306-08-1
Homovanillic acid
CAS: 306-08-1
Molecular Formula: C9H10O4
306-08-1 - Names and Identifiers
| Name | Homovanillic acid |
| Synonyms | HVA Vanilacetic acid Homovanilic acid Vanillacetic Acid Homovanillic acid Homovanillinic acid (4-hydroxy-3-methoxyphenyl)acetate 4-Hydroxy-3-methoxyphenylacetic acid 4-hydroxy-3-methoxy-benzeneaceticaci 4-hydroxy-3-methoxy-Benzeneaceticacid 4-hydroxy-3-methoxyphenyl acetic acid 4-Hydroxy-3-methoxybenzeneacetic acid Acetic acid, (4-hydroxy-3-methoxyphenyl)- Homovanillic acid 4-Hydroxy-3-methoxyphenylacetic acid |
| CAS | 306-08-1 |
| EINECS | 206-176-7 |
| InChI | InChI=1/C9H10O4/c1-13-8-4-6(5-9(11)12)2-3-7(8)10/h2-4,10H,5H2,1H3,(H,11,12)/p-1 |
306-08-1 - Physico-chemical Properties
| Molecular Formula | C9H10O4 |
| Molar Mass | 182.17 |
| Density | 1.1634 (rough estimate) |
| Melting Point | 142-145°C(lit.) |
| Boling Point | 235.56°C (rough estimate) |
| Flash Point | 151.9°C |
| Water Solubility | soluble |
| Solubility | Soluble in water |
| Vapor Presure | 4.36E-06mmHg at 25°C |
| Appearance | White crystalline powder |
| Color | White to beige |
| Merck | 14,4740 |
| BRN | 2213447 |
| pKa | 4.39±0.10(Predicted) |
| Storage Condition | Keep in dark place,Inert atmosphere,Room temperature |
| Stability | Hygroscopic |
| Refractive Index | 1.4209 (estimate) |
| MDL | MFCD00004350 |
| Physical and Chemical Properties | Soluble in water from the human body metabolites. Can be obtained from the reaction of guaiacol and glyoxylic acid. |
306-08-1 - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-23 |
| TSCA | T |
| HS Code | 29189900 |
| Hazard Class | IRRITANT |
306-08-1 - Reference
| Reference Show more | 1. Zhu-Hong Zheng, renyun Zhao, Yuting Ding, et al. Study on sedative and hypnotic activities of different extracts from Baihe Dihuang decoction [J]. Northwest Pharmaceutical Journal, 2019, v.34(03):66-70. 2. Zhu Cai-Xia, Huang Li-Fang Yongqi et al. Effects of β-asarone on behavior and monoamine neurotransmitters in a mouse model of chronic unpredictable mild stimulation [J]. Shi Zhen, National Medicine 2017(04):833-836. 3. [IF = 4.952] Yuxin Hao et al."Stability and mechanism of pH composition from raspberry extract under in vitro gastrointestinal fusion." Lwt Food Sci Technol. 2021 Mar;139:110552 4. [IF = 4.418] Yuan Li et al."Deciphering the Mechanism of the Anti-Hypertensive Effect of Isorhynchophylline by Targeting Neurotransmitters Metabolism of Hypothalamus in Spontaneously Hypertensive Rats."Acs Chem Neurosci. 2020;11(11):1563-1572 5. [IF=4.24] Nana Li et al."Characterization of phenolic compounds and anti-acetylcholinase activity of coconut shells."Food Biosci. 2021 Aug;42:101204 6. [IF=3.512] Yu Sun et al."Integrated Screening of Effective Anti-Insomnia Fractions of Zhi-Zi-Hou-Po Decoction via Drosophila melanogaster and Network Pharmacology Analysis of the Underlying Pharmacodynamic Material and Mechanism."Acs Omega. 2021;6(13):9176-9187 7. [IF=3.361] Ruixue Yu et al."Targeted neurotransmitter metabolomics profiling of oleanolic acid in the treatment of spontaneously hypertensive rats."Rsc Adv. 2019 Jul;9(40):23276-23288 |
306-08-1 - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| a metabolite of dopamine | levodopa (LD) is still the most commonly used drug for the treatment of Parkinson's disease (Parkinso n' s Di sease, PD), which produces dopamine (dopamine ,DA) under the action of dopa decarboxylase in the body. Homovanillic acid ,HVA) is the main metabolite of the monoamine neurotransmitter dopamine. Its chemical name is 3-methoxy-4-hydroxyphenylacetic acid. It is an important biochemical enzyme detection reagent. Urine HVA measurement is one of the methods to detect the functional state of the adrenal medulla and the presence of chromaffin tissue in other parts. If both dopamine and HVA exceed the normal range, it is more likely to indicate malignant pheochromocytoma. The traditional concept is that HVA as a metabolite has no physiological activity, and its clinical significance is only used as an index to evaluate the severity of some diseases and the efficacy of drug treatment. However, some data show that HVA also has certain pharmacological effects. For example, Bertorello A study shows that HVA has inhibitory effect on Na-K-ATPase activity, suggesting that changes in HVA levels in vivo may also have certain physiological and pathological significance. In addition, since homovanillic acid is a metabolite of dopamine, its level in peripheral blood can reflect the activity of dopamine. For example, the level of HVA in cerebrospinal fluid of patients with schizophrenia with family history is significantly higher than that of patients without family history; The cerebrospinal fluid HVA of normal people with family history is significantly higher than that of normal people without family history. Therefore, the determination of HVA in cerebrospinal fluid is very valuable for estimating the risk of schizophrenia in the population; the content of HVA in urine in Parkinson's disease can be used to evaluate the body's manganese poisoning. The research and application of homovanillic acid in biochemistry have been very active. In recent years, there have been many reports on the research as a drug and as an important intermediate in drug synthesis. The phenolic hydroxyl etherification product of homovanillic acid can be used as an immune reagent, its monosodium salt can be used as an absorbent, and its ethyl ester, zinc, epoxy resin, etc. can be used as an adhesive for dental surgery. Various esterification products and amide derivatives of homovanillic acid can be used as anti-inflammatory and analgesic drugs. Fig. 1 is the structural formula of homovanillic acid |
| detection method | homovanillic acid is the main terminal product of catecholamine metabolism in human body. it is excreted in urine. detecting HVA in urine can not only indirectly reflect the secretion of catecholamines in vivo, but also have important significance for early diagnosis and disease monitoring of catecholamine secretion diseases such as pheochromocytoma and neuroblastoma. There are many methods for determining HVA in urine, such as colorimetric thin-layer chromatography and iontophoresis. These methods are time-consuming and cannot quantitatively determine this acid in urine, while gas chromatography requires derivatization. The method is more complicated and is not suitable for the determination of batch samples. Method 1: The recent detection method is mainly high performance liquid chromatography-electrochemical detector method. Chromatographic conditions: reversed-phase liquid chromatography column PLATISIL ODS(250mm * 4.6mm, particle size 5.0 m), injection volume 10 μL, fluorescence detection excitation wavelength 277 nm, emission wavelength 320 nm, column temperature at room temperature, flow phase as shown in the table: the results show that the separation and determination process is completed within 15 min, the retention time of homovanillic acid is 6. 72min; The detection limit of homovanillic acid is 0.15 g/ml; the linear range is 0~25 g/ml; The recovery rate of standard addition is 84.5% ~ 106.1%. The relative standard deviation is less than 3.44%. All indexes of this method meet the requirements of "Guidelines for the Development of Biomaterials Analysis Methods" and can accurately determine the content of homovanillic acid in urine. Method 2: A method based on tripyridine ruthenium (Ru(bpy)32 +) electrochemiluminescence was used to detect HVA. The method is simple, rapid, stable and sensitive. The results have certain guiding significance for early diagnosis and disease monitoring of catecholamine secretion abnormal diseases. The detection mechanism is: |
| Synthetic route | First, vanillin reacts with benzyl chloride under alkaline conditions to produce 3-methoxy-4-benzyloxybenzaldehyde (II),II is reduced by aluminum isopropoxide or sodium borohydride, so that II and formaldehyde are disproportionated in KOH solution to form III;III reacts with sulfoxide chloride to form IV; then it reacts with sodium cyanide to form compound v; Hydrolysis and acidification under alkaline conditions to obtain VI; Finally, 5% Pd-C is used as catalyst, anhydrous ethanol is used as solvent, and I is obtained by catalytic hydrogenolysis at normal temperature and pressure. the specific reaction process is as follows: fig. 2 shows the synthesis route of homovanillic acid |
| application | 1. psychiatric classification: it is generally believed that about 25% ~ 60% of plasma homovanillic acid (pHVA) comes from the central nervous system. it is more feasible to understand the functional state of central DA in schizophrenic patients by measuring the dynamic changes of pHVA. Studies have shown that after treatment with risperidone, the total score of PANSS decreased significantly with the improvement of clinical symptoms, and the content of pHV A also decreased significantly, and there was a positive correlation between the two. Observing the change of p HVA may be used as an observation index of drug efficacy. 2. Neuroblastoma: Neuroblastoma can secrete a large number of catecholamines, of which homovanillic acid is the most important terminal metabolite of catecholamines. Determination of the total amount of 24h urine HVA was once a classic method for diagnosis of neuroblastoma. However, the content of HVA in urine is greatly affected by urine concentration, dilution and other factors, and the result is inaccurate in terms of concentration per unit volume. Therefore, in the past, 24h urine content was measured to indicate its concentration, but it is extremely difficult to accurately retain 24h urine in children. Creatinine (creatinine Cr) is the metabolic end product of creatine, which is excreted by the kidney. The endogenous creatinine content of the human body is extremely constant, so the excretion in 24h urine is generally constant and not affected by 24h urine volume. It is often used to correct the concentration of substances in urine to avoid the influence of urine volume on the concentration of substances. According to this principle, the ratio of homovanillic acid to creatinine (HVA/Cr) is determined by taking random urine, and HVA/Cr is used to express HVA content, which can avoid the influence of urine volume on the determination results, and can also avoid the inconvenience and error of taking 24h urine. 3. Parkinson's disease: homovanillic acid is the main metabolite of monoamine neurotransmitter dopamine, which has potential physiological and pathological significance. Studies have shown that after the administration of levodopa (LD), the concentration of H A in striatum remains at a high level after the LD concentration returns to normal, and is more than 2 times higher than the basic level, suggesting that HVA has an accumulation phenomenon, that is, if the dose is administered at an interval of 6 h, the concentration of central HVA in rats will continue to increase, and whether high concentration of HVA has adverse effects on the body, especially the central nervous system, needs further study. In addition, whether there is accumulation of striatal HVA concentration in patients with Parkinson's disease after long-term clinical application of LD remains to be confirmed by further research. 4. Others: In recent years, homovanillic acid has been reported as an important intermediate in drug synthesis and drug synthesis. The phenolic hydroxyl etherification product of homovanillic acid can be used as an immune reagent, its monosodium salt can be used as an absorbent, and its ethyl ester, zinc, epoxy resin, etc. can be used as an adhesive for dental surgery. Various esterification products and amide derivatives of homovanillic acid can be used as anti-inflammatory and analgesic drugs. (2016-06-17) |
| use | used for content determination/identification/pharmacological experiments, etc. |
Last Update：2024-04-09 20:52:54
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