4396-13-8

Basic information

• Product Name: 2,4,6-trihydroxyisophthalaldehyde
• Synonyms: 2,4,6-trihydroxyisophthalaldehyde;2,4-diforMyl phloroglucinol;Diformylphloroglucinol
• CAS NO: 4396-13-8
• Molecular Formula: C₈H₆O₅
• Molecular Weight: 182
• EINECS: -0
• Mol File: 4396-13-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: 2,4,6-trihydroxyisophthalaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4,6-trihydroxyisophthalaldehyde(4396-13-8)
• EPA Substance Registry System: 2,4,6-trihydroxyisophthalaldehyde(4396-13-8)

Safety Data

• Hazardous Substances Data: 4396-13-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4,6-Trihydroxyisophthalaldehyde is used as an intermediate in the synthesis of Hirsutidin Chloride (H356800), an anthocyanidin found in the Madagascar Periwinkle (Catharanthus Roseus). Hirsutidin Chloride can be used in the preparation of plant-based compounds to lower LDL cholesterol.
Used in Chemical Synthesis:
2,4,6-Trihydroxyisophthalaldehyde is used as a versatile intermediate for the synthesis of various chemical compounds, including pharmaceuticals, dyes, and other organic compounds. Its reactivity and functional groups make it a valuable building block in organic chemistry.

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 26103-97-9 phloroisovalerophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 96573-43-2 1,3-diformyl-5-(3-methyl-butyryl)-2,4,6-trihydroxybenzene 
• 7647-01-0 hydrogenchloride 
• 60-29-7 diethyl ether 

Downstream Products

• 4463-02-9 2,4-dimethylbenzene-1,3,5-triol 
• 1253907-13-9 C₂₆H₄₈N₂O₉Si₂ 
• 959860-49-2 psidial A 
• 1219603-97-0 4,5-diepipsidial A 
• 959860-49-2 guajadial 
• 88130-99-8 robustadial B 
• 88197-30-2 robustadial A 
• 1254173-26-6 (+)-psiguadial B 
• 13383-63-6 1-(2,4,6-trihydroxy-3,5-dimethylphenyl)ethan-1-one 
• 94632-38-9 1,3-Dihydroxy-5-methoxy-2,4-dimethyl-benzol 

Relevant articles and documents

Anticandidal formyl phloroglucinol meroterpenoids: Biomimetic synthesis and in vitro evaluation

Inspired by the diversity-oriented synthesis, some novel formyl phloroglucinol meroterpenoids were synthesized via biomimetic synthesis using essential oils. Eight of them were demonstrated with good in vitro fungicidal activity against Candida albicans a

Isolation and biomimetic synthesis of (±)-Guajadial B, a novel meroterpenoid from Psidium guajava

(±)-Guajadial B (1), an unusual humulene-based meroterpenoid, was isolated as a racemate from the leaves of Psidium guajava, collected from Vietnam. The structure of this novel secondary metabolite was established on the basis of extensive analysis of NMR

Total Syntheses of 4′,6′-Dimethoxy-2'-Hydroxy-3′,5′-Dimethylchalcone Derivatives

Chalcone derivatives afford several pharmacological activities. However, a general synthetic method for 2',4'-dihydroxy-6'-methoxy-3',5'-dimethylchalcone (DMC) derivatives has not been reported thus far. To address this, the preparation of 4',6'-dimethoxy-2'-hydroxy-3',5'-dimethylchalcone (MDMC) derivatives, modified compounds of DMC, in excellent overall yields is reported herein. These compounds have recently attracted growing attention due to their various pharmacological activities. Di-O-methyl-dimethylphloroacetophenone, the key intermediate containing the B-ring moiety, was fabricated by four efficient reaction steps from commercially available phloroglucinol in a 50.1% isolated yield overall. Our synthetic route, which constructs the chalcone skeleton in the final stage via a Claisen–Schmidt condensation of the key intermediate with the desired benzaldehyde derivative, can rapidly produce a vast library of DMC derivatives.

DIMETHYLCHALCONE DERIVATIVES AND PREPARATION METHOD THEREOF

The present invention relates to a dimethalcone (DMC) derivative and a method for producing the same. A compound according to an embodiment of the present invention is represented by chemical formula I: [Chemical Formula I]. In Formula I, R1, R2, and R3 a

DIMETHYLCHALCONE DERIVATIVES AND PREPARATION METHOD THEREOF

The present invention relates to a dimethalcone (DMC) derivative and a method for producing the same. A compound according to an embodiment of the present invention is represented by chemical formula I: [Chemical Formula I]. In Formula I, R1, R2, and R3 are the same as or different from each other, R1 is a hydroxy group or a methoxy group, R2, and R3 are each independently hydrogen, deuterium, a nitro group, a hydroxyl group, a carbonyl group C1?C10, a nitro group, C1?C10 a hydroxyl group, an 'C2?C10 alkyloxy group', an aryloxy C2?C10 group, an aryloxy group, an alkylthioxy group, a silyl group, a boron group, an alkyl group or an C6?C20 aryl group. (C1?C10. The cycloalkyl group, alkenyl group, alkynyl group, aryl group, aralkyl group, aralkyl group, alkylaryl group, alkylamine group. The substituent may be substituted or unsubstituted with 1 or more substituents selected from the group consisting of an aralkylamine group, a heteroarylamine group, an arylamine group, an arylphosphine group, and a heterocyclic group.

Discovery of Anti-TNBC Agents Targeting PTP1B: Total Synthesis, Structure-Activity Relationship, in Vitro and in Vivo Investigations of Jamunones

Twenty-three natural jamunone analogues along with a series of jamunone-based derivatives were synthesized and evaluated for their inhibitory effects against breast cancer (BC) MDA-MB-231 and MCF-7 cells. The preliminary structure-activity relationship revealed that the length of aliphatic side chain and free phenolic hydroxyl group at the scaffold played a vital role in anti-BC activities and the methyl group on chromanone affected the selectivity of molecules against MDA-MB-231 and MCF-7 cells. Among them, jamunone M (JM) was screened as the most effective anti-triple-negative breast cancer (anti-TNBC) candidate with a high selectivity against BC cells over normal human cells. Mechanistic investigations indicated that JM could induce mitochondria-mediated apoptosis and cause G0/G1 phase arrest in BC cells. Furthermore, JM significantly restrained tumor growth in MDA-MB-231 xenograft mice without apparent toxicity. Interestingly, JM could downregulate phosphatidylinositide 3-kinase (PI3K)/Akt pathway by suppressing protein-tyrosine phosphatase 1B (PTP1B) expression. These findings revealed the potential of JM as an appealing therapeutic drug candidate for TNBC.

HALOGEN-SUBSTITUTED DIMETHYLCHALCONE DERIVATIVES AND PREPARATION METHOD THEREOF

The present invention relates to dimethylchalcone (DMC) derivatives substituted with halogen and a method for producing the same. A compound according to an embodiment of the present invention is represented by chemical formula I: [Chemical Formula I]. In Formula I, R1 and R2 are the same as or different from each other, R1, and R2 are each independently selected from the group consisting of hydrogen, methoxy, and methoxy. R3, and R4 are each independently hydrogen or halogen elements, and when R3 is hydrogen, R4 R4 is any one selected from the group consisting of halogen elements R3.

Antioxidative and anti-inflammatory activity of psiguadial B and its halogenated analogues as potential neuroprotective agents

Psiguadial B (8), and its fluoro- (8a), chloro- (8b), and bromo- (8c) derivatives were synthesized using a sodium acetate-catalyzed single step coupling of three components: β-caryophyllene (5), diformylphloroglucinol (11), and benzaldehyde (12). These co

Synthesis of methylophiopogonanone a

Ophiopogon Root (root of Ophiopogon japonicus Ker-Gawler, Liliaceae) is a crude drug used as expectorant, anti-cough and tonic in Kampo medicine (traditional Japanese medicine) as well as other traditional medicines of Asian countries. It contains characteristic homoisoflavonoids with methylated ring A. We synthesized methylophiopogonanone A (1), which is a candidate marker compound for identification test of Ophiopogon Root, from phloroglucinol in 9 steps with overall yield of 11.1%.

Biomimetic Synthesis Enables the Structure Revision of Littordials e and F and Drychampone B

Structural reassignments for littordial E, littordial F, and drychampone B are proposed on the basis of consideration of their biosynthetic origin. The key step in the proposed biosynthesis of each of these meroterpenoids is an intermolecular hetero-Diels-Alder reaction between an o-quinone methide and caryophyllene or humulene. Biomimetic total synthesis of the natural products gave sufficient material to allow their structure revision by NMR studies.