28822-73-3

Usage

Uses

Used in Pharmaceutical Industry:
DL-3,4-Dihydroxyphenyl glycol is used as a pharmaceutical intermediate for the synthesis of various drugs and medications. Its unique chemical structure allows it to be a key component in the development of new therapeutic agents.
Used in Research and Diagnostics:
As a metabolite of catecholamines, DL-3,4-dihydroxyphenyl glycol is used as a research tool and diagnostic marker for studying the metabolism and function of catecholamines in the body. It helps researchers and medical professionals understand the role of catecholamines in various physiological processes and diseases.
Used in Chemical Synthesis:
DL-3,4-Dihydroxyphenyl glycol is used as a starting material or building block in the synthesis of various organic compounds and specialty chemicals. Its unique structure and reactivity make it a valuable component in the development of new chemical products.
Used in Environmental Applications:
DL-3,4-Dihydroxyphenyl glycol can be used in environmental applications, such as in the biodegradation of pollutants or the development of eco-friendly materials. Its unique chemical properties make it a promising candidate for these applications.
Used in Analytical Chemistry:
As a labeled metabolite of catecholamines, DL-3,4-dihydroxyphenyl glycol can be used in analytical chemistry for the detection and quantification of catecholamines and their metabolites. This can be particularly useful in research and clinical settings for the diagnosis and monitoring of various conditions related to catecholamine imbalances.

InChI:InChI=1/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2

Upstream product

• 100434-10-4 1-<3,4-Benzyloxy-phenyl>-aethylenglykol 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 
• 95622-68-7 3,4-Dibenzyloxy-mandelsaeure-aethylester 
• 126644-20-0 3,4-Dibenzyloxy-mandelsaeurenitril-acetat 
• 120-80-9 benzene-1,2-diol 
• 99-40-1 2-chloro-3',4'-dihydroxyacetophenone 
• 29477-54-1 2-hydroxy-3′,4′-dihydroxyacetophenone 
• 122121-92-0 4-(2-hydroxyethyl)cyclohexa-3,5-diene-1,2-dione 
• 10597-60-1 hydroxytyrosol 

Downstream Products

• 959257-37-5 C₂₀H₆F₂₀O₈ 
• 29477-54-1 2-hydroxy-3′,4′-dihydroxyacetophenone 

Relevant academic research and scientific papers

A three-step, gram-scale synthesis of hydroxytyrosol, hydroxytyrosol acetate, and 3,4-dihydroxyphenylglycol

Hydroxytyrosol and two other polyphenols of olive tree, hydroxytyrosol acetate and 3,4-dihydroxyphenylglycol, are known for a wide range of beneficial activities in human health and prevention from diseases. The inability to isolate high, pure amounts of these natural compounds and the difficult and laborious procedures for the synthesis of them led us to describe herein an efficient, easy, cheap, and scaling up synthetic procedure, from catechol, via microwave irradiation.

A two-step process for the synthesis of hydroxytyrosol

A new process for the synthesis of hydroxytyrosol (3,4-dihy-droxyphenylethanol), the most powerful natural antioxidant currently known, by means of a two-step approach is reported. Catechol is first reacted with 2,2-dimethoxyacetaldehyde in basic aqueous medium to produce the corresponding mandelic derivative with > 90 % conversion of the limiting reactant and about 70 % selectivity to the desired para-hydroxyalkylat-ed compound. Thereafter, the intermediate is hydrogenated to hydroxytyrosol by using a Pd/C catalyst, with total conversion of the mandelic derivative and 68 % selectivity. This two-step process is the first example of a synthetic pathway for hydroxytyrosol that does not involve the use of halogenated components or reduction methodologies that produce stoichiometric waste. It also avoids the complex procedure currently used for hydroxytyrosol purification when it is extracted from wastewa-ter of olive oil production.

The metabolic fate of ortho-quinones derived from catecholamine metabolites

ortho-Quinones are produced in vivo through the oxidation of catecholic substrates by enzymes such as tyrosinase or by transition metalions. Neuromelanin, a dark pigment present in the substantia nigra and locus coeruleus of the brain, is produced from dopamine (DA) and norepinephrine (NE) via an interaction with cysteine, but it also incorporates their alcoholic and acidic metabolites. In this study we examined the metabolic fate of ortho-quinones derived from the catecholamine metabolites, 3,4-dihydroxyphenylethanol (DOPE), 3,4-dihydroxyphenylethylene glycol (DOPEG), 3,4-dihydroxyphenylacetic acid (DOPAC) and 3,4-dihydroxyphenylmandelic acid (DOMA). The oxidation of catecholic substrates by mushroom tyrosinase was followed by UV-visible spectrophotometry. HPLC analysis after reduction with NaBH4 or ascorbic acid enabled measurement of the half-lives of ortho-quinones and the identification of their reaction products. Spectrophotometric examination showed that the ortho-quinones initially formed underwent extensive degradation at pH 6.8. HPLC analysis showed that DOPE-quinone and DOPEG-quinone degraded with half-lives of 15 and 30 min at pH 6.8, respectively, and >100 min at pH 5.3. The major product from DOPE-quinone was DOPEG which was produced through the addition of a water molecule to the quinone methide intermediate. DOPEG-quinone yielded a ketone, 2-oxo-DOPE, through the quinone methide intermediate. DOPAC-quinone and DOMA-quinone degraded immediately with decarboxylation of the ortho-quinone intermediates to form 3,4-dihydroxybenzylalcohol (DHBAlc) and 3,4-dihydroxybenzaldehyde (DHBAld), respectively. DHBAlc-quinone was converted to DHBAld with a half-life of 9 min, while DHBAld-quinone degraded rapidly with a half-life of 3 min. This study confirmed the fact that ortho-quinones from DOPE, DOPEG, DOPAC and DOMA are converted to quinone methide tautomers as common intermediates, through proton rearrangement or decarboxylation. The unstable quinone methides afford stable alcoholic or carbonyl products.

PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS

The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.