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Acetaldehyde

puriss. p.a., anhydrous, ≥99.5% (GC)

Synonym: Ethanal

  • CAS Number 75-07-0

  • Linear Formula CH3CHO

  • Molecular Weight 44.05

  •  Beilstein Registry Number 505984

  •  EC Number 200-836-8

  •  MDL number MFCD00006991

  •  PubChem Substance ID 24844966

  •  eCl@ss 39021102

  • Popular Documents:  FTNMR (PDF)  

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Properties

Related Categories A-B, Puriss p.a., Acacia, Aldehydes, Allium sativum (Garlic), Analytical Reagents,
vapor density   1.52 (vs air)
vapor pressure   14.63 psi ( 20 °C)
grade   puriss. p.a.
assay   ≥99.5% (GC)
autoignition temp.   365 °F
quality   anhydrous
expl. lim.   60 %
impurities   ≤0.5% free acid (as CH3COOH)
evapn. residue   ≤0.002%
refractive index   n20/D 1.332(lit.)
  n20/D 1.332
bp   21 °C(lit.)
mp   −125 °C(lit.)
density   0.785 g/mL at 25 °C(lit.)
cation traces   Al: ≤0.5 mg/kg
  Ba: ≤0.1 mg/kg
  Bi: ≤0.1 mg/kg
  Ca: ≤0.5 mg/kg
  Cd: ≤0.05 mg/kg
  Co: ≤0.02 mg/kg
  Cr: ≤0.02 mg/kg
  Cu: ≤0.02 mg/kg
  Fe: ≤0.1 mg/kg
  K: ≤0.5 mg/kg
  Li: ≤0.1 mg/kg
  Mg: ≤0.1 mg/kg
  Mn: ≤0.02 mg/kg
  Mo: ≤0.1 mg/kg
  Na: ≤0.5 mg/kg
  Ni: ≤0.02 mg/kg
  Pb: ≤0.1 mg/kg
  Sr: ≤0.1 mg/kg
  Zn: ≤0.1 mg/kg
storage temp.   2-8°C

Description

Caution

forms easily paraldehyde

Application

Acetaldehyde may be used for the enzymatic synthesis of fatty acids.1

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Acetaldehyde

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Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1089 3 / PGI
WGK Germany 
1
RTECS 
AB1925000
Flash Point(F) 
-38.2 °F
Flash Point(C) 
-39 °C

Protocols & Articles

Articles

Determination of Water Content in Acetaldehyde Using Karl Fischer Titration

Aldehydes have a tendency to form acetals. At the same time water is formed. Water is bound in the bisulfite addition. Short chain aldehydes show a strong tendency to acetal formation, aromatic aldeh...
Keywords: Size-exclusion chromatography, Titrations

Pyruvate Transformations

Depending on the environmental conditions, e.g. whether oxygen is present or not, pyruvate, a product of glucose metabolism, can undergo different biotransformations as shown in Figure 2. Under reduc...
BioFiles 2007, 2.6, 10.
Keywords: Anaerobic, Biofiles, Catalysis, Environmental, Metabolism

Peer-Reviewed Papers

References

Set your institution to view full text papers.

1. THE ENZYMATIC SYNTHESIS OF FATTY ACIDS BY ALDOL CONDENSATION. Brady RO Proc. Natl. Acad. Sci. U. S. A. 44(10), 993-8, (1958)

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Alcohol and lipids. Baraona, E., and Lieber, C.S. Recent Dev. Alcohol. 14, 97-134, (1998)

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Metabolic effects of acetaldehyde. Lieber CS. Biochem. Soc. Trans. 16(3), 241-47, (1988)

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Resolving Some Paradoxes in the Thermal Decomposition Mechanism of Acetaldehyde. Sivaramakrishnan R, Michael JV, Harding LB, et al. J. Phys. Chem. A, (2015)

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Ethanol and acetaldehyde in alcoholic cardiomyopathy: from bad to ugly en route to oxidative stress. Zhang, X., et al. Alcohol 32, 175-186, (2004)

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Alcohol and cancer: genetic and nutritional aspects. Poschl, G., et al. Proc. Nutr. Soc. 63, 65-71, (2004)

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Alcoholic muscle disease and biomembrane perturbations (review). Adachi, J., et al. J. Nutr. Biochem. 14, 616-625, (2003)

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New DNA adducts of crotonaldehyde and acetaldehyde. Hecht, S.S., et al. Toxicology 166, 31-36, (2001)

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The aldol condensation of acetaldehyde and heptanal on hydrotalcite-type catalysts. Tichit D, et al. J. Catal. 219(1), 167-175, (2003)

Carcinogenicity of acetaldehyde in alcoholic beverages: risk assessment outside ethanol metabolism. Lachenmeier DW, Kanteres F, and Rehm J Addiction 104(4), 533-50, (2009)

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A gas chromatographic--mass spectrometric study of profiles of volatile metabolites in hepatic encephalopathy. Goldberg EM, Blendis LM, and Sandler S J. Chromatogr. A 226(2), 291-9, (1981)

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The aldehyde dehydrogenase 2 (ALDH2) Glu504Lys polymorphism interacts with alcohol drinking in the risk of stomach cancer. Matsuo K, Oze I, Hosono S, et al. Carcinogenesis 34(7), 1510-5, (2013)

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Pueraria lobata (Kudzu root) hangover remedies and acetaldehyde-associated neoplasm risk. McGregor NR Alcohol 41(7), 469-78, (2007)

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Alcohol and oral squamous cell carcinoma. Feller L, Chandran R, Khammissa RA, et al. SADJ 68(4), 176-80, (2013)

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[Molluscicidal effect of WPN and MNSC on Lymnaea]. Wang SW, Wang HY, Luo BR, et al. Zhongguo Xue Xi Chong Bing Fang Zhi Za Zhi 25(1), 61-3, (2013)

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[Influence of ethanol-metabolising systems on intensity of lipid peroxidation processes in gastrointestinal tract of rats]. Petushok NÉ, Grokhovskaia TCh, Mel'nichenko NG, et al. Biomed. Khim. 59(1), 76-80, (2013)

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[Molluscicidal effect of suspension concentrate of metaldehyde and niclosamide in fields of mountainous areas in Yunnan Province]. Li BG, Li WB, Feng XG, et al. Zhongguo Xue Xi Chong Bing Fang Zhi Za Zhi 24(5), 564-6, (2012)

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[A patient with a life-threatening disulfiram-ethanol reaction]. Tummers-de Lind van Wijngaarden RF, Havenith T, Hurkens KP, et al. Ned. Tijdschr. Geneeskd. 157(1), A5240, (2013)

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Effect of the allelic variants of aldehyde dehydrogenase ALDH2*2 and alcohol dehydrogenase ADH1B*2 on blood acetaldehyde concentrations. Peng GS and Yin SJ Hum. Genomics 3(2), 121-7, (2009)

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Putative role of brain acetaldehyde in ethanol addiction. Deng XS and Deitrich RA Curr. Drug Abuse Rev. 1(1), 3-8, (2008)

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Pancreatic MAP kinase pathways and acetaldehyde. Apte M, McCarroll J, Pirola R, et al. Novartis Found Symp. 285, 200-11; discussion 211-6, (2007)

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Acetaldehyde adducts in circulation. Niemelä O Novartis Found Symp. 285, 183-92; discussion 193-7, (2007)

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Alcoholic myopathy and acetaldehyde. Preedy VR, Crabb DW, Farrés J, et al. Novartis Found Symp. 285, 158-77; discussion 177-82, 198-9, (2007)

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Pharmacological treatments and strategies for reducing oral and intestinal acetaldehyde. Salaspuro V Novartis Found Symp. 285, 145-53; discussion 153-7, 198-9, (2007)

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[Brain acetaldehyde and ethanol: method of determination and diagnostic significance in ethanol poisoning]. Morozov IuE, Salomatin EM, and Okhotin VE Sud. Med. Ekspert. 45(2), 35-40, (2002)

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Acetaldehyde and gastric cancer. Salaspuro M J. Dig. Dis. 12(2), 51-9, (2011)

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Piecing together the puzzle of acetaldehyde as a neuroactive agent. Correa M, Salamone JD, Segovia KN, et al. Neurosci. Biobehav. Rev. 36(1), 404-30, (2012)

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Acetaldehyde adducts in alcoholic liver disease. Setshedi M, Wands JR, and Monte SM Oxid. Med. Cell. Longev. 3(3), 178-85, (2010)

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Binding of acetaldehyde to human and Guinea pig placentae in vitro. Hard ML, Iqbal U, Brien JF, et al. Placenta 24(2-3), 149-54, (2003)

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The impact of background organic matter and alkalinity on the degradation of the pesticide metaldehyde by two advanced oxidation processes: UV/H₂O₂ and UV/TiO₂. Autin O, Hart J, Jarvis P, et al. Water Res. 47(6), 2041-9, (2013)

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Abuse potential of non-nicotine tobacco smoke components: acetaldehyde, nornicotine, cotinine, and anabasine. Hoffman AC and Evans SE Nicotine Tob. Res. 15(3), 622-32, (2013)

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Epidemiological evidence that acetaldehyde plays a significant role in the development of decreased serum folate concentration and elevated mean corpuscular volume in alcohol drinkers. Yokoyama T, Saito K, Lwin H, et al. Alcohol. Clin. Exp. Res. 29(4), 622-30, (2005)

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The fermentation stress response protein Aaf1p/Yml081Wp regulates acetate production in Saccharomyces cerevisiae. Walkey CJ, Luo Z, Madilao LL, et al. PLoS ONE 7(12), e51551, (2012)

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Aldehyde dehydrogenase 2 deficiency ameliorates alcoholic fatty liver but worsens liver inflammation and fibrosis in mice. Kwon HJ, Won YS, Park O, et al. Hepatology 60(1), 146-57, (2014)

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Alcohol induced hepatic fibrosis: role of acetaldehyde. Mello T, Ceni E, Surrenti C, et al. Mol. Aspects Med. 29(1-2), 17-21, (2008)

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Evaluation of different derivatisation approaches for gas chromatographic-mass spectrometric analysis of carbohydrates in complex matrices of biological and synthetic origin. Becker M, Zweckmair T, Forneck A, et al. J. Chromatogr. A 1281, 115-26, (2013)

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Metaldehyde removal from aqueous solution by adsorption and ion exchange mechanisms onto activated carbon and polymeric sorbents. Tao B and Fletcher AJ J. Hazard. Mater. 244-245, 240-50, (2013)

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Polyamines stimulate the formation of mutagenic 1,N2-propanodeoxyguanosine adducts from acetaldehyde. Theruvathu JA, Jaruga P, Nath RG, et al. Nucleic Acids Res. 33(11), 3513-20, (2005)

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Screening for acetaldehyde dehydrogenase 2 genotype in alcohol-induced asthma by using the ethanol patch test. Matsuse H, Shimoda T, Fukushima C, et al. J. Allergy Clin. Immunol. 108(5), 715-9, (2001)

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Ammonia and formaldehyde participate in the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in addition to creati(ni)ne and phenylacetaldehyde. Zamora R, Alcón E, and Hidalgo FJ Food Chem. 155, 74-80, (2014)

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Acetaldehyde and the genome: beyond nuclear DNA adducts and carcinogenesis. Brooks PJ and Zakhari S Environ. Mol. Mutagen. 55(2), 77-91, (2014)

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Formation of acetaldehyde-derived DNA adducts due to alcohol exposure. Yu HS, Oyama T, Isse T, et al. Chem. Biol. Interact. 188(3), 367-75, (2010)

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Acetaldehyde: déjà vu du jour. Deitrich RA J. Stud. Alcohol 65(5), 557-72, (2004)

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Inhibition of human alcohol and aldehyde dehydrogenases by cimetidine and assessment of its effects on ethanol metabolism. Lai CL, Li YP, Liu CM, et al. Chem. Biol. Interact. 202(1-3), 275-82, (2013)

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Neurotoxicity of acetaldehyde-derived advanced glycation end products for cultured cortical neurons. Takeuchi M, Watai T, Sasaki N, et al. J. Neuropathol. Exp. Neurol. 62(5), 486-96, (2003)

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Influence of genetic variations of ethanol-metabolizing enzymes on phenotypes of alcohol-related disorders. Higuchi S, Matsushita S, Masaki T, et al. Ann. N. Y. Acad. Sci. 1025, 472-80, (2004)

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Differential contribution of clinical amounts of acetaldehyde to skeletal and cardiac muscle dysfunction in alcoholic myopathy. Oba T, Maeno Y, and Ishida K Curr. Pharm. Des. 11(6), 791-80, (2005)

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Universal concept for the implementation of a single cleavable unit at tunable position in functional poly(ethylene glycol)s. Dingels C, Müller SS, Steinbach T, et al. Biomacromolecules 14(2), 448-59, (2013)

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Drinking drivers in Sweden who consume denatured alcohol preparations: an analytical-toxicological study. Jones AW, Lund M, and Andersson E J. Anal. Toxicol. 13(4), 199-203, (1989)

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Relationship between the concentration of ethanol and methanol in blood samples from Swedish drinking drivers. Jones AW and Löwinger H Forensic Sci. Int. 37(4), 277-85, (1988)

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Intracellular accumulation of advanced glycation end products induces apoptosis via endoplasmic reticulum stress in chondrocytes. Yamabe S, Hirose J, Uehara Y, et al. FEBS J. 280(7), 1617-29, (2013)

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Alcohol and acetaldehyde in public health: from marvel to menace. Guo R and Ren J Int. J. Environ. Res. Public Health 7(4), 1285-301, (2010)

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Opposite motor responses elicited by ethanol in the posterior VTA: the role of acetaldehyde and the non-metabolized fraction of ethanol. Martí-Prats L, Sánchez-Catalán MJ, Orrico A, et al. Neuropharmacology 72, 204-14, (2013)

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Use of scented sugar bait stations to track mosquito-borne arbovirus transmission in California. Lothrop HD, Wheeler SS, Fang Y, et al. J. Med. Entomol. 49(6), 1466-72, (2012)

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Risk assessment for the Italian population of acetaldehyde in alcoholic and non-alcoholic beverages. Paiano V, Bianchi G, Davoli E, et al. Food Chem. 154, 26-31, (2014)

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DNA adducts from acetaldehyde: implications for alcohol-related carcinogenesis. Brooks PJ and Theruvathu JA Alcohol 35(3), 187-93, (2005)

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Acetaldehyde adducts in the brain of alcoholics. Nakamura K, Iwahashi K, Furukawa A, et al. Arch. Toxicol. 77(10), 591-3, (2003)

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RNA interference against discoidin domain receptor 2 ameliorates alcoholic liver disease in rats. Luo Z, Liu H, Sun X, et al. PLoS ONE 8(2), e55860, (2013)

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Relationship between omega-3 fatty acids and plasma neuroactive steroids in alcoholism, depression and controls. Nieminen LR, Makino KK, Mehta N, et al. Prostaglandins Leukot. Essent. Fatty Acids 75(4-5), 309-14, (2006)

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Evidence that a metabolic microcompartment contains and recycles private cofactor pools. Huseby DL and Roth JR J. Bacteriol. 195(12), 2864-79, (2013)

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Does acetaldehyde mediate ethanol action in the central nervous system? Mascia MP, Maiya R, Borghese CM, et al. Alcohol. Clin. Exp. Res. 25(11), 1570-5, (2001)

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Serum 7 alpha-hydroxy-4-cholesten-3-one and selenohomocholyltaurine (SeHCAT) whole body retention in the assessment of bile acid induced diarrhoea. Brydon WG, Nyhlin H, Eastwood MA, et al. Eur. J. Gastroenterol. Hepatol. 8(2), 117-23, (1996)

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Vinyl acetate monomer (VAM) genotoxicity profile: relevance for carcinogenicity. Albertini RJ Crit. Rev. Toxicol. 43(8), 671-706, (2013)

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Erythrocyte and plasma protein modification in alcoholism: a possible role of acetaldehyde. Tyulina OV, Prokopieva VD, Boldyrev AA, et al. Biochim. Biophys. Acta 1762(5), 558-63, (2006)

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3,5-Bis(acetaldehyde) substituted BODIPY. Shandura MP, Yakubovskyi VP, and Kovtun YP Org. Biomol. Chem. 11(5), 835-41, (2013)

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Cytotoxicity of acetaldehyde-derived advanced glycation end-products (AA-AGE) in alcoholic-induced neuronal degeneration. Takeuchi M and Saito T Alcohol. Clin. Exp. Res. 29(12 Suppl), 220S-4S, (2005)

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Subchronic exposure to ethyl tertiary butyl ether resulting in genetic damage in Aldh2 knockout mice. Weng Z, Suda M, Ohtani K, et al. Toxicology 311(3), 107-14, (2013)

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Effect of the closure type on the evolution of the physical-chemical and sensory characteristics of a Montepulciano d'Abruzzo Rosé wine. Guaita M, Petrozziello M, Motta S, et al. J. Food Sci. 78(2), C160-9, (2013)

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Ethanol and acetaldehyde action on central dopamine systems: mechanisms, modulation, and relationship to stress. Melis M, Diana M, Enrico P, et al. Alcohol 43(7), 531-9, (2009)

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Scopoletin prevents alcohol-induced hepatic lipid accumulation by modulating the AMPK-SREBP pathway in diet-induced obese mice. Lee HI, Yun KW, Seo KI, et al. Metabolism 63(4), 593-601, (2014)

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Development of industrial brewing yeast with low acetaldehyde production and improved flavor stability. Wang J, Shen N, Yin H, et al. Appl. Biochem. Biotechnol. 169(3), 1016-25, (2013)

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Unexpected properties of NADP-dependent secondary alcohol dehydrogenase (ADH-1) in Trichomonas vaginalis and other microaerophilic parasites. Leitsch D, Williams CF, Lloyd D, et al. Exp. Parasitol. 134(3), 374-80, (2013)

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Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins. Alfonso Pérez-Garrido et al Bioorg. Med. Chem. 17, 896-904, (2009)

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In vitro effects of ethanol, acetaldehyde and fatty acid ethyl esters on human erythrocytes. Tyulina OV, Prokopieva VD, Dodd RD, et al. Alcohol Alcohol. 37(2), 179-86, (2002)

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Photoinduced charge transfer process in p-Cu2O/n-Cu2O homojunction film and its photoelectric gas-sensing properties. Jiang T, Xie T, Yang W, et al. J. Colloid. Interface Sci. 405, 242-8, (2013)

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Acetaldehyde burst protection of ADH1B*2 against alcoholism: an additional hormesis protection against esophageal cancers following alcohol consumption? Israel Y, Rivera-Meza M, Quintanilla ME, et al. Alcohol. Clin. Exp. Res. 35(5), 806-10, (2011)

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Immune response to acetaldehyde-human serum albumin adduct among healthy subjects related to alcohol intake. Romanazzi V, Schilirò T, Carraro E, et al. Environ. Toxicol. Pharmacol. 36(2), 378-83, (2013)

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High cerebral scyllo-inositol: a new marker of brain metabolism disturbances induced by chronic alcoholism. Viola A, Nicoli F, Denis B, et al. MAGMA 17(1), 47-61, (2004)

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The B-vitamins in malnutrition with alcoholism. A model of intervitamin relationships. Dastur DK, Santhadevi N, Quadros EV, et al. Br. J. Nutr. 36(2), 143-59, (1976)

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The identification of degradation products and degradation pathway of malvidin-3-glucoside and malvidin-3,5-diglucoside under microwave treatment. Zhao M, Luo Y, Li Y, et al. Food Chem. 141(3), 3260-7, (2013)

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Role of acetaldehyde in mediating the pharmacological and behavioral effects of alcohol. Quertemont E and Didone V Alcohol Res. Health 29(4), 258-65, (2006)

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Anoxia promotes gravitropic curvature in rice pulvini but inhibits it in wheat and oat pulvini. Azuma T, Inoue Y, Hamada Y, et al. J. Plant Physiol. 170(13), 1158-64, (2013)

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Inhibition of CYP2E1 leads to decreased malondialdehyde-acetaldehyde adduct formation in VL-17A cells under chronic alcohol exposure. Swaminathan K, Clemens DL, and Dey A Life Sci. 92(6-7), 325-36, (2013)

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Acetaldehyde acutely impairs canine testicular testosterone secretion. Boyden TW, Silvert MA, and Pamenter RW Eur. J. Pharmacol. 70(4), 571-6, (1981)

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Nonlinear responses for chromosome and gene level effects induced by vinyl acetate monomer and its metabolite, acetaldehyde in TK6 cells. Budinsky R, Gollapudi B, Albertini RJ, et al. Environ. Mol. Mutagen. 54(9), 755-68, (2013)

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Assays for acetaldehyde-derived adducts in blood proteins based on antibodies against acetaldehyde/lipoprotein condensates. Latvala J, Melkko J, Parkkila S, et al. Alcohol. Clin. Exp. Res. 25(11), 1648-53, (2001)

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Theoretical study of photochemical hydrogen abstraction by triplet aliphatic carbonyls by using density functional theory. Firme CL, Garden SJ, de Lucas NC, et al. J. Phys. Chem. A 117(2), 439-50, (2013)

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Attraction of the orange mint moth and false celery leaftier moth (Lepidoptera: Crambidae) to floral chemical lures. Landolt P, Cha D, and Davis TS J. Econ. Entomol. 107(2), 654-60, (2014)

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Paracoccus denitrificans PD1222 utilizes hypotaurine via transamination followed by spontaneous desulfination to yield acetaldehyde and, finally, acetate for growth. Felux AK, Denger K, Weiss M, et al. J. Bacteriol. 195(12), 2921-30, (2013)

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Short- and long-term effects of acetaldehyde on plasma. Brecher AS and Adamu MT Alcohol 26(1), 49-53, (2002)

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Effects of aldehyde dehydrogenase-2 genotype on cardiovascular and endocrine responses to alcohol in young Japanese subjects. Nishimura FT, Fukunaga T, Kajiura H, et al. Auton. Neurosci. 102(1-2), 60-70, (2002)

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Appearance of aldehydes in the surface layer of lake waters. Dąbrowska A, Nawrocki J, and Szeląg-Wasielewska E Environ. Monit. Assess. 186(7), 4569-80, (2014)

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Locally-generated acetaldehyde is involved in ethanol-mediated LTP inhibition in the hippocampus. Tokuda K, Izumi Y, and Zorumski CF Neurosci. Lett. 537, 40-3, (2013)

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Effect of nine plant volatiles in the field on the sex pheromones of Leguminivora glycinivorella. Hu D, Feng J, Wang Z, et al. Nat. Prod. Commun. 8(3), 393-6, (2013)

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[The possible role of acetaldehyde in the brain damage caused by the chronic consumption of alcohol]. Forn-Frías C and Sanchis-Segura C Rev. Neurol. 37(5), 485-93, (2003)

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Skin regeneration after chemical burn under the effect of taxifolin-based preparations. Shubina VS and Shatalin YV Bull. Exp. Biol. Med. 154(1), 152-7, (2012)

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What is in that drink: the biological actions of ethanol, acetaldehyde, and salsolinol. Deehan GA, Brodie MS, and Rodd ZA Curr. Top. Behav. Neurosci. 13, 163-84, (2013)

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Acetaldehyde links alcohol consumption to cancer. Burton A Lancet Oncol. 6(9), 643, (2005)

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Merck 14,39

Beil. 1,IV,3094

Fieser 1,3

Aldrich MSDS 1, 3:A / Arctander, 3 / Corp MSDS 1 (1), 5:A / FT-IR 1 (1), 465:B / FT-IR 2 (1), 730:B / FT-NMR 1 (1), 727:A / Fenaroli / IR-Spectra (2), 248:B / IR-Spectra (3), 276:B / NMR-Reference 2 (1), 357:A / RegBook 1 (1), 509:B / RegBook 3 (1), 509:B / Sax 6, 74 / Structure Index 1, 73:B:1 / Vapor Phase 3, 551:A

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