ChemicalBook CAS DataBase List 306-08-1

306-08-1

Name	Homovanillic acid
CAS	306-08-1
EINECS(EC#)	206-176-7
Molecular Formula	C9H10O4
MDL Number	MFCD00004350
Molecular Weight	182.17
MOL File	306-08-1.mol

Synonyms

3-METHOXY-4-HYDROXYPHENYL ACETIC ACID 4-HYDROXY-3-METHOXYPHENYLACETIC ACID HOMOVANILLIC ACID HOMOVANIUIC ACID HVA RARECHEM AL BO 0135 4-Hydroxy-3-methoxybenzeneacetic acid 4-hydroxy-3-methoxy-benzeneaceticaci 4-hydroxy-3-methoxy-Benzeneaceticacid Acetic acid, (4-hydroxy-3-methoxyphenyl)- Homovanilic acid Homovanillinic acid Vanilacetic acid Vanillacetic Acid Homovanillic acid 4-Hydroxy-3-methoxyphenylacetic acid 4-HYDROXY-3-METHOXYPHENYLACETIC HOMORANILLIC ACID HomovanillicAcid98% Benzeneacetic acid, 4-hydroxy-3-methoxy- 2-(4-hydroxy-3-methoxy-phenyl)acetic acid

Chemical Properties

Appearance	white to beige crystalline powder
Melting point	142-145 °C(lit.)
Boiling point	235.56°C (rough estimate)
density	1.1634 (rough estimate)
refractive index	1.4209 (estimate)
storage temp.	Store at RT.
solubility	DMSO (Slightly), Methanol (Slightly, Heated)
form	Crystalline Powder
pka	4.39±0.10(Predicted)
color	White to beige
Water Solubility	soluble
Merck	14,4740
BRN	2213447
Stability:	Hygroscopic
Major Application	pharmaceutical
InChI	1S/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)
InChIKey	QRMZSPFSDQBLIX-UHFFFAOYSA-N
SMILES	COc1cc(CC(O)=O)ccc1O
LogP	0.330
CAS DataBase Reference	306-08-1(CAS DataBase Reference)
NIST Chemistry Reference	Benzeneacetic acid, 4-hydroxy-3-methoxy-(306-08-1)
EPA Substance Registry System	306-08-1(EPA Substance)

Safety Data

Symbol(GHS)	GHS07
Signal word	Warning
Hazard statements	H315-H319-H335
Precautionary statements	P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes	Xi
Risk Statements	R36/37/38:Irritating to eyes, respiratory system and skin . less more
Safety Statements	S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . S36:Wear suitable protective clothing . less more
WGK Germany	3
F	10-23
TSCA	T
HazardClass	IRRITANT
HS Code	29189900
Storage Class	11 - Combustible Solids

Raw materials And Preparation Products

Hazard Information

Description

Homovanillic acid (HVA) is a dopamine metabolite. It is formed via deamination of dopamine by monoamine oxidase (MAO) to produce 3,4-dihydroxyphenylacetic acid (DOPAC; Item No. 24912) followed by DOPAC metabolism by catechol-O-methyltransferase (COMT). HVA undergoes hydrogen peroxide-dependent oxidation in the presence of horseradish peroxidase to form a fluorescent dimer that displays excitation/emission maxima of 312/420 nm, respectively. It has been used to quantify hydrogen peroxide production in macrophages and neutrophils.

Chemical Properties

white to beige crystalline powder

Uses

A neuroendocrine tumor marker. Dihydroxyphenylacetic Acid (DOPAC) metabolite.

Uses

Fluorimetric reagent and major catecholamine metaboliteHomovanillic acid is used as a reagent in the determination of oxidative enzymes. It is associated with dopamine levels in the brain. Its presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.

Definition

ChEBI: A monocarboxylic acid that is the 3-O-methyl ether of (3,4-dihydroxyphenyl)acetic acid. It is a catecholamine metabolite.

Biological Activity

Fluorimetric reagent and major catecholamine metabolite. Used for fluorimetric determination of oxidative enzymes including glucose oxidase.

storage

+4°C

References

[1] MIKKO K?ENM?KI. Quantitative role of COMT in dopamine clearance in the prefrontal cortex of freely moving mice[J]. Journal of Neurochemistry, 2010, 114 6: 1745-1755. DOI: 10.1111/j.1471-4159.2010.06889.x
[2] WALTER RUCH Marco B Philip H Cooper. Assay of H2O2 production by macrophages and neutrophils with homovanillic acid and horse-radish peroxidase[J]. Journal of immunological methods, 1983, 63 3: Pages 347-357. DOI: 10.1016/s0022-1759(83)80008-8

Material Safety Data Sheet(MSDS)

Spectrum Detail

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