38515-62-7

Basic information

• Product Name: 1,3-Benzodioxole-5-acetic acid, 2,2-dimethyl-, methyl ester
• Synonyms: 3,4-(dimethylmethylenedioxy)phenylacetate methyl ester;3,4-(dimethylmethylenedioxy)phenylacetic acid methyl ester;2-(2,2-dimethylbenzo[1,3]dioxol-5-yl)acetic acid methyl ester;1,3-Benzodioxole-5-acetic acid,2,2-dimethyl-,methyl ester;2,2-Dimethyl-1,3-benzodioxole-4-acetic Acid Methyl Ester
• CAS NO: 38515-62-7
• Molecular Formula: C12H14O4
• Molecular Weight: 222.241
• Mol File: 38515-62-7.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 1,3-Benzodioxole-5-acetic acid, 2,2-dimethyl-, methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzodioxole-5-acetic acid, 2,2-dimethyl-, methyl ester(38515-62-7)
• EPA Substance Registry System: 1,3-Benzodioxole-5-acetic acid, 2,2-dimethyl-, methyl ester(38515-62-7)

Safety Data

• Hazardous Substances Data: 38515-62-7(Hazardous Substances Data)

Usage

Description

1,3-Benzodioxole-5-acetic acid, 2,2-dimethyl-, methyl ester is an organic compound that serves as an intermediate in the synthesis of Dopal (D533885), which is the reactive metabolite of dopamine (D533780). Dopamine is an endogenous catecholamine with α and β-adrenergic activity.

Uses

Used in Pharmaceutical Industry:
1,3-Benzodioxole-5-acetic acid, 2,2-dimethyl-, methyl ester is used as an intermediate in the synthesis of Dopal (D533885) for its role in the development of pharmaceuticals targeting α and β-adrenergic activity. This makes it a valuable component in the creation of medications that can potentially influence various physiological processes and treat specific conditions related to adrenergic activity.

Upstream product

• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 102-32-9 3,4-dihydroxyphenylacetate 
• 77-76-9 2,2-dimethoxy-propane 
• 25379-88-8 2-(3,4-dihydroxyphenyl)acetic acid methyl ester 

Downstream Products

• 1354701-17-9 (Z)-1-(2-(3,4-dihydroxyphenyl)ethoxy)octadec-9-ene 
• 50602-41-0 3-hydroxy-4-methoxyphenethyl alcohol 
• 2380-78-1 homovanillyl alcohol 
• 1354541-61-9 C₂₀H₁₆N₄O₆ 
• 1332585-62-2 2-(3,4-dihydroxyphenyl)-N-(prop-2-yn-1-yl)acetamide 
• 10597-60-1 hydroxytyrosol 

Relevant articles and documents

Regioselectivity of Cobalamin-Dependent Methyltransferase Can Be Tuned by Reaction Conditions and Substrate

Regioselective reactions represent a significant challenge for organic chemistry. Here the regioselective methylation of a single hydroxy group of 4-substituted catechols was investigated employing the cobalamin-dependent methyltransferase from Desulfitobacterium hafniense. Catechols substituted in position four were methylated either in meta- or para-position to the substituent depending whether the substituent was polar or apolar. While the biocatalytic cobalamin dependent methylation was meta-selective with 4-substituted catechols bearing hydrophilic groups, it was para-selective for hydrophobic substituents. Furthermore, the presence of water miscible co-solvents had a clear improving influence, whereby THF turned out to enable the formation of a single regioisomer in selected cases. Finally, it was found that also the pH led to an enhancement of regioselectivity for the cases investigated.

HYDROXYTYROSOL ETHERS

The invention relates to hydroxytyrosol ethers derived from fatty alcohols and phenolic compounds of olive oil and the salts, solvates and hydrates thereof, which have an affinity for type 1 cannabinoid receptors (CB1) and which can: prevent the oxidation of low-density lipoprotein (LDL); and modulate the actions regulated by said receptor, such as inducing satiety, controlling intake and reducing body fat.

Unsaturated fatty alcohol derivatives of olive oil phenolic compounds with potential low-density lipoprotein (LDL) antioxidant and antiobesity properties

A new route for the synthesis of fatty alcohol derivatives of hydroxytyrosol and other olive oil phenolic compounds was developed to allow the preparation of unsaturated derivatives. The biological activity of synthesized compounds was evaluated. Most of the compounds presented a significant antioxidant activity on low-density lipoprotein (LDL) particles. The activity of the tested products was significantly influenced by the number and position of unsaturations as well as modifications on the polar head of the synthesized compounds. Some of them presented modulation of food intake in rats and, due to their molecular similarity with CB1 endogenous ligands, the endocannabinoid system and PPAR-α were also evaluated as potential targets. The pharmacodynamics could not be totally explained by CB1 and PPAR-α receptor interactions because only two of the four compounds with biological activity showed a CB1 activity and all of them presented low PPAR-α affinity, not justifying its whole in vivo activity. The hydroxytyrosol linoleylether (7) increased LDL resistance to oxidation with a capacity similar to that of hydroxytyrosol and was the most active in vivo compound with a hypophagic effect comparable to that of oleoylethanolamine. We consider that this compound could be a good lead compound for future drug development in obesity treatments.