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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"

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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

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/20 12:51:09」(JST)

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Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C₆H₅CH(OH)CO₂H. It is a white crystalline solid that is soluble in water and polar organic solvents. It is a useful precursor to various drugs. Since the molecule is chiral, it exists in either of two enantiomers as well as the racemic mixture, known as paramandelic acid.

Isolation, synthesis, occurrence

Mandelic acid was discovered while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. The name is derived from the German "Mandel" for "almond". Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase.

Mandelic acid is usually prepared by the acid-catalysed hydrolysis of mandelonitrile,^[3] which is the cyanohydrin of benzaldehyde. Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed:^[4]

Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid and dibromacetophenone.^[5] It also arises by heating phenylglyoxal with alkalis.

It arises from the biodegradation of styrene, as detected in urine.^[6]

Uses

Mandelic acid has a long history of use in the medical community as an antibacterial, particularly in the treatment of urinary tract infections.^[7] It has also been used as an oral antibiotic, and as a component of "chemical face peels", along with other alpha-hydroxy acids (AHAs).

The drugs cyclandelate and homatropine are esters of mandelic acid.

References

^ Merck Index, 11th Edition, 5599.
^ Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.
^ Edwin Ritzer and Rudolf Sundermann "Hydroxycarboxylic Acids, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a13_519
^ Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Org. Synth. ; Coll. Vol. 1, p. 336
^ J. G. Aston, J. D. Newkirk, D. M. Jenkins, and Julian Dorsky (1952). "Mandelic Acid". Org. Synth. ; Coll. Vol. 3, p. 538
^ Engström K, Härkönen H, Kalliokoski P, Rantanen J. "Urinary mandelic acid concentration after occupational exposure to styrene and its use as a biological exposure test" Scand. J. Work Environ. Health. 1976, volume 2, pp. 21-6.
^ Putten, P. L. (1979). "Mandelic acid and urinary tract infections". Antonie van Leeuwenhoek 45 (4): 622. doi:10.1007/BF00403669.

This article incorporates text from a publication now in the public domain: Chisholm, Hugh, ed. (1911). Encyclopædia Britannica (11th ed.). Cambridge University Press.

UpToDate Contents

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English Journal

Enantioseparation of Mandelic Acid Enantiomers With Magnetic Nano-Sorbent Modified by a Chiral Selector.

Tarhan T1,2, Tural B1, Tural S1, Topal G1.
Chirality.Chirality.2015 Nov;27(11):835-42. doi: 10.1002/chir.22524. Epub 2015 Sep 14.
In this study, R(+)-α-methylbenzylamine-modified magnetic chiral sorbent was synthesized and assessed as a new enantioselective solid phase sorbent for separation of mandelic acid enantiomers from aqueous solutions. The chemical structures and magnetic properties of the new sorbent were characteriz
PMID 26370608

In situ immobilization of a general resolving agent on the magnetic multi-wall carbon nanotube for the direct enantioenrichment of dl-mandelic acid.

Tarigh GD1, Shemirani F2.
Talanta.Talanta.2015 Nov 1;144:899-907. doi: 10.1016/j.talanta.2015.07.035. Epub 2015 Jul 14.
l-Threonine (l-thr) as a general chiral selector anchored on the surface of magnetic multi-wall carbon nanotube (MMWCNT) was prepared using an in situ electrostatic adsorption and studied as a new magnetically chiral selector for the separation of chiral dl-mandelic acid (dl-MA) as a model sample. B
PMID 26452906

Multi-residue enantiomeric analysis of human and veterinary pharmaceuticals and their metabolites in environmental samples by chiral liquid chromatography coupled with tandem mass spectrometry detection.

Camacho-Muñoz D1, Kasprzyk-Hordern B2.
Analytical and bioanalytical chemistry.Anal Bioanal Chem.2015 Oct 13. [Epub ahead of print]
Enantiomeric profiling of chiral pharmacologically active compounds (PACs) in the environment has hardly been investigated. This manuscript describes, for the first time, a multi-residue enantioselective method for the analysis of human and veterinary chiral PACs and their main metabolites from diff
PMID 26462925

Japanese Journal

L-アラニンを分割剤としたマンデル酸の光学分割実験

化学と教育 60(7), 320-323, 2012-07-20
NAID 110009490029

ジアステレオマー塩法による光学分割の効率化を目指して

有機合成化学協会誌 69(5), 499-505, 2011-05-01
NAID 10028293252

Low-temperature formation of alpha-alumina from various polyhydroxoaluminum-hydroxy acid composite gels

CERAMICS INTERNATIONAL 37(1), 201-206, 2011-01
NAID 80021522037

「マンデル酸」

Mandelic acid^[1]
Names
	IUPAC name 2-Hydroxy-2-phenylacetic acid
	Other names Mandelic acid; Phenylglycolic acid; α-Hydroxyphenylacetic acid
Identifiers
CAS Number	90-64-2 ; 611-71-2 (R) ; 17199-29-0 (S)
ChEBI	CHEBI:35825
ChEMBL	ChEMBL1609
ChemSpider	1253
EC Number	202-007-6
Jmol interactive 3D	Image
PubChem	1292
RTECS number	OO6300000
UNII	NH496X0UJX
	InChI InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11) Key: IWYDHOAUDWTVEP-UHFFFAOYSA-N ; InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11) Key: IWYDHOAUDWTVEP-UHFFFAOYAD ;
	SMILES O=C(O)C(O)c1ccccc1 ;
Properties
Chemical formula	C8H8O3
Molar mass	152.15 g·mol−1
Appearance	White crystalline powder
Density	1.30 g/cm3
Melting point	119 °C (246 °F; 392 K) optically pure: 132 to 135 °C (270 to 275 °F; 405 to 408 K)
Boiling point	321.8 °C (611.2 °F; 595.0 K)
Solubility in water	15.87 g/100 mL
Solubility	soluble in diethyl ether, ethanol, isopropanol
Acidity (pKa)	3.41
Refractive index (nD)	1.5204
Thermochemistry
Std enthalpy of; formation (ΔfHo298)	0.1761 kJ/g
Pharmacology
ATC code	B05CA06; J01XX06
Hazards
Flash point	162.6 °C (324.7 °F; 435.8 K)
Related compounds
Related compounds	mandelonitrile, phenylacetic acid, vanillylmandelic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

　　[★]

英: mandelic acid
商: ウロナミン、ヘキサミン

概念

参考1

芳香族αヒドロキシ酸の一種。分子式 C8H8O3。形状は白色結晶で、水及び大半の一般的な有機溶媒に溶解する。
マンデル酸は苦扁桃(アーモンド almondの一種)の抽出物を希塩酸で加熱したものから発見されており、ドイツ語のアーモンドを意味するMandelが語源となっている。
抗菌作用を有し、通常マンデル酸塩(マンデル酸ヘキサミン)として膀胱炎、腎盂炎など尿路感染症の尿路消毒剤として用いる。

ヘキサミンが尿中でホルムアルデヒドに分解して防腐作用を発揮し、マンデル酸は尿を酸性化する。

構造

バニリルマンデル酸はマンデル酸をベースとしてバニリン酸の置換基に似ているという意味で命名がなされた？

マンデル酸

バニリン酸

バニリルマンデル酸

臨床関連

スチレン中毒：早期発見のために尿中マンデルさんを測定する。

benzen-ring-CH2=CH2　→　benzen-ring-CH(OH)-COOH

参考

「vanilmandelic acid」

　　[★] バニリルマンデル酸。バニルマンデリン酸

「vanillylmandelic acid」

　　[★] バニリルマンデル酸 VMA

「3-methoxy-4-hydroxymandelic acid」

　　[★] バニリルマンデル酸

[1] Merck Index, 11th Edition, 5599.

[2] Bjerrum, J., et al. Stability Constants, Chemical Society, London, 1958.

[3] Edwin Ritzer and Rudolf Sundermann "Hydroxycarboxylic Acids, Aromatic" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi: 10.1002/14356007.a13_519

[4] Corson, B. B.; Dodge, R. A.; Harris, S. A.; Yeaw, J. S. (1941). "Mandelic Acid". Org. Synth. ; Coll. Vol. 1, p. 336

[5] J. G. Aston, J. D. Newkirk, D. M. Jenkins, and Julian Dorsky (1952). "Mandelic Acid". Org. Synth. ; Coll. Vol. 3, p. 538

[6] Engström K, Härkönen H, Kalliokoski P, Rantanen J. "Urinary mandelic acid concentration after occupational exposure to styrene and its use as a biological exposure test" Scand. J. Work Environ. Health. 1976, volume 2, pp. 21-6.

[7] Putten, P. L. (1979). "Mandelic acid and urinary tract infections". Antonie van Leeuwenhoek 45 (4): 622. doi:10.1007/BF00403669.

リンク元	「マンデル酸」
拡張検索	「vanilmandelic acid」「vanillylmandelic acid」「3-methoxy-4-hydroxymandelic acid」

匿名

検索

案内

案内

mandelic acid