl)methanone 
• 42204-63-7 2,3,4,2'-tetrahydroxy-benzophenone 
• 69-72-7 salicylic acid 
• 5150-42-5 2,3-dimethoxyphenol 
• 579-75-9 2-Methoxybenzoic acid 

Downstream Products

• 110597-41-6 3-benzyloxy-4-hydroxyxanthone 
• 110597-45-0 (+/-)-(2R,3R)-2,3-dihydro-2-(hydroxymethyl)-3-(4-hydroxy-3-methoxyphenyl)-7H-[1,4]dioxino[5,6-c]xanthen-7-one 
• 110597-43-8 ethyl 2-<9H-(3-hydroxy-9-oxo)xanthen-4-yl>oxy-3-hydroxy-3-(4-hydroxy-3-methoxyphenyl)propionate 
• 110597-44-9 2,3-dihydro-2-ethoxycarbonyl-3-(4-hydroxy-3-methoxyphenyl)-7H-1,4-dioxino-<2,3-c>xanthen-7-one 
• 110597-42-7 ethyl 2-<9H-(3-benzyloxy-9-oxo)xanthen-4-yl>oxy-3-oxo-3-(4-benzyloxy-3-methoxyphenyl)propionate 

Relevant articles and documents

DMXAA-pyranoxanthone hybrids enhance inhibition activities against human cancer cells with multi-target functions

Four 5,6-dimethylxanthone-4-acetic acid (D) and pyranoxanthone (P) hybrids (D-P-n) were design-synthesized based on multi-target-addressed strategy. D-P-4 was confirmed as the most active agent against HepG-2 cell line growth with an IC50 of 0.216 ± 0.031 μM. Apoptosis analysis indicated different contributions of early/late apoptosis/necrosis to cell death for both monomers, the combination (D + P in 1:1 mol ratio) and D-P-4. They all arrested more cells on S phase. Western Blot implied that D-P-4 regulated p53/MDM2 to a better healthy state. Moreover, it improved Bax/Bcl-2 signaling pathway to increase cancer cell apoptosis. In all cases studied, D-P-4 showed the best activity and synergistic effect. All the evidences support that D-P-4 is a better anti-cancer therapy with multi-target functions.

Inhibition of protein kinase C by synthetic xanthone derivatives

The modulatory activity of two xanthones (3,4-dihydroxyxanthone and 1-formyl-4-hydroxy-3-methoxyxanthone) on isoforms α, βI, δ, η and ζ of protein kinase C (PKC) was evaluated using an in vivo yeast phenotypic assay. Both xanthones caused an effect compatible with PKC inhibition, similar to that elicited by known PKC inhibitors (chelerythrine and NPC 15437). PKC inhibition caused by xanthones was confirmed using an in vitro kinase assay. The yeast phenotypic assay revealed that xanthones present differences on their potency towards the distinct PKC isoforms tested. It is concluded that 3,4-dihydroxyxanthone and 1-formyl-4-hydroxy-3-methoxyxanthone may become useful PKC inhibitors and xanthone derivatives can be explored to develop new isoform-selective PKC inhibitors.

Synthesis and evaluation of caged Garcinia xanthones

Inspired by the combination of unique structure and potent bioactivities exhibited by several family members of the caged Garcinia xanthones, we developed a synthesis of simplified analogues that maintain the overall caged motif. The caged structure of th

New chiral stationary phases for liquid chromatography based on small molecules: Development, enantioresolution evaluation and chiral recognition mechanisms

Recently, we reported the development of new chiral stationary phases (CSPs) for liquid chromatography (LC) based on chiral derivatives of xanthones (CDXs). Based on the most promising CDX selectors, 12 new CSPs were successfully prepared starting from suitable functionalized small molecules including xanthone and benzophenone derivatives. The chiral selectors comprising one, two, three, or four chiral moieties were covalently bonded to a chromatographic support and further packed into LC stainless-steel columns (150?×?2.1?mm I.D.). The enantioselective performance of the new CSPs was evaluated by LC using different classes of chiral compounds. Specificity for enantioseparation of some CDXs was observed in the evaluation of the new CSPs. Besides, assessment of chiral recognition mechanisms was performed by computational studies using molecular docking approach, which are in accordance with the chromatographic parameters. X-Ray analysis was used to establish a chiral selector 3D structure.

Compound as DMXAA-Pyranoxanthone well as preparation method and application thereof

The invention discloses a DMXAA-Pyranoxanthone heterozygous compound with an anti-tumor effect and a preparation method and application thereof. The DMXAA-Pyranoxanthone heterozygous compound adopts the structural formula shown as a formula I. The preparation method comprises the following steps: preparing DMXAA in three steps, preparing pyranoxanthone in two steps, and combining the DMXAA and the pyranoxanthone into the DMXAA-Pyranoxanthone heterozygous compound in two steps. The DMXAA-Pyranoxanthone heterozygous compound and a DMXAA/pyranoxanthone combined medicine have excellent in-vitro tumor cell proliferation inhibiting activity on breast cancer cells, liver cancer cells, leukemia cells, and can induce apoptosis of tumor cells through multiple targets. The DMXAA-Pyranoxanthone heterozygous compound and the DMXAA/pyranoxanthone combined medicine can be applied to preparation of cancer treating medicines.

Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them

34 Xanthones were synthesized by microwave assisted technique. Their in?vitro inhibition activities against five cell lines growth were evaluated. The SAR has been thoroughly discussed. 7-Bromo-1,3-dihydroxy-9H-xanthen-9-one (3-1) was confirmed as the most active agent against MDA-MB-231?cell line growth with an IC50 of 0.46?±?0.03?μM. Combination of 3-1 and 5,6-dimethylxanthone-4-acetic acid (DMXAA) showed the best synergistic effect. Apoptosis analysis indicated different contributions of early/late apoptosis and necrosis to cell death for both monomers and the combination. Western Blot implied that the combination regulated p53/MDM2 to a better healthy state. Furthermore, 3-1 and DMXAA arrested more cells on G2/M phase; while the combination arrested more cells on S phase. All the evidences support that the 3-1/DMXAA combination is a better anti-cancer therapy.

* One derivative containing nitrogen and its preparation method and application (by machine translation)

The invention discloses a formula (I) of formula (II) containing nitrogen mouth Shan Tong derivative and its preparation method and application, A new synthesis of this invention containing nitrogen mouth Shan Tong derivatives of the salt and its acid salt, increased solubility, active research indicates part of the compound at the same time with treating and/or preventing diabetes and complications from diabetes mellitus the role of the, can further carry out development research as a model for treating and/or preventing diabetes caused by the complications of diabetes medicine. (by machine translation)

Microwave-assisted synthesis of xanthones promoted by ytterbium triflate

Xanthones represent a class of naturally occurring compounds with valuable and promising reported pharmacological activities. One of the main disadvantages in the use of such products is related to the difficulties in their chemical synthesis. In this Letter a new and improved method for the chemical synthesis of xanthones is described. The title compounds have been synthesized in good yields under microwave irradiation from substituted 2-hydroxybenzoic acids and phenols in the presence of Yb(OTf)3 hydrate as the catalyst.

Pyranoxanthones: Synthesis, growth inhibitory activity on human tumor cell lines and determination of their lipophilicity in two membrane models

The benzopyran and dihydrobenzopyran moieties can be considered as "privileged motifs" in drug discovery being good platforms for the search of new bioactive compounds. These moieties are commonly found fused to the xanthonic scaffold belonging to the bio

Microwave-assisted efficient and green synthesis of hydroxyxanthone in water

An efficient and green procedure has been developed for the synthesis of hydroxyxanthones from substituted 2,2-dihydroxybenzophenone precursors via microwave-assisted base-catalyzed cyclization in water. This method provides excellent yields of products in a short time, making it a useful strategy for the synthesis of structurally diverse hydroxyxanthones.