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Benzilic acid is an organic compound with formula C
₁₄H
₁₂O
₃ or (C
₆H
₅)₂(HO)C(COOH). It is a white crystalline aromatic acid, soluble in many primary alcohols.

Preparation

Benzilic acid can be prepared by heating mixture of benzil, ethanol and potassium hydroxide.

Another preparation, performed by Liebig in 1838, is the dimerization of benzaldehyde, to benzil, which is transformed to the product by the benzilic acid rearrangement reaction.^[1]

Uses

Benzilic acid is used in the manufacture of glycollate pharmaceuticals including Clidinium, Dilantin, and Flutropium, which are antagonists of the muscarinic acetylcholine receptors.

It is used in manufacture of the incapacitating agent 3-quinuclidinyl benzilate (BZ) and is regulated by the Chemical Weapons Convention. It is also monitored by law enforcement agencies of many countries, because of its use in the manufacture in hallucinogenic drugs.^[2]

References

^ Liebig, J. (1838). "Ueber Laurent's Theorie der organischen Verbindungen". Annalen der Chemie. 25: 1–31. doi:10.1002/jlac.18380250102.
^ "Nerve Agent Precursors: Benzilic acid and Methyl Benzilate", Factsheets on Chemical and Biological Warfare Agents, Chemical precursors.

External links

Safety MSDS data
Solubility in alcohols
Converting Benzaldehyde to Benzilic Acid
Synthesis of Benzilic Acid

UpToDate Contents

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1. 化学テロ：早急な認識および初回薬物治療マネージメント chemical terrorism rapid recognition and initial medical management

English Journal

Hydroxylation versus Halogenation of Aliphatic C-H Bonds by a Dioxygen-Derived Iron-Oxygen Oxidant: Functional Mimicking of Iron Halogenases.

Chatterjee S1, Paine TK2.
Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2016 Jun 27;55(27):7717-22. doi: 10.1002/anie.201509914. Epub 2016 Jan 28.
An iron-oxygen intermediate species generated in situ in the reductive activation of dioxygen by an iron(II)-benzilate complex of a monoanionic facial N3 ligand, promoted the halogenation of aliphatic C-H bonds in the presence of a protic acid and a halide anion. An electrophilic iron(IV)-oxo oxidan
PMID 26822989

Effects of novel tacrine-related cholinesterase inhibitors in the reversal of 3-quinuclidinyl benzilate-induced cognitive deficit in rats--Is there a potential for Alzheimer's disease treatment?

Misik J1, Korabecny J2, Nepovimova E2, Kracmarova A2, Kassa J2.
Neuroscience letters.Neurosci Lett.2016 Jan 26;612:261-8. doi: 10.1016/j.neulet.2015.12.021. Epub 2015 Dec 18.
Inhibitors of cholinesterase are important drugs for therapy of Alzheimer's disease and the search for new modifications is extensive, including dual inhibitors or multi-target hybrid compounds. The aim of the present study was a preliminary evaluation of pro-cognitive effects of newly-developed 7-M
PMID 26708634

The effects of novel 7-MEOTA-donepezil like hybrids and N-alkylated tacrine analogues in the treatment of quinuclidinyl benzilate-induced behavioural deficits in rats performing the multiple T-maze test.

Misik J1, Korabecny J1, Nepovimova E1, Cabelova P1, Kassa J1.
Biomedical papers of the Medical Faculty of the University Palacký, Olomouc, Czechoslovakia.Biomed Pap Med Fac Univ Palacky Olomouc Czech Repub.2015 Dec;159(4):547-53. doi: 10.5507/bp.2015.006. Epub 2015 Feb 10.
AIMS: The number of approved drugs for the clinical treatment of Alzheimer disease remains limited. For this reason, there is extensive search for novel therapies. Of these, cholinesterase inhibitors have some proven benefit in slowing the disease progression and still remain the first-line therapeu
PMID 25690521

Japanese Journal

Structure of the human M2 muscarinic acetylcholine receptor bound to an antagonist

Haga Kazuko,Kruse Andrew C.,Asada Hidetsugu,Yurugi-Kobayashi Takami,Shiroishi Mitsunori,Zhang Cheng,Weis William I.,Okada Tetsuji,Kobilka Brian K.,Haga Tatsuya,Kobayashi Takuya
Nature, 2012-01-25
… The antagonist 3-quinuclidinyl-benzilate binds in the middle of a long aqueous channel extending approximately two-thirds through the membrane.The orthosteric binding pocket is formed by amino acids that are identical in all five muscarinic receptor subtypes, and sharesstructural homology with other functionally unrelated acetylcholine binding proteins from different species. …
NAID 120003752107

Assessment of Novel Muscarinic Acetylcholine Receptors in Rat Cerebral Cortex by a Tissue Segment Binding Method

Lee Kung-Shing,Nishimune Atsushi,Yoshiki Hatsumi [他],ANISUZZAMAN Abu Syed Md,SUZUKI Fumiko,WANG Mao-Hsien,CHENG Juei-Tang,MURAMATSU Ikunobu
Journal of pharmacological sciences 112(4), 444-451, 2010-04-20
… [3H]-Quinuclidinyl benzilate (QNB, a hydrophobic ligand) specifically bound to mAChRs in the cortex segments. …
NAID 10027909139

The Forefront for Novel Therapeutic Agents Based on the Pathophysiology of Lower Urinary Tract Dysfunction: Bladder Selectivity Based on In Vivo Drug-Receptor Binding Characteristics of Antimuscarinic Agents for Treatment of Overactive Bladder

Yoshida Akira,Fujino Tomomi,Maruyama Shuji [他],Ito Yoshihiko,Taki Yuko,Yamada Shizuo
Journal of Pharmacological Sciences 112(2), 142-150, 2010
… In vivo quantitative autoradiography using (+)N-[11C]methyl-3-piperidyl benzilate in rats showed significant occupancy of brain muscarinic receptors on intravenous injection of oxybutynin, propiverine, solifenacin, and tolterodine. …
NAID 130000160421

Related Pictures

★リンクテーブル★

リンク元	「ベンジル酸」「ベンジラート」
拡張検索	「3-quinuclidinyl benzilate」「quinuclidinyl benzilate」

「ベンジル酸」

Benzilic acid
Names
	IUPAC name Hydroxy(diphenyl)acetic acid
	Other names α,α-Diphenyl-α-hydroxyacetic acid, α,α-Diphenylglycolic acid, α-Hydroxydiphenyl acetic acid, 2,2-Diphenyl-2-hydroxyacetic acid, 2-Hydroxy-2,2-diphenylacetic acid, Diphenyl glycolic acid, Hydroxydiphenyl acetic acid
Identifiers
CAS Number	76-93-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:39414 ;
ChEMBL	ChEMBL578171 ;
ChemSpider	6220 ;
ECHA InfoCard	100.000.904
PubChem CID	6463;
	InChI InChI=1S/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16) Key: UKXSKSHDVLQNKG-UHFFFAOYSA-N ; InChI=1/C14H12O3/c15-13(16)14(17,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,17H,(H,15,16) Key: UKXSKSHDVLQNKG-UHFFFAOYAV ;
	SMILES O=C(O)C(O)(c1ccccc1)c2ccccc2 ;
Properties
Chemical formula	C14H12O3
Molar mass	228.25 g·mol−1
Appearance	white solid
Density	1.08 g/cm3
Melting point	150 to 152 °C (302 to 306 °F; 423 to 425 K)
Boiling point	180 °C (356 °F; 453 K) (17.3 hPa)
Solubility in water	2 g/l (20 °C)
Hazards
R-phrases (outdated)	R22
S-phrases (outdated)	S23, S24, S25, S28, S36, S37, S45
NFPA 704	1 2 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references