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H0131

Sigma-Aldrich

DL-4-Hydroxy-3-methoxymandelic acid

≥98% (HPLC), powder

Synonym(s):

α,4-Dihydroxy-3-methoxybenzeneacetic acid, VMA, Vanillomandelic acid, Vanillylmandelic acid, Vanilmandelic acid

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About This Item

Linear Formula:
HOC6H3(OCH3)CH(OH)CO2H
CAS Number:
55-10-7
Molecular Weight:
198.17
Beilstein/REAXYS Number:
2213227
EC Number:
200-224-0
MDL number:
MFCD00004235
UNSPSC Code:
12352106
PubChem Substance ID:
24277743
NACRES:
NA.77

assay

≥98% (HPLC)

form

powder

color

white to off-white

mp

132-134 °C (dec.) (lit.)

solubility

H2O: ~50 mg/mL

storage temp.

2-8°C

SMILES string

OC1=C(OC)C=C(C(O)C(O)=O)C=C1

InChI

1S/C9H10O5/c1-14-7-4-5(2-3-6(7)10)8(11)9(12)13/h2-4,8,10-11H,1H3,(H,12,13)

InChI key

CGQCWMIAEPEHNQ-UHFFFAOYSA-N

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Biochem/physiol Actions

Epinephrine and norepineprine metabolite.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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D Fraser Davidson et al.
Annals of clinical biochemistry, 48(Pt 4), 358-366 (2011-06-15)
Neuroblastoma is the most common extracranial solid tumour in childhood (8% of all childhood cancers), the most frequently diagnosed in infancy, and has one of the highest death rates, while chromaffin tumours rarely present in childhood. Both tumour types produce
Xiaoquan Lu et al.
The Analyst, 137(6), 1416-1420 (2012-02-01)
Electrochemiluminescence (ECL) of Ru(bpy)(3)(2+) using metabolites of catecholamines: homovanillic acid (HVA) and vanillylmandelic acid (VMA) as co-reactants were investigated in aqueous solution for the first time. When HVA and VMA were co-existent in the buffer solution containing Ru(bpy)(3)(2+), ECL peaks
Kai Li et al.
Journal of investigative surgery : the official journal of the Academy of Surgical Research, 25(2), 86-92 (2012-03-24)
This study assesses the clinical features of neuroblastoma and survival. Data for 98 patients between January 2000 and December 2006 at Children's Hospital of Fudan University, Shanghai, China, were retrospectively analyzed. Diagnostic methods included imaging, 24-hr urine catecholamines, bone marrow
Wayne L Furman et al.
Investigational new drugs, 30(4), 1660-1670 (2011-07-29)
Gefitinib potently inhibits neuroblastoma proliferation in vitro, and the gefitinib/irinotecan combination shows greater than additive activity against neuroblastoma xenografts. This Phase II pilot study estimated the rate of response to two courses of intravenous irinotecan plus oral gefitinib in children
W P Tormey et al.
Irish journal of medical science, 164(2), 146-150 (1995-04-01)
A study of the case notes from 101 of the 113 instances where at least one of the results was abnormal from the analysis of 24 hr urinary collections for noradrenaline, adrenaline, and dopamine and their metabolites 4-hydroxy-3-methoxy-mandelic acid (HMMA)
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