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Sigma-Aldrich

DL-3,4-Dihydroxymandelic acid

95%

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About This Item

Linear Formula:
(HO)2C6H3CH(OH)CO2H
CAS Number:
14883-87-5
Molecular Weight:
184.15
EC Number:
238-956-8
MDL number:
MFCD00004231
UNSPSC Code:
12352100
PubChem Substance ID:
24849152
NACRES:
NA.22

Assay

95%

mp

136-137 °C (dec.) (lit.)

SMILES string

OC(C(O)=O)c1ccc(O)c(O)c1

InChI

1S/C8H8O5/c9-5-2-1-4(3-6(5)10)7(11)8(12)13/h1-3,7,9-11H,(H,12,13)

InChI key

RGHMISIYKIHAJW-UHFFFAOYSA-N

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General description

Metabolite of norepinephrine.

Application

DL-3,4-Dihydroxymandelic acid was used in the simultaneous analysis of 4-hydroxy-3-methoxymandelic acid and 4-hydroxy- 3-methoxyphenylacetic acid in urine. It was also used to study the changes in body temperature.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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W I Cranston et al.
The Journal of physiology, 223(1), 59-67 (1972-05-01)
1. The imino-dibenzyl drugs, imipramine and desipramine, which inhibit the uptake by neurones of noradrenaline, were injected into the lateral cerebral ventricles of cats and rabbits: changes in body temperature resulted which were different for the two species, but nevertheless
W X Dong et al.
Journal of the autonomic nervous system, 44(2-3), 109-117 (1993-08-01)
Pre-synaptic endings of the sympathetic nervous fibers control the metabolism of catecholamines, particularly inactivating norepinephrine after its neuronal recapture. The present study was carried out to investigate this segment of the metabolism of catecholamines through measurements of DHPG, DOMA and
J N Rodríguez-López et al.
Analytical biochemistry, 195(2), 369-374 (1991-06-01)
A continuous spectrophotometric method for the rapid determination of diphenolase activity of tyrosinase is described. It uses 3,4-dihydroxymandelic acid (DOMA) as the substrate of tyrosinase and measures the final product, 3,4-dihydroxybenzaldehyde (DOBA). The spectrum of this product shows a bathochromic
Andrea E Schwaninger et al.
Toxicology letters, 202(2), 120-128 (2011-02-08)
3,4-Methylenedioxymethamphetamine (MDMA, Ecstasy) is excreted in human urine mainly as conjugates of its metabolites 3,4-dihydroxymethamphetamine (DHMA) and 4-hydroxy-3-methoxymethamphetamine (HMMA). The glucuronidation kinetics of HMMA showed high capacities, but also high K(m) values, unlikely to be reached after recreational user's doses.
M Sugumaran et al.
The Biochemical journal, 281 ( Pt 2), 353-357 (1992-01-15)
Mushroom tyrosinase, which is known to convert a variety of o-diphenols into o-benzoquinones, has been shown to catalyse an unusual oxidative decarboxylation of 3,4-dihydroxymandelic acid to 3,4-dihydroxybenzaldehyde [Sugumaran (1986) Biochemistry 25, 4489-4492]. The mechanism of this reaction was re-investigated. Although
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