DL-3,4-Dihydroxymandelic acid

Name: <SC>DL</SC>-3,4-Dihydroxymandelic acid
Brand: ALDRICH
Price: 150 USD
Availability: InStock

95%

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About This Item

Linear Formula:

(HO)₂C₆H₃CH(OH)CO₂H

CAS Number:

14883-87-5

Molecular Weight:

184.15

NACRES:

NA.22

PubChem Substance ID:

24849152

UNSPSC Code:

12352100

EC Number:

238-956-8

MDL number:

MFCD00004231

Assay:

95%

Key Documents

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InChI key

RGHMISIYKIHAJW-UHFFFAOYSA-N

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)

SMILES string

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

assay

95%

mp

136-137 °C (dec.) (lit.)

functional group

carboxylic acid, hydroxyl

Quality Level

100

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This Item	A7256	55520	92591
Sigma-Aldrich 151610 DL-3,4-Dihydroxymandelic acid	Sigma-Aldrich A7256 DL-Norepinephrine hydrochloride	Sigma-Aldrich 55520 3-Hydroxymandelic acid	Sigma-Aldrich 92591 DL-2,6-Diaminopimelic acid
assay 95%	assay ≥97% (TLC)	assay ≥97.0% (T)	assay ≥95% (TLC)
Quality Level 100	Quality Level 200	Quality Level 100	Quality Level 100
mp 136-137 °C (dec.) (lit.)	mp -	mp 128-132 °C	mp -
functional group carboxylic acid	functional group -	functional group carboxylic acid, hydroxyl	functional group -

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[1]. It was also used to study the changes in body temperature[2].

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Neuronal metabolism of catecholamines: plasma DHPG, DOMA and DOPAC.

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

p-Hydroxyphenylacetic Acid Metabolism in Pseudomonas putida F6.

K E O'Connor et al.

Journal of bacteriology, 183(3), 928-933 (2001-02-24)

Pseudomonas putida F6 was found to metabolize p-hydroxyphenylacetic acid through 3,4-dihydroxyphenylacetic acid, 3,4-dihydroxymandelic acid, and 3,4-dihydroxybenzaldehyde. Cell extracts of P. putida F6 catalyze the NAD(P)H-independent hydroxylation of p-hydroxyphenylacetic acid to 3,4-dihydroxyphenylacetic acid which is further oxidized to 3,4-dihydroxymandelic acid. Oxidation

Mechanistic studies on tyrosinase-catalysed oxidative decarboxylation of 3,4-dihydroxymandelic acid.

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

A continuous spectrophotometric method for the determination of diphenolase activity of tyrosinase using 3,4-dihydroxymandelic acid.

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

Sulfation of the 3,4-methylenedioxymethamphetamine (MDMA) metabolites 3,4-dihydroxymethamphetamine (DHMA) and 4-hydroxy-3-methoxymethamphetamine (HMMA) and their capability to inhibit human sulfotransferases.

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.

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