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3,4-Bis(methoxymethoxy)benzaldehyde is an organic compound that serves as a crucial intermediate in the synthesis of various bioactive molecules. It is characterized by its unique structure, featuring a benzaldehyde core with two methoxymethoxy groups attached at the 3,4-positions. 3,4-Bis(methoxymethoxy)benzaldehyde plays a significant role in the development of pharmaceuticals and other applications due to its versatile chemical properties.

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  • 6515-06-6 Structure
  • Basic information

    1. Product Name: 3,4-Bis(methoxymethoxy)benzaldehyde
    2. Synonyms: 3,4-Bis(methoxymethoxy)benzaldehyde
    3. CAS NO:6515-06-6
    4. Molecular Formula: C11H14O5
    5. Molecular Weight: 226.23
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 6515-06-6.mol
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 354.209 °C at 760 mmHg
    3. Flash Point: 157.278 °C
    4. Appearance: /
    5. Density: 1.161 g/cm3
    6. Vapor Pressure: 0mmHg at 25°C
    7. Refractive Index: 1.519
    8. Storage Temp.: N/A
    9. Solubility: Dichloromethane;
    10. CAS DataBase Reference: 3,4-Bis(methoxymethoxy)benzaldehyde(CAS DataBase Reference)
    11. NIST Chemistry Reference: 3,4-Bis(methoxymethoxy)benzaldehyde(6515-06-6)
    12. EPA Substance Registry System: 3,4-Bis(methoxymethoxy)benzaldehyde(6515-06-6)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 6515-06-6(Hazardous Substances Data)

6515-06-6 Usage

Uses

Used in Pharmaceutical Industry:
3,4-Bis(methoxymethoxy)benzaldehyde is used as a key intermediate in the synthesis of Okanin (O515750), a natural product extracted from Dalbergia sissoo Roxb. leaves. Okanin exhibits potent antibacterial properties and has potential anti-inflammatory effects, making it a valuable compound for the development of new drugs to combat bacterial infections and inflammation.
Used in Organic Synthesis:
3,4-Bis(methoxymethoxy)benzaldehyde is used as a versatile building block in the synthesis of chalcones, which are a class of compounds known for their diverse range of biological activities. Chalcones have been extensively studied for their anti-inflammatory, antioxidant, and anticancer properties, among others. The presence of the methoxymethoxy groups in 3,4-Bis(methoxymethoxy)benzaldehyde allows for the facile synthesis of various chalcone derivatives with potential therapeutic applications.
Used in Cancer Research:
3,4-Bis(methoxymethoxy)benzaldehyde is also utilized as a precursor in the development of anti-cancer agents. Its unique structure allows for the synthesis of novel compounds with potential to target cancer cells and inhibit their growth and proliferation. 3,4-Bis(methoxymethoxy)benzaldehyde's ability to be modified and functionalized makes it an attractive candidate for the design of new anticancer drugs with improved efficacy and reduced side effects.

Check Digit Verification of cas no

The CAS Registry Mumber 6515-06-6 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 6,5,1 and 5 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 6515-06:
(6*6)+(5*5)+(4*1)+(3*5)+(2*0)+(1*6)=86
86 % 10 = 6
So 6515-06-6 is a valid CAS Registry Number.
InChI:InChI=1/C11H14O5/c1-13-7-15-10-4-3-9(6-12)5-11(10)16-8-14-2/h3-6H,7-8H2,1-2H3

6515-06-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 3,4-bis(methoxymethoxy)benzaldehyde

1.2 Other means of identification

Product number -
Other names Benzaldehyde,3,4-bis(methoxymethoxy)

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:6515-06-6 SDS

6515-06-6Relevant articles and documents

Synthetic hispidin, a PKC inhibitor, is more cytotoxic toward cancer cells than normal cells in vitro

Gonindard,Bergonzi,Denier,Sergheraert,Klaebe,Chavant,Hollande

, p. 141 - 153 (1997)

The trypanocidal activity of naturally occurring 6-(3,4-dihydroxystyryl)-4-hydroxy-2-pyrone (hispidin) prompted us to examine its cytotoxic activity toward normal and cancerous cells in culture. Hispidin synthesized in our laboratory to a high degree of purity (checked by 1H and 13C NMR spectroscopy) was shown to be cytotoxic (between 10-3 mol/L and 10-7 mol/L) toward normal human MRC-5 fibroblasts, human cancerous keratinocytes (SCL-1 cell line), and human cancerous pancreatic duct cells (Capan-1 cell line). Interestingly, addition of hispidin in three successive doses (between 10-5 mol/L and 10-7 mol/L) led to a 100-fold increase in activity with an enhanced activity on cancer cells compared to normal cells (50%). Synthetic hispidin was found to inhibit isoform β of protein kinase C (IC50 of 2 x 10-6 mol/L), but not E. coli and placental type XV alkaline phosphatases. The enhanced activity of hispidin toward the cancerous cell lines is discussed.

Structural elucidation of in vitro metabolites of bavachinin in rat liver microsomes by LC-ESI-MSn and chemical synthesis

Xie, Fan,Du, Guoxin,Ma, Shunan,Li, Yiming,Wang, Rui,Guo, Fujiang

, p. 296 - 306 (2016)

1. Bavachinin isolated from Psoralea corylifolia has various activities, such as antimicrobial, antiallergic, antitumor and so on. Our previous study showed that natural bavachinin exhibits peroxisome proliferator-activated receptor γ-agonist activity.2.

Microbial Transformation of Broussochalcones A and B by Aspergillus niger

Xiao, Yina,Han, Fubo,Kim, Myeong Ji,Lee, Kwang Youl,Lee, Ik-Soo

supporting information, p. 601 - 607 (2021/02/16)

Broussochalcones A (BCA, 1) and B (BCB, 2) are major bioactive constituents isolated from Broussonetia papyrifera, a polyphenol-rich plant belonging to the family Moraceae. Due to their low yields from natural sources, BCA (1) and BCB (2) were prepared sy

Tethered aryl groups increase the activity of anti-proliferative thieno[2,3-b]pyridines by targeting a lipophilic region in the active site of PI-PLC

Barker, David,Haverkate, Natalie A.,Leung, Euphemia,Pilkington, Lisa I.

, (2021/12/02)

The compounds 2-amino-3-carboxamido-thieno[2,3-b]pyridines have demonstrated excel-lent anti-proliferative activity against human cancer cell lines, including the triple-negative breast cancer cell line MDA-MB-231. In this study, 81 novel thieno[2,3-b]pyridines were synthesised in four series to further improve their anti-proliferative activity, in particular by targeting an adjacent lipophilic pocket in the putative target enzyme phosphoinositide phospholipase C (PI-PLC). Overall, it was found that appending a propyl-aryl group at C-5 on 2-amino-3-carboxamido-thieno[2,3-b]pyridine resulted in compounds with potent biological activity, exhibiting IC50 values in the nanomolar range. The propyl linker could be an α,β-unsaturated ketone or a saturated propyl ketone, but the highest activity was obtained when allylic alcohols were the tether between thieno[2,3-b]pyridine and the appended aryl group, with compound 21r having IC50 values lower than 50 nM. Compounds with one extra carbon in the tether (i.e., a four-atom chain) were found to be considerably less active. Molecular modelling revealed this propyl tether places the newly introduced aryl ring in an untargeted lipophilic pocket within the active site of the phosphoinositide phospholipase C (PI-PLC) enzyme.

Exploring the 2′-hydroxy-chalcone framework for the development of dual antioxidant and soybean lipoxygenase inhibitory agents

Detsi, Anastasia,Hadjipavlou-Litina, Dimitra,Karadendrou, Maria-Anna,Kostopoulou, Ioanna,Kritsi, Eftichia,Liargkova, Thalia,Polyzos, Nestor-Ioannis,Pontiki, Eleni,Tzani, Andromachi,Zoumpoulakis, Panagiotis

, (2021/05/29)

2′-hydroxy-chalcones are naturally occurring compounds with a wide array of bioactiv-ity. In an effort to delineate the structural features that favor antioxidant and lipoxygenase (LOX) inhibitory activity, the design, synthesis, and bioactivity profile of a series of 2′-hydroxy-chalcones bearing diverse substituents on rings A and B, are presented. Among all the synthesized derivatives, chalcone 4b, bearing two hydroxyl substituents on ring B, was found to possess the best combined activity (82.4% DPPH radical scavenging ability, 82.3% inhibition of lipid peroxidation, and satisfac-tory LOX inhibition value (IC50 = 70 μM). Chalcone 3c, possessing a methoxymethylene substituent on ring A, and three methoxy groups on ring B, exhibited the most promising LOX inhibitory activity (IC50 = 45 μM). A combination of in silico techniques were utilized in an effort to explore the crucial binding characteristics of the most active compound 3c and its analogue 3b, to LOX. A common H-bond interaction pattern, orienting the hydroxyl and carbonyl groups of the aromatic ring A towards Asp768 and Asn128, respectively, was observed. Regarding the analogue 3c, the bulky (-OMOM) group does not seem to participate in a direct binding, but it induces an orientation capable to form H-bonds between the methoxy groups of the aromatic ring B with Trp130 and Gly247.

Antibacterial activity of a new monocarbonyl analog of curcumin MAC 4 is associated with divisome disruption

Polaquini, Carlos R.,Marques, Beatriz C.,Ayusso, Gabriela M.,Mor?o, Luana G.,Sardi, Janaína C.O.,Campos, Débora L.,Silva, Isabel C.,Cavalca, Lúcia B.,Scheffers, Dirk-Jan,Rosalen, Pedro L.,Pavan, Fernando R.,Ferreira, Henrique,Regasini, Luis O.

, (2021/02/22)

Curcumin (CUR) is a symmetrical dicarbonyl compound with antibacterial activity. On the other hand, pharmacokinetic and chemical stability limitations hinder its therapeutic application. Monocarbonyl analogs of curcumin (MACs) have been shown to overcome these barriers. We synthesized and investigated the antibacterial activity of a series of unsymmetrical MACs derived from acetone against Mycobacterium tuberculosis and Gram-negative and Gram-positive species. Phenolic MACs 4, 6 and 8 showed a broad spectrum and potent activity, mainly against M. tuberculosis, Acinetobacter baumannii and methicillin-resistant Staphylococcus aureus (MRSA), with MIC (minimum inhibitory concentration) values ranging from 0.9 to 15.6 μg/mL. The investigation regarding toxicity on human lung cells (MRC-5 and A549 lines) revealed MAC 4 was more selective than MACs 6 and 8, with SI (selectivity index) values ranging from 5.4 to 15.6. In addition, MAC 4 did not demonstrate genotoxic effects on A549 cells and it was more stable than CUR in phosphate buffer (pH 7.4) for 24 h at 37 °C. Fluorescence and phase contrast microscopies indicated that MAC 4 has the ability to disrupt the divisome of Bacillus subtilis without damaging its cytoplasmic membrane. However, biochemical investigations demonstrated that MAC 4 did not affect the GTPase activity of B. subtilis FtsZ, which is the main constituent of the bacterial divisome. These results corroborated that MAC 4 is a promising antitubercular and antibacterial agent.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

Carlet, Federica,Bertarini, Greta,Broggini, Gianluigi,Pradal, Alexandre,Poli, Giovanni

supporting information, p. 2162 - 2168 (2021/04/02)

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Neuroregenerative Potential of Prenyl- And Pyranochalcones: A Structure-Activity Study

Aigner, Ludwig,Bieler, Lara,Couillard-Despres, Sebastien,Priglinger, Eleni,Riepl, Herbert M.,Urmann, Corinna

supporting information, p. 2675 - 2682 (2021/10/12)

Loss of neuronal tissue is a hallmark of age-related neurodegenerative diseases. Since adult neurogenesis has been confirmed in the human brain, great interest has arisen in substances stimulating the endogenous neuronal regeneration mechanism based on ad

Sterubin: Enantioresolution and Configurational Stability, Enantiomeric Purity in Nature, and Neuroprotective Activity in Vitro and in Vivo

Hofmann, Julian,Fayez, Shaimaa,Scheiner, Matthias,Hoffmann, Matthias,Oerter, Sabrina,Appelt-Menzel, Antje,Maher, Pamela,Maurice, Tangui,Bringmann, Gerhard,Decker, Michael

supporting information, p. 7299 - 7308 (2020/05/18)

Alzheimer′s disease (AD) is a neurological disorder with still no preventive or curative treatment. Flavonoids are phytochemicals with potential therapeutic value. Previous studies described the flavanone sterubin isolated from the Californian plant Eriodictyon californicum as a potent neuroprotectant in several in vitro assays. Herein, the resolution of synthetic racemic sterubin (1) into its two enantiomers, (R)-1 and (S)-1, is described, which has been performed on a chiral chromatographic phase, and their stereochemical assignment online by HPLC-ECD coupling. (R)-1 and (S)-1 showed comparable neuroprotection in vitro with no significant differences. While the pure stereoisomers were configurationally stable in methanol, fast racemization was observed in the presence of culture medium. We also established the occurrence of extracted sterubin as its pure (S)-enantiomer. Moreover, the activity of sterubin (1) was investigated for the first time in vivo, in an AD mouse model. Sterubin (1) showed a significant positive impact on short- and long-term memory at low dosages.

Total synthesis of novel skeleton flavan-alkaloids

Simon, James E.,Wu, Qingli,Zhen, Jing

, (2020/10/18)

The first total synthesis of novel skeleton natural compounds kinkeloids A and B, a group of newly discovered flavan alkaloids isolated fromthe African plant Combretum micranthum, are described in this study. The key and final step are achieved by Mannich reaction, through which the piperidine moiety couples to the flavan moiety. The identities of synthesized kinkeloids were further confirmed through a comparison with the ones in the plant leaves extract using LC/MS.

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