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Chemical Compound Review

BENZOIN     2-hydroxy-1,2-diphenyl- ethanone

Synonyms: Aerozoin, DL-BENZOIN, SureCN145, CCRIS 75, PubChem20784, ...
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Disease relevance of BENZOIN


Psychiatry related information on BENZOIN


High impact information on BENZOIN

  • The quantitative effect of cosolvents on the water solubility of hydrophobic substrates can be correlated with the effect on reaction rates to determine the geometries of transition states for Diels-Alder reactions, the benzoin condensation, and alkylations of phenoxide ions and aniline [7].
  • The experiments of decades have finally resulted in successful enantioselective benzoin condensations and enantioselective intramolecular Stetter reactions as important examples of carbene catalyzed asymmetric nucleophilic acylation processes [8].
  • In this process, no benzoin products from carbonyl anion dimerization are observed [9].
  • Another broad range of chiral analytes (beta-blockers, phenoxypropionic acid, benzoin derivatives, PTH-amino acids, benzodiazepinones) studied also provided improved chiral separation at low pH compared to high-pH conditions [10].
  • In addition, comparative studies on the enantioseparation of benzoin-related compounds with SI-S-beta-CD and with randomly sulfate-substituted beta-CD were made [11].

Biological context of BENZOIN


Anatomical context of BENZOIN


Associations of BENZOIN with other chemical compounds

  • Specifically, the photolysis of 1-phenyl-3-p-tolyl-propan-2-one and benzoin ethyl ether and photodimerization of acenaphthylene were conducted [17].
  • Precolumn fluorescence derivatization of the antagonist [Arg6,D-Trp7,9,MePhe8]-substance P[6-11] with benzoin in high-performance liquid chromatography and selective detection of arginine-containing fragments in its degradation products [18].
  • Precolumn fluorescence derivatization for the determination of the antagonist [Arg6,D-Trp7,9,MePhe8]-Substance P¿6-11¿ (antagonist G) using benzoin in HPLC was studied [18].
  • In the case of benzoin and propiomazine binding to human serum albumin, capacity factors were observed to always decrease upon addition of organic modifiers, although the effects of 1- and 2-propanol suggest a possible specific interaction or modification of the protein conformation [19].
  • The guanidino compounds in urine or deproteinized serum after ultrafiltration are converted to the fluorescent derivatives with benzoin in an alkaline medium, and the derivatives are separated simultaneously within 25 min on a reversed-phase column (mu Bondapak Phenyl) with a linear gradient elution of methanol in aqueous mobile phase (pH 8.5) [20].

Gene context of BENZOIN

  • The consecutive analysis of the neutral compound, benzoin, by the OVM-encapsulated column showed good repeatability in the retention time (RSD = 1.23% for the first peak, N = 10) [21].
  • The intact BSA column gave a higher enantioselectivity than the BSA-FG75 column for most of the compounds tested, whereas the BSA-FG75 column gave a higher enantioselectivity than the intact BSA column for lorazepam and benzoin, and had a higher capacity for benzoin [22].
  • The package insert of the type most commonly used (Steri-Strip), indicates that the application of compound tincture of benzoin, U.S.P. (CTB) increases strip adhesion [23].
  • Conversely, the BFD S26A variant was unable to cleave benzoin [24].
  • The author presents a survey of his experience with the use of benzoin as an aid to prevent and to treat wound complications as: CSF leakage ruptured meningoceles, prevention of leakage and wound infections, during the use of external cranial drainage, indwelling catheters or implanted cannulas and electrodes [25].

Analytical, diagnostic and therapeutic context of BENZOIN

  • The mechanism of cross silyl benzoin addition is proposed in detail and is supported by crossover studies and a number of unambiguous experiments designed to ascertain the reversibility of key steps [26].
  • A quantitative relationship between capacity factor and selector concentration in capillary electrophoresis and high performance liquid chromatography: evidence from the enantioselective resolution of benzoin using human serum albumin as a chiral selector [27].
  • To investigate the reason for this we have measured retention (k') of a neutral solute (racemic benzoin) in HPLC and EKC using an identical range of BGE/mobile phase conditions in both techniques [27].
  • Coumarinic and benzoin derivatives, as well as (+/-)-1, 1'-binaphthyl-2,2'-dihydrogen phosphate (BNP) were used as test analytes for MEKC experiments [28].
  • 42 (60.9%) of these patients were placed on 20% podophyllin on tincture of benzoin, 17 (24.6%) on cryotherapy and 1 (1.5%) on both [29].


  1. Benzaldehyde lyase, a novel thiamine PPi-requiring enzyme, from Pseudomonas fluorescens biovar I. González, B., Vicuña, R. J. Bacteriol. (1989) [Pubmed]
  2. Contact dermatitis owing to tincture of benzoin. Coskey, R.J. Archives of dermatology. (1978) [Pubmed]
  3. Allergic contact dermatitis to compound tincture of benzoin. James, W.D., White, S.W., Yanklowitz, B. J. Am. Acad. Dermatol. (1984) [Pubmed]
  4. An unusual necrotizing dermatitis after a single application of topical benzoin and pressure bandage for enucleation of an eye. Tripathi, R.C., Fekrat-Polascik, S., Tripathi, B.J., Ernest, J.T. Lens and eye toxicity research. (1990) [Pubmed]
  5. Nasal papillomas: successful treatment with podophyllin. Bennett, R.G., Grist, W.J. South. Med. J. (1985) [Pubmed]
  6. Evaluation of massage with essential oils on childhood atopic eczema. Anderson, C., Lis-Balchin, M., Kirk-Smith, M. Phytotherapy research : PTR. (2000) [Pubmed]
  7. Determining the geometries of transition States by use of antihydrophobic additives in water. Breslow, R. Acc. Chem. Res. (2004) [Pubmed]
  8. Nucleophilic carbenes in asymmetric organocatalysis. Enders, D., Balensiefer, T. Acc. Chem. Res. (2004) [Pubmed]
  9. Catalytic conjugate additions of carbonyl anions under neutral aqueous conditions. Myers, M.C., Bharadwaj, A.R., Milgram, B.C., Scheidt, K.A. J. Am. Chem. Soc. (2005) [Pubmed]
  10. Polymeric Sulfated Amino Acid Surfactants: A Class of Versatile Chiral Selectors for Micellar Electrokinetic Chromatography (MEKC) and MEKC-MS. Rizvi, S.A., Zheng, J., Apkarian, R.P., Dublin, S.N., Shamsi, S.A. Anal. Chem. (2007) [Pubmed]
  11. Migration behavior and enantioseparation of hydrobenzoin and structurally related compounds in capillary zone electrophoresis with a dual cyclodextrin system consisting of heptakis-(2,3-dihydroxy-6-O-sulfo)-beta-cyclodextrin and beta-cyclodextrin. Lin, C.E., Lin, S.L., Cheng, H.T., Fang, I.J., Kuo, C.M., Liu, Y.C. Electrophoresis (2005) [Pubmed]
  12. Intramolecular gamma-hydroxylations of nonactivated C-H bonds with copper complexes and molecular oxygen. Schönecker, B., Zheldakova, T., Lange, C., Günther, W., Görls, H., Bohl, M. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  13. Cyanide-catalyzed cyclizations via aldimine coupling. Reich, B.J., Justice, A.K., Beckstead, B.T., Reibenspies, J.H., Miller, S.A. J. Org. Chem. (2004) [Pubmed]
  14. Kinetics of the thiazolium ion-catalyzed benzoin condensation. White, M.J., Leeper, F.J. J. Org. Chem. (2001) [Pubmed]
  15. The genetic toxicology of benzoin and caprolactam. Brady, A.L., Stack, H.F., Waters, M.D. Mutat. Res. (1989) [Pubmed]
  16. Caprolactam and benzoin: tests for induction of chromosome aberrations and SCEs in mouse bone marrow. McFee, A.F., Lowe, K.W. Mutat. Res. (1989) [Pubmed]
  17. Dendrimers as photochemical reaction media. Photochemical behavior of unimolecular and bimolecular reactions in water-soluble dendrimers. Kaanumalle, L.S., Ramesh, R., Murthy Maddipatla, V.S., Nithyanandhan, J., Jayaraman, N., Ramamurthy, V. J. Org. Chem. (2005) [Pubmed]
  18. Precolumn fluorescence derivatization of the antagonist [Arg6,D-Trp7,9,MePhe8]-substance P[6-11] with benzoin in high-performance liquid chromatography and selective detection of arginine-containing fragments in its degradation products. Cui, H., Reubsaet, J.L., Bult, A. Journal of chromatography. A. (1996) [Pubmed]
  19. Effect of organic modifiers on retention and enantiomeric separations by capillary electrophoresis with human serum albumin as a chiral selector in solution. Ahmed, A., Lloyd, D.K. Journal of chromatography. A. (1997) [Pubmed]
  20. High-performance liquid chromatographic measurement of guanidino compounds of clinical importance in human urine and serum by pre-column fluorescence derivatization using benzoin. Kai, M., Miyazaki, T., Ohkura, Y. J. Chromatogr. (1984) [Pubmed]
  21. A protein-encapsulation technique by the sol-gel method for the preparation of monolithic columns for capillary electrochromatography. Kato, M., Sakai-Kato, K., Matsumoto, N., Toyo'oka, T. Anal. Chem. (2002) [Pubmed]
  22. Enantioselectivity of bovine serum albumin-bonded columns produced with isolated protein fragments. Haginaka, J., Kanasugi, N. Journal of chromatography. A. (1995) [Pubmed]
  23. Reinforcement of surgical adhesive strips. Mikhail, G.R., Selak, L., Salo, S. The Journal of dermatologic surgery and oncology. (1986) [Pubmed]
  24. Exploring the active site of benzaldehyde lyase by modeling and mutagenesis. Kneen, M.M., Pogozheva, I.D., Kenyon, G.L., McLeish, M.J. Biochim. Biophys. Acta (2005) [Pubmed]
  25. Multiple use of benzoin as an aid in neurosurgical practice: the watertight benzoin dressing. Marino Júnior, R. Arquivos de neuro-psiquiatria. (1979) [Pubmed]
  26. Mechanism and scope of the cyanide-catalyzed cross silyl benzoin reaction. Linghu, X., Bausch, C.C., Johnson, J.S. J. Am. Chem. Soc. (2005) [Pubmed]
  27. A quantitative relationship between capacity factor and selector concentration in capillary electrophoresis and high performance liquid chromatography: evidence from the enantioselective resolution of benzoin using human serum albumin as a chiral selector. Lloyd, D.K., Ahmed, A., Pastoré, F. Electrophoresis (1997) [Pubmed]
  28. Enantioselectivity of alcohol-modified polymeric surfactants in micellar electrokinetic chromatography. Tarus, J., Agbaria, R.A., Morris, K., Billiot, F.H., Williams, A.A., Chatman, T., Warner, I.M. Electrophoresis (2003) [Pubmed]
  29. Prevalence of human papilloma virus genital infections in sexually transmitted diseases clinic attendees in Ibadan. Okesola, A.O., Fawole, O.I. West African journal of medicine. (2000) [Pubmed]
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