27738-46-1

Basic information

• Product Name: 1,3-BENZODIOXOLE-5-GLYCOLIC ACID
• Synonyms: 1,3-BENZODIOXOLE-5-GLYCOLIC ACID;3,4-METHYLENEDIOXYMANDELIC ACID;ALPHA-HYDROXY-1,3-BENZODIOXOLE-5-ACETIC ACID;TIMTEC-BB SBB008591;α-hydroxy-1,3-benzodioxole-5-acetic acid;3,4-(METHYLENEDIOXY)MANDELIC ACID 98+%;(1,3-Benzodioxol-5-yl)hydroxyacetic acid;2-(2H-1,3-benzodioxol-5-yl)-2-hydroxyacetic acid
• CAS NO: 27738-46-1
• Molecular Formula: C₉H₈O₅
• Molecular Weight: 196.16
• EINECS: 248-628-6
• Mol File: 27738-46-1.mol
• Article Data: 12

Chemical Properties

• Melting Point: 158-162 °C
• Boiling Point: 403.5 °C at 760 mmHg
• Flash Point: 169.2 °C
• Appearance: /
• Density: 1.553 g/cm³
• Vapor Pressure: 3.1E-07mmHg at 25°C
• Storage Temp.: Hygroscopic, Refrigerator, Under inert atmosphere
• Solubility: Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Sonicated)
• PKA: 3.39±0.11(Predicted)
• Stability: Hygroscopic
• BRN: 209546
• CAS DataBase Reference: 1,3-BENZODIOXOLE-5-GLYCOLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-BENZODIOXOLE-5-GLYCOLIC ACID(27738-46-1)
• EPA Substance Registry System: 1,3-BENZODIOXOLE-5-GLYCOLIC ACID(27738-46-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 27738-46-1(Hazardous Substances Data)

Usage

Description

1,3-Benzodioxole-5-glycolic Acid is an organic compound characterized by the presence of a benzene ring with a dioxole group at positions 1 and 3, and a glycolic acid group at position 5. It is a 2-hydroxy monocarboxylic acid derivative of mandelic acid, where positions 3 and 4 on the benzene ring are substituted by a methylenedioxy group. This unique structure endows it with potential applications in various fields.

Uses

Used in Pharmaceutical Industry:
1,3-Benzodioxole-5-glycolic Acid is used as a starting reagent for the synthesis of various bioactive compounds, such as (-)cephalotaxine, (+)harringtonine, and (-)drupacine. These compounds have demonstrated significant pharmacological properties, making them valuable in the development of new drugs for the treatment of various diseases.
Used in Pest Control:
1,3-Benzodioxole-5-glycolic Acid is used as a chemosterilant agent for controlling the population of tobacco budworm, an agricultural pest that causes significant damage to tobacco crops. By disrupting the reproductive system of the insect, this compound helps in reducing the overall population and minimizing the damage caused by these pests.

InChI:InChI=1/C9H8O5/c10-8(9(11)12)5-1-2-6-7(3-5)14-4-13-6/h1-3,8,10H,4H2,(H,11,12)/p-1/t8-/m0/s1

Upstream product

• 115124-42-0 benzo[1,3]dioxol-5-ylhydroxyacetic acid ethyl ester 
• 120-57-0 piperonal 
• 75-25-2 Bromoform 
• 274-09-9 Methylenedioxybenzene 
• 108-10-1 4-methyl-2-pentanone 
• 78-93-3 butanone 
• 5137-55-3 Aliquat 336 
• 120-80-9 benzene-1,2-diol 
• 147030-72-6 benzo[1,3]dioxole-5-carboxylic acid methoxymethylamide 
• 3162-29-6 1-(benzo[d][1,3]dioxol-6-yl)ethanone 
• 94-53-1 Piperonylic acid 
• 533-31-3 Sesamol 
• 298-12-4 Glyoxilic acid 
• 6000-59-5 glyoxalic acid monohydrate 

Downstream Products

• 120-57-0 piperonal 
• 223438-61-7 benzyl 3-((1S)-1-(1,3-benzodioxol-5-yl)-2-{[(2-methoxy-4-methylphenyl)sulfonyl]amino}-2-oxoethyl)-1-methyl-1H-indole-6-carboxylate 
• 223438-59-3 benzyl 3-[(1S)-2-amino-1-(1,3-benzodioxol-5-yl)-2-oxoethyl]-1-methyl-1H-indole-6-carboxylate 
• 370104-34-0 (2S)-1,3-benzodioxol-5-yl{6-[(benzyloxy)carbonyl]-1-methyl-1H-indol-3-yl}ethanoic acid 
• 199589-50-9 3-(1-{[(2-methoxy-4-methylphenyl)sulfonyl]carbamoyl}-1-(3,4-methylenedioxyphenyl)methyl)-1-methyl-1H-indole-6-carboxylic acid 
• 199589-43-0 methyl 3-{1-(1,3-benzodioxol-5-yl)-2-[(2-methoxy-4-methylphenyl)sulfonyl-amino]-2-oxoethyl}-1-methyl-1H-indole-6-carboxylate 
• 2861-28-1 1,3-benzodioxole-5-acetic acid 

Relevant articles and documents

[3,3] Sigmatropic rearrangements of benzyl vinyl ethers. Model studies directed toward the total synthesis of cephalotaxine

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Structure-activity relationships, biological evaluation and structural studies of novel pyrrolonaphthoxazepines as antitumor agents

Microtubule-targeting agents (MTAs) are a class of clinically successful anti-cancer drugs. The emergence of multidrug resistance to MTAs imposes the need for developing new MTAs endowed with diverse mechanistic properties. Benzoxazepines were recently identified as a novel class of MTAs. These anticancer agents were thoroughly characterized for their antitumor activity, although, their exact mechanism of action remained elusive. Combining chemical, biochemical, cellular, bioinformatics and structural efforts we developed improved pyrrolonaphthoxazepines antitumor agents and their mode of action at the molecular level was elucidated. Compound 6j, one of the most potent analogues, was confirmed by X-ray as a colchicine-site MTA. A comprehensive structural investigation was performed for a complete elucidation of the structure-activity relationships. Selected pyrrolonaphthoxazepines were evaluated for their effects on cell cycle, apoptosis and differentiation in a variety of cancer cells, including multidrug resistant cell lines. Our results define compound 6j as a potentially useful optimized hit for the development of effective compounds for treating drug-resistant tumors.

Method for preparing heliotropin

The invention discloses a method for preparing heliotropin. The preparation method comprises the following steps: (a) preparing dilute sulfuric acid from concentrated sulfuric acid and water, adding the dilute sulfuric acid into a flask, adding glyoxylic acid, and cooling the mixed solution by using ice water; (b) adding benzodioxole into the mixed solution in a certain period of time, reacting for some time at the temperature of 0 DEG C, diluting by using water, separating out the precipitate, filtering, washing, drying in the shade, thereby obtaining white 3,4-methylenedioxymandelic acid; and (c) adding the 3,4-methylenedioxymandelic acid and dilute nitric acid into the three-neck flask, heating and stirring in a boiling water bath for some time, extracting by using diethyl ether, taking the organic phase, neutralizing and washing by using aqueous solution of sodium hydroxide, and finally, drying the organic phase by using anhydrous sodium sulfate, boiling off the organic solvent, cooling to obtain solids, recrystallizing by using methanol, thereby obtaining the heliotropin crystals. The method disclosed by the invention is fewer in preparation processes, low in input cost, good in yield effect and safe to operate, has excellent prospects and is suitable for large-scale industrial production.

Sesamol intermediate product process for preparing Piperonal and application

The invention belongs to the field of food additives and provides a preparation method of a sesamol intermediate heliotropin. The preparation method is convenient to use by taking nitric acid as a decarboxylating agent; the product, namely the sesamol intermediate heliotropin is good in purity; especially the decarboxylation efficiency is high, so that the decarboxylation reaction can be efficiently carried out to directly influence the synthesis yield of the overall preparation route; compared with other synthesis routes, the heliotropin synthesis route disclosed by the invention has considerable advantage on the cost, and the product competitiveness is relatively strong. The synthesis method disclosed by the invention has the advantages of cheap raw materials, simple reaction process and high yield and can be applied to large-scale synthesis of sesamol.