Vanillyl mandelic acid

Names

[ CAS No. ]:
55-10-7

[ Name ]:
Vanillyl mandelic acid

[Synonym ]:
dl-α,4-dihydroxy-3-methoxyphenylacetic acid
Hydroxy(4-hydroxy-3-methoxyphenyl)acetic acid
Vanilmandelic Acid
4-Hydroxy-3-methoxy-DL-mandelic acid
DL-VANILLOMANDELIC ACID
Vanilinmandelic Acid
DL-Vanillylmandelic acid
4-Hydroxy-3-methoxyphenyl(hydroxy)acetic acid
QVYQR DQ CO1
(4-Hydroxy-3-methoxyphenyl)glycolic acid
UNII:0DQI268449
Vanillomandelic Acid
α,4-Dihydroxy-3-methoxybenzeneacetic acid
EINECS 200-224-0
Vanillinemandelic acid
4-hydroxy-3-methoxy-phenylglycolic acid
3-methoxy-p-hydroxymandelic acid
VMA
VANILLYLMANDELIC ACID
Benzeneacetic acid, α,4-dihydroxy-3-methoxy-
4-Hydroxy-3-methoxymandelic acid
3-methoxy-4-hydroxymandelic acid
4-Hydroxy 3-methoxymandelic acid
HYDROXYMETHOXYMANDELICACID
MFCD00004235
Vanillinmandelic acid

Biological Activity

[Description]:

Vanillylmandelic acid is the endproduct of epinephrine and norepinephrine metabolism. Vanillylmandelic acid can be used as an indication of the disorder in neurotransmitter metabolism as well. Vanillylmandelic acid has antioxidant activity towards DPPH radical with an IC50 value of 33 μM[1].

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Signaling Pathways >> Others >> Others

[In Vitro]

Vanillylmandelic acid has antioxidant activity, the IC50 value is determined as the amount of VMA required to reduce 50% of the starting concentration of free radical is 33*10-6 M in the UV-Vis decolourisation DPPH assay[1].

[In Vivo]

Vanillylmandelic acid (intra-arterial injection over 1 min; 1, 10 and 100 mg/kg; the 60 min-observation period) produces a significant difference between vanillylmandelic acid groups and controls. Vanillylmandelic acid decreases the heart rate by 17.5%, 17.9% and 18.9% after 1, 10 and 100 mg/kg, respectively. Mean blood pressure is decreased by 13.5% in control animals as compared to 37%, 23% and 26% after 1, 10 and 100 mg/kg, respectively, in wistar rats[1].

[References]

[1]. Michalis K Kolentinis, et al.Cardiovascular effects of vanillylmandelic acid in rats. Eur J Pharmacol. 2013 Mar 5;703(1-3):46-52.

[2]. Dušan Dimić, et al. Experimental and theoretical elucidation of structural and antioxidant properties of vanillylmandelic acid and its carboxylate anion. Spectrochim Acta A Mol Biomol Spectrosc. 2018 Jun 5;198:61-70.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
421.3±45.0 °C at 760 mmHg

[ Melting Point ]:
132-134 °C (dec.)(lit.)

[ Molecular Formula ]:
C₉H₁₀O₅

[ Molecular Weight ]:
198.173

[ Flash Point ]:
173.7±22.2 °C

[ Exact Mass ]:
198.052826

[ PSA ]:
86.99000

[ LogP ]:
-0.11

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.606

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
26-36-37/39

[ RIDADR ]:
UN 1993 3/PG 3

[ WGK Germany ]:
3

[ RTECS ]:
CY9033750

[ Packaging Group ]:
III

[ Hazard Class ]:
3

[ HS Code ]:
29036990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 29036990

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