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151610

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

Quality Level

100

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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Related Categories

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
S J Ley et al.
Research in veterinary science, 61(2), 172-173 (1996-09-01)
The threshold response to a mechanical nociceptive stimulus was significantly lower on the lame hind limb of lame cows than on the same limb of sound cows. There were no significant differences between the concentrations of cortisol, noradrenaline, adrenaline or
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
T R Kingsley et al.
Journal of gerontology, 46(4), B135-B141 (1991-07-01)
Adrenal catecholamines (CA) were measured in 6-, 18-, and 30-mo Lobund-Wistar rats (LWR) maintained under germ-free or conventional conditions and fed either ad libitum or a restricted (70% of adult ad libitum) diet. Levels of dopamine (DA), norepinephrine (NE), epinephrine
T H Czapla et al.
Biochimica et biophysica acta, 1077(3), 400-406 (1991-04-29)
Cyclic voltammetric and chronoamperometric data are consistent with a process in which 3,4-dihydroxymandelic acid (DOMA) is oxidized initially in a two-electron step to its corresponding o-benzoquinone. This species is unstable and undergoes the rate-determining loss of CO2 (k = 1.6
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