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V2375 Sigma

Vanillin

Synonym: 4-Hydroxy-3-methoxybenzaldehyde, Vanillic aldehyde

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Properties

Related Categories Aldehydes, Building Blocks, C8, Carbonyl Compounds, Cell Biology,
vapor density   5.3 (vs air)
vapor pressure   >0.01 mmHg ( 25 °C)
assay   ≥98%
bp   170 °C/15 mmHg(lit.)
mp   81-83 °C(lit.)
Gene Information   rat ... Ar(24208)

Description

Price and Availability

Suggested Laboratory Gloves


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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xi
Risk Statements (Europe) 
36
Safety Statements (Europe) 
26
WGK Germany 
1
RTECS 
YW5775000
Flash Point(F) 
307.4 °F
Flash Point(C) 
153 °C

Protocols & Articles

Peer-Reviewed Papers

References

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Impact of induced fit on ligand binding to the androgen receptor: a multidimensional QSAR study to predict endocrine-disrupting effects of environmental chemicals. Markus A Lill et al J. Med. Chem. 48, 5666-74, (2005)

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Vanillin and vanillin analogs relax porcine coronary and basilar arteries by inhibiting L-type Ca2+ channels. Raffai G, Khang G, and Vanhoutte PM J. Pharmacol. Exp. Ther. 352(1), 14-22, (2015)

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Determination of vanillin in commercial food product by adsorptive stripping voltammetry using a boron-doped diamond electrode. Yardım Y, Gülcan M, and Şentürk Z Food Chem. 141(3), 1821-7, (2013)

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Novel approaches to the biosynthesis of vanillin. Walton NJ, Narbad A, Faulds C, et al. Curr. Opin. Biotechnol. 11(5), 490-6, (2000)

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Serotonergic activity-guided phytochemical investigation of the roots of Angelica sinensis. Shixin Deng et al J. Nat. Prod. 69, 536-41, (2006)

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Influenza A (H(1)N(1)) Antiviral and Cytotoxic Agents from Ferula assa-foetida. Chia-Lin Lee et al J. Nat. Prod. 72, 1568-72, (2009)

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Study on the constituents of Mexican propolis and their cytotoxic activity against PANC-1 human pancreatic cancer cells. Feng Li et al J. Nat. Prod. 73, 623-7, (2010)

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Vanillin. Walton NJ, Mayer MJ, and Narbad A Phytochemistry 63(5), 505-15, (2003)

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Mixed-ligand Cu(II)-vanillin Schiff base complexes; effect of coligands on their DNA binding, DNA cleavage, SOD mimetic and anticancer activity. Tabassum S, Amir S, Arjmand F, et al. Eur. J. Med. Chem. 60, 216-32, (2013)

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Biotechnological production of vanillin. Priefert H, Rabenhorst J, and Steinbüchel A Appl. Microbiol. Biotechnol. 56(3-4), 296-314, (2001)

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Cytotoxic flavonoids from the leaves of Cryptocarya chinensis. Tsung-Hsien Chou et al J. Nat. Prod. 73, 1470-5, (2010)

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Overexpression of O-methyltransferase leads to improved vanillin production in baker's yeast only when complemented with model-guided network engineering. Brochado AR and Patil KR Biotechnol. Bioeng. 110(2), 656-9, (2013)

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Increased significance of food wastes: selective recovery of added-value compounds. Reis IA, Santos SB, Santos LA, et al. Food Chem. 135(4), 2453-61, (2012)

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Antitubercular constituents from the stem wood of Cinnamomum kotoense. Fu-Chi Chen et al J. Nat. Prod. 68, 1318-23, (2005)

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On the factors affecting product distribution in laccase-catalyzed oxidation of a lignin model compound vanillyl alcohol: experimental and computational evaluation. Lahtinen M, Heinonen P, Oivanen M, et al. Org. Biomol. Chem. 11(33), 5454-64, (2013)

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Effects of lignin-derived phenolic compounds on xylitol production and key enzyme activities by a xylose utilizing yeast Candida athensensis SB18. Zhang J, Geng A, Yao C, et al. Bioresour. Technol. 121, 369-78, (2012)

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Melanogenesis inhibitors from the desert plant Anastatica hierochuntica in B16 melanoma cells. Souichi Nakashima et al Bioorg. Med. Chem. 18, 2337-45, (2010)

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Biovanillin from agro wastes as an alternative food flavour. Zamzuri NA and Abd-Aziz S J. Sci. Food Agric. 93(3), 429-38, (2013)

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Investigation of the Amycolatopsis sp. strain ATCC 39116 vanillin dehydrogenase and its impact on the biotechnical production of vanillin. Fleige C, Hansen G, Kroll J, et al. Appl. Environ. Microbiol. 79(1), 81-90, (2013)

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Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica. Jih-Jung Chen et al J. Nat. Prod. 71, 1016-21, (2008)

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3D-QSAR and molecular docking studies of benzaldehyde thiosemicarbazone, benzaldehyde, benzoic acid, and their derivatives as phenoloxidase inhibitors. Chao-Bin Xue et al Bioorg. Med. Chem. 15, 2006-15, (2007)

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Toxicity and synergic repellency of plant essential oil mixtures with vanillin against Aedes aegypti (Diptera: Culicidae). Kim SI, Yoon JS, Baeck SJ, et al. J. Med. Entomol. 49(4), 876-85, (2012)

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A comprehensive review on vanilla flavor: extraction, isolation and quantification of vanillin and others constituents. Sinha AK, Sharma UK, and Sharma N Int. J. Food Sci. Nutr. 59(4), 299-326, (2008)

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CYP53A15 of Cochliobolus lunatus, a target for natural antifungal compounds. Barbara Podobnik et al J. Med. Chem. 51, 3480-6, (2008)

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Effect of enzymatic deamidation of soy protein by protein-glutaminase on the flavor-binding properties of the protein under aqueous conditions. Suppavorasatit I and Cadwallader KR J. Agric. Food Chem. 60(32), 7817-23, (2012)

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Automated method for determination of olive oil phenols and metabolites in human plasma and application in intervention studies. Orozco-Solano MI, Ferreiro-Vera C, Priego-Capote F, et al. J. Chromatogr. A 1258, 108-16, (2012)

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Prenatal chemosensory learning by the predatory mite Neoseiulus californicus. Peralta Quesada PC and Schausberger P PLoS ONE 7(12), e53229, (2012)

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Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core. Harini ST, Kumar HV, Rangaswamy J, et al. Bioorg. Med. Chem. Lett. 22(24), 7588-92, (2012)

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Synthesis and antioxidant properties of dendritic polyphenols. Choon Young Lee et al Bioorg. Med. Chem. Lett. 19, 6326-30, (2009)

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Inhibition by capsaicin and its related vanilloids of compound action potentials in frog sciatic nerves. Tomohiro D, Mizuta K, Fujita T, et al. Life Sci. 92(6-7), 368-78, (2013)

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Biotechnological and molecular approaches for vanillin production: a review. Kaur B and Chakraborty D Appl. Biochem. Biotechnol. 169(4), 1353-72, (2013)

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Flavoring extracts of Hemidesmus indicus roots and Vanilla planifolia pods exhibit in vitro acetylcholinesterase inhibitory activities. Kundu A and Mitra A Plant Foods Hum. Nutr. 68(3), 247-53, (2013)

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Impact of flavour solvent (propylene glycol or triacetin) on vanillin, 5-(hydroxymethyl)furfural, 2,4-decadienal, 2,4-heptadienal, structural parameters and sensory perception of shortcake biscuits over accelerated shelf life testing. Yang N, Hort J, Linforth R, et al. Food Chem. 141(2), 1354-60, (2013)

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New decontamination method based on caprylic acid in combination with citric acid or vanillin for eliminating Cronobacter sakazakii and Salmonella enterica serovar Typhimurium in reconstituted infant formula. Choi MJ, Kim SA, Lee NY, et al. Int. J. Food Microbiol. 166(3), 499-507, (2013)

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Validated determination of primulasaponins in primula root by a high-performance-thin-layer-chromatography densitometric approach. Coran SA and Mulas S J. Pharm. Biomed. Anal. 70, 647-51, (2012)

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Enhancement of pancreatic lipase inhibitory activity of curcumin by radiolytic transformation. Tae Hoon Kim et al Bioorg. Med. Chem. Lett. 21, 1512-4, (2011)

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Inhibitory property of the Piper betel phenolics against photosensitization-induced biological damages. Soumyaditya Mula et al Bioorg. Med. Chem. 16, 2932-8, (2008)

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Optimization of enzymatic process for vanillin extraction using response surface methodology. Gu F, Xu F, Tan L, et al. Molecules 17(8), 8753-61, (2012)

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Vanillin suppresses Kupffer cell-related colloidal carbon-induced respiratory burst activity in isolated perfused rat liver: anti-inflammatory implications. Galgani JE, Núñez B, and Videla LA Food Funct. 3(12), 1319-23, (2012)

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Exploration of Vanilla pompona from the Peruvian Amazon as a potential source of vanilla essence: quantification of phenolics by HPLC-DAD. Maruenda H, Vico Mdel L, Householder JE, et al. Food Chem. 138(1), 161-7, (2013)

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Anti-UV activity of lignin-carbohydrate complex and related compounds. Nanbu T, Shimada J, Kobayashi M, et al. In Vivo 27(1), 133-9, (2013)

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Simultaneous analysis of guaiacol and vanillin in a vanilla extract by using high-performance liquid chromatography with electrochemical detection. Takahashi M, Sakamaki S, and Fujita A Biosci. Biotechnol. Biochem. 77(3), 595-600, (2013)

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Characterization of an isoeugenol monooxygenase (Iem) from Pseudomonas nitroreducens Jin1 that transforms isoeugenol to vanillin. Ryu JY, Seo J, Park S, et al. Biosci. Biotechnol. Biochem. 77(2), 289-94, (2013)

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Effect of enzymatic protein deamidation on protein solubility and flavor binding properties of soymilk. Suppavorasatit I, Lee SY, and Cadwallader KR J. Food Sci. 78(1), C1-7, (2013)

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Fenugreek extract as an inducer of cellular death via autophagy in human T lymphoma Jurkat cells. Al-Daghri NM, Alokail MS, Alkharfy KM, et al. BMC Complement Altern. Med. 12, 202, (2012)

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Inhibition of GABA shunt enzymes' activity by 4-hydroxybenzaldehyde derivatives. Yun-Hai Tao et al Bioorg. Med. Chem. Lett. 16, 592-5, (2006)

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Anti-biofouling property of vanillin on Aeromonas hydrophila initial biofilm on various membrane surfaces. Ponnusamy K, Kappachery S, Thekeettle M, et al. World J. Microbiol. Biotechnol. 29(9), 1695-703, (2013)

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Thermal tolerance and survival of Cronobacter sakazakii in powdered infant formula supplemented with vanillin, ethyl vanillin, and vanillic acid. Yemiş GP, Pagotto F, Bach S, et al. J. Food Sci. 77(9), M523-7, (2012)

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Vanillin differentially affects azoxymethane-injected rat colon carcinogenesis and gene expression. Ho KL, Chong PP, Yazan LS, et al. J. Med. Food 15(12), 1096-102, (2012)

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Mining biologically-active molecules for inhibitors of fatty acid amide hydrolase (FAAH): identification of phenmedipham and amperozide as FAAH inhibitors. Fabien Vincent et al Bioorg. Med. Chem. Lett. 19, 6793-6, (2009)

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Key odorants in cured Madagascar vanilla beans (Vanilla planiforia) of differing bean quality. Takahashi M, Inai Y, Miyazawa N, et al. Biosci. Biotechnol. Biochem. 77(3), 606-11, (2013)

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Statistical media and process optimization for biotransformation of rice bran to vanillin using Pediococcus acidilactici. Kaur B and Chakraborty D Indian J. Exp. Biol. 51(11), 935-43, (2013)

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Synthesis, antifungal activity and structure-activity relationships of vanillin oxime-N-O-alkanoates. Ahluwalia V, Garg N, Kumar B, et al. Nat. Prod. Commun. 7(12), 1635-8, (2012)

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Diastereoselective synthesis of 5-hydroxy-8-methoxy-1-oxaspiro[5,5]undeca-7,10-diene-9-one. Plourde GL and Scully TW Molecules 18(1), 1174-80, (2013)

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Synthetic-biology firms shift focus. Hayden EC Nature 505(7485), 598, (2014)

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Merck 14,9932

Beil. 8,IV,1763

Aldrich MSDS 1, 1831:A / Arctander, 3067 / Corp MSDS 1 (2), 3593:D / FT-IR 1 (2), 120:D / FT-IR 2 (2), 2545:A / FT-NMR 1 (2), 959:A / Fenaroli / IR-Spectra (3), 919:G / IR-Spectra (2), 805:C / RegBook 67 (2), 1725:H / RegBook 1 (2), 1725:H / Sax 6, 2720 / Sigma FT-IR 1 (2), 971:B / Structure Index 1, 274:B:6 / Vapor Phase 3, 1301:D

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