- 関
- homovanillic acid、HVA
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/09/07 23:30:37」(JST)
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Homovanillic acid
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| Names |
| IUPAC name
2-(4-Hydroxy-3-methoxy-phenyl)acetic acid
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| Identifiers |
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CAS Registry Number
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306-08-1 Y |
| ChEBI |
CHEBI:545959 Y |
| ChEMBL |
ChEMBL1562 Y |
| ChemSpider |
1675 Y |
InChI
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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) Y
Key: QRMZSPFSDQBLIX-UHFFFAOYSA-N Y
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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)
Key: QRMZSPFSDQBLIX-UHFFFAOYAZ
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| Jmol-3D images |
Image |
| KEGG |
C05582 Y |
| MeSH |
Homovanillic+acid |
| PubChem |
1738 |
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| Properties |
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Chemical formula
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C9H10O4 |
| Molar mass |
182.18 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Y verify (what is: Y/N?) |
| Infobox references |
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Homovanillic acid (HOC6H3(OCH3)CH2COOH; synonyms: 3-methoxy-4-hydroxyphenyl acetic acid; HVA; 4-hydroxy-3-methoxy-benzeneacetic acid; 4-hydroxy-3-methoxyphenylacetic acid) is a major catecholamine metabolite and is produced throughout the body.[1] It is used as a reagent to detect oxidative enzymes, and is associated with dopamine levels in the brain.
In psychiatry and neuroscience, brain and cerebrospinal fluid levels of HVA are measured as a marker of metabolic stress caused by 2-deoxy-D-glucose.[2] HVA presence supports a diagnosis of neuroblastoma and malignant pheochromocytoma.
Fasting plasma levels of HVA are known to be higher in females than in males. This does not seem to be influenced by adult hormonal changes, as the pattern is retained in the elderly and post-menopausal as well as transsexuals according to their genetic sex, both before and during cross-sex hormone administration. Differences in HVA have also been correlated to tobacco usage, with smokers showing significantly lower amounts of plasma HVA.[3]
See also
References
- ^ Lambert, G.W.; Eisenhofer, G.; Jennings, G.L.; Esler, M.D. "Regional homovanillic acid production in humans". Life Sciences 53 (1): 63–75. doi:10.1016/0024-3205(93)90612-7.
- ^ Marcelis M, Suckling J, Hofman P, Woodruff P, Bullmore E, van Os J (September 2006). "Evidence that brain tissue volumes are associated with HVA reactivity to metabolic stress in schizophrenia". Schizophr. Res. 86 (1–3): 45–53. doi:10.1016/j.schres.2006.05.001. PMID 16806836.
- ^ Giltay E, Kho K, Blandjaar B, Verbeek M, Geurtz P, Geleijnse J, Gooren L (July 2005). "The sex difference of plasma homovanillic acid is unaffected by cross-sex hormone administration in transsexual subjects". J Endocrinol 187 (1): 109–16. doi:10.1677/joe.1.06307. PMID 16214946.
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Neurotransmitter metabolic intermediates
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| catecholamines |
Anabolism
(tyrosine→epinephrine) |
- Tyrosine → Levodopa → Dopamine → Norepinephrine → Epinephrine
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Catabolism/
metabolites |
| dopamine: |
- DOPAL
- DOPAC
- MOPET
- Hydroxytyrosol
- 3-Methoxytyramine
- Homovanillic acid
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| norepinephrine: |
- 3,4-Dihydroxymandelic acid
- Normetanephrine
- Vanillylmandelic acid
- 3-Methoxy-4-hydroxyphenylglycol
- Dihydroxyphenylethylene glycol
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| epinephrine: |
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| tryptophan→serotonin |
| anabolism: |
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| catabolism: |
- 5-Hydroxyindoleacetic acid
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| serotonin→melatonin |
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Index of the central nervous system
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| Description |
- Anatomy
- meninges
- cortex
- association fibers
- commissural fibers
- lateral ventricles
- basal ganglia
- diencephalon
- mesencephalon
- pons
- cerebellum
- medulla
- spinal cord
- Physiology
- Development
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| Disease |
- Cerebral palsy
- Meningitis
- Demyelinating diseases
- Seizures and epilepsy
- Headache
- Stroke
- Sleep
- Congenital
- Injury
- Neoplasms and cancer
- Other
- Symptoms and signs
- head and neck
- eponymous
- lesions
- Tests
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| Treatment |
- Procedures
- Drugs
- general anesthetics
- analgesics
- addiction
- epilepsy
- cholinergics
- migraine
- Parkinson's
- vertigo
- other
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Tumor markers
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| Blood |
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| Endocrine |
| Thyroid cancer |
- Thyroglobulin
- Medullary thyroid cancer (Calcitonin
- Carcinoembryonic antigen)
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| Pheochromocytoma |
- Normetanephrine
- Enolase 2
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| Neuroendocrine tumors |
- Synaptophysin
- Chromogranin A
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| Neuroblastoma |
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| Nervous system |
| Brain tumor |
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| Astrocytoma |
- Glial fibrillary acidic protein
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| NC/Melanoma |
- S100 protein
- Melanoma inhibitory activity
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Cardiovascular/
respiratory |
| Lung cancer |
- Carcinoembryonic antigen
- Enolase 2
- Autocrine motility factor
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| Hemangiosarcoma (endothelium) |
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| Digestive |
| Colorectal cancer |
- CA19-9
- Carcinoembryonic antigen
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| Pancreatic cancer |
- CA19-9
- Carcinoembryonic antigen
- CA 242
- Tumor-associated glycoprotein 72
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| Hepatocellular carcinoma |
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Reproductive/
urinary/
breast |
| Ovarian tumor |
- Surface epithelial-stromal tumor
- EC
- EST
- Choriocarcinoma
- Dysgerminoma
- Sertoli-Leydig cell tumour
- GCT
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| Testicular cancer |
- βhCG
- Alpha-fetoprotein/AFP-L3
- CD30
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| Prostate cancer |
- Prostate-specific antigen
- Prostatic acid phosphatase
- Glutamate carboxypeptidase II
- erbB-3 receptor
- Early prostate cancer antigen-2
- SPINK1
- GOLM1
- PCA3
- TMPRSS2
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| Germ cell tumor |
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| Bladder cancer |
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| Breast cancer |
- CA 15-3
- erbB-2 receptor
- erbB-3 receptor
- Cathepsin D
- Ca 27-29
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| General histology |
| Sarcoma |
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| Carcinoma (epithelium) |
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| Musculoskeletal |
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Index of neoplasms and cancer
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| Description |
- Tumor suppressing and oncogenes
- Tumor markers
- Carcinogen
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| Disease |
- Neoplasms and cancer
- Symptoms and signs
- Paraneoplastic
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| Treatment |
- Radiotherapy
- Drugs
- Immunotherapy
- intracellular chemotherapeutics
- extracellular chemotherapeutics
- adjuvant detoxification
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UpToDate Contents
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English Journal
- Minimal residual disease monitoring in neuroblastoma patients based on the expression of a set of real-time RT-PCR markers in tumor-initiating cells.
- Hartomo TB, Kozaki A, Hasegawa D, Pham TV, Yamamoto N, Saitoh A, Ishida T, Kawasaki K, Kosaka Y, Ohashi H, Yamamoto T, Morikawa S, Hirase S, Kubokawa I, Mori T, Yanai T, Hayakawa A, Takeshima Y, Iijima K, Matsuo M, Nishio H, Nishimura N.SourceDepartment of Epidemiology, Kobe University Graduate School of Medicine, Kobe, Japan.
- Oncology reports.Oncol Rep.2013 Apr;29(4):1629-36. doi: 10.3892/or.2013.2286. Epub 2013 Feb 12.
- Minimal residual disease (MRD) is derived from tumor-initiating cells (TICs) and is responsible for tumor relapse. Neuroblastoma is characterized by extreme tumor heterogeneity, and more than half of high-risk patients experience tumor relapse. To overcome tumor h
- PMID 23417100
- Adult vitamin D deficiency leads to behavioural and brain neurochemical alterations in C57BL/6J and BALB/c mice.
- Groves NJ, Kesby JP, Eyles DW, McGrath JJ, Mackay-Sim A, Burne TH.SourceEskitis Institute for Cell and Molecular Therapies, Nathan, Queensland, Australia.
- Behavioural brain research.Behav Brain Res.2013 Mar 15;241:120-31. doi: 10.1016/j.bbr.2012.12.001. Epub 2012 Dec 10.
- Epidemiological evidence suggests that low levels of vitamin D may predispose people to develop depression and cognitive impairment. While rodent studies have demonstrated that prenatal vitamin D deficiency is associated with altered brain development, there is a lack of research examining adult vit
- PMID 23238039
- Increased melatonin may play dual roles in the striata of a 6-hydroxydopamine model of Parkinson's disease.
- Lin L, Meng T, Liu T, Zheng Z.SourceResearch Center of Neurobiology, Fujian Medical University, Fuzhou 350004, China; Department of Biochemistry and Molecular Biology, Fujian Medical University, Fuzhou 350004, China.
- Life sciences.Life Sci.2013 Mar 12;92(4-5):311-6. doi: 10.1016/j.lfs.2013.01.007. Epub 2013 Jan 16.
- AIMS: To investigate dynamic changes and roles of melatonin (MLT) in the striata of 6-hydroxydopamine (6-OHDA)-treated rats.MAIN METHODS: A Parkinson's disease (PD) rat was established by a unilateral injection of 6-OHDA into the right substantia nigra pars compacta (SNc) and the right medial forebr
- PMID 23333823
Japanese Journal
- Brain Science(117)統合失調症患者の認知機能障害をカテコラミン代謝産物,脳由来神経栄養因子との関連から探る : 抗精神病薬治療からの検討
- うつ病における血漿モノアミン代謝産物濃度の変化と臨床症状の関連の検討
- 野崎 啓子,渡辺 研弥,曽田 恵美 [他]
- 日本生物学的精神医学会誌 = Japanese journal of biological psychiatry 25(1), 44-49, 2014
- NAID 40020058331
- 家族歴にMenkes病を認める新生児3例の臨床像の検討
- 八木 麻理子,楠 典子,李 知子,粟野 宏之,森岡 一朗,児玉 浩子,竹島 泰弘,飯島 一誠
- 脳と発達 46(1), 26-29, 2014
- 【目的】Menkes病 (MD) 早期診断の手がかりを検討する. 【方法】家族歴にMDを認め罹患リスクのある男児3例 (罹患児1例, 非罹患児2例) の新生児期の臨床像を比較した. 【結果】MDに特徴的なkinky hairは, 出生直後は極軽微で見逃す危険性があった. 血清銅は, 罹患児では経時的に低下したが, 非罹患児では上昇した. MDで上昇するとされる尿HVA/VMA比は, 罹患児ではc …
- NAID 130005005676
Related Links
- ho·mo·va·nil·lic ac·id (HVA), (hō'mō-vă-nil'ik as'id), 4-Hydroxy-3-methoxyphenylacetic acid; a phenol found in human urine; produced through the ... Determination of vanillylmandelic acid, vanillactic acid, and homovanillic acid in dried ...
- Sigma-Aldrich offers Sigma-H1252, Homovanillic acid for your research needs. Find product specific information including CAS, MSDS, protocols and references. ... Biochem/physiol Actions Metabolite of dihydroxyphenylacetic acid ...
Related Pictures
★リンクテーブル★
[★]
ホモバニリン酸 HVA
