バニリルマンデル酸。バニルマンデリン酸
WordNet
- street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
- any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
- having the characteristics of an acid; "an acid reaction"
PrepTutorEJDIC
- 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2017/08/11 17:08:59」(JST)
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Vanillylmandelic acid
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Names |
IUPAC name
(RS)-hydroxy(4-hydroxy-3-methoxy-phenyl)acetic acid
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Other names
α,4-Dihydroxy-3-methoxybenzeneacetic acid, VMA, Vanillomandelic acid, Vanillylmandelic acid, Vanilmandelic acid
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Identifiers |
CAS Number
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3D model (JSmol)
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- Interactive image
- Interactive image
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Beilstein Reference
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2213227 |
ChEBI |
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ChemSpider |
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ECHA InfoCard |
100.000.204 |
EC Number |
201-701-6 |
IUPHAR/BPS
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MeSH |
Vanilmandelic+acid |
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InChI
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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) Y
Key: CGQCWMIAEPEHNQ-UHFFFAOYSA-N Y
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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)
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SMILES
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COC1=C(C=CC(=C1)C(C(=O)O)O)O
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O=C(O)C(O)c1cc(OC)c(O)cc1
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Properties |
Chemical formula
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C9H10O5 |
Molar mass |
198.173 g/mol |
Appearance |
White powder |
Melting point |
133 °C (271 °F; 406 K) |
Hazards |
Safety data sheet |
MSDS at Sigma Aldrich |
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 YN ?) |
Infobox references |
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Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings[1] and is an end-stage metabolite of the catecholamines, epinephrine, and norepinephrine. It is produced via intermediary metabolites.
Contents
- 1 Chemical synthesis
- 2 Biological elimination
- 3 Clinical significance
- 4 References
Chemical synthesis
VMA synthesis is the first step of a two-step process practiced by Rhodia since the 1970s to synthesize artificial vanilla.[1] Specifically the reaction entails the condensation of guaiacol and glyoxylic acid in an ice cold, aqueous solution with sodium hydroxide.
Biological elimination
VMA is found in the urine, along with other catecholamine metabolites, including homovanillic acid (HVA), metanephrine, and normetanephrine. In timed urine tests the quantity excreted (usually per 24 hours) is assessed along with creatinine clearance, and the quantity of cortisols, catecholamines, and metanephrines excreted is also measured.
Norepinephrine degradation. Vanillylmandelic acid is shown at top right. Enzymes are shown in boxes.
[2]
Clinical significance
Urinary VMA is elevated in patients with tumors that secrete catecholamines.[3]
These urinalysis tests are used to diagnose an adrenal gland tumor called pheochromocytoma, a tumor of catecholamine-secreting chromaffin cells. These tests may also be used to diagnose neuroblastomas, and to monitor treatment of these conditions.
Norepinephrine is metabolised into normetanephrine and VMA. Norepinephrine is one of the hormones produced by the adrenal glands, which are found on top of the kidneys. These hormones are released into the blood during times of physical or emotional stress, which are factors that may skew the results of the test.[citation needed]
References
- ^ a b Fatiadi, Alexander; Schaffer, Robert (1974). "An Improved Procedure for Synthesis of DL-4-Hydroxy-3-methoxymandelic Acid (DL-"Vanillyl"-mandelic Acid, VMA)" (PDF). Journal of Research of the National Bureau of Standards Section A. 78A (3): 411–412. doi:10.6028/jres.078A.024. Retrieved 19 December 2013.
- ^ Figure 11-4 in: Rod Flower; Humphrey P. Rang; Maureen M. Dale; Ritter, James M. (2007). Rang & Dale's pharmacology. Edinburgh: Churchill Livingstone. ISBN 0-443-06911-5.
- ^ Magera MJ, Thompson AL, Matern D, Rinaldo P (May 2003). "Liquid chromatography-tandem mass spectrometry method for the determination of vanillylmandelic acid in urine". Clin. Chem. 49 (5): 825–6. PMID 12709381. doi:10.1373/49.5.825.
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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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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UpToDate Contents
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English Journal
- Maternal diet of polyunsaturated fatty acid altered the cell proliferation in the dentate gyrus of hippocampus and influenced glutamatergic and serotoninergic systems of neonatal female rats.
- Tang M1,2, Zhang M1,2, Cai H1, Li H3, Jiang P4, Dang R4, Liu Y1, He X1,2, Xue Y1,2, Cao L1,2, Wu Y1,2.
- Lipids in health and disease.Lipids Health Dis.2016 Apr 5;15(1):71. doi: 10.1186/s12944-016-0236-1.
- BACKGROUND: Long-chain polyunsaturated fatty acids (PUFAs) are major components of the phospholipids that forming the cell membrane. Insufficient availability of PUFAs during prenatal period decreases accretion of docosahexaenoic acid (DHA) in the developing brain. DHA deficiency is associated with
- PMID 27048382
- Enhanced FGF23 production in mice expressing PI3K-insensitive GSK3 is normalized by β-blocker treatment.
- Fajol A1, Chen H1, Umbach AT1, Quarles LD1, Lang F1, Föller M2.
- FASEB journal : official publication of the Federation of American Societies for Experimental Biology.FASEB J.2016 Feb;30(2):994-1001. doi: 10.1096/fj.15-279943. Epub 2015 Nov 2.
- Glycogen synthase kinase (GSK)-3 is a ubiquitously expressed kinase inhibited by insulin-dependent Akt/PKB/SGK. Mice expressing Akt/PKB/SGK-resistant GSK3α/GSK3β (gsk3(KI)) exhibit enhanced sympathetic nervous activity and phosphaturia with decreased bone density. Hormones participating in phospha
- PMID 26527066
- Is Preoperative Biochemical Testing for Pheochromocytoma Necessary for All Adrenal Incidentalomas?
- Jun JH1, Ahn HJ, Lee SM, Kim JA, Park BK, Kim JS, Kim JH.
- Medicine.Medicine (Baltimore).2015 Nov;94(45):e1948. doi: 10.1097/MD.0000000000001948.
- This study examined whether imaging phenotypes obtained from computed tomography (CT) can replace biochemical tests to exclude pheochromocytoma among adrenal incidentalomas (AIs) in the preoperative setting.We retrospectively reviewed the medical records of all patients (n = 251) who were admitt
- PMID 26559265
Japanese Journal
- やせの女子学生におけるエネルギー代謝と自律調節機能
- Expression of Human Organic Anion Transporters in the Choroid Plexus and Their Interactions With Neurotransmitter Metabolites
- LC/MSによる精度管理用標準溶液中の Homovanillic Acid (HVA) 及び Vanilmandelic Acid (VMA) の同時定量
- 日本マス・スクリーニング学会誌 = Journal of Japanese Society for Mass-screening 13(2), 63, 2003-09-01
- NAID 10017000852
★リンクテーブル★
[★]
- 英
- vanillylmandelic acid VMA, 3-methoxy-4-hydroxymandelic acid
- 同
- バニルマンデリン酸 vanilmandelic acid
- 関
- マンデル酸、バニリン酸、ホモバリニン酸