3343-19-9

Usage

Uses

Used in Neurology and Psychiatry Research:
DL-3,4-Dihydroxyphenyl glycol is used as a biomarker for measuring dopamine levels in the body, which aids in the study and diagnosis of various neurological and psychiatric disorders. Its analysis helps researchers and clinicians to better understand the role of dopamine in these conditions.
Used in Diagnostic Applications:
DHPG is utilized as a diagnostic tool for assessing dopaminergic activity, which can be crucial in identifying and monitoring the progression of conditions such as Parkinson's disease, depression, and schizophrenia.
Used in Therapeutic Target Research:
DL-3,4-Dihydroxyphenyl glycol has been investigated for its potential as a therapeutic target for the treatment of neurological and psychiatric disorders. Understanding its role in dopamine metabolism may lead to the development of new treatments and interventions for these conditions.

InChI:InChI=1/C8H10O4/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8-12H,4H2/t8-/m1/s1

Upstream product

• 100434-10-4 1-<3,4-Benzyloxy-phenyl>-aethylenglykol 
• 51-41-2 norepinephrine 
• 29477-54-1 2-hydroxy-3′,4′-dihydroxyacetophenone 
• 99-40-1 2-chloro-3',4'-dihydroxyacetophenone 
• 120-80-9 benzene-1,2-diol 
• 122121-92-0 4-(2-hydroxyethyl)cyclohexa-3,5-diene-1,2-dione 
• 10597-60-1 hydroxytyrosol 
• 126644-20-0 3,4-Dibenzyloxy-mandelsaeurenitril-acetat 
• 95622-68-7 3,4-Dibenzyloxy-mandelsaeure-aethylester 
• 5447-02-9 3,4-dibenzyloxybenzaldehyde 

Downstream Products

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

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.

A kinetic investigation of the pulmonary metabolism of dopamine in rats shows marked differences compared with noradrenaline

The aim of this study was to investigate the deamination of dopamine in the intact pulmonary circulation of isolated lungs of the rat. The first part of the study showed that dopamine is not converted to noradrenaline by dopamine-β-hydroxylase (DBH) when dopamine is perfused through isolated lung preparations with monoamine oxidase (MAO) and catechol-O-methyltransferase (COMT) inhibited. Hence, it was not necessary to inhibit DBH in subsequent experiments. The metabolite profile for deamination of dopamine in the lungs was examined by determining whether MAO and semicarbazide-sensitive amine oxidases (SSAO) contribute to the deamination of dopamine (and noradrenaline), and by determining the activity of MAO (k(MAO)) for the metabolism of dopamine. Lungs were perfused with 1 nmol/l 3H-dopamine or 3H-noradrenaline with COMT inhibited and, in experiments to determine the contribution of SSAO to deamination, with MAO inhibited. Inhibition of MAO reduced the deamination of dopamine and noradrenaline by 99.8% and 98.6%, respectively, indicating that MAO, and not SSAO, was responsible for deamination of the catecholamines in the lungs. The k(MAO) value for deamination of dopamine was 3.89 min-1. Further experiments were carried out to determine the contributions of MAO-A and MAO-B to the deamination of dopamine in lungs perfused with 1 nmol/l3H-dopamine and 100 nmol/l lazabemide or 300 nmol/l Ro41-1049, respectively. The values of k(MAO-A) and k(MAO-B) were 3.05 min-1 and 0.626 min-1, respectively.