vanilmandelic acid

バニリルマンデル酸。バニルマンデリン酸

WordNet

1. 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
2. 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
3. having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

1. 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

Names
IUPAC name (RS)-hydroxy(4-hydroxy-3-methoxy-phenyl)acetic acid
Other names α,4-Dihydroxy-3-methoxybenzeneacetic acid, VMA, Vanillomandelic acid, Vanillylmandelic acid, Vanilmandelic acid
Identifiers
CAS Number	55-10-7 Y
3D model (JSmol)	Interactive image Interactive image
Beilstein Reference	2213227
ChEBI	CHEBI:20106 Y
ChemSpider	1207 Y
ECHA InfoCard	100.000.204
EC Number	201-701-6
IUPHAR/BPS	6645
MeSH	Vanilmandelic+acid
PubChem CID	1245
InChI 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 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)
SMILES COC1=C(C=CC(=C1)C(C(=O)O)O)O O=C(O)C(O)c1cc(OC)c(O)cc1
Properties
Chemical formula	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).
Y verify (what is YN ?)
Infobox references

Vanillylmandelic acid (VMA) is a chemical intermediate in the synthesis of artificial vanilla flavorings and is an end-stage metabolite of the catecholamines, epinephrine, and norepinephrine. It is produced via intermediary metabolites.

Chemical synthesis

VMA synthesis is the first step of a two-step process practiced by Rhodia since the 1970s to synthesize artificial vanilla. 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.

Clinical significance

Urinary VMA is elevated in patients with tumors that secrete catecholamines.

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.

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

• 日本健康医学会雑誌 13(1), 11-17, 2004-04-30
• NAID 110009562981

• Expression of Human Organic Anion Transporters in the Choroid Plexus and Their Interactions With Neurotransmitter Metabolites

• Journal of pharmacological sciences 93(4), 430-436, 2003-12-01
• NAID 10011953460

• 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

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★リンクテーブル★

リンク元	「バニリルマンデル酸」

「バニリルマンデル酸」

　　[★]

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

HVA	ホモバニリン酸 homovanillic acid	ドパミンの代謝産物
VMA	バニリルマンデル酸 vanillylmandelic acid	ノルアドレナリン、アドレナリンの代謝産物